Toast, Inc.Inheriting a struggling sales rep who had cycled through four managers in five months, I faced a performance crisis that demanded both urgency and precision. This rep was in the bottom 10% of the org, sitting in a formal performance management track, and had grown deeply negative about their prospects after months of inconsistent leadership. In my first two weeks, I conducted a deep dive into their last 10 months of performance data while simultaneously observing their day-to-day selling to diagnose the real root causes: a difficult headspace, specific skill gaps, and a lack of personal accountability — including holding their own customers accountable. I had a direct, honest conversation with them about what was at stake and whether they were willing to fight for their role, which became the foundation for a clear accountability and coaching plan.
To close the gaps, I built an intensified version of the operating system I run across my team, tailored to the severity of this situation. This included three weekly syncs (start, middle, and end of week) to track progress against goals, daily productivity readouts, and deep deal-by-deal coaching to make up for months of missed development — reviewing or shadowing roughly two calls per week and spending significant time on pipeline review. Recognizing that top-of-funnel volume was also a problem, I tracked daily prospecting pace and built a targeted account plan focused on deals above a certain size threshold. I also leaned on the broader team's culture of excellence, having teammates step in to support this rep when I was bandwidth-constrained, reinforcing that poor performance couldn't hide on our team.
The turnaround was dramatic and sustained: this rep went from roughly 60% quota attainment to 110%+ for three consecutive months, more than doubling their personal compensation quarter over quarter. Top-of-funnel volume increased 50% versus their historical baseline, average deal size improved by 50%, and they moved themselves out of the bottom 10% and off performance management entirely — the only one of four reps org-wide in that same situation to do so at the time of writing.
