Upmarket Push: Doubling Enterprise ARR via Win-Loss Insights

We started with the win-loss program we already had in place—30-minute interviews with closed-won and closed-lost champions—paired with quantitative splicing of deals in spreadsheets and pivot tables (industry, persona, incumbent solution). Key insights emerged: strong traction in sub-verticals like medical devices and banking; a legacy competitor forcing painful migrations that created inbound; and the reality that above-the-line personas (VP Finance, Head of FP&A, sales leaders) actually drove deals, while sales-comp analysts were eager users but lacked organizational sway.

Those findings let us reframe messaging around “return on incentives” / ROI—positioning commissions as a strategic GTM lever that aligns reps to new products, services, or markets—rather than just “make the analyst’s job easier.” The narrative worked for both the champion (elevating their role) and the economic buyer.

We then operationalized it across the full GTM motion: sub-industry campaigns and landing pages, customer interviews and case studies, tailored demo environments and talk tracks with sales engineers, and enablement so marketing, sales, and CS all spoke the same language. I later codified the whole process as my 4Rs framework—Research (qual + quant), Refine (insights → positioning & message-tested narrative), Ready (marketing campaigns + sales playbooks + CS readiness), Report (look back on what worked).