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 professionThe new abundance of opportunities for mentorship and individual developmentThe direct roadmap of sales roles to leadership positions

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 uncertaintyNavigating the cost of indecision (COI)Leaning into processes during good and bad economic times

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 aheadWhy 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

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 innovationThe effect of AI on sales trends, efficiency, and account retention and growthThe importance of post-sale structure (and how it can make your business stronger)

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

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.

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

How can sales leaders become trusted advisors and overcome the challenges of an elongated sales process while accounting for ever-evolving buyer behavior?In this episode of Winning The Challenger Sale, Krysten Conner shares effective strategies for building strong client relationships and solutions that drive retention and account growth. Krysten shares her remarkable journey from being a middle school teacher to becoming a top-selling expert at multiple unicorn companies. Together, Andee and Krysten explore the challenges sales leaders face, the shifting landscape towards better retention models, the power of personalization in customer relations, and the pivotal role of discovery calls in setting the stage for the future.Discussed in this episode:The obstacles and industry language challenges that sales leaders encounter and how to overcome them for better resultsThe quantification of the cost of inaction (COI)The role of personalized sales strategies using customer data, and the importance of understanding and addressing the unique needs of different customer personas

What’s the top predictor of customer loyalty? It’s not service. It’s not even a great product (although that doesn’t hurt). It’s an exceptional sales experience — and that only happens when you bring all of the elements of the customer experience together, from product to marketing. And when you align sales, marketing, customer experience, customer onboarding, and support against the customer journey, magic happens. When Amrita Mathur took on the role of VP of Marketing at Superside, she prioritized intertwining product and marketing, aligning Superside’s approach to gaps they viewed in the market and their ICP. Much of the company’s success can be attributed to this cohesive approach, and other companies should follow suit. Join us as we discuss:The importance of doing deep discovery to identify market gaps, then putting in the work to fill themWhy the experience prospects have needs to carry over throughout their journey as buyers and customersWhy your business needs a customer community and advisory board

When you speak with a client, do they think you’re there to help them, or to drive them to a close? Because buyers can tell. They hunger for sellers who deliver insights that support their goals and their business — and not a pop-in with bagels and coffee. The most effective sellers understand that they need to sell with purpose — and It all starts with your SKO. Our guest, Lisa Earle McLeod, founder of McLeod & More and author of five bestselling books, including Selling With Noble Purpose, talks about the concept of selling with purpose and how sales leaders can bring this concept into their SKO.. She shares three tips for creating an unforgettable SKO that celebrates success, while bringing sellers together to achieve higher performance. Here’s a hint: it all starts with understanding the difference that selling makes in your customer’s lives. Join us as we discuss:Transforming SKOs and sales culture with a purpose-driven approachPrioritizing emotional connection throughout SKOs to drive home purposeThe importance of reinforcement

With weeks of prep work, exciting itineraries, and top-notch speakers, SKOs are usually an epicenter of excitement after a grueling end-of-year rush.But despite the traditional approach to designing SKOs as a rallying cry for motivation, they truly serve two main purposes: resetting and refocusing the team by providing clarity and creating energy, commitment, and movement around action items.Paul Stansik, operating partner at ParkerGale Capital returns to the show to discuss designing the most effective SKO. He wants CROs to focus in on two overlooked facets of a successful SKO: clarity and purpose, with follow-up. When your sales team doesn’t understand the main problem you’re trying to address or the strategy you’re implementing, it leaves them in a whirlwind of energy with no direction to point it in. And when you don’t build in touchpoints and reminders throughout the year, the SKO becomes just another event on the calendar. Particularly in a remote environment where SKOs may be the only opportunity to meet with teammates and collaborate, these events are crucial in assuring team-wide alignment and enabling sellers to show up with the right knowledge. Industry-rattling speakers are fantastic for rallying the team together, but without clarity, SKOs will fall flat. Join us as we discuss:The importance of balancing clarity and motivation, and how you can attain bothIdentifying and addressing the company's biggest bottlenecks as guiding factors in designing a stellar SKOBuilding collaboration and continuous improvement with mid-year meet-ups and hybrid approaches

Diversity, equity, inclusion, and belonging are simple—but getting it right is not easy.Creating a truly inclusive environment where your sales team reflects the diverse pipeline you have (or hope to build) requires a high level of intentionality. You can’t build an inclusive environment with just one initiative. A quarterly workshop won’t give you the results you’re looking for. In fact, most blanket efforts won’t. In this episode, we’re joined by Cynthia Barnes, founder and CEO of the National Association of Women Sales Professionals (NAWSP), the first Black woman to deliver the keynote at Outbound 2022 — and a changemaker challenging the status quo across the sales industry. According to Cynthia, a truly inclusive sales environment can only exist when built upon clear definitions and intentions, strong leadership, and realistic goal setting.When we stop approaching diversity as a matter of equality and shift to an approach of equity and individualization, we can foster cultures that enable each and every individual to bring their best selves to work. We discuss:The difference between equity and equality (and how to incorporate what’s most important into your DEI initiatives)Practical measures you can take today to build diversity, equity, inclusion, and belonging to your organization and your pipelineWhy a commitment to diversity matters in sales and marketing

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, opportunities, and networking, and training that she wishes she had when she started in sales to women from diverse backgrounds. Now with more than 5,000 members, Sistas in Sales hopes to build a more inclusive, well-rounded profession for generations to come.Join us as we discuss:Why failing to build a diverse sales team leaves important, problem-solving perspectives — and money— on the tableHow the best leaders trust their sellersWhy it’s important to build psychological safety