Checkr’s in-app messaging was applied indiscriminately to all users regardless of relevance. Users were complaining. Messages from Sales, Support, Customer Success, and Customer Education were uncoordinated, creating a noisy and frustrating experience that undermined the product.
The underlying problem was organizational as much as technical: five separate teams were sending messages through a crude shared mechanism with no targeting, no ownership, and no alignment. Legal had unresolved compliance concerns. Nobody had the mandate or the appetite to fix it.
I brought together six groups — VP of Sales, Customer Education, Customer Support, Customer Success, Legal, and Product — around a shared problem definition. The framing mattered: this was a product quality issue affecting users, not an internal tooling dispute.
I ran a structured three-stage vendor evaluation: reviewed three vendors, required each to conduct a live demo, then put the top candidates through one-month trials with real usage across the stakeholder groups.
By the time we reached the decision meeting, every group had already invested a month in making their preferred option work. The vote for Pendo was straightforward. Legal’s compliance concerns had been built into the evaluation criteria from the start — which turned them from a blocker into a champion.