Three Critical Trends for Sales Leaders to Address in the Age of AI

Q&A with Robert Blaisdell, VP Analyst, Chief of Research, Gartner

As the sales landscape rapidly evolves, CSOs are facing unprecedented challenges—and opportunities—driven by the rise of AI, the demand for greater productivity, and the need to manage costs. The path to 2026 will require sales leaders to rethink their strategies, embrace new technologies, and reimagine how their teams engage with customers

We spoke with Robert Blaisdell, VP Analyst, Chief of Research in the Gartner Sales practice, to explore the essential actions CSOs must take to thrive in the age of AI - from harnessing AI for genuine productivity gains to transforming go-to-market motions and empowering sales managers.

Q: What are the three critical trends that chief sales officers (CSOs) must address in 2026 as they strive to lead sales in the AI era?

A: To drive commercial growth in 2026 and beyond, CSOs must contend with significant headwinds impacting their organization - increased productivity demands, a never-ending and often increasing slate of change initiatives, demand for transformation at high speed, and effectively managing or even reducing costs.

With these challenges, we’ve identified the top trends for CSOs to address as we head into 2026:

• Drive sales productivity by leading the creation of a sales-centric AI portfolio roadmap.

• Enhance seller effectiveness and buyer engagement by transforming go-to-market (GTM) motions to align with buyer preferences.

• Improve seller performance by maximizing the impact of sales managers with role clarity and organizational support.

Q: With AI adoption accelerating across sales organizations, what practical steps should CSOs take to ensure their AI strategy delivers real productivity gains, rather than just technological hype?

A: Highlighting our first trend, to deliver genuine productivity gains from AI, CSOs must develop a sales-centric AI strategy that is tightly linked to commercial outcomes. This starts with assessing current revenue goals and aligning with IT leadership on the existing tech and AI stack capabilities.

CSOs should then define the desired transformation outcomes from AI adoption—whether that means reducing the cost of sales, accelerating revenue growth, or achieving both objectives. With these goals in mind, they can create a strategic roadmap with clear milestones for seamless AI integration. Rather than adopting AI for its own sake, CSOs need to ensure that AI serves as a true productivity partner, driving efficiency and effectiveness across their sales organization.

Q: As buyer behaviors shift toward rep-free and information-rich experiences, how can CSOs transform their go-to-market motions to better engage and build trust with increasingly skeptical buyers?

A: With this second trend, CSOs must transform their GTM motions to align with new buyer preferences, as a majority of B2B buyers prefer rep-free experiences and come armed with extensive—though not always trustworthy—information.

To counteract low engagement, CSOs should leverage AI to enhance the effectiveness and personalization of seller outreach, making it more prescriptive and tailored to individual buyer needs. This means moving away from volume-based outreach and focusing on relevance, as buyers increasingly avoid suppliers who send too many or irrelevant messages.

Building trust requires thoughtful engagement and leveraging AI to provide buyers with credible, targeted information that addresses their specific concerns.

Q: Given the critical role of sales managers as performance multipliers, what organizational changes and support structures are needed to maximize their impact in an AI-driven sales environment?

A: This is the third trend that CSOs must address in 2026. Maximizing the impact of sales managers requires a fundamental redesign of their role to act as amplifiers of seller effectiveness. While CSOs dedicate significant time, resources, and investment to boosting seller effectiveness, they often underestimate the importance of providing comparable support and development for sales managers themselves.

CSOs should focus on hiring and developing sales managers based on specific mindsets and competencies, rather than simply promoting top sellers. Investment in enablement programs and appropriate technologies is essential to empower sales managers, allowing them to provide personalized support and coaching.

Organizational support should also address the gap between managers' formal job descriptions and their day-to-day responsibilities, ensuring they have the right tools and clarity to drive performance in an increasingly complex, AI-enabled sales landscape.

Q: How can CSOs overcome the challenge of limited influence over AI initiatives within their organizations and earn a seat at the table for driving strategic technology adoption?

A: To gain greater influence over AI initiatives, CSOs must proactively engage in technology strategy discussions and demonstrate their understanding of how AI can drive commercial outcomes. Building a sales-centric AI strategy and presenting a clear vision for AI’s role in sales productivity will help CSOs earn credibility with CEOs and other C-suite leaders.

By aligning their goals with IT leadership and showcasing the business impact of AI adoption, CSOs can position themselves as essential contributors to the organization's broader technology strategy, increasing their accountability and influence over AI-driven transformation.