
99 episodes

Winning the Challenger Sale Challenger
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- Business
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4.6 • 46 Ratings
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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: https://www.challengerinc.com/events/
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#99: Orchestrating Success in Q4
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 behaviorOrchestrating selling team dynamics — from CEO involvement to team motivationGuiding buyers, building confidence, and leveraging buyer verifiers -
#98: Closing Complex Deals in a Changing Economic Landscape
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 alertHow to set your team up for a strong end-of-yearWhy a mix of in-person and virtual communication is key -
#97: Tackling Q4: Sales Strategies from an NFL Pro Turned Sales Leader
Does AI hold the key to your end-of-year success? What are the effective ways that organizations are using it to drive results? Explore the role of AI in sales strategy, from identifying in-market accounts to streamlining processes, and discover innovative prospecting tactics that drive success, even in these challenging times.
In this episode, Andee is joined by former NFL player turned sales leader Ernest Owusu, now senior director of sales development at 6sense, He shares his insights on building successful sales development programs.
Join us as we discuss:
What Ernest believes the NFL and B2B sales have in commonInsights into leveraging AI for personalized sales approaches and efficient decision-making.Effective prospecting strategies and team motivation techniques to keep your sales team on track for a successful year-end close. -
#96: Seal the Deal with Customer-Centric Experiences
What’s the key to creating end-of-year momentum? Creating the best buyer experience, prioritizing the right deals, and implementing feedback. Invest in these three strategies, and your sales team will optimize their performance in the final weeks of 2023 and launch into the new year with confidence.
Sam Senior, co-founder and CEO at Testbox, joins the Andee this week to discuss all things necessary to finish the year strong. He emphasizes the importance of identifying red and green flags for sales focus, building better communications for sales enablement, and leaning into the “give-to-get” mindset. With limited time and resources, Sam shares the insights you need to close Q4 successfully.
Join us as we discuss:
Engaging the stakeholders who truly matter with customer-led buying experiences and personalized sales approachesImproving sales experiences with real-time communication — both digital and in-personSales strategies for startups to land on Day One lists -
#95: Customer Messaging that Seals the Deal
Think of your sales pipeline as less like a funnel and more like a subway map — your sellers can take multiple routes to close, as long as they head in the right general direction. It’s up to you to identify each customer’s unique journey — and that can’t be done without explicit efforts to foster relationships and customer-led growth.
Building trust with customers is essential for the future — yet many sales professionals take a shortsighted view that extends only to closing deals. Moving away from a transactional mindset and toward customer-led growth is all about how we view and treat the pipeline, according to Matt Heinz, President of Heinz Marketing.
In today’s episode, Andee and Matt confront the many misconceptions surrounding customer relationships, highlighting the necessity of challenging customers to uncover their true needs and the crucial role of the user committee and user journey alongside the buying committee in B2B deals.
Matt underscores the significance of sales and marketing alignment for complex deals, shedding light on the collaborative approach between the two teams and the pivotal role of tailored content in securing customer engagement and loyalty. This episode is full of practical tips and examples of effective sales positioning, common pitfalls in discovery, and the transformative power of community in customer retention.
In this episode:Challenging customer assumptions for business success and treating each customer like a VIPHow cross-departmental alignment around customer engagement bring clarity and profitabilityCrafting tailored content and community building to expand and deepen your customer base -
#94: Want Account Growth? Make Your Business Indispensable
Today’s market is complex and unpredictable, but one thing is certain — retention matters more now than ever before. By embracing the role of a trusted advisor and focusing on overall profitability over top-line growth, sales leaders can navigate the rollercoaster days ahead.
In this episode, Andee Harris sits down with Marinus Maris, industry veteran and VP of international sales at Challenger. Marinus provides a unique perspective on the current landscape of sales culture, skills, and growth strategies. Drawing inspiration from his journey, Marinus provides details into the necessary shift toward profitable growth and the art of building and retaining customer loyalty.
In this episode, Marinus and Andee break down:
Why focusing on profitability is the new norm in sales.How sellers can leverage curiosity, storytelling, and proactive account planning to achieve profitable growthStrategies that prioritize profitable customer segments for long-term growth
Customer Reviews
Sales Gems with Jen & Mike
Love this show! Jen and Mike always drop some serious sales wisdom. It's my go-to for insights, and I can't help but share it with my team. Keep it coming, you two!
This show provides a different perspective
This is one of the best sales podcasts out there because of the perspective it provides. Jen Allen is not only a top seller, she’s a great interviewer. She asks questions of her guests (and thus her audience) to get them thinking about the sales process from a different point of view. Think differently, and you’ll sell differently.
Thoughtful and informative
Loving the practical applications of the Challenger book and thoughtfulness Mike and Jen bring to each episode!