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 concerns about the existing approach that hadn’t been resolved.
Stakeholder Alignment: Brought together six groups — VP of Sales, Customer Education, Customer Support, Customer Success, Legal, and Product — around a shared problem definition. Established that this was a product quality issue affecting users, not just an internal tooling question
Rigorous Vendor Evaluation: Ran a structured three-stage selection process: 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
Decision Facilitation: Brought all stakeholders together at the conclusion of the trial period to make a collective decision. Pendo was selected
Legal Resolution: Ensured Legal’s compliance and privacy concerns were addressed as part of the evaluation criteria — turning a blocker into a champion
Key Insight: Tooling decisions that touch multiple teams are really alignment problems in disguise. The vendor evaluation process wasn’t just due diligence — it was the mechanism for building shared ownership. By the time stakeholders voted on Pendo, they had already invested a month in making it work. That’s not consensus-building; that’s commitment-building.