Toast, Inc.In early 2024, I inherited a sales team in crisis: average tenure was just 9 months, our most senior rep was returning from leave, and within my first quarter, two reps attrited, forcing an urgent rehire. I was simultaneously adapting to a new goal structure, new management, and I needed a process from the ground up
To rebuild the team, I developed my own hiring criteria to identify strong internal talent and proactively engaged XDR teams to pull qualified candidates into the interview pipeline as soon as they became eligible. This let me get new hires performing at a fully-ramped level within 3 months. On the management side, I simplified the role down to two core objectives and built an entire operating system — including custom KPIs that better measured true success — around driving those objectives.
The results were dramatic: we went from 3rd-worst of 18 teams to #1 by the end of 2024, finishing 10% ahead of the next-best team. Individually, my reps hit goal 42% more often in H2 of 2024 and booked over $5 million in revenue in FY24. In 2025, as the rest of the org's performance declined, we sustained our edge — reps hit goal at nearly 2x the rate of their peers. When headcount grew 60% that year, I refined the operating system further, doubling down on hiring for "urgency" and instituting a signature weekly coaching cadence for every rep. The team closed 2025 with over $6 million in booked revenue
