Case Study: WePay achieves scalable sales coaching and faster deal alignment with 15Five

Growing Your Sales Organization Beyond The Deal

WePay, a fast-growing payments provider for online platforms, expanded from about 65 to over 200 people and faced common sales challenges: tribal knowledge trapped in individuals, inconsistent deal-level coaching, and gaps in sales enablement that left managers unsure where deals were getting stuck. Chief Revenue Officer Kurt Bilafer needed a way to capture insights across reps, standardize feedback, and develop frontline managers so the team could scale without losing top talent.

WePay adopted 15Five’s automated 5-15 weekly check-ins, setting consistent questions to surface deal details, objections, and themes. That data let Kurt pinpoint coaching needs, accelerate cross-functional fixes (marketing used captured objections to build new materials), reduce time spent on status updates, and focus on talent development. The result: faster issue identification, more effective coaching, stronger team alignment and culture, and improved retention of high performers.

WePay

Kurt Bilafer

Chief Revenue Officer