Winning the Challenger Sale

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.

Dan Dal Degan, operating executive at Marlin Equity Partners, 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

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 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

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 indecision (COI)
• Leaning into processes during good and bad economic times

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 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

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 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

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 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

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 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)

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 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 Amazon.

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, 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

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. 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