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Winning the Challenger Sale

  • #107: Mentoring the Next Generation of Successful Sales Leaders

    27 FEB 2024 · The sales profession has evolved, but one thing has remained the same: the power and importance of mentorship. Where sales leaders once learned in person from each other in unstructured meetings — office banter, going to lunch, connecting at conferences or networking events — many of today’s professionals now work primarily from home. So how can we foster growth and success in today’s sales leaders? The answer remains the same, but the execution looks a little different., operating executive at, is a skilled mentor with a strong commitment to returning the energy and input he received as an up-and-coming professional. In the last episode of Winning the Challenger Sale podcast before a hiatus, Andee and Dan reflect on how mentorship has evolved, where sales professionals should look for growth today, and the current (and future) state of the field. Join us as we discuss: - Raising awareness of the sales profession - The new abundance of opportunities for mentorship and individual development - The direct roadmap of sales roles to leadership positions
    40 min. 41 sec.
  • #106: Accelerating Pipeline with a Unified ABM Strategy

    13 FEB 2024 · 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., president of, 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 with less. We discuss: - The importance of ABM and how you can use it to double your revenue - How to develop doubt-proof business cases for client expansion and gaining client trust - Achieving a holistic team effort utilizing cross-departmental strategy and integration
    25 min. 1 sec.
  • #105: Balancing the Art and Science of Selling

    30 GEN 2024 · For sellers, the past few years have shown that feast or famine, repeatable and dependable sales process wins every time., CEO at, 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 indecision (COI) - Leaning into processes during good and bad economic times
    32 min. 30 sec.
  • #104: How Challengers Thrive in a Fear-Driven Market

    23 GEN 2024 · 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, key account executive at, suggests the problems aren’t from the final mile, but from tactical approaches earlier in the buying process. In this episode, he and Andee Harris break down: - Strategies to combat indecision in a fear-driven market - Tactical tips to identify Talkers, Blockers, and Mobilizers (and what to do with that knowledge) - The importance of understanding and leveraging prospect timelines
    34 min. 34 sec.
  • #103: Positive Paranoia with Matt Doyon

    16 GEN 2024 · 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,, co-founder and CEO of and author of “,” 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 year to thrive. We discuss: - Tactical advice for reps to implement today for a successful year ahead - Why there’s no room left for the lowest-performing reps (and how you can ensure you’re not one of them) - Why this year spells disaster for the “Lone Wolf,” and why the Challenger will come out on top
    30 min. 27 sec.
  • #102: From Stalled to Sealed: Winning Sales Strategies For Today

    9 GEN 2024 · 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, 40-60% of deals are lost to this nearly-invisible force. This week on WTCS we’re joined by, founding partner at and co-author of, 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 indecision, and what you can do about it - Sales techniques for building trust and navigating customer concerns - Balancing buyer expectations in practical, achievable outcomes — and transformative possibilities
    32 min. 51 sec.
  • #101: Insights from the Frontline at Challenger

    19 DIC 2023 · Throughout 2023, businesses experienced tightening budgets, layoffs, increasing numbers of stakeholders, longer deal cycles — yet expectations remain as high as ever., 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 sellers can expect in the coming months regarding buyer preference, economic navigation, and technological innovation - The effect of AI on sales trends, efficiency, and account retention and growth - The importance of post-sale structure (and how it can make your business stronger)
    23 min. 32 sec.
  • #100: Can You Actually be Authentic at Work?

    12 DIC 2023 · In this special 100th episode of Winning The Challenger Sale podcast, we’re joined by, Principal at and co-author of, 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 balance company values and employee voice - Prioritizing intangibles to retain top-tier talent with inclusive culture and KPIs - The Importance of communication and power of the inclusive language matrix Ramsey’s book, The Mentorship Engine, is available on
    30 min. 56 sec.
  • #99: Orchestrating Success in Q4

    28 NOV 2023 · What makes an efficient and successful modern selling machine? Customized, personalized tactics aligned directly to the customer journey., founder and “chief sales energizer” at 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, Challenger COO Alli Manning, to share how sellers can embrace this mindset to close out the year strong and keep pace for the coming year. We discuss: - Modern sales techniques for adapting to today’s buyer behavior - Orchestrating selling team dynamics — from CEO involvement to team motivation - Guiding buyers, building confidence, and leveraging buyer verifiers
    33 min. 13 sec.
  • #98: Closing Complex Deals in a Changing Economic Landscape

    21 NOV 2023 · 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., CEO at, 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. Testifying in the case for in-person sales meetings, Jeb explains the results he’s witnessed and how face-to-face interactions fuel stronger sales. Join us as we discuss: - Sales strategies in a volatile economy and how to avoid a state of alert - How to set your team up for a strong end-of-year - Why a mix of in-person and virtual communication is key
    28 min. 21 sec.

Win the sales moments that matter, every day. Take a deep dive into the day-to-day skills and behaviors proven to win in complex selling and buying environments. Hosted by the...

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Win the sales moments that matter, every day. Take a deep dive into the day-to-day skills and behaviors proven to win in complex selling and buying environments. Hosted by the team that brought you the best-selling books, "The Challenger Sale" and "The Challenger Customer."

Learn more about our "Winning the Challenger Sale" webinar series here:
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