When I stepped into the Account Management function at Toast, I inherited a team of approximately 25 account managers struggling to support over 3,000 customers. The function was fundamentally broken: segmentation was virtually non-existent, many team members lacked either the technical aptitude or strategic account management skills needed for the role, and processes were entirely ad hoc. There was no performance management system, no competency framework, minimal enablement or training, and zero accountability. The team spent every day firefighting with no capacity for proactive customer work or revenue expansion opportunities.
I prioritized ruthlessly, starting with the foundational building blocks in my first 90 days. I implemented performance management and competency frameworks to establish clarity around expectations and capabilities, then moved quickly to segmentation and territory redesign to ensure customers were matched with appropriately skilled account managers. This required some difficult decisions: we moved underperformers out who couldn't level up, and simultaneously recruited high-caliber talent to raise the bar. I also designed a new compensation model that rewarded high performance through bonuses and included an effective commission structure on upsells, creating clear incentives aligned with business outcomes. Territory design became sophisticated, taking into account account manager level, tenure, compensation, and the strategic importance of each customer.
The transformation was dramatic. Upsells improved by double-digit percentages quarter-over-quarter throughout the first 12 months, while customer churn remained remarkably low despite the organizational upheaval. Beyond the revenue impact, we achieved a massive cultural overhaul—several of the rockstar hires I brought in have leveled up tremendously and moved into increasingly senior management roles across Toast. Perhaps most gratifying was that many of the people processes we incubated on my team—including competency maps, the performance management system, and upward manager surveys—were borrowed and scaled across the entire company, creating lasting organizational impact far beyond my immediate function.