Upmarket Push: Doubling Enterprise ARR via Win-Loss Insights

This case study was created from an episode of the Product Marketing Adventures Podcast. It has been adapted into Dusted's case study format to preserve and showcase the guest's real-world experience. Written to preserve the voice of the true author, Quintin Smith.

I joined CaptivateIQ as the founding PMM (fourth on the marketing team) right before the Series C that raised $100M at a unicorn valuation. At the time, CaptivateIQ was commission software that displaced spreadsheets for incentives and sales performance management. We had strong traction with lookalike hyper-growth SaaS startups and mid-market companies—logos like Gong—and were at the classic “cross the chasm” juncture as the business matured and built out more robust marketing and sales functions.

We started seeing opportunistic enterprise logos and larger deals (e.g., $200K ARR versus our typical ~$30K deals, plus a nearly won $600K deal). Everyone got excited about the shiny-object potential of repeating those wins, especially since our flexible, spreadsheet-like product resonated with complex enterprise needs. The real challenge was turning a handful of one-off large deals into a repeatable upmarket motion without spreading the startup too thin or chasing distractions that could lead to churn. We needed intentional focus, dollars, marketing, and enablement pointed at enterprise so we could systematically find and close more of them.