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One of the most significant trends over the past decade has been the explosion in the number of companies in the software as a service (SaaS) industry. Today, there’s SaaS products to support virtually every business function, and increasingly for specific segments too.

Several forces have combined to make this a reality - chief among them is the mass migration to cloud computing from on-premise software, and the fact that it’s never been easier, quicker or cheaper to launch a SaaS company. In short, Marc Andreessen has been proved right, and his assertion that “software is eating the world” has well and truly come to pass.

Another significant trend is the widespread consumerization of IT - functional business leaders have displaced chief information offices (CIOs) as the main purchasers of IT and software. The role of the CIO has evolved and become decentralised - CIOs now advise, guide and empower, rather than directly make purchasing decisions (although, they often retain the power of veto). CIOs now play a different, broader and more impactful role.

As a result most departments now have their own budget for software purchases and are building their own technology stack. Traditionally, a “technology stack”, was a list of all the technology services used to build and run one single application, but in recent years it has expanded to encompass the technology used by a team, department or company. Under the hood of every successful SaaS company is a stack of tools which power their teams.

The chart below shows the sales technology landscape - there are over 800 vendors listed and 38 different categories. With so many tools available, third-party review websites, such as G2 Crowd, TrustRadius and Capterra have come to prominence. Just as people browse reviews for everything from restaurants to films to jobs, they also seek reviews for software. We humans leverage social proof to aid decision-making in both our personal and working lives.

Source: Sales Hacker

It’s fair to say that the sales enablement category has mirrored the impressive growth of the sales technology landscape as a whole. There are now many vendors selling excellent products. I’m fortunate that in my role I regularly get to speak with vendors - this front row seat gives me the opportunity to research, demo, evaluate, purchase and rollout sales enablement tools. I also make time to read analyst reports, speak with industry colleagues, follow venture capitalist (VC) activity and generally, try to keep up with the pace of change within the sales enablement space.

As a result, I’ve been thinking long and hard about what a sales enablement technology stack should look like and the types of challenges it should solve.

The growth of sales enablement
There’s never been a better time to be a sales enablement professional. The role is rapidly growing and it’s a new frontier of sorts. There are several signs which point to a promising future - just look at the rise of the Sales Enablement Society, level of VC funding flooding into the category, the growing number of sales enablement tools, and, the increasing number of sales enablement teams and practitioners.

According to Aragon Research, sales enablement technology is expected to be a $5B industry by 2021. If you require one piece of research to explain the large influx of VC cash in the sales enablement category and the emergence of sales enablement tools, then this is it. The market conditions are hugely attractive - increasing numbers of sales enablement teams are launching, their budgets are growing, most are using outdated tools and there’s no category leader. There’s a big unmet need.

What is a sales enablement technology stack?
There’s currently no agreed upon definition of what constitutes a sales enablement technology stack is, however, I think the description below effectively sums it up:

“A sales enablement technology stack is a grouping or “stack” of technologies that sales organisations leverage to conduct and improve their activities. Often, the focus of these tools and technologies is to increase sales rep effectiveness, efficiency and productivity, so that they are equipped to sell.”

Sales enablement technology categories
As I’ve mentioned there’s a plethora of tools which fall under the umbrella of sales enablement, however, in order to construct a technology stack, I think it’s helpful to first consider how, when and why sales reps will leverage specific tools. For example, it’s likely sales rep going through onboarding and who needs to learn about forecasting will have different needs to a tenured sales rep looking for a sales deck - so it stands to reason that they will also use different tools.

Sales enablement is often poorly defined and subsequently misunderstood, so there’s many technologies which fall under that umbrella. Broadly speaking, I think there are eight categories that can be described as sales enablement technology, plus “miscellaneous”, as there’s always new and peripheral technology, which can be applied to sales enablement. These tools all have different use cases and can be the building blocks of a sales enablement technology stack.

The sales enablement technology categories are:

  • Customer relationship management (CRM)

  • Learning management systems (LMS)

  • Learning reinforcement

  • Sales coaching

  • Sales readiness

  • Sales productivity

  • Sales engagement

  • Sales asset management

  • Miscellaneous

Before we progress any further I’m keen to stress that there’s huge overlap between the categories. Very few tools play in just one area, so you won’t need to go out and buy eight new tools.

However, I do believe it’s important to broadly categorise sales enablement technology. This makes it easier to see where it fits within your technology stack - otherwise you can feel like you’re going around in circles (as the chart below shows).

To bring some order to the chaos that is buying sales enablement technology, it’s valuable to think about the moments when a sales reps will use the software. In my experience, a good starting point is during a sales rep’s onboarding, which is typically between one and four weeks and the ramp period which starts when onboarding ends and often lasts up to six months. Thirdly, you should also consider the period when sales reps are fully ramped and selling. There’s lots happening at these different milestones and it’s likely they will need different technology.

For instance, some sales enablement tools have learning reinforcement, sales coaching and sales readiness functionality as standard, while others lean heavily towards sales productivity and sales engagement.

The chart below shows the different categories of sales enablement technology which make up a sales enablement technology stack:

Sales enablement technology explained
Below are explanations and examples of the different types of activity you would expect each type of sales enablement tool to help you accomplish:

CRM
A CRM helps businesses track interactions with prospects and customers. Sales reps can typically send emails and make calls within their CRM, as well as add notes and track deals from start to finish. A CRM is a critical business tool and is used to provide detailed reporting and forecasting to business leaders, and is often a company’s system of record.

At many organisations the CRM is owned by a business operations team, however, an increasing number of sales enablement teams are also taking on this responsibility. I’ve included CRM within this post for that reason, plus the fact it is often the foundation on which other tools sit.

A CRM typically helps businesses:

  • Track deals

  • Manage pipeline

  • Log activity

  • Communicate with leads and customers (calls and emails)

  • Report on activity


LMS
An LMS is a tool to help employees learn through a variety of methods. Leading LMS products offer everything from instructor-led training (ILT) right the way through to online learning to just-in-time learning (JIT). An LMS provides people with customised learning paths based on their role, experience and tenure and often has the means for companies to reinforce learning through quizzes, as well as track proficiency and award certifications.

An LMS typically has the following functionality:

  • Customised learning paths

  • ILT and JIT

  • Quizzes and certification

  • Analytics and reporting

  • Mobile functionality


Learning reinforcement
As its name suggests, a learning reinforcement tool enables employees to retain what they have learnt. This is important as there’s a large body of research which shows people forget what they’re been taught without repetition, reinforcement and practice (up to 90% of information can be forgotten within 31 days). A learning reinforcement tool typically takes a microlearning approach, which helps people retain only the most important parts of a training session.

A learning reinforcement tool typically has the following functionality:

  • Spaced reinforcement

  • Microlearning

  • Quizzes and certification

  • Analytics and reporting

  • Mobile functionality


Sales coaching
Sales coaching tools helps sales reps improve key competencies, such as perfecting an elevator pitch, articulating a value proposition or delivering a demo. They work by providing a test environment, where sales reps can practice and managers can grade the sales rep and provide structured feedback, all of which is tracked within the tool.

Sales coaching tools often enable sales reps to make recordings or upload live calls to the tool for feedback, and some of the leading vendors use machine learning and artificial intelligence (AI) to transcribe recordings and provide coaching recommendations to the manager.

A sales coaching tool typically has the following functionality:

  • Coaching platform

  • Call recording

  • Call insights and recommendations

  • Best practice library

  • Video challenges


Sales readiness
A sales readiness tool helps sales reps to prepare for selling, and is typically used for onboarding new hires and during the ramp period. The leading solutions enable people to participate in both online and ILT, discover the latest updates and receive coaching. Another benefit of sales readiness tools is that they allow you to meet the needs of the modern learner (overwhelmed and distracted) with a microlearning or JIT learning approach.

An example of a JIT approach would be a sales rep trying to create a quote within your CRM. They may have covered how to do this in their onboarding, but by the time they need to create a quote, they may have forgotten what they’ve learnt. A sales readiness tool can provide JIT learning in the form of video and text instructions on how to perform tasks, such as creating a quote.

A sales readiness tool typically has the following functionality:

  • Microlearning and JIT learning

  • Sales playbooks

  • Quizzes and certification

  • Analytics and reporting

  • Mobile functionality


Sales productivity
A sales productivity tool helps automate low value tasks - freeing up people’s time to focus on speaking with prospects and customers. There are many sales productivity tools out there, and they typically reduce the time that sales reps spend on repetitive activities, such as sending emails to prospects and setting up meetings. Advanced tools help sales reps spend their time more efficiently with intelligent notifications, such as when leads visit a web page or take a high intent action.

A sales productivity tool typically has the following functionality:

  • Email sequences

  • Meeting scheduling

  • Lead notifications

  • Email tracking

  • Workflow automation


Sales engagement
Sales engagement tools help sales reps to connect with people in a more effective way. These tools are particularly prevalent among SaaS inside sales teams that are chasing relatively high volume, but low value deals. Sales teams in that type of environment require a highly engineered and repeatable sales processes - and these tools often make it possible to accomplish that.

The best sales engagement tools provide personalisation at scale and they leverage data to identify what makes a successful connection, such as time of day, subject line and type of communication.

A sales engagement tool typically has the following functionality:

  • A/B testing

  • Email templates

  • Email scheduling

  • Text messaging

  • Video functionality


Sales asset management
A sales asset management tool helps sales and marketing teams to share the right content with the right audience at the right time. Best of all, sales asset management tools provide detailed analytics - so you can understand what content is consumed, shared and ultimately, what helps win deals.

A sales asset management tool typically has the following functionality:

  • Content management

  • Content recommendations

  • Content personalisation

  • Compliance

  • Content analytics


Miscellaneous
There’s a large number of tools out there which can be used for sales enablement, but aren’t necessarily positioned as such. My advice is to keep your eye on the sales enablement and peripheral vendor space, and keep some budget aside each year for potential projects.

Over the past 12 months, I’ve been interested in tools in the following space (I believe they are worth investigating further):

  • Sales rep knowledge base

  • Chatbot

  • Data enrichment

  • Meeting intelligence

  • Pipeline automation


Building your sales enablement technology stack
Each company will have its own needs and requirements when building a sales enablement technology stack. However, I believe there’s a process you can follow to ensure you’re building a stack that truly meets the needs of your sales organisation. The steps are as follows:

1. Understand the jobs to be done
Before making any technology purchases you need to understand the key activities your sales reps undertake (e.g. book meetings) and what the intended outcome of the activity is (e.g. close deals more quickly). This will give you a baseline to understand what they’re doing and what could be improved.

2. Audit existing technology
You should also audit your existing technology, and seek to understand what it does, how it’s used, as well as strengths and weaknesses. By understand the jobs to be done and tools currently used, it’s then possible to identify gaps that new technology could help fill.

As an aside, I’ve worked in organisations where it’s been difficult to audit technology (many tools were being paid for, but not used), so this may also be an opportunity to put some rigour around future technology purchases.

3. Define your needs
Next up is defining your needs, and listing at a high level what you want the tool to do for your business. At this stage my advice is to think about the outcomes and what results the tool will help you achieve. Once you’ve defined these high level requirements, you can then think about features and functionality.

4. Agree what functionality is essential and what is nice to have
Now it’s time to get granular. You need to decide what features and functionality are essential and those which are only nice to have. Be warned - people can often be swayed by nice to haves, but they’re often a distraction. To combat this I suggest creating a scorecard that is weighted heavily towards what is essential.

5. Evaluate vendors
You’re now ready to reach out and start speaking with vendors. I suggest involving key stakeholders and end users in the evaluation process, if they’re not already. Buying technology is one thing, but successfully rolling it out is quite another. Involving the right people early on, being thoughtful about communication and gaining “buy in” is hugely important.

There you have it. That’s how I’m thinking about sales enablement technology. However, I want to conclude with a word of caution. As the role of sales enablement continues its ascent and more technology becomes available, it’s going to become even more important that we remain strategic and thoughtful about the purchases we make and the value they help us create. That’s how the role of sales enablement will continue its journey to gaining a seat at the top table.

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Retention truly is the foundation of growth for software as a service (SaaS) companies, but oftentimes, it is overlooked and undervalued. This is always a huge mistake. High churn is a corollary of poor retention - but it can creep up unannounced, and rather than deal a single fatal blow, it causes death by a thousand small cuts.

A high churn rate is highly undesirable as it shackles growth, is a source of friction and (rightly) raises tough questions about product/market fit. You need to understand retention and optimise for it.

So why is retention so vital to the wellbeing, growth and success of a SaaS company? Well, it all comes down to basic economics. Put simply, it is considerably cheaper to retain customers than acquire new ones. There’s little point in acquiring new customers if churn is out of control. Think of it like a leaky bucket - you need to fix the hole, rather than continually filling the bucket with more water.

The image below shows how high churn can quickly derail the growth of a SaaS company. If businesses with high churn continue to acquire new customers they’re going to waste time and resource, and have little to show for it.

Source: HubSpot

Retention trumps acquisition
While new client acquisition often captures the attention of business leaders, in my experience, many companies are taking the wrong approach. They overestimate the importance of the initial sale and underestimate the importance of a client’s lifetime value (LTV). Now don’t get me wrong - the sales organisation plays a vital role acquiring customers, but when you have a services organisation that typically retains clients for several years, you begin to realise that services is where the big money is made.

In my mind, retention trumps acquisition and Tom Tunguz, venture capitalist (VC) at Redpoint shared five reasons why fixing churn is a better bet than chasing growth. Despite this, most SaaS leaders rank acquisition over retention. While they care about retention, it’s clearly less of a priority.

Source: ProfitWell

We’ve covered why high churn is undesirable, but let’s turn our attention to why low churn is important and what it means for a SaaS business. Put simply, if you’re acquiring customers, and the rate at which they buy more is greater than the revenue lost from churn, then you’ve built a highly desirable business. A business that doesn’t have to sell anything new, but still grows is the holy grail of SaaS.

The key takeaway is to make tackling churn a priority early on, rather than reacting after the event.

Calculating churn
As I hope you’ll agree by now, churn matters and understanding how it’s calculated is really important. It may not be immediately apparent, but there’s some important differences between monthly and annual churn. Allow me to explain. A 5% annual churn rate means that monthly churn is 0.42%, whereas a 5% monthly churn equates into a hugely troubling 46% annual churn rate. Or put another way, a 5% monthly churn rate means that if you started January with 100 customers you’d only have 54 customers left at the end of December. In order to record any kind of growth you’d have to acquire another 47 new customers.

While each industry and company is different, a 5% monthly churn rate isn’t a solid foundation for a SaaS business, and in all honesty a business in that situation should seek to ramp up retention and dial down acquisition. Otherwise, it’s literally burning through money. High churn becomes even more troublesome if you have a limited total addressable market (TAM) - when businesses acquire customers and then lose them, it’s nigh on impossible to re-win their trust and business.

LTV:CAC for SaaS businesses
LTV:CAC is perhaps the most important of all SaaS metrics, so it’s invaluable to know how churn impacts it. LTV:CAC is the lifetime value of a customer divided by the customer acquisition cost. Looking at these numbers as a ratio helps you understand how effective a business is at making money. You can clearly see what the return will be from every dollar, euro or pound invested. An LTV:CAC of 3:1 is widely regarded within the SaaS industry as the foundation of a solid business (an even greater LTV is better).

SaaS businesses have unique characteristics which means it makes sense for them to be measured differently. They typically incur high up-front costs to deliver products and acquire customers, but follow the path to profitability by retaining and adding customers over time, many of whom upgrade or buy more. SaaS businesses often operate on a subscription basis, so monthly or yearly subscription value is low, but lifetime value is high. This makes retention and keeping a handle on churn absolutely vital.

SaaS growth levers
At a high level, retention matters as there’s only ever three levers to grow a SaaS business:

  1. Increase number of customers

  2. Increase average revenue per user (ARPU)

  3. Reduce customer churn

Let’s take a look at the results businesses can achieve by optimising each lever. Although, the scenarios below are completely theoretical, the table shows how each growth lever acts as a multiplier and that incremental improvements can have a transformational impact on the performance of a SaaS business.

Seemingly small improvements or a few percentage points improvement can have a dramatic impact on the health and success of a SaaS company.

Metric

Scenario A

Scenario B

Difference

ARPU

$100K

$120K

+20%

Number of customers

1K

1.K

+20%

Annual churn rate

10%

5%

-50%

ARR

$90M

$136.8M

+52%

Where SaaS businesses choose to invest their time, energy and money is hugely important. They need to strike the fine balance between customer acquisition, retention and account growth. The best companies understand how to retain customers, all the while increasing ARPU, and once these metrics have created a flywheel effect, they then (and only then) double down on customer acquisition with sales and marketing. That’s the winning growth playbook followed by the leading SaaS businesses.

The importance of customer success
I’m sure it’s abundantly clear by now, but SaaS companies need to invest in some form of customer success. But what should “customer success” include? While it’s hard to generalise, for lower cost products customer success will likely include self guided education, such as videos, forums and FAQs pages and at the higher end it will mean dedicated staff, such as a customer success manager or professional services, while the middle will take a blended approach.

Businesses need to remember the “services” part of SaaS - too often they forget they’re not just selling software. After all, the act of purchasing software never makes a customer successful. They need education, training and support to leverage it effectively. Once they’ve acquired this knowledge (or hired a third party with it), then and only then, are they on the way to achieving success.

Calculating customer success
One of the best ways to understand the success of your customer base is net promoter score (NPS). It’s an index ranging from -100 to 100 that measures the willingness of customers to recommend a company's products or services.

While NPS may lack detail and qualitative data, it does provide an effective indicator of the health of a client and if they’re a churn risk. For those unfamiliar with NPS, its scoring system means that you’re penalised heavily for poor a rating (0-6 are classified as detractors), receive nothing for mediocre ratings (7-8 are classified as passives) and are only rewarded for high ratings (9-10 are classified as promoters).

Source: Wootric

What represents a “good” NPS changes between industry and product, however, you should track your own NPS, as well as conduct research to track and benchmark key competitors.

For SaaS businesses to turn a profit they need clients to succeed and continue paying for their products over a long period of time. This is easier said than done, but is what increases LTV, retention and recurring revenue. By investing in customer success teams to provide strategic guidance, account management and support, businesses are well placed to reduce churn and increase spend per client. Customer success is a vital cog in the SaaS sales engine - it has the potential to generate considerably more recurring revenue than the original sale.

Strategies to help SaaS companies reduce churn
Based on my experiences at HubSpot, Indeed.com and Automation Anywhere, I’ve identified five high impact strategies to lower churn:

1. Develop an integration ecosystem
There’s much data to suggest that integrations with other products help SaaS businesses to reduce churn. This makes perfect sense - integrations often provide customers with more value, which in turn increases usage and gives them more reasons to engage with your product. It’s a virtuous circle, and you should consider building or enabling other companies to build products that integrate with yours.

The graph below shows that customer retention is closely tied to the number of integrations they have - in fact, just one integration seemingly has a significant impact on retention.

Source: ProfitWell

Integrations are an important weapon in your armour as they give your clients more ways and reasons to use your product - this typically leads to higher usage, which creates more value and ultimately greater retention.

2. Optimise your qualification process
There’s a school of thought which states that only poor fit customers churn. I don’t quite see things as clear cut as that, however, the fact remains - by optimising your qualification process you can screen out poor fit clients early on and defend against churn further down the line.

You can get started with optimising your qualification process by looking at the profile of successful customers and unsuccessful ones. Depending on what you uncover it could lead you to take action such as, focussing on targeted accounts like the Fortune 1000, or refining your value proposition. This could mean moving away from being perceived as a money saving product to one that helps companies make money or increases productivity. It could also lead you to focussing on specific job roles or moving from mid-market to enterprise.

The key learning here is to recognise that your qualification process needs to be in a continual state of optimisation. There’s no guarantee what worked yesterday will continue to work in the future. You need to understand who wins (and loses) with your product.

3. Increase ARPU with up and cross-selling
There’s a large body of research which shows that higher ARPU leads to less churn. Perhaps understandably, if a client is continuing to spend a high amount of money, it stands to reason they’re deriving value and therefore less likely to churn.

Source: ProfitWell

SaaS businesses have two options when it comes to increasing ARPU - they can either upsell, meaning to sell more of the same product, a higher value plan or add-ons. The second way to increase ARPU is by cross-selling, which is to sell a suite of different products to the customer.

Up and cross-selling matters as you’re more likely to be successful selling to existing customers than new ones - the book Marketing Metrics: The Definitive Guide to Measuring Marketing Performance states that the probability of a successful sale with a new prospect is 5%-20%, whereas the probability of a successful sale with an existing customer is a lofty 60%-70%. Again, this makes a lot of sense - you’ve already established trust and credibility with existing customers, so it stands to reason they’d buy from you again.

Source: Marketing Metrics

In the interests of fairness, it’s important to understand that higher ARPU deals often have inherent characteristics which help mitigate churn. For instance, it’s not uncommon for larger value deals to have minimum contract lengths, such as 12 months, and in some cases, multi-year. This is often less to do with churn and more typically a reflection of how long it takes for the customer to see value.

By way of example, there are many differences between MailChimp and Oracle Eloqua, and this is reflected in their respective go-to-market (GTM) strategies:

GTM Strategy

MailChimp

Oracle Eloqua

Ideal persona

Small business

Enterprise

Buying process

Touchless

Field sales rep

Price

Low

High

Onboarding

Self-serve

In-person training

Contract terms

Contractless

Minimum 12 month contract

Before implementing a strategy to increase ARPU it’s important to consider your growth stage. If you have 100 customers and your ACV is low, it’s likely a better investment to focus on acquisition, but if you have 100K customers and ACV is low or moderate, then increasing ARPU should be explored.

4. Build a customer success early warning system
As the name suggests, most SaaS companies have a customer success team whose role is to ensure clients succeed and therefore mitigate churn. To achieve this goal, customer success teams need to identify, track and defend against red flag metrics - the numbers which indicate if a client is likely to churn (usage rates, last login date and customer satisfaction are potential examples).

By tracking user behaviour it becomes easier to predict when someone is at risk of churning. Casey Armstrong, chief marketing office (CMO) at ShipBob sums it up well, “Before cancellation ever happens, there are clear signals that a customer is in danger of churning.” He adds, “Engagement lags, and your product or service goes from an everyday occurrence to being used once a week, then once a month. Finally, they decide it’s a waste of money altogether.”

Intercom’s Des Traynor shares a similar outlook, “ Typically customers gradually stop using products, from using it every morning to every week to once a month...At some point down the road you’ll remember you’re paying for something you don’t need and don’t use, and then you ‘churn’, even though the decision was made months ago.”

It’s hard to prescribe what the right red flag metrics will be, (although ZOKRI lists 16 in this blog post) - instead, you should look at customers that have churned and identify trends between them. Then it’s time to act. You need to invest time in both the discovery and then running programmes to defend against red flag metrics.

5. Request an annual or multi-year commitment
One foolproof way to lower churn is by reducing the frequency of renewals - this can best be achieved by requesting an annual or multi-year commitment from clients. The chart below shows that SaaS companies with annual contracts report lower churn than those with monthly contracts - by requesting an annual or multi-year deal over monthly (or contractless), you’re reducing the number of purchasing decisions per year and opportunities to churn.

Source: ProfitWell

While this is an effective approach, it obviously needs to be acceptable within your market. The good news is that as SaaS companies grow there’s often a move towards enterprise clients, which typically means larger ACV, as well as a move away from monthly billing to annual or multi-year. The chart below shows that products with smaller ACV tend to be on monthly contracts and larger ACV products have multi-year deals.

Source: SaaS Capital

You also need to consider your company’s growth stage - if you’re still finding product/market fit, giving customers the option to upsticks and leave each month can provide you with invaluable feedback much more quickly than an annual contract.

It’s also important to understand when is the appropriate time to request a longer commitment. Discounting is a big challenge within the SaaS industry, so companies typically request a longer contract in exchange for giving a discount. Therefore,..

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Everybody likes to win. And while it’s true that you learn lots about your skills, attributes and character from losses, there’s nothing quite like that sense of satisfaction when your team secures a hard earned victory.

I’ve been fortunate, both as an individual contributor and as part of a team to have racked up some important wins (jobs, promotions, new business and awards), but in truth, there’s only been three periods where I’ve been part of teams where there’s been an expectation of winning.

Teams that expect to win are unlike anything else. By definition, winning organisations are the rarest of beasts (there can only ever be one winner), but in addition to their talents, successful teams possess an exceptional work ethic, the highest standards, unshakable confidence, and a determination that literally sets them apart from the competition.

Winning teams breathe rarefied air and there’s something special about them - magical almost. While winning organisations are undoubtedly talented, it’s the management which are responsible for creating the environment for the team to thrive. The best organisations have managers with an uncanny habit of getting the best out of their team, but also the ability to attract, develop and retain talent. Seemingly, once you manage to crack the winning formula, develop that winning habit or start a winning run, you then create a level of momentum, which garners attention and fashions a reputation – all of which combines to keep that winning sequence going. It’s not for nothing people say, “success breeds success”.

In my experience successful teams also have an uncommon bias for action, hold each other accountable and are remarkably consistent in their work. Winning teams recognise the importance of consistently high performance - and that you’re only as good as your last match, deal, or quarter, and that you must show up, time and time again. This grittiness and the ability grind out results, often in the face of adversity or when the chips are down is one of the hallmarks of a winning team.

I’m fascinated by winning teams and the values, structure and organisation which bind them. It’s rare for a winning organisation to be thrown together – when you look, and I mean, really look under the surface there’s often a leader with a clear vision, a strong culture and set of shared values. These leaders are very deliberate about these components and when you combine that with talented individuals, you have the building blocks of a successful team.

How winning teams are constructed is timely, as in my role leading sales enablement at Automation Anywhere, shortly we’ll be growing the team, and I want to be thoughtful about the work we do, the candidates we hire and the culture we foster on what we hope and expect to be a winning team.

As previously mentioned, I’ve been privileged to have played a small part in some winning organisations – these experiences have taught me a lot, and undoubtedly shape my leadership style. The next few paragraphs hone in on these experiences – you’ll have to both excuse and indulge me a little, but they’re pertinent and provide an important frame of reference for how I perceive “winning”.

The first truly successful team that I was part, happened during my teenage years, when I played for an all-conquering football (soccer) team. In one eight week period during a summer, I won more trophies than in my previous eight years, such were the team’s numerous skills and talents.

And then as a graduate, I was part of a tremendously successful team at Edelman, the world’s largest public relations (PR) agency - and now first billion dollar agency. There was a 12 month period where our Edelman team won every pitch and candidly, it felt like they swept all before them. More recently I worked at HubSpot during a period of historical hypergrowth, where we won the battle to conquer the marketing software space, as well as launched new and exciting sales, CRM and services products.

While it may seem fanciful (I did say you’ll have to indulge me) to talk about a junior sports team in the same breath as billion dollar companies, I’m a firm believer that parallels can be drawn between different areas and lessons learnt. For instance, all three organisations had an expectation that we would work hard, leverage our talents to the full and perhaps most importantly, continually seek to improve performance. These teams set out to win their respective leagues and markets, and were successful in achieving that.

I’ve also worked in other businesses that would consider themselves successful, even though they didn’t win their respective markets. Chill Insurance is a disruptive challenger brand, that innovated and took market share off slower moving incumbents. While Indeed.com became the world’s de facto job search engine and stole the lunch of many job boards along the way. However, they’re still some way off displacing LinkedIn – and it’s only going to get more competitive and exciting now Google has entered the fray.

The characteristic of winning teams
When I draw upon my experiences of winning teams, it’s clear they all share some key characteristics. They are:

1. Talent
This may seem obvious, but it still needs to be said. All the high performing and successful teams I’ve been part of, have been packed full of talented people. While there may have been stars on each team, even the weakest players were strong. This meant that the average ability was always high - and thanks to the excellent recruitment strategies these organisations employed, there was always a conveyor belt of talent available.

2. Growth mindset
The most successful people I’ve worked or played alongside never rest on their laurels. They want to be the best in their respective role, stay in that coveted top position and actively take ownership of their growth. These people have the potential and will to improve, and are proactive about it. They are purposeful when it comes to self-improvement and carve out and protect time dedicated to it. The lesson here is to recruit people not only for the job they’ll do today, but for tomorrow and beyond.

3. Discipline
One of the most undervalued attributes of high performing teams is discipline - top teams are extremely disciplined and keep high standards in how they approach their work. It could be arriving early to a training session, having a keen eye for the smallest of details or hitting monthly goals. Disciplined teams work hard for each other to “get shit done” and they execute on the basics consistently, and to the highest standards. They also share a level of pride in the work and are disciplined about maintaining high standards.

4. Consistency
A natural outcome of discipline is consistency. If you have the discipline to put the hours in (and of course, the required talent) it stands to reason that you’ll see improved and consistent results. The best teams, whether they be sporting or within the software as a service (SaaS) industry have high standards and consistently meet them. They’re on top form most of the time and winning is their default setting.

Top teams recognise that to win and perform at the top level they need to put in the “reps and sets”. To be absolutely clear, doing the same activity over and over again is often tough, boring, unsexy or a combination of all three – and that’s why discipline is so crucial.

5. Fight
There’s nothing quite like it when you have a team all pulling in the same direction and fighting for, rather than with each other. Losing upsets them, offends them even, and they want to go about setting it right. The most successful teams have a squad of people who all have each other’s back – they are willing to go the extra mile to help each other out. It’s rare to work in that kind of environment, but when you do, cherish it – you’re onto something special.

How winning teams are led
When I think back to the winning teams I’ve been on, there was always an effective leader behind the scenes, who created an environment for us to thrive. There were many similarities in how these teams were led and structured, and I’ve listed the most important below:

1. Freedom
The best leaders give their teams the freedom to express themselves and come up with the goods. They do this by giving clear instruction and direction (strategy) on what the expected outcome should be - and then let the person figure out how to achieve it (tactics) or provide coaching when it’s needed. By giving freedom, leaders avoid micromanagement, show a high level of trust and give people the opportunity to let their creative sparks flying.

2. Accountability
High performing teams are made up of people who hold themselves and their colleagues accountable. This means speaking up when something is not right or when standards slip, as well as providing constructive, but candid feedback - and expecting the same from others. Creating a truly accountable organisation is easy to talk about, but in practise, it’s hard to implement.

It’s often overlooked, but if you truly value freedom and want autonomy in your role, then you need to display accountability and take responsibility. Freedom comes as a result of accountability - you can’t have one without the other. 

3. Vision
The most effective leaders craft and share a vision for their team that is easily understood. They articulate this vision, work to gain buy-in and repeat the vision frequently, so people are left in no doubt what direction the team is heading in. The importance of repetition cannot be underestimated - leaders of winning teams are adept at communicating their vision. They have a vision for the organisation that people believe in and want to be part of.

4. Culture
The importance of culture and culture-fit cannot be overlooked. While you obviously want to avoid Groupthink and creating a monoculture, you do want to establish principles for how you’ll work and what your organisation’s values will be. The key takeaway here is to aim for diversity in all its various forms - background, thought, personality and more, but gain alignment and understanding on how work will be done.

I would go as far say that a strong culture is essential for high performing teams. While my football team and Edelman had high hiring bars, HubSpot went a step further and codified what it looked for in its employees (HubSpot hires for HEART - people that are humble, empathetic, adaptable, remarkable and transparent). It’s a bold move, but it has paid HubSpot back in spades.

5. Humility
Top teams have a healthy respect for the competition. From not disparaging the competition in a sales pitch to shaking hands after a match, it’s important to retain a high level of humility at all times. Some of the best advice I ever received on this topic was to, “watch, but don’t fear the competition”. Instead, you should understand the strengths and merits of the competition, and use this as motivation to get and stay ahead of the them.

Winning teams possess what I consider to be a healthy paranoia and appreciate that what they have today, could be gone tomorrow – that sense of fear is what (partly) feeds their discipline.

There you have it. I’ve been thinking for some time about the winning teams I’ve been part of and just what made them so successful. I’m pleased to have finally organised and synthesised my thoughts in this way. By digging into the teams’ characteristics and distilling them, I hope it makes them more applicable and replicable.

But here’s the thing - writing about winning is the easy part, the real challenge is doing it, and doing it consistently. That takes all the characteristics I’ve written about and some more. However, if I were to pick one attribute of a winning team it would be the ability to execute on strategy – the best teams have a narrow gap between strategy and tactics. Talk (or should that be writing) is cheap – action, delivery and results is what matters most.

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One of the questions I get asked most frequently is around building a sales enablement strategy and what that might look like. While each company, context and industry is different, I believe that there are some fundamentals that should form the blueprint of any sales enablement strategy.

At a high level the strategy should convey what your team does, how it does it, goals and main initiatives for the year ahead. However, here’s the thing - as sales enablement is such an emerging area, there’s a distinct lack of sales enablement thought leadership, best practices and models available, let alone materials that specifically cover strategy. My hope is that this post and the sales enablement strategy template I’ve created will help right that wrong, and generate conversation and critical feedback within the sales enablement community.

Rather than reinvent the wheel, I’ve chosen to build upon what is already a successful and valuable strategy template. As there’s such a dearth of sales enablement materials we shouldn’t be afraid to borrow, adapt and reuse successful tools from other fields. A good idea is a good idea after all.

What I’ve adapt is a simplified one page strategic plan that we used at HubSpot or “MSPOTs” as they were called. Each year every team had to create an MSPOT, and  they were published on the company wiki, for all employees to see, question and provide feedback on. These documents were and are a hugely valuable tool for a number of reasons - they communicate in simple terms what can often be a complex area. But the real value of these plans is that they drive alignment - they make it easy to see what each team, department and organisation is working on, omitting and their respective goals.

Sales enablement strategy
While there’s no industry-wide agreement on what a sales enablement strategy should include, to me the key components and fundamentals are:

  • Mission

  • Strategy

  • Serving

  • Plays

  • Targets

  • Responsibilities

  • Omissions

You can see a completed example of the sales enablement strategy template below, as well as detailed explanation on each stage of the strategy:

Download the Sales Enablement Strategy Template in Google Drive and PowerPoint.

Mission
Your sales enablement team mission should be aspirational and explain what your team aspires to do. It should focus on the long term and rarely change (if at all). In my experience, the best teams have a mission that is clearly understood and often repeated. A long term sales enablement mission acts as a North Star - everyone can see where the team wants to get to, even if they’re unsure of the route they’ll take to get there.

Strategy
A sales enablement team’s strategy should be simple to understand, encapsulate what the team does, and will likely change on an annual basis. In the first instance, when crafting your strategy and committing it to paper, it’ll probably be too lengthy. You’ll have to spend time making it more succinct, and boil it down into a couple of digestible themes which tie back to an important goal that your team wants to hit.

Serving
The role of sales enablement, as its name suggests is to enable, partner with and ultimately, serve others. You should take the time to identify and communicate who your key stakeholders are (it’s likely to be sales leadership and sales reps). Who your sales enablement teams serves should be reviewed annually and will likely expand as the business evolves.

Plays
This is the fun part. You should list the key plays that’ll bring your strategy to life and help the sales organisation succeed. The plays are best thought of as the big initiatives that the sales enablement function will focus on each year. While you can mention specific sales enablement activities and tactics within the template, it’s often more valuable to describe broad themes, as you’ll likely be running several activities per theme.

Targets
There are a plethora of sales enablement metrics that can be tracked, however you will first need to spend time figuring out what the key challenges are, and then build a plan to overcome them. Once you have taken these steps, it’s then time to consider goals and measurement.

At a high level, the most important factors to consider when setting sales enablement goals are:

  • Are they aligned with business and sales objectives?

  • Do they influence revenue?

  • Are they trackable?

Follow these goal-setting principles and you’ll have a solid foundation on which to build a sales enablement function.

Responsibilities
Sales enablement is a broad area, so a key part of building a sales enablement function is defining the team’s responsibilities. Sales enablement is often poorly defined and subsequently misunderstood, so clearly defining your responsibilities and communicating this to the business is essential.

To illustrate the point, a sales enablement function can be responsible for any and all of these areas:

  1. Onboarding

  2. Sales process and methodology

  3. Sales playbooks

  4. CRM

  5. Sales tools and technology

  6. Sales content

  7. Ongoing training and development

  8. Competitive intelligence

  9. Sales projects and campaigns

  10. Deal support


Omissions
One of the most important, but overlooked parts of every sales enablement strategy is deciding and communicating what work will be omitted. Omissions are the projects that will not be funded each year. There’s rarely a lack of good ideas and work to be found, but it’s important to decide what work won’t be tackled.

By clearly communicating your omissions you can help drive alignment and set the right expectations with other teams and stakeholders. At HubSpot, CEO Brian Halligan frequently reminded employees that “companies are more likely to die of indigestion than starvation.” What he meant was, as software as a service (SaaS) companies grow there’s always the temptation to do more, but if you’re not strategic you risk becoming slow, bloated and losing focus. This lesson is as true for sales enablement as it is for any function.

Other important areas to consider
The sales enablement strategy template is designed to be easily understood, but the reality is creating any kind of strategy is tough and requires more detail. I also recognise that there are a number of important questions and areas to consider when creating a sales enablement strategy that are not covered in the template including:

  • Will you support channel partners? What does sales enablement look like for them?

  • How will you support international markets and different languages?

  • Do you plan to prioritise some teams over others? Why?

  • Are you responsible for supporting sales reps throughout the sales process or just parts of it?

  • Are you responsible for sales rep development throughout their whole time at your company or just a part of it?

  • How do you enable other teams to enable the sales organisation?

I’ve listed below some important operational areas that warrant consideration when building a sales enablement team.

Prioritisation
When leading a sales enablement team it can be easy to get caught up and slowed down in what sales reps say they want, rather than what they need - or worse still, supporting those with the loudest voice, most seniority or highest salary. You need a tool to prioritise work.

I’ve found that the best way to navigate this challenge is by prioritising work based on estimated revenue and number of sales reps impacted. If you’re having a tough or heated discussion, I suggest bringing it back to this. In my experience this approach typically creates an understanding and acceptance of a decision, if not wholehearted support.

At HubSpot I use a simple 2X2 grid to rank projects based on estimated revenue and impact on sales reps - put simply, I always focus on activity that will most likely influence revenue. I often share (in jest) that working in sales enablement has taught me to say “no” a 1,000 different ways - quite simply we’ll never have the resources to implement all the ideas, suggestions and projects (even the good ones) that sales managers and sales reps champion, so having a process to categorise and rank work, which is shared with your stakeholders is crucial.



Scheduling and mindshare
The most effective sales enablement teams both create and curate - they instinctively understand the needs of the sales organisation and share what’s most important, rather than trying to share everything, and risk overwhelming sales reps. To combat this challenge you need to think strategically about the programmes you run.

Best-in-class sales enablement functions like LinkedIn accomplish this by imposing a limit on how much sales rep time or “mindshare” they’re allowed each quarter. By limiting themselves to 20 hours per quarter, which equates to just over 90 minutes per week, the LinkedIn team is forcing itself to prioritise what’s most important.

Sales tools and technology
By now I’m confident we’ve established that sales enablement is a broad and varied area. Depending on the challenges you want to solve, you’re going to need to invest in best of breed sales tools. Some of the most impressive sales tools I’ve come across are HubSpot, Outreach, Chorus, Articulate, Troops, Brainshark, Highspot, Clearslide, Mindtickle and ToutApp.

You should familiarise yourself with these vendors, the types of problems they help solve and also rank, just how important those problems are for your business to solve. It may be that sales acceleration and engagement tools like HubSpot and Outreach will solve the most urgent pain point and setting up e-learning like Articulate is less of a priority for your business. Or vice versa.

Measuring learning
Most training at most companies is flash in the pan and it’s difficult to understand if the information shared has been understood, let alone applied. Best practice is to have people take part in some form of learning, give them time to practice what they’ve learnt and then test what they’ve learnt with a certification or quiz. You should also be able to tie this activity back to business metrics.

For instance, if sales reps are discounting too heavily, you could run negotiation training classes. These trainings would be both theoretical and practical, and the practical exercise would require sales reps to role play specific negotiation scenarios with colleagues. Once sales reps have honed their skills, they’d then have to become “negotiation certified”, by successfully handling a tough negotiation role play with a sales manager. While running a programme like this you could track who is becoming negotiation certified, but also measure what impact it has on important business metrics like discounting.

Enabling others
I’m a firm believe that no single team owns “enablement”. While sales enablement should own the strategy, they should also empower other teams to create enablement materials by sharing best practices, planning models and consulting on what good looks like. For instance, product marketing, learning and development (L&D) and sales managers are already likely to be creating some enablement materials. Sales enablement can scale their impact by enabling others to enable the sales organisation.

Communication
Ideally, one team should own communication with the sales organisation. This team should have a process for categorising and prioritising announcements, so sales reps receive the right information at the right time on the right platform. I believe sales enablement can and should own this function.

However, communication should not be one way. You should also invite feedback in a formal way, so that you have a tight feedback loop and sense of what’s happening on the sales floor. You should consider forming a panel of sales reps that you can share ideas with, test new tools and use as a sounding board.

Lastly, if you’d like a copy of the Sales Enablement Strategy Template, I’ve made it available to download in both Google Slides and PowerPoint. There’s no forms to complete or anything like that, but if you do download it, I’d appreciate any feedback you have - good, bad or indifferent. The template is editable, so I’m keen for others to adapt and make the template more relevant for their organisation.

As I’ve mentioned, there’s a real lack of sales enablement planning models available - I hope by publishing these templates, I can make a small contribution to helping others figure out how to build a high performing sales enablement function at their business. By sharing what we’re doing and inviting critical feedback, we can help elevate the role of sales enablement to where it truly belongs.

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I’ve been working within the software as a service (SaaS) industry for more than five years now. During this period I’ve learnt more than I ever thought possible and my personal growth has accelerated with each passing year.

Working with fast-growing technology companies HubSpot and Indeed.com has taught me how two very different companies can come to dominate their respective industries. Importantly, these experiences have shown me what is required for a SaaS business to launch, grow and ultimately, succeed in new markets. I’ve also become well-acquainted with a number of “rules” or truisms that SaaS businesses are run by - some of which are well known within the industry, but others which have been largely kept under wraps, until now.

Before we dig into the rules, I just want to say that in my mind rules are made to be broken, and should be thought of more as a guide, template or guardrail. My advice is to use them as a starting point of discussion at your business, rather than follow them blindly.

Let’s get down to it. Here are the key rules I’ve learnt to run a successful SaaS business by:

1. Rule of 40 - finding the right blend of growth and profitability
Perhaps the most famed SaaS rule of all, is the rule of 40. It’s a simple calculation to help you quickly and easily understand the health of a SaaS business. The rule states that a businesses annual revenue growth rate, plus its profit should equal 40%.

For example, if a company’s growth rate is 20%, then profit should be 20% or if the growth rate is 40%, then breaking even is absolutely fine, or indeed any other permutation, so long as the growth rate and profit equals 40%. The chart below shows a number of industry leading SaaS companies that have achieved the rule of 40.

Source: For Entrepreneurs

What I like about this rule is that it takes into consideration the twin challenges of growth and profitability, and can be applied regardless of growth stage. Why does growth stage matter? Well, sometimes investing heavily in the pursuit of growth is the right move for a company, especially in a winner-takes-all market, but at other times, particularly in more mature markets, monetization and profit will likely be the right call. The rule of 40 accounts for both scenarios and everything in between.

2. Rule of 3 and 10 - everything breaks when you grow
It’s important to recognise (and plan for) that how you operate will fundamentally change as your business grows. What works with 50 employees will creak heavily at 500 and come crashing down with 5,000. As you grow you’re going to need new processes, people, playbooks and additional layers of management.

Put simply, the rule of 3 and 10 means that when a company trebles in size everything breaks. The number of employees when things get particularly troublesome are three, 10, 30, 100, 300 and 1,000 - before company headcount hits these milestones you’ll need to rethink how you operate. Just think, the skills and attributes which are required of a marketing leader at a 10 person company are much different, and indeed could be a potential weakness at a 1,000 person company.

3. LTV:CAC needs to be 3:1 (or greater)
Throughout the SaaS world, there’s two metrics that business leaders keep a close eye on at all times - they are lifetime value (LTV) and customer acquisition cost (CAC). These metrics immediately give insight into the health and likely success of a SaaS business.

LTV:CAC is the lifetime value of a customer divided by the customer acquisition cost. LTV as its name suggests is the total lifetime value to the business of a customer and the CAC is the costs associated with maintaining the product, as well as marketing and sales costs.

Looking at these numbers as a ratio helps you understand how effective a business is at making money. You can clearly see what the return will be from every dollar, euro or pound invested. An LTV:CAC of 3:1 is desirable within the SaaS industry (an even greater LTV is better).

4. Keep annual churn <7%
In my mind, churn is the most important of all SaaS metrics. There’s no point acquiring new clients if churn is out of control. Think of it like a leaky bucket - you need to fix the hole, rather than continually filling the bucket with more water. Churn matters and understanding how it’s calculated and the causes behind it is really important.

It may not be immediately apparent, but there’s some important differences between monthly and annual churn. Allow me to explain. A 5% annual churn rate means that monthly churn is 0.42%, whereas a 5% monthly churn equates into a hugely troubling 46% annual churn rate. Or put another way, a 5% monthly churn rate means that if you started January with 100 customers you’d only have 54 customers left at the end of December. In order to record any kind of growth you’d have to acquire another 47 new customers.

While each industry and company is different, a 5% monthly churn rate isn’t a solid foundation for a SaaS business, and in all honesty a business in that situation should seek to ramp up retention and dial down acquisition. Otherwise, it’s literally burning through money. To avoid this situation you obviously want churn to be as low as possible, but SaaS businesses which require a 12 month, upfront commitment should aim to keep annual churn under 7%.

Remember that churn is the silent SaaS killer - often sales and marketing receive all the attention and glory, but services is where the predictable recurring revenue is made and kept. Retention trumps acquisition.

5. Track your NPS closely
One of the best ways to understand the success of your customer base is net promoter score (NPS). It’s an index ranging from -100 to 100 that measures the willingness of customers to recommend a company's products or services.

While NPS may lack detail and qualitative data, it does provide an effective indicator of the health of a client, and was widely used at both HubSpot and Indeed.com. For those unfamiliar with NPS, its scoring system means that you’re penalised heavily for poor a rating (0-6 are classified as detractors), receive nothing for mediocre ratings (7-8 are classified as passives) and are only rewarded for high ratings (9-10 are classified as promoters).

Source: Wootric

What represents a “good” NPS changes between industry and product, however, you should track your own NPS, as well as conduct research to track and benchmark key competitors. To build upon my previous point - churn is really important and NPS is a metric SaaS businesses can and should use to identify customers that are at risk of quitting.

6. Create a discounting process
Discounting tends to be a big challenge within the SaaS industry - it’s literally one of the quickest and easiest ways to maximise or damage revenue potential. To manage discounting effectively you need some guiding principles and a process in place.

For starters, you should always sell on the basis of the value that your product will create, rather than features or functionality. And if you do find yourself in a negotiation, it is advisable to take a “give-to-get” approach and request a greater commitment (more product, multi-year contract, payment upfront) in return for a discount. You should also have predefined limits about who can authorise what level of discount - for instance, a sales rep can sanction 5%, a sales manager 10% and sales director 10%+.

While principles are valuable, you also need a process for sales reps to follow when entering a negotiation - a clearly defined process ensures that sales reps avoid discounting at every stage of a deal.

At HubSpot we rolled out the following discount process. Sales reps explain to prospects that the first four steps must be completed before a discount can be discussed:

  1. The prospect agrees that their challenge needs to be solved now.

  2. The prospect agrees that HubSpot solves their challenge and not a competitor.

  3. The prospect shares the desired start date and procurement process.

  4. The key decision-maker is part of the sales process.
     

  5. Only now can a discount be discussed.

7. Have a framework to evaluate investments
Over the next 12 months should you build a new product line, open your first international office or acquire a competitor? Understanding what, when and where to place your bets is hugely important. You need a system to help guide your investments so you not only succeed today, but in the future.

During my time at HubSpot there’s been two frameworks which have stood out as strategic ways to make important decisions. The first is the idea of S Curves - all products, markets and business models follow a predictable cycle of growth, maturity and decline (the pattern often looks like an “S”, hence its name). After a period of growth, maturation strikes as price competition emerges, the most attractive customers are acquired and businesses see diminishing returns.

To overcome this challenge, the best companies continually innovate and create new products to offset the maturation and decline of existing ones. The lesson here is to view your products in terms of S Curves and ensure you’re investing in your next greatest hit.

Source: Accenture

The second model is the Horizons Framework developed by McKinsey. It offers a way to focus on short, mid and long-term growth opportunities, and the eagle-eyed among you will notice that (see chart below), visually, it shares some similarities with the S Curve diagram.

The Horizons Framework is an effective way to categorise projects, which in turn helps with assigning budget, headcount and timelines. The framework requires you to categorise work that is either a horizon one, two or three. Horizon one represents core products and services readily identified with the company and those that provide the greatest profits.

Horizon two covers emerging opportunities like new products and acquisitions, moves that are likely to generate substantial profits in the future, but that could require considerable investment. And Horizon three contains ideas for profitable growth further down the road. For instance, this could be research projects, pilot programmes and investments in other businesses.

Source: McKinsey

The key point is, you need to have a framework for categorising and investing in future growth opportunities for your SaaS business.

8. Decrease your CAC with a freemium offering
While most SaaS companies focus on increasing the LTV of clients and simply controlling CAC, they should not be afraid to disrupt their existing go to market strategies in order to reduce CAC.

HubSpot applied its marketing product to the S Curve framework and saw it was reaching maturation. The tool remains the company’s greatest hit and what it’s best known for, however, it is a high touch sale with a high CAC, and has an increasing number of competitors. In order to create another line of business while reducing CAC, HubSpot launched sales, CRM and more recently, customer service tools.

Importantly, free, low touch versions are available for the marketing, sales and CRM tools (see image below) - people can test a light version of the product, see value and then graduate to the paid version.

Source: HubSpot

The beauty of this freemium strategy is that HubSpot can use its free products to acquire large numbers of users, a percentage of which will be converted into paying customers at a later date. This approach means HubSpot has a new source of highly qualified leads at a much lower CAC (in comparison to other acquisition channels).

Adopting a freemium strategy lowers CAC for several reasons. First up, while free products require development time and ongoing maintenance, the potential reach is vast and products are more scalable than other acquisition channels, albeit less predictable. Secondly, free users often want to upgrade “touchlessly” without speaking to a sales rep, and for those that do want to speak with somebody, they often require less sales rep interaction than a regular sale - both of which reduce CAC and time to sell.

9. Hire for stage fit, not experience
Let’s face it, when you boil it down, most problems are people problems. Hiring matters. A lot. One of the biggest mistakes a fast-growing SaaS company can make is hiring for experience over stage fit.

For example, it’s not uncommon for a 100 person company fresh off a funding round to go and hire a VP of Sales from a Fortune 500 company. While this can work, you need to ensure that you’re hiring somebody for their ability to do the job today - as I said, it can work, but in all likelihood it’s unlikely a VP at a Fortune 500 company will succeed at a 100 person company. You need the right people for your company’s growth stage.

Businesses need to make hires based on people’s ability to execute in the short and mid-term, not on the fact that they worked at a publicly listed SaaS company.

10. Avoid overeating - as your business grows do more of less
At HubSpot, CEO Brian Halligan frequently reminded employees that “companies are more likely to die of indigestion than starvation.” What he meant was, as SaaS companies grow there’s always the temptation to do more, but if you’re not strategic you risk becoming slow, bloated and losing focus.

HubSpot communicates its goals in a document called MSPOT, which is published on the company wiki for all to see. It stands for mission, strategy, projects, omissions and tracking:

  • Mission: Rarely changes.

  • Strategy: Annually changes.

  • Projects: 4 or 5 big annual initiatives.

  • Omissions: Projects we decided not to fund.

  • Tracking: Numbers we are looking at to see if we are on track.

Halligan adds,“The most important part of the document is probably the “Omissions” part. These are the projects we are not going to fund this year. This is how the organisation limits my appetite so I don’t overstuff us.” The key learning here is that’s important to have a simple document which spells out the strategy for the year ahead, plus the initiatives that very deliberately won’t happen. That’s how you create alignment and focus.

There you have it. These are the rules I’ve learnt from my time within the SaaS industry. Both HubSpot and Indeed.com have not only survived, but thrived during this period and recorded record growth. I’d love to hear what rules, principles and truisms you use to lead your SaaS business. The SaaS industry is still very much in its first act - by sharing this information we will uncover new best practices, dispel myths and define what good looks like. It’s my belief that the best is yet to come from the SaaS industry and I’m excited about the second act and beyond.

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Today, everyone working in and around sales and marketing knows that bots are hot, in vogue and quite simply, of the moment. That’s no secret.

After years of thinking, talking and let’s be honest, dreaming about what might just be possible, over the past 12-18 months numerous software as a service (SaaS) companies from around the globe have taken their respective bot offerings to market.

It’s been an exciting period as discussion around bots has (finally) moved on from the peripheral to the mainstream, or put another way, from the realms of sci-fi to reality. While innovators and early adopters are embracing the opportunities afforded by bots, the fact remains that too much work within sales and marketing is still manual - too few teams are thinking of ways to automate, eliminate or optimise. Spreadsheets, documents and email are all too often, still the norm, rather than the exception, as most people at most companies continue doing their job, rather than figuring out ways to improve how their work is done.

In my role leading sales enablement at HubSpot in EMEA, we deliberately carve out time to think about ways to leverage tools, technology and software that will make sales reps more effective. And as a company we value people that have the ability to continually reimagine ways of working and attach great importance to this attribute.

Indeed, a large part of my remit is not just responding to the needs of sales reps today, but thinking big and anticipating future trends, and subsequently our sales reps’ needs in the future. The best sales enablement teams implicitly understand what a sales organisation wants, but more importantly what it needs (they’re not necessarily the same), often before even the sales organisation comes to that realisation.

While the most effective sales enablement leaders leverage data, study trends and speak with both sales reps and sales managers to develop a true sense of the sales organisation, and how they can best support it. With this in mind I built and launched a sales enablement bot for HubSpot sales reps.

It’s hosted within our private HubSpot Slack channel and answers sales rep questions related to competitive intelligence, case studies, sales collateral and more.

To use Silicon Valley parlance, the bot was built to “scratch my own itch”. I needed to somehow answer the numerous and ever increasing questions that I was asked each day by sales reps, while remaining productive. The bot works by answering questions within Slack, as well as pointing the sales rep towards more detailed information (outside of Slack), if required.

Building the bot within Slack was really important to us - it’s the internal communication platform of choice for sales reps at HubSpot and they feel comfortable using it everyday. Building a tool on a platform where your audience already are, is nearly always more successful than building it elsewhere. We had a large and engaged audience on Slack, which helped massively with adoption of the bot.

Slack’s sleek design and intuitive user interface (UI) means our sales reps can simply click on the options suggested by the bot or type in what they’re looking for, and they will be guided towards the answer to their question. While the bot is freeing up my time, more importantly it provides sales reps with the information they need, at any time of the day and across any device.

Here are some examples of what queries the bot can help with. HubSpot sales rep can either ask these requests verbatim or try a different variation:

  • Marketo competitive intelligence

  • Infusionsoft information

  • How do we beat SharpSpring?

  • Who are Intercom?

  • How we beat Act-On?

  • Tell me about Zoho

  • Strengths of MailChimp

  • Sales Hub competitors

  • SaaS case studies

  • Case studies on manufacturing

  • Education clients

  • Customer reference call request form

  • ROI of HubSpot

  • GDPR information

  • Sales deck

  • HubSpot proposal

  • Send me sales collateral

  • Show me some review websites

  • G2 Crowd reviews

  • Where do we rank on TrustRadius?

You can watch a demonstration of the bot in action below:

The Sales Enablement Bot I Built at HubSpot - YouTube

There are many more ways the sales enablement bot can help, plus some carefully hidden “Easter Eggs” for sales reps to discover. You’ll also notice that we named the bot, “Ben Botton”. The name was suggested by a sales manager (in case you didn’t notice, it’s a play on my name, Ben Cotton), and while it’s fun, what’s more important is the Ben Botton moniker makes the bot memorable, which in turn increases adoption by sales reps. It’s easy to overlook, but what you call and how you brand your bot matters. My advice is to think carefully about this from the beginning, and avoid making it an afterthought.

Background
Let’s now cover in detail how, why and when I build the bot. Here’s goes. As an individual contributor (IC) partnering with over 100 sales reps, I’m always thinking about ways to effectively scale the services I offer to the sales organisation. Scale is hugely important (although, we shouldn’t chase scale at the expense of impact and revenue), and there’s two forces, in particular which keep me focussed on it.

The first is related to the business and pretty obvious - as HubSpot grows we’re going to recruit more and more sales reps - certainly at a faster rate than we’ll make sales enablement hires. That’s to be expected. The less obvious factor is related to my role, and where I invest my time. A large amount of my day can be spent answering sales rep questions. Now, don’t get me wrong, I think an important part of my role is partnering with sales reps, coaching them and where needed, answering questions, but the answer doesn’t necessarily need to come from a human. That’s where bots, and more generally, automation comes in.

Like many people I’ve been intrigued by the potential utility of bots for a long, long time. Leveraging automation is not only interesting, but important - after all, if a SaaS company’s headcount growth exceeds revenue growth, it impacts its ability to invest in product, and if that happens, things can start to go awry. The solution is to achieve leverage via automation, and that’s a part bots will play.

Automating sales enablement
The way I see it, not all sales rep questions are created equal (far from it). In fact, most questions I’m asked each day by sales reps can be split into one of two categories:

  1. Consultant - low volume, high value questions that require a bespoke response.
  2. Agent - high volume, low value questions that require a templated response.

The consultant-type questions are when a sales rep wants advice, guidance or coaching. This is a good use of my time, and where possible, is where I invest it. However, the agent-type questions, such as suggesting case studies, sharing competitive intelligence, sales decks or links to various resources still need to be answered, but I think a bot can and should help lighten the load. Frankly, this work is far less valuable, more unskilled and more tactical in nature.

As I’ve said before, there’s a significant difference between data and insight. Bots are ideal to turn to when seeking to answer a clear cut question, but anything that involves judgement, empathy or shades of grey is where a human will be required. Bots provide data and answers to inform decision-making, but a human is needed to distill that data into actionable insight. Bot technology will help complete simple tasks quickly and efficiently, but they won’t close a deal or dream up a marketing campaign. Data is to knowledge as insight is to wisdom.

Goals of the bot
I had heard my HubSpot colleague Brian Bagdasarian talk about how bots should take on “fragments of jobs”, rather than replace them entirely, and it really resonated. I see the sales enablement bot as a way for sales reps and sales enablement to become more productive in two important ways:

  1. Help sales reps get the answer to agent questions quickly.

  2. Reduce the volume of agent questions I get asked - freeing up time work on consultant questions.

It’s always difficult to set SMART goals for a new initiative such as this, however, we set ourselves the goal of the bot answering 500+ sales reps questions per month, which equates to five questions per month, per sales rep.

Results
It’s fair to say we’ve been delighted with the results. The bot answers (well) over 500 questions per month from HubSpot sales reps in EMEA. Importantly, that’s 500+ questions that would have needed to be answered by a human (either myself or a colleague).

Using some back of a napkin math you can begin to quantify the impact and benefit of the bot. For example, if each question a sales reps asks would take five minutes to respond to (research suggests that the true number is 20+ minutes, especially, once you factor in the time to regain concentration and flow), then you can begin to see how the efficiencies quickly add up.

Now don’t get me wrong, I still do answer sales reps questions, but there’s been a significant change in the type of questions that bubble up to me - sales reps now ask for recommendations, coaching and advice, rather than links, sales decks and case studies. Candidly, recommendations, coaching and advice are much higher value activities and the right place for me to invest my time.

Not only is the bot making me more productive, but the bot is providing sales reps with answers to their questions immediately. The bot is making me more efficient and freeing up sales rep time, so they can focus on doing what they do best, which is high value tasks like speaking and meeting with prospects.

What the bot can and can’t do
It’s fair to say there’s much hype around bots at the moment, but the reality is humans, from the Industrial Revolution onwards have systematically sought out ways to eliminate manual tasks via automation - and the rise of bots is just the latest incarnation of that trend. In a sales and marketing context we should consider bots an enabling technology that will replace parts of, rather than entire jobs. For the moment, bots are a time saver, rather than true value creator.

The bot that I built directs sales reps to the right place. It works by “signposting” sales reps to places that answer their questions. However, there’s lots the bot does not do. It’s by no means comprehensive and certainly doesn’t have every use or edge case covered, but it does answer the majority of agent-type questions I’m asked. I have continued to iterate on the bot since its launch and plan to add more functionality in the future.

The future
Looking ahead, I’d love to see the bot evolve from something that is essentially reactive to become proactive and predictive. Currently a sales reps inputs a question and it outputs a response. This is somewhat rudimentary, and while it hints at the future power of bots, it clearly has its limitations.

The next step is to leverage artificial intelligence and machine learning so that the bot can proactively make suggestions. The future bot won’t wait for a sales reps to come to it with a question or problem - instead, the bot will proactively reach out with a recommendation. At a high level, making the move from tools which are reactive to those which are dynamic, proactive and learn is how we’ll create more value for the sales organisation and business.

I’m truly passionate about bots and the promise of this new technology, but while there’s a lot to look forward and ideas to be dreamt up, we need to realise that we’re still in the first act of bots and what’s possible. This is exactly what makes sales enablement exciting and the reason I work in this emerging field - we get the opportunity to create a small part of the future and think about just what might be possible in the sales industry.

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One of the exciting aspects of working in an emerging area like sales enablement is that, today, nobody knows or indeed, has all the right answers. In many respects we’re “building the plane while flying it”, as we collectively figure out what good looks like.

As a result there’s a refreshingly high level of collaboration, modesty and openness among industry colleagues - in my experience fellow sales enablement professionals are generous with their time, humble and willing to help each other out.

Admittedly, I’m also fortunate to work at a company like HubSpot - it opens a lot of doors and people are always interested to hear how we approach sales enablement. Candidly, setting up meetings with sales enablement leaders at interesting companies is rarely difficult. That’s why twice a year I take a couple of days out of the office to visit other sales enablement professionals at their place of work - it genuinely is the best time I invest each year. As an aside, there’s little formal sales enablement training available, so this opportunity for peer learning, ideation, feedback and discussion is incredibly valuable.

Indeed, over the past 18 months I’ve met with talented people (several times) at Google, Facebook, LinkedIn, Stripe, AdRoll, Dropbox, Zendesk, Intercom, LogMeIn, Procore, DocuSign and Xerox to chew the fat over all things sales enablement. During these meetings I’ve shared my point of view on sales enablement, gained critical feedback and developed some of my ideas - all of which has helped sharpen what I consider to be my sales enablement best practices and guiding principles. They’re by no means definitive, but they act as a starting point for how I approach my work at HubSpot.

Let’s get down to it - here are my sales enablement best practices:

1. Consider sales reps your customers and get close to them
I wholeheartedly believe that those companies which get closest to the customer will win. The same is true of sales enablement - by considering sales reps your clients and trying to remain in close proximity to them, you’ll become more understanding and empathetic to the needs, want and challenges of the sales organisation.

At HubSpot I very deliberately go and sit by sales reps for a part of each day. Being physically close to the sales team means I have a closer relationship with them, I’m more attuned with the mood on the sales floor, and can use this insight to provide a more valuable service to the sales organisation. But physical proximity is only half the battle - you need to consider and treat sales reps as cherished clients - ultimately, this means ensuring they’re successful, rather than happy (happy clients often leave, whereas successful ones seldom do).

2. Be a strategic consultant, not a tactical order taker
The most effective sales enablement teams are akin to consultants, rather than order takers. The key point to understand is that what a sales team says it wants may not necessarily be what it needs. This may sound like a minor semantic difference, but once I realised the difference between wants and needs, it had an immeasurable impact on how I work.

For instance, a sales manager may say they want more case studies for their region, but once you truly uncover the challenge, you may find out that buyers are more conservative in their market, so what they actually need is more evidence of social proof (this could be third party review websites like TrustRadius and G2 Crowd, customer testimonials, videos and of course, case studies).

In the same way that a doctor listens to a patient before making a diagnosis and then suggesting a remedy, sales enablement works best when it is free to analyse a problem, suggest recommendations and then build a programme to make those recommendations a reality. In short, if you focus on uncovering true needs you’ll elevate yourself to the position of a strategic consultant, but if you solely focus on wants, you’ll be stuck as a tactical order taker.

3. Understand the importance of revenue responsibility
Let’s be honest. When it comes to winning an argument, revenue trumps everything else. The best sales enablement teams are focussed on revenue - whether that be quota attainment, influenced revenue, productivity per rep (PPR) or another sales related metric.

What the best teams have figured out is that by focussing on revenue you will have the biggest impact. Or put another way, if you’re not influencing revenue, then you’re on the way to becoming an overhead and expense. And teams which fall into this category are often “nice to haves”, rather than “must haves”.

Ultimately, teams which lose their focus on the bottomline often see their budget reduced, sphere of influence diminished and impact minimised. In contrast, the best sales enablement leaders are rightly fixated on revenue and how they can increase it. I literally can’t overstate the importance of a sales enablement function having some form of revenue responsibility. Make it your focus and keep it front and centre for your team.

4. Define your service offering to the business
Generally, sales enablement is poorly defined within businesses and subsequently misunderstood. This means that it’s crucial you clearly communicate to the business what areas your sales enablement function will own.

It’s not hard to see how misunderstandings happen. When I think about the scope of a sales enablement team it can legitimately cover content, training, technology, deal support, the company’s customer relation management (CRM) tool, sales playbooks, sales methodology and more. Clearly, that’s a big list of important initiatives, and in reality, any team from sales enablement, sales operations, sales strategy, training and learning and development (L&D) could rightly claim it as part of their remit.  

Subsequently, one of the first and most important jobs when building a sales enablement team is defining what areas you will cover, but of equal importance communicating what work sales enablement will not do. Both defining what you will own and omit will bring a lot of clarity and focus to your organisation.

5. Shared goals are the one true way to drive alignment
One of the most impactful, but simplest changes I ever made was to share the same goals as the sales organisation. In my mind, sharing goals are the one true way to drive alignment and more teams should do this. Yet the reality is much different - shared goals between different teams are often the exception, rather than the rule.

Having the same goals as the sales leadership makes sense on a number of levels. It brings much needed clarity, simplicity and intellectual honesty - ultimately, it means everyone is pulling in the right direction - we’re both winning, and by definition losing together. However, the opposite is unfortunately all too common. Oftentimes, a sales enablement (or marketing) team will be hitting their goals (which are different to the sales organisation), yet the sales organisation is failing to hit their goals.

My point is that, can a sales enablement team ever truly consider itself a success if the sales organisation is failing to hit quota? My gut feeling is that it can’t, but my recommendation is that you can avoid much of the finger pointing, by having everyone share the same goal.

6. Base decisions on revenue and number of sales reps impacted
As I’ve already mentioned, when leading a sales enablement team it can be easy to get caught up and slowed down in what sales reps say they want, rather than what they need - or worse still, supporting those with the loudest voice, most seniority or highest salary.

I’ve found that the best way to navigate this challenge is by making decisions based on estimated revenue and number of sales reps impacted. If you’re having a tough or heated discussion, I suggest bringing it back to this. In my experience this approach typically creates an understanding and acceptance of a decision, if not wholehearted support.

At HubSpot I use a simple 2X2 grid to rank projects based on estimated revenue and impact on sales reps - put simply, I always focus on activity that will most likely influence revenue. I often share (in jest) that working in sales enablement has taught me to say “no” a 1,000 different ways - quite simply we’ll never have the resources to implement all the ideas, suggestions and projects (even the good ones) that sales managers and sales reps champion, so having a process to categorise and rank work, which is shared with your stakeholders is crucial.

7. Take a blended approach to measurement
Some sales enablement activities are easy to measure and attribute, while others are not. That’s the cold, hard truth of the matter, and it’s for that reason I recommend teams take a blended approach to sales enablement measurement.

Although, sales enablement plays and tactics, such as content, training and technology are easy to understand, measuring the impact, success and effectiveness of a sales enablement team is less straightforward. On the one hand it can be simple to identify a metric that has high business impact, such as quota attainment, but often it is challenging to attribute precisely how much influence sales enablement actually had on said metric.

And on the other hand, you can have metrics that are easily attributable like net promoter score (NPS) of a training session or tool adoption, but often these have less impact on the business. It’s for these reasons I believe a blended approach to sales enablement measurement is needed.

If you’re interested, the metrics I’m measured by at HubSpot are monthly quota attainment of the EMEA sales organisation and I personally carry an influenced revenue goal from deal support. Thirdly, I run an NPS survey at the beginning of each month, to understand how sales reps felt I performed the previous month. This trifecta of goals keeps me focussed on important business metrics (quota attainment), ensures I am personally influencing revenue, and that I provide a good service to the sales organisation.

8. Be comfortable with some hand to hand combat
Working at a fast-growing software as a service (SaaS) company like HubSpot has taught me to deeply appreciate and value scale. While scale is important we should not seek it all costs - we need to also recognise and be comfortable with the fact that some enablement activity doesn’t scale, and frankly, never will.

The key takeaway here is to find the right blend between one-to-many, lower value and one-to-one, higher value activities. Most importantly, we should always seek to optimise for impact and revenue, not scale. Occasionally, it feels like scale is the very first question that sales enablement professionals ask, when really we should figure out if something will work first, and then tackle scale later.

Or put another way, would you rather run a programme that helps a cohort of 10 sales reps at your company improve their quota attainment by 20%, or one that helps all 100 people on of your sales organisation improve by 1%? Sometimes a higher impact programme for a smaller number of sales reps can be the right approach.

9. Be honest about your level of sales enablement maturity
Sales enablement is a rapidly emerging, but immature function. Many companies are investing in the creation of sales enablement teams, but as they’re so new, there’s a distinct lack of thought leadership, standardised measurement and best practices available.

To try and bridge this gap I often meet with sales enablement professionals at other SaaS companies. While the discussions are often uniquely insightful, some patterns typically emerge based on how long the respective sales enablement teams have been operational. Their teams can nearly always be categorised as being in one of the following stages: set up, tactical, reset, strategic and best-in-class (you can read more about the five stages of sales enablement maturity here).

By truly understanding your level of maturity you can understand where you are today, but more importantly where you want to be tomorrow.

10. Recognise that you’re in the business of influence
Strategic communication is an integral part of successful sales enablement. And the success (or failure) of a sales enablement function is intertwined with its ability to influence a sales organisation and change behaviour.

While it may not be immediately apparent, communicating well with and managing stakeholders is a prerequisite for successful sales enablement. Therefore, you need to be thoughtful about communication, as getting it right helps a sales enablement team earn trust and build credibility, which over time expands its scope of influence. This is important as ultimately, there’s just two states that a sales enablement team can ever be in. Either the sales leadership rates the sales enablement team and think they add value - or they don’t.

Sales enablement is a unique function, with its own opportunities, challenges and pressures, however, I think it shares many parallels with the role of a management consultant. Just like consultants, we sales enablement professionals are in the business of problem solving by providing counsel and guidance, but ultimately, we are reliant on other teams to execute.

But merely problem solving and managing stakeholders is not enough - to be successful, sales enablement leaders must influence via persuasion, coaching and cajoling, so people take action and change their behaviour. Ultimately, that’s what drives results.

These are my sales enablement best practices - what are yours?
So there you have it. These are the sales enablement best practices that I operate by at HubSpot. It’s my operating system if you will, and I’d love to discover how other sales enablement professionals are thinking about this too. Admittedly, these best practices are by no means definitive, nor are they applicable to every business, but they’ve given me a solid foundation to build a high-performing function. They will likely evolve over time, but today, they give me the framework to make the right decisions to help our sales organisation succeed.

I hope that you find these best practises valuable, but more importantly, I hope they spark discussion at your organisation around the role sales enablement can, should and will play. Critically evaluating and talking about sales enablement is how we’ll elevate the role to where it truly belongs. I’m proud to play a small part in what is a big moment for those of us working in and around sales enablement.

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