As we think about sales evolution in 2025, we saw consensus form around a handful of topics — how Challenger can shift and evolve in our current error, building inclusive sales cultures, the need for modern account growth strategies — but no trend compared to the role that artificial intelligence can (and will) play in sales performance in 2025.

Much of the attention paid to AI in 2023 and 2024 revolved around its efforts in automating routine tasks or taking the guesswork out of creating content like cadences or social posts. Nearly two years ago, HubSpot reported that 68% of business leaders called AI tools important to their overall business strategy. That number has likely grown… yet the truth is that sales leaders struggle to fit the growing capabilities of these tools into a well-rounded strategy to grow pipeline and closed-won deals.

We received more questions about AI than any other trend. And the best one came from Klaus J., a director of a global center of excellence for a digital supply chain company. He asked:

What role, if any, do you see AI and machine learning having on sales planning and execution in 2025 and beyond?

Andrea Grodnitzky, CMO at Richardson Sales Performance, shared with us her thoughts on this question, digging into how these capabilities have expanded and the true impact they can have for sales organizations, particularly around forecast accuracy and upskilling and coaching.

Andrea notes that there are six areas where generative AI can transform sales organizations:

• Automating repetitive tasks: Freeing sales teams from administrative work, allowing more time for high-value tasks and customer interactions.
• Personalization at scale: Creating tailored content based on individual communication styles and preferences.
• Providing intelligent insights: Analyzing vast datasets to prioritize accounts, leads, and strategies for growing strategic accounts.
• Content creation: Generating compelling pitches, cold emails, and other sales materials informed by historical data.
• Pipeline management and forecasting: Enhancing deal tracking, communication analysis, and forecasting accuracy.
• Coaching and upskilling: Personalized learning pathways, real-time feedback, and insights to improve seller performance and close skill gaps.

“We know no two sellers are alike. They have different levels of skill and competencies. So creating personalized learning pathways is really powerful to help upskill your team more quickly and make the content more relevant for them,” Andrea said.

“AI can analyze reps’ performance data, their individual skill gaps, and then based on that, recommend individual personalized learning pathways and training content. Certainly, AI can be used for real-time, in-the-moment coaching embedded in places like your CRM workflows [to] guide reps on things that are basic, like how to handle customer objections, all the way up to advancing deals and deal strategy.”

A lot has changed since we published “The Challenger Sale” in 2011 — and while the principles that underpin the Challenger methodology hold true, no one succeeds by doing the same thing over and over again. After all, we’re on the record that the status quo needs disrupting and that a seller’s job is to build continuous business improvement and ROI.

With that in mind, Tony M., a senior sales effectiveness manager, asked us:

Based on the way sales will evolve in 2025, how should we adapt and change the Challenger sales methodology?

We took it straight to Lauren Graves, Head of Learning Design at Challenger, who not only helped develop Challenger’s initial learning experiences but also continues to apply her expertise to innovating and updating Challenger’s content and products.

Though the initial research took place in 2011, Challenger revalidated key points in 2019, finding that the single biggest driver of customer loyalty — the sales experience — hasn’t changed. But how sales leaders drive teams to deliver meaningful sales experiences will evolve. Adapting to modern challenges is essential. Lauren told us this means:

• Tackling customer indecision: Develop strategies to guide buyers through overwhelming choices and complexities.
• Embedding learning into tools: Utilize platforms like Salesforce or Gong to reinforce skills and provide tactical support.
• Upskilling sales teams: Equip sellers to handle new buying behaviors and decision-making patterns with adaptive training methods.

“You don’t necessarily need to switch out your toolset for each new project. A screwdriver can still be the right tool for the task, but it is fair to think about how we might need to adapt the tools in our box for the job at hand,” Lauren advises. “A lot has changed to make buying harder, and that in turn makes selling harder. We’re continuing to see growing buying groups, shortening amounts of buyer time and attention, and the impact that all of this plays in the rise of indecision.”

Lauren suggests that adapting training for the changing landscape might actually mean thinking about how people learn best. The way people consume information has changed dramatically, and that means meeting learners where they are.

Creating an environment that works for everyone is tricky, but building a sales culture that welcomes everyone and supports them to do their best work can’t be, if an organization wants to be successful. Related to this, Bill B., an SVP of sales and partnerships, asked us:

How do we navigate challenges in sales training like teaching in multi-generational workplaces or connecting with neurodivergent team members?

Here, Lauren again turns to the importance of agile, adaptive training programs and leading with empathy.

“Climate is the environment that individual leaders and managers create in their teams by virtue of what they say and what they do. This is where empathy and authenticity shine,” she notes. “It’s going to be easier for a manager or leader to really listen to their people, to listen and figure out what support they can offer… There’s magic in a group of people going through an experience together, especially ones who think and see the world differently.”

Practically speaking, this means embracing:

• Individualized learning approaches: Recognize different learning preferences but balance them with collaborative experiences like role-playing.
• Empathy-driven leadership: Foster a supportive team climate where managers listen and adapt to individual needs.
• Cultural sensitivity: Ensure training materials and methods resonate with all team members while promoting shared understanding and respect.
• Adaptive technology: Leverage AI-driven tools to tailor training paths, making learning accessible and engaging for everyone.

In doing so, sales leaders create an environment that prioritizes authenticity and allows sellers to embrace all types of learning, knowing that it will lead to becoming the best salesperson they can be.

As a new year comes closer, sales leaders’ minds often drift toward new strategies, new tools, and the change management needed to implement them. But as important as strategic planning and learning can be, operationalizing it — and embedding it in your culture — is just as important.

That’s exactly what Alex A., a senior sales enablement manager, asked us about:

What best practices, tools, and techniques can you share to overcome resistance to change and more successful embedding of the Challenge mindset?

Charryse Bigger, an Enterprise Account Executive at Challenger, notes that this is a question she hears a lot. “I get this in every sales process we do, anytime we’re talking about change management. And it’s about culture.”

Her advice for leading an organization through change and making it stick falls into three categories:

• Executive communication: Ensure top-down messaging reinforces the importance of new approaches.
• Frontline involvement: Empower individual contributors to champion the change with quick wins and success stories.
• Structured processes: Embed consistent processes for call planning, execution, and follow-ups to create a repeatable framework for success.

Charryse also offers a key internal Mobilizer to pursue: the rep who looks askance at everything.

“I love a skeptic,” she laughs. “The second you convert that skeptic… they are your biggest ally. Converting that person converts way more people. It’s well worth your time as an enablement leader.”

Many of our questions for 2025 focused on high-level, big picture change. But Michelle P., a senior director, raised one of the most popular questions we get at Challenger:

We have a great product and great service, but our account growth rates are flat. What are we doing wrong?

For companies struggling with flat growth rates, Charryse emphasized shifting focus from excellent service to demonstrating measurable business impact.

“Service and product, they’re table stakes. When we over-index on providing excellent service, thinking it will lead to growth for our business, it’s wasted effort,” Charryse notes, adding that a lot of people ask this. “What outperforms anything else is, ‘Am I helping you be better as a company?’”

Many sales organizations rightly see that expanding existing accounts is a path for growth, but they make the mistake of thinking it’s as easy as checking boxes rather than searching for new growth opportunities.

As sales leaders consider how to grow their accounts, they need instead to focus on the following:

• Align your value with client goals: Highlight how your product influences their key business metrics and revenue targets.
• Train account managers: Develop skills for sales-focused conversations that emphasize ROI and the cost of inaction.
• Expand relationships: Look beyond the current scope to uncover new opportunities for partnership and growth.
• Utilize customer data: Leverage insights from client interactions to identify trends and proactively offer solutions tailored to their evolving needs.

By shifting the focus to measurable outcomes, organizations can unlock sustainable account growth.

“This is something account managers haven’t always been trained to do,” Charryse said. “You need to upskill those account managers to have more sales-focused conversations so that you’re really talking about customer improvement of your client, which also gives you customer improvement at your company. Account growth and account management are an ongoing relationship with a client, which means always looking for additional ways to partner together.”

The sales landscape continues to rapidly evolve with integrating AI and machine learning at the forefront, followed by welcoming adaptive and agile learning, building inclusive cultures, and making it operational by embedding it in day-to-day activities.

By embracing these changes, leveraging new technologies, and focusing on measurable client outcomes, organizations can thrive in 2025 and beyond.

And as 2025’s changes turn into 2026 and beyond, Challenger and Richardson will continue to adapt and bring you Insights and agility that help sales organizations continue to thrive.

As go-to-market (GTM) teams have grown and evolved, so too have our perceptions of “pre-sale” and “post-sale” roles. Customer success and account managers must now focus beyond retention to emphasize expansion and growth.

These new rules of account growth dictate a new approach. To meet their goals, account managers need to channel new logo sellers. But don’t panic: By learning to challenge customers and deliver Insights, Challengers set themselves in front of the competition and find new approaches to grow business. Let’s dig into the shifts in account management that necessitated this change, what it means for GTM teams, and easy strategies to get started.

The evolution of customer success

The idea of customer support isn’t new, but client success and account management functions are, relatively speaking. The first CS role emerged in 1996 at a company called Vantive. In 2005, as Salesforce grew rapidly and acquired both new customers and other companies, they recognized a need to address increasing levels of customer churn and built out a real customer success team. This team reflected the early function of CS teams: focusing on renewals and retention for CRM companies.

Eventually, venture capital investors recognized the value of scrutinizing retention plans in the same way they prioritized a startup’s approach to new business. After all, it’s much easier to grow business from existing accounts than to start fresh with new ones, right? Well, that’s overstating it a little.

What really drives account growth?

Today, as the CS field grows, account managers and customer success teams face new challenges. Increasingly, they must balance retention and service delivery with growth. In this clip, Challenger Account Director Megan Dolan looks at how renewals and expansion fit into a typical AD’s quota in 2021 and how those expectations evolved in 2024 in our recent Winning The Challenger Sale Webinar “Reframing Account Management for Growth.”

So, what strategies can help them get there? In 2018 and again in 2023, Challenger surveyed account managers and sales leaders to find out what they thought contributed to growth. Eighty-eight percent of those account managers replied that great service was the biggest driver. Yet, our research shows that only 28% of sales leaders are regularly reporting meeting account growth targets.

In short, while reps report that service yields growth, sales leaders report that strategy isn’t working. How do we explain that discrepancy?

As we know from the original Challenger research, it all comes back to the customer experience. The sales experience is the single biggest driver of customer loyalty. A Challenger sale sets your company up as the kind of trusted advisor that can partner with clients to bring them Insights they aren’t seeing elsewhere. Carrying that support forward is key to growing accounts. As Marinus Maris, our General Manager of International Sales, says, the key is not customer service but customer improvement.

“The metric you want your customers to have in their mind is, ‘I can’t live without this person because what they’re bringing to me is insightful,’” Marinus says.

For Challenger sellers, this means continually bringing Insights to the table, looking ahead to unforeseen blockers, and helping them navigate internal and external threats.

“It’s far more profitable to go after your existing base,” Marinus says. “One of the expressions that we use in the team here is that the customers you want are like the customers you already have.”

Yet, as Megan shared, it’s not enough to deliver Insights and improvement.

Strategies for approaching expansion like new business

First, we recognize that most CS professionals didn’t choose that career path because they enjoy cold calling or even engaging in sales conversations. At the same time, most sellers — unless they’re those fantastic Problem Solvers — don’t thrive in a post-sale environment.

That’s why the first step in successfully growing revenue with existing accounts is a strategic shift in the way your GTM team approaches growth. Just look at how sales leaders attending our recent webinar responded when we asked how their teams shake out.

Whether you divide your teams into pre and post-sale or not, it’s critical that everyone sees growth as a shared responsibility of a holistic GTM team. From there, leaders can begin coaching their CS and AD teams to push the boundaries of what they might naturally consider “account management.”

Dig into your clients’ success metrics

According to research from LinkedIn and Ipsos, 78% of B2B buyers rated sellers “aligning with [them] on success metrics related to purchase” as very important in a sales engagement. Customer success and AD teams tasked with growth should know those metrics, too — and should use their ongoing connection with customers to dive beneath the surface.

Hear more in this clip from Megan.

Get comfortable moving beyond the main points of contact

Next, CS and AD teams must partner and plan to break into new business units at existing clients. Often, that means getting comfortable moving outside their main POCs.

When Megan wants to begin a conversation with a stakeholder in a new business unit, she reaches out on LinkedIn and sends resources to key contacts. Crucially, these resources aren’t about the product — they’re directly related to those stakeholders’ interests. She also asks for introductions and sometimes makes them herself.

“I’m often connecting people at the same organizations and actually brokering meetings between them,” Megan says. “It’s up to us to create that bridge, that off-ramp, to get them to the same destination.”

Of course, your points of contact may not welcome this approach, at least at first. You may hear them ask, “Why are you reaching out to so-and-so?” But remember that Challenger sellers don’t pursue relationship building for its own sake. They build relationships, yes, but they build them around commercial growth.

“It’s about those interactions between the workshop or the training where we can help them overcome roadblocks they weren’t even aware of,” Megan says.

Deeply understand the business and identify new opportunities

To grow accounts, account managers must understand what the customer cares about across multiple business units. Look at the company website, understand its segments and organizational charts, and speak to the broader problems facing the industry. Don’t forget to read financial statements and annual reports. Megan particularly likes turning to podcasts, LinkedIn posts, or product launch videos.

“It’s a minute and thirty seconds straight from a C-Level or from an executive,” Megan says. “When you reach out to that person, you can let them know you saw their video.”

Then, return to your Challenger skills and use that knowledge to disrupt their status quo. This is about identifying the problems they haven’t thought about, and it allows account directors to elevate their credibility and build a path to growth.

“Then they can think back to: Megan helped me with this,” she says. “And that sets up that fantastic experience that we discussed, one that’s based not on service, but on growth.”

Turning account growth into a strategy that wins

The new rules of account growth dictate that pre- and post-sale teams must align closely together if they want to achieve ambitious growth goals. As the lines between sales and CS begin to blur and disappear, Challenger-trained account managers and CSMs will find themselves a step ahead. They can use tailored Insights to build on a strong sales experience in a way that centers relationships around customer improvement, not just customer service.

For more, check out our on-demand Winning The Challenger Sale Webinar, “Reframing Account Management for Growth.”

What do color theory and sales have in common?

They are both a combination of art and science designed to achieve a specific result and enact a sense of emotion, need, or desire inside of another. If you know where to look, you’ll find creativity throughout the business world.

It’s tempting to balk at being creative in today’s tumultuous market — tightening the reins, whittling strategies down to the bare bones, and leaning too far into science alone seem the more practical ways to reach goals on deadline.

But you need both the art and the science to survive and thrive.

Kendra Tucker, CEO at Truckstop has picked up more than a few tips and tricks during her time in private equity and as a sales leader, equipping her with the mindset to win, even in economic downturns.

Kendra believes sellers need both the science of procedure and the panache to deliver that process in a way that connects to customers to close deals and win.

Listen to “#105: Balancing the Art and Science of Selling” on Spreaker.

Not ready to listen right now? Head over to your preferred podcast platform and like/download the episode.

Understanding your role as a seller

How are you delivering your solution? Where does value factor into the overall system?

“Value-based selling is not a one-time or even a few times a year training experience,” Kendra says. “It truly is a system. It can’t just be, ‘I’ve got a star seller who knows how to insert value and customer voice into their sales process.’”

Kendra says value-based selling should permeate every level of the sales process, from enablement to operations to delivery.

“Whether it’s a tough period for sales or an awesome period for sales, that type of baseline rigor is really important,” she continues.

One of Kendra’s cornerstone questions for sales leader candidates is: How do you structure your team?

“I’m listening for a sales leader to say, ‘I always need to have my right-hand person, and that’s my sales operations leader.’ The metrics are so important,” she says.

Sales leaders should be holistic — motivational, and operational in their performance, also known as art and science.

Both elements are necessary for sales team success. Sales leaders need a partner who can sort through the weeds and pull out trends.

When budgets are tight and times are hard, that type of precision is invaluable. If your team is uncertain about where their focus should be and what they should be doing, your customers will be tool.

Honing in on sales obstacles in 2024 (and how to combat them)

Indecision and uncertainty are not the only trials to watch out for in the coming months, but — keeping on trend from 2023 — we should prepare for another year where those obstacles take center stage.

“There’ll be a lot of experimentation around how we communicate the value of our product, how we help our customers achieve real ROI through our product,” Kendra says. “Even this year, I’ve been talking to our product team and our product marketing team, getting really crisp about what our product delivers.”

Clarity can be worth its weight in gold in times of economic turmoil, and Kendra has first-hand experience leveraging that strategy.

How Truckstop navigated extreme demand and high volume

From the second half of 2020 into the first half of 2022, Truckstop experienced a boom of growth that demanded precise procedures. Kendra dug in and held fast with her team to come out the other side stronger.

“We took that moment to augment and solidify some of the sales processes,” she says. “We have an incredibly high velocity, high volume selling process, and there had been some process in place, but we took it as an opportunity to ensure that we had the right process, so we added value-based selling into our approach.”

When the boom times stopped, the groundwork Kendra and her team designed proved to be even more valuable in the aftermath of high volume. It gave them a clear idea of how their managers were leading, how they defined their roles, the effectiveness of training procedures, and what, if anything, needed further tweaking.

“In our business, if we have just one off-selling day, it can mess with the numbers for the whole month. You’ve got to be on your game,” she says. “So having managers who are paying close attention to input and output metrics, understanding when they need to jump into a seller’s day and unstick something, is really important.”

Creating a solid foundation for your team built on clarity and strong operations, mixed with that oh-so-critical dash of art and creativity, lends to a healthy and thriving sales process that gets results and earns you the wins you’re looking for to navigate calm and stormy seas alike.

Want to learn more about finding the balance between art and science in sales? Listen to the full episode of Winning the Challenger Sale to hear Kendra’s perspective on failsafes to leverage in times of difficulty, how to build a strong sales team, and more.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.

You know your territory. You memorize your conversion rates. Every time you pick up the phone or check your email, your prospects are positive, seemingly as invested in the deal as you are.

So, why is the pen not hitting the paper?

In this fear-driven market of tight budgets, many leaders are looking to upskilling and doubling down on demos training. But could they be asking the wrong questions?

Geoff Hendricks, key account executive at Challenger, suggests looking at a different foundational element.

Geoff believes sellers who are losing deals they should win should pay closer attention to the beginning stages of the sales process. On Episode 104, he joins Challenger CEO Andee Harris to discuss how the major mistakes made in the early stages of the sales process can impact close. Geoff shares his tips for heading off disaster early, getting ahead of indecision, and more when fear is at the forefront of buyers’ minds.

Listen to “#104: How Challengers Thrive in a  Fear-Driven Market” on Spreaker.

Not ready to listen right now? Head over to your preferred podcast platform and like/download the episode.

The pitfalls of qualification frameworks

When economic conditions threaten to derail a sales team’s progress, managers often step in to shepherd deals through to completion. But Geoff sees this micromanagement leading to a transactional mindset among sellers.

“They begin chasing month-to-month and quarter-to-quarter pipeline,” Geoff says. “They start discounting deals to get them across the line — deals that probably shouldn’t have ever been forecasted in the first place.”

When sales leaders feel stuck, they push sub-par deals. This may stabilize numbers in the short term, at the cost of their team’s morale over the long term.

Often, sales leaders will try to head off this predicament by adopting a qualification framework. Yet, the added paperwork can frustrate sellers just as much as it helps them.

Geoff suggests sales leaders avoid frustration by emphasizing exactly how these frameworks will help sellers build pipelines and meet their goals.

Combating indecision

Geoff notes that, previously, sellers were attempting to sway clients into selecting their product amongst a handful of their competitors. Now, the problem seems much larger and more complex: is the client going to decide at all?

If you are talking to a buyer who is below the line or part of the committee, it is unlikely they will be making the decision themselves. While they may see the intrinsic value of your product, the real decision-makers might disagree.

When your buyer does not have direct access to the budget, you will likely face financial surprises in the final mile. However, those final mile roadblocks are often obvious at the starting line – if sellers know where to look. It starts with knowing your buyer’s type.

 

Blockers, Talkers, and Mobilizers (and how to navigate them)

Buyer types

Challenger places buyer personality types into one of three categories: blockers, talkers, and mobilizers.

Blockers stand in the way, but Talkers and Mobilizers can seem extremely similar on the surface.

However, Talkers never sign deals. Instead, they take you to the last mile and then disappear.

Mobilizers are the buyers who sign. They have the power to close the deal and the budget to back it.

Gauge your buyer’s reaction

So, how do you determine whether your buyer is a Talker or a Mobilizer?

First, consider what happens when you offer an unexpected insight. If the buyer consistently agrees, they may be a Talker. A Mobilizer, on the other hand, will challenge your insight out of a true desire to understand.

Mobilizers look at the process of buying the product as a potential reality, so they will ask the hard questions to ensure your product fits their needs.

Multithreading and understanding the org chart

There are only a few key players in an organization that can manage internal politics, and identify and bring major stakeholders into meetings — and they’re the Mobilizers.

If you walk into a roundtable meeting with a stack of declined invites and empty chairs, you’re likely dealing with a Talker.

Multithreading helps sellers identify their buyers’ position in the org chart, and further determine whether they’re Talkers or Mobilizers. By leaning into the Mobilizers in their pipeline, they will make contact with the decision-making committee (and those that hold the keys to the budget).

Geoff’s secrets to the signature

Once you complete these processes, what’s next?

Geoff says the next step, and one of the most important ones, is to set the close date.

“So, let’s assume that we’ve done our due diligence, we have the cost of inaction, we’ve identified a Mobilizer, and they’ve got the right people involved. This brings us to a very important point: what do they care about? What is the date they need to make a change?” Geoff says.

It may be a meeting, conference, or training date they are aiming to set. Once you understand the buyer’s goals, align them with your goals and begin working back from that date.

“Consider it your kickoff moment. This is the moment you realize value. Then, there are all of these steps that have to happen before the date to make it a reality,” Geoff says.

While there may be legal or financial roadblocks, arm your Mobilizer with the information and a concrete date so everyone is invested in moving the deal forward.

Want to learn more about identifying Mobilizers and finding deals that are sure to close? Listen to the full episode of Winning the Challenger Sale where Geoff reveals more about the personas to look for, how to enable them, and more.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.

 

The best salespeople take on the Tom Brady mindset.

After playing college football at Michigan, Tom Brady was selected by the New England Patriots in the 6th round of the 2000 NFL Draft, coming in as the overall 199th pick.

He went on to win 6 Super Bowls with the Patriots, a 7th with the Tampa Bay Buccaneers, and just about every award the NFL has to offer.

His secret? He never took the chip off of his shoulder. He always stuck to the basics, trusted the process, and never got too comfortable. After all, he was passed over for most of the draft and deemed unworthy of playing on most teams.

Even though he is now commonly accepted as the greatest football player of all time, Brady kept to his fundamental skills — always working to make sure his career did not fall apart, landing him back where he started as the 199th pick.

According to Matt Doyon, Co-Founder and CEO of Triple Session, the best sellers take on the Tom Brady share this drive. On a new episode of Winning The Challenger Sale, our guest Matt shares lessons from more than two decades of sales experience. They’re also featured in his book Revenue Revolution.

Listen to “#103: Positive Paranoia with Matt Doyon” on Spreaker.

Not ready to listen right now? Head over to your preferred podcast platform and like/download the episode.

Building a strategy for 2024

The truth is the sales landscape of today is entirely unique — mostly because the environment for the last 20 years is what Matt calls “artificial.”

Baby Boomers were the largest generation in US history, and they offered boatloads of capital to the market, with the last two decades bringing their time of highest earnings with the lowest costs.

While in their 50s and 60s, Baby Boomers had their homes paid off, their kids out of their homes, and more available money than ever before. Now, they’re retiring by the masses — and they’re taking their money out of the market with them.

This is not a temporary shift. Matt expects this to become the normal environment over the next 15 years or more. This is why he believes we need to have what he’s coined the “Revenue Revolution.”

“We need to rethink the way that we rebuild our sales and customer success organizations and focus on operationalizing them for maximum efficiency. With that, it takes a new strategy. What got us here will not get us to the next level,” Matt says.

So, what should the new strategy look like? Matt believes adapting to the new market begins with embracing fundamentals.

Moving the needle with a day-by-day schedule

Most sales personnel and managers work on quarterly goals, and some even break those down into monthly milestones. Instead, Matt encourages us to drill down into the daily inputs from a team perspective, then for each individual on the team.

“Those daily inputs are the only things we can control,” Matt says.

To return to the sports analogy, great teams do not put blinders on and hyper-fixate on the upcoming game — instead, they focus on today’s practice.

In other words, what moves the needle closer to the goal between 8 a.m. and 6 p.m.?

Those components may look different for everyone, but Matt believes there are some tried and true best practices that spark small changes in your daily routine that promise major improvements to your outcomes.

• Step one: This step starts the night before. Finish your day with at least a 15-minute preview of the day ahead. Matt encourages us to understand what is coming up on the horizon, ensure we are prepared, and add extra time for necessary prep work.
• Step two: Schedule 15 minutes in the morning to get your head in the game. Matt tells us that we need to sharpen and wake up our brains in the morning — and scheduling that into our day sets us up for success.

Matt suggests approaching this as a quick learning “micro session.” Listening to a thought leader, building a skill, or having a thoughtful conversation with a manager will set the tone for success for the day.

“So much of our success rests on preparation and finding that flow state. It’s not an accident when things fall into place, it is a skill that can be harnessed, and we can hardwire ourselves to get into those types of flow states as much as we possibly can,” Matt says.

Understanding and getting ahead of trends

When discussing clients who may be apprehensive about changing their ways, Matt explains that no one is required to adopt these changes — but they should at least consider it.

Matt looks back on the advent of the electronic calculator in 1961. While many were ecstatic with the new technology options available, there were still some accountants who were keen on sticking to their old-school, paperwork-based ways.

“You could do that, but by 1962, you’d be going out of business,” Matt says.

With the calculator, companies became faster and smarter, had fewer errors, and could take on all of their competitors.

“So, can you see around the corner? The name of the game is understanding where the trends are and getting ahead of them. We can’t rely on what got us here to get us where we want to go,” Matt says.

With a new economic environment and technological advancements such as AI, sales teams are going to have to change their methods to remain cutting-edge.

Formalizing personal skills

One important area of growth lies in coaching sellers, especially those new to the job. Matt contends that college isn’t enough to prepare these new sellers for their careers. Luckily, formal, technical on-the-job training is available. From prospecting to discovery to running demos, new sales reps will likely encounter systems to teach them these skills. What’s harder to acquire is the professional and personal skills those new sellers will also need to succeed.

“If we are going to be great sales professionals or great business professionals in general, we also have to be great humans,” Matt says.

That takes learning “soft skills” such as time management, business acumen, professional communication skills, and more. Managers must pass their knowledge of these skills down to their team members, just as they might teach them how to use a CRM. That means getting comfortable addressing topics such as emotional intelligence, growth, accountability, and work ethic.

When managers take on these topics and present them to their teams, they can experience holistic, team-wide growth.

The perpetual “positive paranoia” mindset

Matt compares sales to driving. With more experience, drivers become more complacent and comfortable. That means we’re actually becoming worse drivers over time, rather than constantly improving our skills.

The same is true in sales. When a rep gets several deals closed and appears to be at the top of their game, they start skipping steps of the sales process and missing cues and opportunities.

This means they become worse at sales over time unless they stick to the process. Instead, Matt says, winning sellers must constantly be asking “what did I miss?”

“It is that perpetual paranoia where they constantly believe they are not good enough. The best-in-class AEs will thrive in this new environment,” Matt says.

That means honing in on the basic questions every single time. “Did I miss a step? Am I connecting? Do I need to drill deeper here?”

Paranoia doesn’t have to be negative. By adding a bit of “positive paranoia” to the year ahead, we can ensure that yesterday’s wins don’t roll into tomorrow’s losses.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.

Why aren’t you winning?

Between 40 and 60% of lost deals are victims of quiet indecision. It’s a consistent problem exacerbated by tough macroeconomic conditions. But it isn’t inescapable.

In fact, the process of moving through this roadblock can serve as a great opportunity to meaningfully connect with your client.

Ted McKenna, founding partner at DCM Insights and co-author of The JOLT Effect, joined the Winning The Challenger Sale podcast to discuss why indecision occurs, what amplifies indecision, and how reps can steer around it for a strong close.

Listen to “#102: From Stalled to Sealed: Winning Sales Strategies For Today” on Spreaker.

Not ready to listen right now? Head over to your preferred podcast platform and like/download the episode.

Today’s environment of indecision

Ted and co-author Matt Dixon published The JOLT Effect in September of 2022 using research performed during the pandemic. While their research hinted that the problem of indecision would naturally grow over time, the last 18 months accelerated that trend.

“The macroeconomic environment has only exacerbated some of these trends,” Ted says.

The problems of indecision have particularly worsened in technology and SaaS circles. As venture capital dries up and investors look to tighten the purse strings, buyers want to avoid risk. The easiest thing to do is nothing at all.

Yet, Ted says, buyers remain curious. They still want visits and demos, meaning the pipeline stays full — of clients who are stalling in later stages of the cycle.

“It feels like everyone is vibing, then they go cold. You’re left scratching your head wondering as to why that might be,” Ted says.

Navigating omission bias

Omission bias, according to the National Library of Medicine, is “people’s tendency to evaluate harm done through omission as less morally wrong and less blameworthy than commission when there is harm.”

Omission bias is rampant in B2B sales, Ted says.

“We see so many situations happen where it felt like the buyer was excited to move forward. They had stated their intent to purchase. They even selected the vendor. The seller was doing all the things you would have expected and hoped. Still, the deal stalled,” Ted says.

In The JOLT Effect, Ted and his co-author write that sellers can lose to omission in two ways.

Loss of the error of omission is when someone chooses not to do something and, as a result, they miss out. For example, if all of your friends invested in cryptocurrency and you chose not to do so, loss of the error of omission would sit in when you see all of your friends have hit it rich.

The error of commission happens when someone chooses to do something and it ends horribly wrong — and this one weighs heavily on buyers.

When thinking of past purchase regrets, buyers become more and more hesitant to sign on the dotted line. They worry not only about the product but also about their company’s ability to reach desirable outcomes.

Leveraging healthy amounts of fear

Can this level of client fear be leveraged to make a difference in sales?

The answer is yes, but only if done so tactfully in a way that is designed to build trust.

The kicker is that clients do not lay out their personality, fears, and weaknesses on a silver platter for the sales team. Truthfully, they may not even be able to pinpoint these specific attributes themselves, much less feel comfortable and confident to openly share them with others.

“It becomes almost an obstacle on an emotional level to a purchase, even though rationally they’re excited about the concept,” Ted says.

Even in B2B sales, this is a rare area of opportunity for sellers to rely on personal experiences to self-identify what a buyer is going through at the moment, as the seller has likely experienced the factors leading to and resulting from indecision as well.

So, what skills can a salesperson utilize to navigate indecision in their clients?

“We came up with what we call pings and echoes. The seller uses their ability to ping the buyer and understand what’s going on under the surface of the water, to understand the size, depth, and breadth of that indecision,” Ted says. “Then, using that to inform them of the quality of the opportunity and the type of indecision they have. Knowing more can help the seller treat the indecision in a more precise way.”

The truly impressive aspect of the pings and echo concept is that, even if the pings are off, the system can still work.

When clients put forth an honest, transparent conversation, clients will likely notice the seller’s dedication (and active listening skills) — leading to a sense of relief for the buyer.

Apart from active listening and relying on personal experiences, Ted believes that high-quality, realistic expectation-setting is crucial for avoiding decision paralysis and keeping your pipeline flowing smoothly.

 

Want to learn more about how to navigate indecision and continue to close deals? Listen to the full episode of Winning the Challenger Sale where Ted reveals more of the necessary skills to build trust with clients, how to effectively build and maintain safety nets, and more.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.

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.

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.

Marinus and Andee break down:

• Why focusing on profitability is the new norm in sales
• How sellers can leverage customer improvement for profitable growth
• Strategies that prioritize profitable customer segments for long-term growth

Listen to “#94: Want Account Growth? Make Your Business Indispensable” on Spreaker.

Not ready to listen right now? Head over to your preferred podcast platform and like/download the episode.

Why focusing on profitability is the new norm in sales

We’ve seen sales leaders react to volatile economic conditions by moving their focus from top-line growth to profitable growth. Focusing on profitable growth includes accountability for efficiency alongside effectiveness — how do sales reps apply that strategy in the long term?

“The sales teams doing this really well are not focusing on the idea of sales,” Marinus says. “First and foremost, they’re focusing on customer creation and retention, which is a little bit of a different ballgame.”

The sales world focuses on selling; in the sphere of customer creation and retention, the focus is solving specific customer problems. The difference lies in the mindset. To problem solve, it takes: 

• Genuine curiosity
• Storytelling
• Proactive account planning

Sellers typically ask “How do I sell more of this product/service?” When the focus shifts to retention, the key question becomes “What problems need to be solved within this organization, and what can I teach them about these problems that they might not understand?”

Taking on an advisor role is far more beneficial in the long run than settling for a quick sale. To be an effective advisor, a rep must understand every facet of the customer’s problem areas and goals.

How sellers can leverage customer improvement for profitable growth

When companies consistently meet a buyer’s needs at the right time, and with the right outcomes, they will almost undoubtedly choose to stay in that customer relationship. 

“The metric you want your customers to have in their mind is, ‘I can’t live without this person because what they’re bringing to me is insightful,’” Marinus says.

One critical element for providing insightful advice? Focus on customer improvement — offer new perspectives on issues, help them look around the corner, and open their eyes to new possibilities and solutions.

“It’s far more profitable to go after your existing base,” Marinus continues. “One of the expressions that we use in the team here is that the customers you want are like the customers you already have.”

What are the commonalities across those customers? Where is the common ground for high-spending accounts? What is the total addressable market within each of those accounts?

“Really start to think about, ‘Where’s the ICP here? Does it exist? Do we have champions in certain accounts?’ When you start to take those into account, you start to see your Champion League of accounts, your division one and your division two of accounts you want to be going after.”

Mobilizers — aka Champions — are essential for account growth and retention. Identifying who will help champion positive business results throughout the organization can spread into more leads in the relevant pool. Working together yields the most rewards.

Strategies that prioritize profitable customer segments for long-term growth

Without an on-their-game Account Director, even the best-suited customers can struggle to achieve their goals. It takes a dedicated leader to retain customers and maintain customer improvement.

“The best account directors are asking for accountability, which is to say, ‘I want to be able to build this amount of pipeline, I want to be able to ask for this many referrals, I want to make sure I’m doing this quality follow up,’ or so on and so forth, ‘I need your help to hold me accountable to these things,’” Marinus says. 

When everyone understands the objectives and has clear steps forward, that clarity transfers to customers, helping them to overcome challenges and leading to positive growth.

Want to learn more about how to effectively and efficiently problem-solve for customers? Listen to the full episode of Winning the Challenger Sale where Marinus reveals more about the art of building and retaining customer loyalty, working as a team, leveraging mobilizers, and more.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.

Quarter four will be here before you know it — and those three months of excitement lead right into the sales kickoff. 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. 

Many organizations are still balancing 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 make for a standout SKO. 

Sailpoint continuously goes above and beyond to 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

Listen to “#88: A Practical Guide to Creating a Kick-Ass SKO” on Spreaker.

   

Fully visualizing your SKO with tools, tricks and a t-shirt cannon

Before you can build a truly impactful SKO, you have to start with a vision. While many build their vision with a top-down approach, Barrett suggests flipping that on its head.

“Our SKOs would never be successful without the team, because they get so engaged and excited. They help build the vision as well,” Barrett says. “We start by going up the ladder first, then pushing downstream.”

Barrett, Robin and their team begin by deciding the top three things they want to push across the entire SKO. These will be major takeaways the entire event can be built around. Most importantly, they work together across teams to decide which top points are most important for driving the team forward throughout the following year. 

“We define our vision for the year around three or four things we can drop down throughout the theme of any event we do. From there, we build a vision deck,” says Barrett.

The vision deck is vital for ensuring each event, activity or speaker at the SKO is in complete alignment with the main goals and ideas the team needs to embrace throughout the year. It’s a living document that can be revisited again and again throughout the event planning process. 

The art of drawing people in

Once you identify your central vision, you can shift your focus to building excitement and drawing in people. According to Robin, a T-shirt cannon never hurts. 

“Having fun with those moments in between the more serious or inspiring messaging, and giving the event some levity can really go a long way to make guests feel comfortable, welcome and valued,” Robin says.

Robin and her team make sure to set the stage with something unexpected — their tactics go beyond the traditional opening of the top speaker entering the room. Instead, Sailpoint shares something of a ‘commercial’ using creative video at the start of the event and again when returning from breaks. 

They also conclude the event with a creative element, gamify as much as possible and close out with awards and recognition.

Why a whiteboard belongs in every office for SKO planning

When it comes to planning out the specific events and agenda of an SKO the most important tools you can use are a whiteboard, a large room with plenty of space to pace, and collaboration. 

“We work best when we can collaborate well and brainstorm together,” Robin says. “A whiteboard is really helpful to visualize the whole event. Map out the different topics, your agenda, the days — last year we even mapped out the floorplans of the hotel.”

When working with a document or spreadsheet, you’re often limited by what you can see visually. By writing down the time, dates and locations of events, speakers and timeline, you can see how they will work together to drive your vision home across the team.

The team at Sailpoint used the whiteboard as their event planning source of truth. And while they found themselves redesigning, even wiping the board clean and starting over once or twice, the tool was crucial for providing a visual that allowed all team members to collaborate and brainstorm to design the best SKO possible. 

Following up with measurement

Building community and excitement are key for an impactful SKO. However, without measurement and feedback, there is no way to ensure the event is effective, and perhaps more importantly, can be iterated upon to truly drive home the vision.

By incorporating reinforcement throughout and following an event, you can ensure your team grasps the important concepts incorporated throughout the event. If any gaps are revealed, measurement also creates an opportunity to tailor follow-up training or meet-ups throughout the year for an SKO that will drive value in all four quarters.

Navigating unexpected challenges in the shift from virtual back to in-person

During the pandemic Sailpoint, like many organizations, had to shift their SKOs online. After completing two virtual SKOs, they shifted back to in-person — which proved more challenging than expected. 

Like many businesses—Challenger included—their leaders found that virtual training can actually be more effective. Taking tools and tricks learned from designing virtual training and translating them for use throughout in-person SKOs can be incredibly helpful for retention and engagement.

The shift back to in-person events elicited a mix of reactions from Sailpoint’s sellers. Many people enjoyed the virtual events because they could play, replay, pause and restart whenever they wanted. It was acceptable to get up, grab a coffee and let their dog out. In-person events are typically more rigid, and traditionally, include sessions as long as 8 hours. 

“That’s one thing we’ve taken from virtual,” Barrett says. “Eight-hour long sessions are no longer a thing for us. We try to do short, quick sessions unless they’re breakouts. We try to keep those about 30 minutes, because any longer and you lose attention.”

How to create a sense of community with creative elements, networking opportunities and injecting fun throughout your event

One of the largest benefits of shifting SKOs back to in-person is the added value of networking. In addition to focusing on the themes and vision for the SKO, leaning into the benefits of networking by incorporating brainstorming sessions, break-outs and specified time for connection build camaraderie and motivation for the year to come. 

Sailpoint also relies heavily on creativity when designing and executing SKOs. Gamification is a major way the team injects fun into the event.

Over their two previous virtual SKOs, Robin and Barrett’s teams leveraged apps, platforms and outside teams to gamify the events. When shifting back to in-person, they worked with outside agencies to retain the fun and creativity throughout their live event.

“It’s helpful to think outside the box and outside your team,” Robin says. “It’s about the experience for your audience. How can you make it the best event possible, while also keeping in mind that budget?”

What matters most when identifying the right speaker mix

When deciding on keynotes, speakers and activities it is essential to consider diversity. When sellers see themselves represented on stage, it can be incredibly empowering. Sellers need to see themselves throughout the event, whether through speakers, awards or leadership roles.

“We integrate stories and speakers from all over the world,” says Barrett. “We really try to pay attention to our global partners so they have an opportunity to be on stage and talk about how well we work together, how the relationship contributed to the win of a deal.” 

In addition to featuring stories and leaders from all over the world, Robin emphasizes the importance of featuring a diverse set of voices. 

“As far as representation we highlight our rockstar sellers, men and women,” she says. “We give our women leaders a platform to give a keynote or hold a session.”

By representing the diversity of your sales team throughout your SKO, you invite all attendees to recognize they are a critical part of the community and will play an instrumental role in achieving the overall vision for the year. Without diversity, you risk devaluing your overall message. 

Want to learn more about designing a kick-ass SKO? Listen to the full episode of Winning the Challenger Sale where Barrett and Robin reveal more about incorporating lessons learned from virtual events into live, injecting fun, community and creativity throughout, and ramping up diversity for ultimate motivation and representation.

To hear this episode, and many more like it, you can subscribe to the Winning The Challenger Sale podcast on our website, Apple Podcasts, Spotify, or just search for it in your favorite podcast player.