In early June, SBI hosted three high-impact Sales Enablement workshops, one in San Francisco hosted by Laurel Tanner and Ray Makela, another in New York City led by David Hecht and Rick Karlton, and one in Seattle hosted by Greg Steward, Ray Makela, and Kelly Lewis. These events brought enablement leaders together to tackle the most pressing challenges in equipping sellers for today’s complex buying environment.
The discussions centered around three strategic imperatives: addressing buyer friction, measuring enablement’s impact on high-priority commercial initiatives, and how AI-enabled solutions are changing the role of enablement.
SBI’s research, The Next Era of Commercial Differentiation, confirmed that buying has become more difficult in today’s environment due to increased levels and sources of buyer friction. Today's B2B buyers are overwhelmed by internal pressure, larger buying committees, and an increase in executive scrutiny. This complex buying environment is slowing down decisions and threatening growth.
Enablement leaders raised a new perspective. Buyers lack experience purchasing complex AI-enabled or platform-based solutions. Sellers must be equipped to educate buyers on how to buy and adapt their own behaviors to progress the deal. The conversations highlighted the role enablement plays in bridging this gap by arming sellers with the tools, content, and training to lead confident, consultative conversations.
As the market has shifted away from point solutions toward platforms, participants emphasized the need to move away from traditional sales tactics. Sellers often revert to recommending disconnected features or offering a shopping list of point solutions, missing the broader opportunity to tie their comprehensive solution to the buyer’s strategic goals.
Leaders at the sessions noted that this challenge goes beyond sales execution. Organizations must align messaging, pricing, website content, and packaging around holistic platform value, rather than fragmented features or stand-alone offerings. Enablement leaders must ensure that this shift is embedded into sales training and buyer-facing content.
A central theme across both events was the increasing pressure to demonstrate sales enablement’s contribution to top-line outcomes. SBI facilitated a planning exercise where participants mapped their company’s “Big Bets,” identified corresponding seller behaviors, and determined measurable enablement actions to support those behaviors.
Staying aligned on driving results toward the organization’s goals, rather than fulfilling non-measurable requests, is essential for enablement to seen as a strategic partner. Additionally, leaders must avoid the trap of tracking easy-to-measure outputs that don’t move the needle. Top-performing enablement teams measure metrics that focus on both leading and lagging indicators, painting a clear picture of enablement’s impact. AI tools can be used to help streamline measurement, but enablement professionals are still navigating which tools to trust in a rapidly evolving tech landscape.
Another recurring topic was the underutilized influence of frontline sales managers in driving behavioral change. SBI’s research shows that companies that offer dedicated frontline manager training see a 7% boost in quota attainment (potentially thousands of dollars in lost revenue for those that don’t). This served as a call to action for enablement leaders to offer dedicated training and support to sales managers, as many are promoted to their position without the skills needed to drive success.
Participants also aligned on the need to treat frontline managers as partners when introducing new skills, techniques, and behaviors to the sales team. Without frontline manager support and adoption, enablement initiatives fall flat and deliver little impact. However, bringing frontline managers along and encouraging them to continue 1:1 coaching can bring lasting change.
Both workshops concluded with a look to the future. AI-enabled tools are being used to scale, personalize, and measure enablement. This rapidly evolving environment forces enablers to self-educate and attempt to stay ahead. As one participant put it, the way sellers consume knowledge is changing fast. Traditional courses may soon give way to more fluid, on-demand learning formats.