People in a meeting

Table of Contents

    Everybody knows someone who peaked in high school. They may have been exceptionally talented, but ultimately stopped progressing.

    All high-growth businesses inevitably encounter the same problem: the strategies that initially resulted in success are no longer enough to support them at scale.

    So many companies come out of the gates hot, quickly grow to a certain scale, and then struggle. Win rates plummet; sales teams churn. What’s happening here? And, more importantly, how can you avoid it?

    As Highspot’s Vice President of Strategic Services, I shared in a new three-part series how you can confront this challenge and successfully overcome it.

    PART I

    In the first installment, let’s explore the three key issues businesses face at scale — how to address the first one.

    Part II

    In part two of the digital transformation series, let’s take a look at how businesses can meet the needs of these new buyers and adapt successfully.

    Part III

    In this third and final installment, let’s cover how top sellers handle common challenges as the business scales — from their approach to qualifying to how they navigate deals.

    DIGITAL TRANSFORMATION STARTS NOW

    Most high-growth companies will eventually reach a point where growth gets hard. Met with new challenges, some businesses may attempt to get back to their former glory by doubling down on the strategies that worked yesterday. But that’s almost never successful. Instead, the best companies recognize that they’re playing a new game on a new field and proactively work to navigate that change.

    Steve Hallowell

    Steve Hallowell is the former Vice President of Professional Services at Highspot, where he focused on helping go-to-market leaders elevate the performance of their customer-facing teams. Steve’s expertise lies in delivering strategic guidance, enabling organizations to unlock the full value of their sales enablement efforts.

    Related Resources

    10 popular B2B sales automation use cases for reps
    Blog
    10 popular B2B sales automation use cases for reps
    With AI-powered B2B sales automation tools, enterprise go-to-market teams can elevate their enablement efforts and better support reps.
    The metrics that matter most for predictable GTM success in 2026
    Blog
    The metrics that matter most for predictable GTM success in 2026
    Forecasts shouldn’t rely on gut feel. Learn which GTM metrics reveal deal momentum, stalled risks, and real performance before it’s too late.
    How AI streamlines win-loss analysis for GTM leaders
    Blog
    How AI streamlines win-loss analysis for GTM leaders
    The best AI go-to-market tools simplify win-loss analysis for B2B revenue leaders by offering instant, in-depth insights on recent deals.