Winning the Challenger Sale (Challenger)

In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Nate Nasralla, Founder of Fluint. They discuss how to sell with your buyers, not to them.

The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Amy Hrehovcik to discuss how to manage the inevitable buying group conflict and dysfunction that arises when you have multiple customer stakeholders getting either directly or indirectly involved in a deal.

In this episode of Winning the Challenger Sale, hosted by Jen, Will Aitken, Sales Evangelist at Sales Feed, discusses opportunity prioritization in prospecting. They discuss the need to prioritize prospects to focus major efforts on the discussions and clients that are most likely to result in a successful sale. Aitken elaborates on how to distinguish your top prospects from a list of several hundred potential clients.

In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Amy Volas, Founder & CEO of Avenue Talent Partners, discusses achieving long-term success in recruiting, marketing and sales. Often, individuals prioritize self-promotion to attract prospects, which is usually rooted in short-term fulfillment goals such as now-now sales. But, what if, with a thorough understanding of a niche's issue, one could engage an audience in a substantive discussion, leading to meaningful interaction, resulting in genuine value to a customer? Amy goes into great detail about the impact of short-term approaches on sales outcomes.

On this month's episode, hosts Mike Randazzo and Jenn Allen talk all about building a case for change. Change initiatives or purchases are hard for customers to commit to, especially in uncertain times. But what does it take to get a risk averse buyer to move off of their status quo in this environment? The answer: a rock solid business case for change built not only on rational, quantitative evidence, but also on an appeal to the emotional drivers of purchase decision making.

The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Caroline Franczia to explore how star sellers prepare negotiables and anticipate curve balls ahead of negotiation conversations. In addition, they discuss the similarities and differences between MEDDIC and the Challenger selling method, as well as the roles that early stakeholder engagement, discovery, and salesperson energy have in facilitating a successful sales process.

In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Nick Capozzi, Head of Storytelling at Demostack. They discuss how to use descriptive words and ideas to help prospects visualize themselves as part of your story and relate better to the ideas or products you're selling.

The theme for December on Winning the Challenger Sale is a recap of the best insights from 2022. WTCS host, Jen Allen, is joined by Dr. Howard Dover to explore the major themes that have disrupted the status quo of selling this year.

In this episode of Winning the Challenger Sale, hosted by Jen, Johnathan Bald, Area Vice President of Large Enterprise Sales Netwitness - Canada & US East at RSA Security, discusses the fundamentals of qualifying, disqualifying, and prioritizing opportunities. Johnathan explains how the unique market fit and the maturity of an organization influence the likelihood of qualifying or disqualifying a prospect, and factors that influence internal opportunity prioritization.

On this episode of the Winning the Challenger Sale podcast, hosts John Shea and Mike Randazzo discuss the importance of  showing up with credibility in your first interaction with a new client or prospect. Our first guest Jen Allen, Key Account Executive at Challenger, will share her experience with demonstrating credibility and making a strong first impression on the first sales interaction with a prospect, and the prep work you can do to make sure you're prepared.Our second guest, Kristina Jaramillo, Founder and President of Personal ABM will be talking all how you can build credibility with social selling techniques. 

In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Mor Assouline, Founder of FDTC and Creator of Saas Talks: From Lead to Close Podcast. They discuss sales strategies that convert interested buyers into advocates. How to approach a demo boost consumer delight so that they can proactively recommend your company's products and services to other stakeholders or potential customers.

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.

The theme for September on Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by Amelia Taylor to discuss how sales representatives can motivate action in mid to late-stage opportunities, especially when progress stalls.

On this episode of the Winning the Challenger Sale podcast, hosts John Shea and Mike Randazzo and guest, Jennifer Allen, break down how to get the discovery call right. Discovery is a critical component of most sales processes, yet it's often misunderstood or overlooked in its importance. Listen to learn strategies and tactics sales professionals can use to unlock information and deliver value in early stage discovery calls with prospects and customers. 

The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Howard Brown to discuss nontraditional ideas for how sellers can manage the inevitable buyer dysfunction that happens when multiple stakeholders are involved in the decision.

In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Jeff Bajorek, Founder, Advisor, and Coach to B2B Sales Leaders at Parabola Consulting and Host of Rethink The Way You Sell. They discuss how you can take a single interested stakeholder and aid them in their efforts to advocate for you with the broader buying.

The theme for this special episode on Winning the Challenger Sale is Avoiding Death by Discovery. WTCS host, Jen Allen, is joined by Doug Landis to explore the major themes, such as “anti-discovery,” that disrupted the status quo of selling throughout the year 2022.

On this episode of the Winning the Challenger Sale podcast, Andee Harris, CEO of Challenger, recaps highlights from the second most popular theme from the podcast last year. The goal is to help you kickstart the year on a solid foundation while riding on the wings of these clips. This time, she walks us through deep insights from the theme “Turning Interest into Advocacy.” Tune in to learn how to convert a single interested stakeholder into an advocate for you among the broader buying team from interviews with Mor Assouline, Jeff Bajorek, Nate Nasralla, and Brandon Fluharty.

In this episode of Winning the Challenger Sale, hosts Mike Randazzo and Jen Allen discuss social selling in depth. They discussed how important it is to include the human element in the sales and marketing process and deliver value that engages customers and prospects. They investigate factors that influence great sales, such as how easily customers connect with stories, especially ones that highlight challenges they are facing and how you have enabled better outcomes for other customers like them.

On this month's episode, hosts Mike Randazzo and Jen Allen talk demos. The good, the bad and the ugly. Every sales person needs to demo their product or solution in some way, at some point, but the reality is there is much more that can go wrong with demos than right. Listen as  Mike and Jen discuss demo traps to avoid, and the characteristics of best in class demos to keep in mind as you lead them at any stage of the sales process.

The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host Jen Allen is joined by Geoff Hendricks to discuss the importance of ensuring you're on the same page with your buyer about what needs to be done before closing a deal.

On the first episode of the Winning the Challenger Sale podcast, hosts John Shea and Mike Randazzo talk all about negotiations - one of the aspects of the sales process that sellers are least confident in. Joined by guest Lauren Graves, Challenger's Head of Learning and Design, they discuss 'sizing the pie' versus 'protecting the pie', how Challengers deal with curveballs, and how to handle the anxiety called "torschlusspanik" in advance of the negotiation.

On this special 2022 Year in Review episode of the Winning the Challenger Sale podcast, our new host Andee Harris, CEO of Challenger, runs through the highlights of our most popular episodes from this year. Tune in to hear the best clips from Ravi Rajani, Brandon Fluharty, Jeff Bajorek, Sam McKenna, Will Allred, and Tom Alaimo as they discuss major themes that have disrupted the status quo of selling this year.

In this episode of Winning the Challenger Sale, Jen is joined by Ravi Rajani, Founder of Ravi Rajani Consulting and Host of The Influential Communicator Podcast. They explore some persuasive ideas for how sellers can use storytelling to motivate action and convey the human impact of the customer problem we're solving.

In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Richard Perez, Lead Advisor for Sales and Go-to-Market Practice at Apax, presented ideas on how to approach C-level buyers, how to deal with problems by offering unique insights into their viewpoints, and how to turn those insights into practical solutions. He shares his views on how to engage with C-level buyers on a human level, as well as the significance of prior preparation for a meaningful conversation with them.

The theme for September on Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by John Shea to discuss how creating urgency allows salespeople to provide customers with real value—by getting the prospects to realize that every day, week, or month without the proposed solution hurts their business, their income, safety, or peace of mind. Hence, they are compelled to take action as quickly as possible.

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.

In this episode, hosts Mike Randazzo and Jen Allen talk all about late-stage negotiations. You're wrapping up late-stage deals that you've been working on for months, you're in the final mile, and then... procurement throws you a curveball. An unexpected request, demand, or ultimatum that you weren't anticipating and you're rushing to come up with a response at the moment. But, what if the perfect response is actually no response at all? Or a delayed response? Listen to hear Mike and Jen unpack what high-performing sellers do differently than their average or core performers peers when it comes to handling curveballs that are thrown their way in late-stage negotiations.

The theme for September on the Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by Florin Tatulea to discuss how understanding the buyer's position and trying to speak the buyer's language can assist sales professionals uncover the urgency for the buyer to take the necessary action and some strategies for SDRs and AEs to be successful in sales.

In this episode of Winning the Challenger Sale, WTCS host Jen Allen recounts the June theme of persuasive storytelling. She discusses her sales journey and highlights common mistakes salespeople make when telling their stories that leave a buyer in a "no decision" position. She also recommends practical storytelling techniques that are strategic, effective, and beneficial.

In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Ian Koniak, Founder & President at Ian Koniak Sales Coaching, shares how to engage C-level buyers, convince them to take the meeting, and then ensure those meetings are productive. He shares his formula for cold emailing, what to say during those meetings, and then how to connect with C-level buyers on both a human and professional level.

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 conditions
• Unexpected yet simple ways to differentiate post-pandemic
• Behaviors that high-performing sellers are using to navigate this economy
• What’s in the crystal ball for the sales universe in the next five years

Be sure to rate and review the podcast on your favorite podcast platform!

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 competition
• How sales and marketing can better understand one another and work towards shared goals
• What sales leaders need to understand about fostering a culture of inclusivity

You 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!

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 success
• How common goals, “open and real” communications, consistent execution, and a shared narrative lead to better sales and marketing partnership
• The importance of coaching to realize behavior change at scale
• Ways to ensure marketing content is actually useful to sales

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 alignment
• Breaking down departmental silos with an enterprise-wide mindset
• Hunting for insight to inspire innovation with your frontline, customer-facing teams

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 buyers

In 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 narrative
• The misconceptions both teams have about one another’s roles in the sales process
• The rise of sales enablement and how it’s helping to bridge the sales and marketing divide

Remember to rate the podcast on your favorite podcast platform!

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 profiles
• Owning your unique voice and getting over the discomfort of promoting yourself on social
• Using social media to test new ideas and messages, then learning from the response
• New ways of thinking around the content you post on LinkedIn

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 media
• Using content to teach people something and avoiding engagement for engagement’s sake
• How to be part of the conversation—either in the comments or in dark social channels
• Social selling as the key to engaging your buyers before they engage with sales

Be sure to check out Sam’s previous appearance on Winning The Challenger Sale!

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-mouth
• The undeniable value of product-led growth
• Segmenting and executing your sales process based on buyer intent

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 media
• Social selling as a massive opportunity for commercial teams across all funnel stages
• Demystifying the ROI of social selling, including the strength of its halo effect on your brand and sales cycle

You 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.

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 outreach
• How SDRs can connect with today’s B2B buyer
• Why 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)

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 overload
• Instilling confidence in the post-sale customer experience to win deals in a downturn
• Building rapport in a digital selling environment and using collaboration and interactivity for stronger virtual meetings

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 precision
• Outbound isn’t dead—but your outbound strategy might be
• Predictions for AI applications in sales and marketing (and how people are using AI wrong today)

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 group
• Shaping discovery strategies according to specific buyer readiness
• All 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

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 product
• Managing perceived risk and uncertainty in your deals to avoid no-decision losses
• The importance of gaining visibility into the sales experience from the buyer’s perspective at every stage of the deal

In 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.

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 discovery
• How 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

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 deals
• Getting back to the roots of knowing one another as people, while also driving sales and marketing forward as a team
• The power of narrative and storytelling in differentiation

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 conversations
• Taking relationship selling to the next level with Commercial Insight and Teaching
• Designing your pitch deck as an accessory to lead to your solution, not with your solution

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 buyers
• Diversity across teams and in the pipeline, and why it’s so important

Truth bomb 💣 A lot of sellers fail because they fail to follow up.

Your outbound can be on point, but unless it’s absolutely phenomenal, you’re not likely to close many deals with a single email. You’ve got to come back a few times, remind your buyer who you are, and show them exactly why they should execute your CTA.

And guess what—tech can help without scaring prospects away with a robotic tone 🤖

When is outbound a losing game? Is there a golden number of emails you should send? Craig Jordan, Founder and CEO at SaaScend and our guest on the latest episode of Winning the Challenger Sale podcast, says he won’t respond until he’s received four emails, at minimum. And more importantly—the intention and attention behind the email (seen with interesting, well-written, personalized copy) are much more important than whether robots are involved in the development.

Join us as we discuss:

• Utilizing tech to power and personalize your communications (while avoiding complacency and tech stack fatigue)
• How to build a killer tech stack from scratch without overextending resources
• Building mentorship and collaboration into culture for cascading system success

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 growth
• Addressing tech stack fatigue by asking the right hard questions
• Integrating new sales tech in a way that enables legacy professionals

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 analysis
• Striking a balance between standardizing practices and respecting regional differences
• Empowering sales professionals by encouraging self-reflection and embracing vulnerability

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 cut
• The future of tech in sales and beyond—tangible outcomes, increased attribution and empowered teams

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 mindset
• Why failing to coach your sellers is costing your business
• How to create highly-human interactions in the age of AI
• The first steps to becoming an aspirational leader

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 table
• How the best leaders trust their sellers
• Why it’s important to build psychological safety

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 business
• Addressing the skill, hill, or will challenge of social selling

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 pipeline
• Why a commitment to diversity matters in sales and marketing

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 table
• Counterintuitive habits that set high performers apart from the rest

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 both
• Identifying and addressing the company's biggest bottlenecks as guiding factors in designing a stellar SKO
• Building collaboration and continuous improvement with mid-year meet-ups and hybrid approaches

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 SKO
• How to navigate the unexpected challenges in the shift from virtual to in-person
• The importance of fun, creative elements, and networking opportunities throughout your SKO to create a sense of community
• Identifying the right speaker mix — from ensuring diversity to reinforcement and inspiration

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 approach
• Prioritizing emotional connection throughout SKOs to drive home purpose
• The importance of reinforcement

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-in
• How to design the perfect SKO theme to build consistency
• The importance of cross-team collaboration
• Empowering managers with coaching tools and resources to ensure sellers keep up to date with takeaways throughout the year.

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 them
• Why the experience prospects have needs to carry over throughout their journey as buyers and customers
• Why your business needs a customer community and advisory board

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 customer
• Proven strategies for customer retention and holistic account health monitoring
• The importance of understanding and retaining high-value customers with segmenting, listening, and iteration

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 results
• The 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

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 growth
• Strategies that prioritize profitable customer segments for long-term growth

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 VIP
• How cross-departmental alignment around customer engagement bring clarity and profitability
• Crafting tailored content and community building to expand and deepen your customer base

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 approaches
• Improving sales experiences with real-time communication — both digital and in-person
• Sales strategies for startups to land on Day One lists

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 common
• Insights 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 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

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

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.

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)

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

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

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

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

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

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

In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Geoff Hendricks, Key Account Executive at Challenger, and Ari Brinson, Business Development Associate at Challenger, discuss their views and experiences with email marketing and present a framework for producing effective emails that customers love to engage with.

Insight-selling in a one-to-one customer conversation is one thing. But how do we do it effectively in front of the entire buying group? Check out this month's podcast to learn more.

In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Josh Braun, Founder of Josh Braun Sales Training, shares his perspective on social selling and how to engage with prospects in a way that flips their defense mechanism to traditional sales processes and allows them to open up to the solution you have to offer.

The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host Jen Allen is joined by Ryan Scalera to discuss how star sellers prepare to open negotiations and anticipate curve balls ahead of negotiation conversations.

In this episode of Winning the Challenger Sale, Jen Allen hosts Mike Randazzo's farewell session, which is his final episode as a co-host. They talk about the key concepts behind the Challenger sales strategy, as well as the most memorable experiences and discoveries they've had over the years. Mike discusses his experiences, techniques, and dilemmas while working with Challenger. He also highlights the fundamental concepts and timeless strategic differentiators in sales approaches.

In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Will Allred, Co-Founder and COO of Lavender, presents ideas on writing emails that people want to respond to. They discuss interesting factors that influence customer reaction to email outreach.

In this episode of Winning the Challenger Sale, Jen is joined by Brent Adamson, the Global Head of Research and Communities at Ecosystems and former Distinguished Vice President at Gartner. They discuss persuasive storytelling from the perspective of using emotional selling to start a conversation, pique interest, influence purchasing decisions, and build long-term relationships by focusing on a customer's feelings rather than logic or the product's features.

In this episode of Winning the Challenger Sale, Jen is joined by Tom Alaimo, Growth Account Executive at Gong/Millennial Sales and Pavilion Podcast Host. They discuss approaches for optimal opportunity identification, assessment, and prioritization. Tom shares personal experiences and vivid illustrations of why he believes it’s important to be transparent about value propositions. He suggests establishing a clients' stance early in a sales conversation before validating any possibility. Spending time verifying the possibility is preferable to leaving things to chance and assuming the sale goes through.

The theme for November on Winning the Challenger Sale is Preparing for Negotiations. WTCS host, Jen Allen, is joined by Niko Papademetriou to discuss techniques used by star salespeople to prepare for negotiations and any surprises that may come up.

In this episode of Winning the Challenger Sale, hosts Mike Randazzo and Jen Allen dive deep into this week's theme of "engaging C-level buyers". They investigate factors that will make selling difficult in 2022, focusing on the complexity of the expanding buyer's side as a result of increased risk aversion to the traditional solo buyer role. Listen to Mike and Jen explain the shift from the traditional perspective of autonomous purchase consideration by the C-level suite to the need of the seller to develop compelling insights through other sensitive factors that influence success.

Does this sound familiar? You're too expensive. The timing isn't right. We're happy with the solution we have. If there's one topic that's truly universal in B2B selling, both in terms of how often sellers face it and one of things sellers hate the most, it's objection handling. But what if we told you that most sellers approach objection handling all wrong? On this episode, Mike and Jen share a completely different way to approach customer or prospect objections.

In this episode of Winning the Challenger Sale, hosts Mike Randazzo and Jen Allen discuss engaging prospects via email marketing using both the strategic and human approaches. They investigate ways to improve the email recipient’s experience by arousing their curiosity with findings obtained from your interest in the relevant issue, eventually inspiring a natural response.

The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host, Jen Allen, is joined by Leslie Venetz to discuss the role of a mutual close plan in driving sales success. She sees the close plan as an opportunity to guide a buyer through the buying process towards an outcome beneficial for them and, hopefully, for you.

The theme for September on Winning the Challenger Sale is Driving Urgency for Change. WTCS host, Jen Allen, is joined by Carl Ferreira to discuss approaches for creating healthy urgency in mid- to late-stage opportunities, especially when progress stalls.

Have I earned the right to ‘teach’ my customer yet?Listen to hear hosts Mike Randazzo and Jen Allen discuss how Challengers leverage credibility building and effective questioning to then introduce the right insight, at the right time.

The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Charles Muhlbauer to discuss the role that curiosity and discovery play for a seller leading a group meeting in front of a buying group.

The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host, Jen Allen, is joined by Aaron Evans to discuss how to map out and mutually agree with a customer on the final steps toward closing a deal.

In this episode of Winning the Challenger Sale, hosted by Jen and Mike, Sam McKenna, Founder at #samsales Consulting, discusses differentiation strategies for sales emails. They delve into finding the proper balance between personalization and relevance in email outreach. Sam explains in detail her ‘Show Me You Know Me’ approach. You don’t want to miss this!

In this episode of Winning the Challenger Sale, WTCS host Jen Allen is joined by Brandon Fluharty, Founder of Be Focused. Live Great. and Facilitator at Make More Hustle Less Club. They discuss consensus-based selling and how you can take a single interested stakeholder and aid them in their efforts to advocate for you with the broader buying team.

The theme for October on Winning the Challenger Sale is Creating a Mutual Close Plan. WTCS host, Jen Allen, is joined by Anthony Natoli to discuss the importance of mutual close plans; why and how salespeople should use them to enhance their sales processes.

The theme for August on the Winning the Challenger Sale is Resolving Buying Group Conflict. WTCS host, Jen Allen, is joined by Luigi Prestinenzi to discuss how to manage the inevitable buyer group conflict and dysfunction that arises when you have multiple customer stakeholders involved either directly or indirectly in a deal.