How Will Sales Evolve in 2025? Trends & Expert Insights From Richardson & Challenger

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.