What does account-based marketing (ABM) look like in 2024? For most people, they talk about it as a platform, and not a strategy. When you embrace ABM as a critical part of your GTM strategy, you can break down internal barriers and bring marketing, sales and customer together to create the ultimate account experience. Kristina Jaramillo, president of Personal ABM, argues that this team approach creates top-tier account experiences, allowing teams to work in unison to drive greater revenue, and expand and retain existing clients, ultimately diminishing the continued challenge to do more wit ..read more

For sellers, the past few years have shown that feast or famine, repeatable and dependable sales process wins every time. Kendra Tucker, CEO at Truckstop, joins Challenger CEO Andee Harris on this episode to talk about what she’s learned from her experience in private equity and as a sales leader. Kendra talks about how process guided Truckstop through the turbulent pandemic era, the cost of inaction, and brings advice for sellers and sales leaders to navigate this unusual economy (and win more deals). Join us as we discuss: Closing deals when buyers face uncertainty Navigating the cost of ..read more

Sales leaders, let’s try an exercise: if given a blank sheet of paper, can you write down three “superpowers” for each of your reps? The best sales leaders aren’t those who force reps to sell like them. Sales teams that consistently win lean into diversity through supportive leadership that enables psychological safety and amplifies individual strengths. By intentionally welcoming diverse voices into the room, these leaders bring more solutions to the table. In this episode, we’re joined by Chantel George, founder & CEO of Sistas In Sales, which she founded to bring the mentorship, oppo ..read more

You know your conversion rates, historical conversion rates, and territory inside and out. You have more data at your fingertips than ever before and your buyers keep saying yes — but then they don’t sign (or worse, disappear.). As sales leaders look back at 2023, many of them find themselves asking where things went wrong with customers during the final mile and what they can do in 2024 to improve their forecast accuracy. In this episode, our guest Geoff Hendricks, key account executive at Challenger, suggests the problems aren’t from the final mile, but from tactical approaches earlier in t ..read more

2024 promises more obstacles than ever for sellers, with increasingly elongated sales cycles, creeping increased indecision and tighter budgets. But what exactly does that mean for you and your sales team? Despite this bleak outlook, Matt Doyon, co-founder and CEO of Triple Session and author of “Revenue Revolution,” has a striking forecast: this year, the top 20% of sales professionals will have their best year yet. The middle 60% will struggle. And bottom 20%? They’re likely to find themselves out of a job. Fortunately, you have the power to push yourself into the top tier, making 2024 a ye ..read more

Why aren’t you winning? For so many modern sellers, the answer is only visible once it’s too late. According to research published in The JOLT Effect, 40-60% of deals are lost to this nearly-invisible force. This week on WTCS we’re joined by Ted McKenna, founding partner at DCM Insights and co-author of The JOLT Effect, to break down indecision’s impact on your win rates. Ted and Andee address the key steps sales teams can take to unlock stalled deals and push through to a successful close, even when key players are mired in indecision. We discuss: The major role of omission bias in buyer ..read more

Throughout 2023, businesses experienced tightening budgets, layoffs, increasing numbers of stakeholders, longer deal cycles — yet expectations remain as high as ever. Nader Pishdad, principal executive advisor at Challenger, joins Challenger CEO Andee Harris to dive into trendand hypotheses for the coming year from both buyers and sellers — and what to expect as the sales world continues to evolve. As we close out with Winning the Challenger Sale podcast’s final episode of the year, we take a look back at lessons learned and how we can use those lessons to shape 2024. We discuss: What sell ..read more

In this special 100th episode of Winning The Challenger Sale podcast, we’re joined by Ramsey Jay, Jr., Principal at Ramsey Jay, Jr. and Associates and co-author of The Mentorship Engine, who shares how to shift sales teams’ mindsets and build successful, optimized workplace cultures to supercharge sales teams heading into 2024. Host Andee Harris, CEO of Challenger, celebrates this milestone episode and then she and Ramsey dive deep on inclusivity, mentorship, and the power of love and service — and how embracing these means better business. We discuss: Building authenticity into culture to ..read more

What makes an efficient and successful modern selling machine? Customized, personalized tactics aligned directly to the customer journey. Alice Heiman, founder and “chief sales energizer” at Sales Strategies for CEOs has helped countless CEOs shift their mindset from traditional methods to a modernized approach — leading the way with strong collaboration and insight to navigate today’s evolving buyers. The secret? Sellers must orchestrate their internal team, from leadership to subject matter experts, and build custom strategies to meet the needs of their prospects. Alice joins our guest host ..read more

What marks the difference between a prepared seller and an unprepared rep? Whichever one follows the fundamentals of sales during times of ease will be the one who successfully navigates volatile markets. Intentionality, strategy, discovery — remember those cornerstones and your sales team will rise above any coming adversity. Jeb Blount, CEO at Sales Gravy, joins Andee this week to discuss avoiding slipping into a state of alert as the year comes to a close. He emphasizes the importance of qualifying deals, focusing on engagement, and matching efforts to land the right deal at the right time ..read more