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

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 revenueHow to develop doubt-proof business cases for client expansion and gaining client trustAchieving 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 uncertaintyNavigating 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 marketTactical 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 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

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 itSales techniques for building trust and navigating customer concernsBalancing 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 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)

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 voicePrioritizing intangibles to retain top-tier talent with inclusive culture and KPIsThe 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 behaviorOrchestrating selling team dynamics — from CEO involvement to team motivationGuiding 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 alertHow to set your team up for a strong end-of-yearWhy a mix of in-person and virtual communication is key

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.

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

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

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

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

80% of your revenue comes from 20% of your customer base, and retaining those customers comes at a fraction of the price of acquiring new ones. Yet, many sales and marketing efforts are still locked on closing new leads with metric-centric objectives.While new customers will always be essential for growth, retention is the only way to achieve the status of a profitable, valuable, growth-oriented company.Therese Parkes, industry director for technology B2B at Google joins the show to share how to build a thoughtful retention strategy that allows you to get a deeper, wider concentration of customers across your organization to delight, retain, and pursue upselling opportunities.Join us as we discuss:Shifting your ABM strategy to move beyond leads to signals to meet the needs of the modern digital customerProven strategies for customer retention and holistic account health monitoringThe importance of understanding and retaining high-value customers with segmenting, listening, and iteration

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

Here's a controversial idea: Your SKO is not a massive training event. According to Peter Zink, Senior Director of Revenue Enablement at Sprout Social, it's a time for people to come together, see each other, celebrate and align on a few critical concepts to take into the new year. To build an effective SKO today, Peter argues that you begin with a theme that can be used as a rallying cry, then build an event that pushes your business forward and sustains your trajectory throughout the entire year. Join us as we discuss:Creating a culture of top-down and bottom-up buy-inHow to design the perfect SKO theme to build consistencyThe importance of cross-team collaborationEmpowering managers with coaching tools and resources to ensure sellers keep up to date with takeaways throughout the year.

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

Q4 will be here before you know it — and right after those three months of excitement comes the sales kickoff. And if you want to make sure your SKO brings your sellers together and sends them into 2024 with clarity and purpose, now is the time to begin planning it. Covid continues to impact the SKO planning process, as many organizations balance the advantages of virtual and hybrid events with the community building that takes place when you bring your team together in one room. Whatever path makes the most sense for your organization, our guests today make it clear that the place to start is with a vision statement — and from there you can layer on the creative elements, education, content, speakers, and swag that makes for a standout SKO. Sailpoint continuously goes above and beyond as they deliver top-quality SKOs that fuel growth. So it was a genuine delight to bring in Barrett Sellers, VP of global revenue enablement, and Robin Barde, associate manager of global revenue enablement to discuss the practical and replicable approaches they take to designing a kick-ass SKO, which you can emulate as you launch your team into the new year. We discuss:Why you need a vision deck, a whiteboard (or two), and a t-shirt cannon to fully visualize your SKOHow to navigate the unexpected challenges in the shift from virtual to in-personThe importance of fun, creative elements, and networking opportunities throughout your SKO to create a sense of communityIdentifying the right speaker mix — from ensuring diversity to reinforcement and inspiration

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

A seller's greatest enemy? It's not “no.” It's “We'll see.” The average seller loses between 40% and 60% of their qualified pipeline to no decision. Matt Dixon, founding partner of DCM Insights and co-author of The Challenger Sale, The Effortless Experience, and The Challenger Customer. Matt and his co-author analyzed 2.4 million sales calls over the course of 18 months, which they turned into the definitive guide to overcoming customer indecision — The JOLT Effect. They dove into the underpinnings of no-decision losses, uncovering exactly how they happen and the surprising approaches that top-performing sales professionals take to shift customers out of hesitation and into action...In this bonus episode, Matt joins us to talk about what The JOLT Effect uncovered about buyer psychology and intent, the role fear of failure plays in customer indecision, and how sales teams can employ the JOLT Effect to push customers past their fear of failure to an unqualified yes.We discuss:The three major drivers behind the fear of failure that leads to no-decision losses (and how the JOLT process can help mitigate them)Creating flexible, shared decision-making for buyers while taking inaction off the tableCounterintuitive habits that set high performers apart from the rest

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

Game up on one screen, Discord on the other, thousands of people are connecting with one another at any given moment. Whether you like dodging red shells and drifting across iterations of rainbow road or you have an interest in specialized aircraft simulation, there's an online community and gaming system for you.Evan Patterson, Marketing Consultant & Freelancer Marketer at Evan Patterson Consulting accidentally found his way into marketing through online gaming communities. His gatherings for gamers quickly grew and garnered the attention of gaming platforms, companies, and enthusiasts alike.Evan now uses his hands-on expertise in social selling to enable B2B SaaS companies to foster communities and connections with the same spark. He joined us to explain how social selling is best fueled by authentic connection, and how sales leaders can build healthy, high-performing teams by harnessing the power of social selling.We discuss:How a simple question can help leaders move beyond “equality” and toward true “equity.”How authentic allyship does (and doesn't) show up in businessAddressing the skill, hill, or will challenge of social selling

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

We've all heard that culture eats strategy for breakfast. But how can sales teams nurture a stronger culture among individual sellers? Start with mindset.Changing the way your organization sees its sellers—and the way those sellers see themselves—can unlock impressive sales growth. Our guest Catherine Brown, Founder of ExtraBold Sales, shares how managers can begin shifting away from the stereotype of sales people who push and coerce, and towards a culture that taps into each seller's ‘why.' After all, a strong culture is made up of thriving individuals—all of whom aregrowing toward the best version of themselves. In her recent book, How Good Humans Sell, Catherine breaks down the importance of enabling your sellers to develop into their best selves. Our conversation delves into her practical tips for building high performance ,starting at the granular human level.Join us as we discuss:Closing more sales with a simple shift in company mindsetWhy failing to coach your sellers is costing your businessHow to create highly-human interactions in the age of AIThe first steps to becoming an aspirational leader

Sales teams now see sales tech like Gong and Showpad as staples for high-performing organizations.But these platforms are just the beginning. Fringe tech, enabled by AI and cross-platform collaboration, can automate and streamline administrative tasks, freeing up your sales team to invest in, you know, selling. The robots aren't coming for your sales team — but they are coming to help. Embracing innovative tech differentiates the best of the best from the average seller in the modern sales world.Jeff Rosset, founder and CEO of Sales Assembly, joined the show to discuss how leaders best leverage tech (tailored to their strategy and environment) to allow sales teams to dive deeper into social selling, better understand their prospects and hone new skills to emphasize and create authentic connections.In sales, AI and fringe tech aren't just shiny tools to take up space in the stack — they create opportunities to calibrate and reach your full potential.Join us as we discuss:Opportunities to utilize tech for efficiency (and common misconceptions)What sets successful social selling teams apart from those who won't make the cutThe future of tech in sales and beyond—tangible outcomes, increased attribution and empowered teams

Over the past few years, there have been astounding advancements in tech with no sign of slowing down—and we all have a choice to make: Terminator or Iron Man.As a sales leader (or any type of business leader, really), you have two options. You can choose to treat these innovations as a threat, run away and hide from technology, automation, and AI as if they are the Terminator, out for your job and livelihood. Or, you can embrace the superpowers these innovations can offer and become a modern business Iron Man.Danny Wasserman, Director of GTM Enablement at Gong says those who run and hide will be left behind. But those who embrace the endless possibilities and benefits of modern tech will be able to become the best version of themselves, ultimately elevating their personal and professional lives.When you leverage tech to gather, isolate and analyze data, you can identify strengths and weaknesses with ease and speed that has never before been possible.So which will it be—Terminator or Iron Man?Join us as we discuss:Achieving higher win rates by leveraging revenue intelligence and data analysisStriking a balance between standardizing practices and respecting regional differencesEmpowering sales professionals by encouraging self-reflection and embracing vulnerability

You're marching into battle, armored allies by your side. Together, you have to decide how to reign as champion, but to do that you have to share your knowledge. How much do you give away without revealing your biggest strategic strengths (and weaknesses)? After all, your ally in battle may also be your competition in other realms of life.Like allies on a battlefield, business partners must navigate prospects with precision, sharing data and insights as needed. But in reality, you only have 50% of the data you need to make an informed decision. Even the best partner in the world doesn't want to share their entire customer list (let alone their whole pipeline). Bob Moore, Co-Founder and CEO at Crossbeam had a revolutionary idea—what if partners could exchange all the right data without giving away so much information they lose their strategic edge? Bob joins us to discuss how partners, like allies on a battlefield, can be enabled with data to win any war together, all while retaining individual privacy, security and compliance.We discuss:The importance and potential of partnership ecosystem-led growthAddressing tech stack fatigue by asking the right hard questionsIntegrating new sales tech in a way that enables legacy professionals

Truth bomb

You've identified a problem you want to solve for your organization. You've done the research and narrowed it down to two promising solutions. After visiting the websites for both, you click ‘book a call' and wait.The first SDR spends an hour talking to you about our organization and needs—it sounds like you're a great fit, at least from their perspective. So they schedule another call with you the following week for a demo. You hang up and wait some more, with very little knowledge to sway your solution decision.The second SDR jumps right in, they're already familiar with your organization and ask about team priorities, immediately jumping into a demo. You leave the call with a clear understanding of whether or not this solution is the perfect fit.Which sounds like the better buying experience? If you said the first, you're likely to be the only human who also enjoys trips to the DMV.We speak with Ashley Zagst, Senior Account Executive at Chili Piper about the power of demo-ing on the first call (and how it benefits the buyer and seller). Join us as we discuss:The role demoing plays in the sales process (and how to leverage it to your advantage)Creating safe space for sellers to build a foundation of trust with buyersDiversity across teams and in the pipeline, and why it's so important

You rely on the school bus to get your child to and from school safely every single day. You expect the bus to be outfitted with the best, most reliable parts and fuel. So how would you feel if your child was unexpectedly late coming home? And more—you found out the bus broke down because it was using cheap engine oil that causes higher ash buildup over the premium option.Your child's well-being is worth more than the cost-savings of discount oil, and you'll be hard-pressed to find anyone that disagrees. Which is the story that Christine Cox, North America Sales Methodology Specialist at Chevron, used to sell a heavy duty engine oil to a maintenance manager for a school bus company. Probably not where you thought that was going, was it?In this episode of the Winning The Challenger Sale podcast, Andee talks to Christine about using stories like this one to humanize the sale and as part of the Commercial Teaching choreography, which will help you better connect with buyers and set yourself apart from competitive solutions in your industry.Listen to the full episode for:Putting the buyer as a human at the center of your sales conversationsTaking relationship selling to the next level with Commercial Insight and TeachingDesigning your pitch deck as an accessory to lead to your solution, not with your solution

Your alarm goes off and you grab your phone, silencing the noise to scroll social media for a few minutes before getting ready for the day.You stream music and eat breakfast—flipping through recipes and meal plans (paper or digital, be real) and planning your grocery list. You hop in the car and head to work or the gym or wherever you start your day.From the moment we wake up to the moment we close our eyes, we are bombarded with endless information. So much so, much of it has become white noise.When was the last time you actually noticed the video ads between reels, voice ads on streaming platforms or printed ads on the billboards you drive past daily? And when you have noticed them, do they make you feel seen and understood? Or do they feel like a generic sales pitch? When it comes to being a beacon of clarity in the sea of noise, you have to provide information that will actually be valuable to your audience. And to catch their attention, you'll need to do so with a strong narrative, according to our guest Cody Gillund, VP of Marketing at Open Lending. She shares the power of storytelling in shaping meaningful touchpoints to drive sales and ultimately give back to the community.We discuss:Using the Deal Accelerator program to move forward difficult dealsGetting back to the roots of knowing one another as people, while also driving sales and marketing forward as a teamThe power of narrative and storytelling in differentiation

Sales has long been in fierce competition with other sellers and the status quo, losing customers to other companies and inaction. But today, we're also up against every department head across our prospect's businesses. With everyone lobbying for a slice of the budget, if the problem you solve isn't a top priority in your prospect's business today, you won't close a sale.In Ep. 74 of Winning the Challenger Sale podcast, we talk with Collin Mitchell, VP of Sales at Leadium about what it takes to dig deep enough to shape a discovery so well you can take full charge of your sales process.We discuss:The importance of flexing the curiosity muscle throughout discoveryHow to unstick the most stuck deals (and avoid them altogether by prioritizing discovery)Understanding and adapting to customer personalities and dismissing all excuses around not understanding your buyer

When it comes to winning with today's B2B buyers, our guest on the Winning The Challenger Sale podcast this week has some serious mic-dropping comments:“If it's not solving a problem, it's a non-starter.”“If it's a great product, but there's not a great story to tell behind it, there's no point in really even selling it.”“Buyers can tell when you're not as into the product as maybe your competitor is.”Yep, you read that right. You can't sell something you don't believe in… at least not very well. And without a strong voice and a great story about the problem your product is solving, you might as well quit before you start.In this episode, Challenger's very own VP of Product, Gina Slesar, brings a unique perspective to the discussion about who today's B2B buyer is. As an experienced product leader, Gina explains what B2B buyers are looking for in the products they purchase, which in today's volatile, uncertain economy, we know that connecting with buyers takes a lot more than a quality product and a decent offer.Listen to the full episode to hear Andee and Gina discuss:The three foundational components required to be successful selling a productManaging perceived risk and uncertainty in your deals to avoid no-decision lossesThe importance of gaining visibility into the sales experience from the buyer's perspective at every stage of the dealIn case you missed it: Andee and Gina also presented a webinar on the latest Challenger research into B2B buyer behavior and trends, which you can watch on-demand here.

Your phone charger is frayed and bent.Wires exposed, you twist it slightly to the right and balance your phone just so to get it to charge.A new cord has been on your list for weeks, but let's be honest, the situation isn't quite urgent enough for you to hit “buy now.” It's still charging, isn't it?Until it isn't.This strange habit of putting something off until it's truly broken isn't a personality flaw—it's just human nature.And according to Hannah Ajikawo, CEO and Founder of Revenue Funnel, it exists in modern sales, too. Getting today's B2B buyers to convert before things crash and burn is incredibly tough, but that's what sellers should reach for. To do that, your reps need to understand exactly where your prospect is in their buying journey.Once you know that, Hannah says, you must proactively shape your discovery strategy, meet your buyer where they're at, and guide them to the next step. This tailored discovery is a surefire way to differentiate from the first conversation and establish your value as a credible partner in a competitive buying situation.Listen to the full episode to learn more about:How to avoid being overhasty when it comes to building consensus in a buying groupShaping discovery strategies according to specific buyer readinessAll the best tips for discovery: two mistakes that all sellers make, the one question you MUST ask in discovery, the question you need to STOP asking, and how to do better introductions in a first sales call

We think we know our customers… but what if they're in an entirely different universe than we imagine?Each layer of customer understanding unveils a new truth that should ultimately shape how sales and marketing connect with buyers. But too often, there is a complete disconnect between what a customer knows about your product and what your sellers are communicating to the market. So how can we close this gap when we can't even gauge how many light-years away our ICP is?According to our latest guest, Jordan Crawford, Founder of Blueprint, if you take the time to hear customer stories, they'll tell you something you've never even thought of. You can shortcut years of learning by asking customers what they already know. That is what it takes to bridge the divide and connect with today's B2B buyers.Join us as we discuss:Using customer stories and experiences to launch conversations with precisionOutbound isn't dead—but your outbound strategy might bePredictions for AI applications in sales and marketing (and how people are using AI wrong today)

Would you show up to a street race with a bicycle? That's probably what it feels like as a seller up against today's digitally-enabled buyers.B2B buyers have almost everything they need to make informed buying decisions on their own. They're in the driver's seat… and sellers are stuck pedaling behind, trying to catch up.Luckily, it doesn't have to be this way. Hendrik Isebaert, CEO at Showpad and our guest on the Winning The Challenger Sale podcast this week, is a former seller himself and a wealth of knowledge on taking control of the buyer's journey, particularly in a virtual selling environment.His tips on preparation for virtual sales calls, selling on business impact, and building rapport in the digital space are everything you need to ditch the bike and hop in with the buyer to navigate together towards the purchasing finish line.Listen to the full episode to learn more about:Engaging with today's increasingly digital B2B buyer by embracing an omnichannel sales experience to avoid information overloadInstilling confidence in the post-sale customer experience to win deals in a downturnBuilding rapport in a digital selling environment and using collaboration and interactivity for stronger virtual meetings

Imagine your buyers all live in a gated community. A cold call is like showing up to the gatehouse without an invitation and expecting the security guard to let you in.But the buyer moved into that neighborhood for a reason, and it definitely wasn't so that SDRs could show up unannounced.Instead, you need to get to know your buyers to turn that cold call into a warm call. Bump into them at the gym. Find out their favorite coffee shop. Heck, move in next door! (Okay, maybe this metaphor is getting a little too creepy.)Putting aside the stalker vibes, there's still a lesson here. And today's guest on the Winning The Challenger Sale podcast, Tom Slocum, Founder of The SD Lab, has plenty of lessons to share about connecting with B2B buyers.Today's B2B buyers want relationships, community, and personalized solutions. Anyone can learn the skills needed to be an SDR, but to be a great one, you must become your ICP. That means doing your research, joining their communities, and adding value in every interaction.Building a community-like connection is more important than ever. And Tom shares exactly what your team can do to stop the “spray and pray” and instead… get an invite to the neighborhood BBQ!Listen as Tom and Andee discuss:What the modern (and more informed) B2B buyer actually wants from sales outreachHow SDRs can connect with today's B2B buyerWhy your sales development team should transition from cold calling to a warm calling approach (and how to use Tom's 3x3 method to do so)

The bar has been raised for sellers and feels like it keeps rising. The amount of information modern buyers have is at an all-time high, buyers' expectations from sellers have grown and changed, meaning sellers must now add more value than ever to help buyers along their purchasing journey.According to our latest guest, Ryan Barretto, President of Sprout Social, social media has quickly become one of the best platforms available to add that extra value.If your commercial organization isn't prioritizing social selling, you're missing a massive opportunity. (And don't try to tell us that you don't believe in the ROI—Ryan has some great counterpoints to that.)As a seller, if you can become adept at social selling, you can fast-forward building a connection with buyers and understanding what they care about so that you can provide a tailored and differentiated sales experience.It's a win-win.Join Ryan and our host and Challenger CEO, Andee Harris, on this episode of the Winning The Challenger Sale podcast, where they discuss:How the role of a salesperson must change and adapt to the modern buyer, particularly in how they want to use and experience social mediaSocial selling as a massive opportunity for commercial teams across all funnel stagesDemystifying the ROI of social selling, including the strength of its halo effect on your brand and sales cycleYou can also watch Ryan and Andee present on unlocking the lead gen potential of social media in a recent webinar from our Leading The Challenger Sale webinar series. Watch the recording here.

Word-of-mouth has long fueled the success of countless companies, big and small. But over the past several years, through the rise of the digital age, word-of-mouth has evolved into something with unlimited potential — something known as dark social. Now, a recommendation (or negative feedback) can reach millions with a single click of a ‘share' button.On this episode of Winning the Challenger Sale, we speak with Chris Walker, CEO of Refine Labs, who, as a pioneer of dark social, explains just how far a single share can go. Modern buyers want to make their own decisions and look for recommendations from trusted sources — we dive into just how you can leverage that to maximize your reach and growth.Join us as we discuss:How dark social's scale far outweighs word-of-mouthThe undeniable value of product-led growthSegmenting and executing your sales process based on buyer intent

Social selling is the key to engaging with your buyers before they're interested in talking to sales, before they're even in the market for your solution. But what's the key to successful social selling? Authenticity.Forget the “algorithm hacks.” Forget engagement for engagement's sake. Showing up as your authentic self on social is what truly matters because that's what will help you cut through the noise and form meaningful connections with your audience, and ultimately, your buyers.When you approach social media with authenticity and add value to each conversation, you can generate an affinity that will bring people back to your thought leadership again and again.This week on the Winning The Challenger Sale podcast, our guest is someone who excels at building connections and creating repeating engagement on social media. We're joined by Sam McKenna, the Founder of #samsales Consulting, who discusses how today's social media platforms are the next great avenues of prospecting in sales and marketing.Join as we discuss:The importance of authenticity when building your brand and presence on social mediaUsing content to teach people something and avoiding engagement for engagement's sakeHow to be part of the conversation—either in the comments or in dark social channelsSocial selling as the key to engaging your buyers before they engage with salesBe sure to check out Sam's previous appearance on Winning The Challenger Sale!

Buying and selling have always been social activities.Except nowadays, most of that socializing happens digitally and in virtual networking spaces.What we've learned through the rise of social media platforms is that there's a right way to approach your presence on social that will help you form real connections and have meaningful conversations with buyers. And our guest on the Winning The Challenger Sale podcast this week gives us the foundational elements of that “right way” to enable you to be successful at social selling.In this episode, Suzanne Muchin, Co-Founder of Bonfire Women, drops some knowledge about selling yourself and your ideas on social media in ways that are authentic and relatable and help you cut through the noise to reach your desired audience.Join as we discuss:How to spice up your “About” section of your social media profilesOwning your unique voice and getting over the discomfort of promoting yourself on socialUsing social media to test new ideas and messages, then learning from the responseNew ways of thinking around the content you post on LinkedIn

Sales and marketing have perhaps the most well-known tension since cats and dogs—only, it's far more important that they get along.Short of couples therapy or family counseling (which will make more sense once you listen to the episode), how do you cut the tension between these teams and create a symbiotic relationship leading to stronger sales messaging that consistently wins over buyersIn this episode, we're speaking with Michael Schaumberger, who is both a Principal Executive Advisor and the Global Lead for Insights and Messaging at Challenger, heshares the secrets to bringing your sales and marketing teams together to build an insight-led selling approach.We discuss:Marketing's role developing a sales narrativeThe misconceptions both teams have about one another's roles in the sales processThe rise of sales enablement and how it's helping to bridge the sales and marketing divideRemember to rate the podcast on your favorite podcast platform!

Too often, sales, marketing and customer success exist in silos—and it's stifling progress.When all three forces align, businesses thrive and customers get what they actually want and need. When they don't, it's easy for business to get “stuck.”On this episode of the Winning The Challenger Sale podcast, we're joined by Margaret Mueller, Board Director, President, and CEO at The Executives'​ Club of Chicago, who reminds us of a commonly underutilized tactic for unlocking business potential: utilizing sales for customer insight and innovation.With sales on the frontlines and marketing the compelling force behind engagement, both can benefit immensely from sharing data and gaining symbiosis, especially in turbulent times such as an acquisition, brand consolidation, or uncertain economic conditions.Join us as we discuss:Learnings from what can go wrong in pursuit of alignmentBreaking down departmental silos with an enterprise-wide mindsetHunting for insight to inspire innovation with your frontline, customer-facing teams

With your car, bad tire alignment causes uneven tire wear, diminishing suspension quality, and steering problems that could cause an accident.The same goes for bad sales and marketing alignment—metaphorically, at least.All too often, commercial leaders ignore when two of their most important wheels—sales and marketing—veer off in completely opposite directions. Different goals. Different metrics. Little to no communication. And the longer they go without a wheel alignment, the costlier that misalignment becomes.In this episode, we're speaking with a world-class “mechanic” when it comes to sales and marketing alignment. Jon Perera, Chief Marketing Officer at Highspot, joins the show to share his secrets for getting sales and marketing working better together.We discuss:Achieving alignment across the “four wheels of the car”—sales, marketing, enablement, and customer successHow common goals, “open and real” communications, consistent execution, and a shared narrative lead to better sales and marketing partnershipThe importance of coaching to realize behavior change at scaleWays to ensure marketing content is actually useful to sales

Sales success is built on understanding others.If you don't know your buyers, you're going to struggle to make the sale. If you can't put yourself in the shoes of your colleagues in marketing, it's going to be impossible to align. And if you can't create a culture of inclusivity on your sales team, you miss out on a range of diverse perspectives that would strengthen your business.In this episode, we speak with Lori Richardson, CEO and Founder of Score More Sales, about her career-long advocacy for inclusivity in sales and what she has learned about building a more empathetic and understanding sales team.We discuss:Why understanding your buyer is the key to differentiating yourself and beating the competitionHow sales and marketing can better understand one another and work towards shared goalsWhat sales leaders need to understand about fostering a culture of inclusivityYou can order Lori's book “She Sells: Attract, Promote, and Retain Great Women in B2B Sales” here! Be sure to rate and review the podcast on your favorite podcast platform!

Will there be a recession this year? It seems not even economists can agree, but regardless of how likely it is, the simple fact that it's possible is brewing uncertainty. So what's a seller to do?Here to help answer that question is the latest episode of “Winning the Challenger Sale,” where host Andee Harris, CEO of Challenger, is joined by Tim Kocher, Director of Business Development at West Monroe Partners, for a discussion on how to navigate economic uncertainty in a way that actually drives sales growth and captures market share.Tim shares his wisdom from selling and leading sales teams through four recessionary periods and drops a serious truth bomb… Sellers can't be as successful solely relying on technology and virtual selling. He also highlights two areas of focus: account-based growth and engaging Mobilizers in your deals.Tim and Andee close it out by exploring how the sales universe is changing and the potential impact of generative AI on marketing and sales in the future.Join as we discuss:How to sell amidst uncertainty and why you need to play offense even during difficult market conditionsUnexpected yet simple ways to differentiate post-pandemicBehaviors that high-performing sellers are using to navigate this economyWhat's in the crystal ball for the sales universe in the next five yearsBe sure to rate and review the podcast on your favorite podcast platform!

The theme for this month on Winning the Challenger Sale is Selling When No One is Buying. WTCS Host Andee Harris, CEO of Challenger, is joined by Shannon Poole, CFO at Challenger, to discuss the roles CFOs play in executive deals, how they protect a business from negative impacts, and the skillsets a CFO needs to make financial decisions. She also talks about cost of inaction (COI) vs return on investment (ROI), which is more critical to business growth. Shannon offers guidance to salespeople who do most of their business via an organization and the best practices for CFOs. Tune in to learn more about selling when no one is buying.

The theme for this month on Winning the Challenger Sale is Selling When No One is Buying. WTCS Host, Andee Harris, CEO of Challenger, is joined by Paul Stansik, Operating Partner at ParkerGale Capital, to discuss the sales executives' role and the pressures they face to increase sales during slow periods of business, and the skills they need to succeed in today's competitive sales environment. They further discuss how to improve customer retention in a business and win over investors. Tune in to learn more about selling when no one is buying.

On this episode of the Winning the Challenger Sale podcast, Andee Harris, CEO of Challenger, is joined by Rebecca Grimes, Chief Revenue Officer at Ruby, to discuss skills such as listening skills, storytelling skills and others that are necessary to possess for sales when the market is tough. They also discuss how agility and being a human first can help you to sell. Tune in now to hear all about selling during uncertain times.