Toast, Inc.In 2022, Toast shifted its sales organization's compensation model from booked revenue to live revenue, a change designed to better align individual contributor incentives with the business's true goal: getting quality revenue actually activated for the company. That same year, I was tasked with selling not just the single complex product I had specialized in, but an entirely new suite of products, including payroll services, one of the most operationally complex offerings in our portfolio. Within an org of roughly 25-30 reps, this meant learning to sell and activate a new line of business while adapting to a metric that rewarded successful customer go-lives over signed contracts.
To succeed under this new model, I operated on the principle that a deal wasn't truly done until the project was live. I ran thorough discovery during the sales process and was willing to disqualify customers who I felt weren't positioned to succeed post-signature, rather than overpromising for a quick close. My biggest lever, however, was building an above-average level of alignment with the onboarding (OC) team through constant, proactive communication: after signing a customer, I compiled detailed lists of potential risks and asks based on my direct experience with that account, giving onboarding teams visibility most sales reps never provided. I also matched account complexity to OC seniority, advocating in advance to pair more complex customers with more senior onboarding specialists. Throughout implementation, I held customers accountable to their deliverables, set clear expectations to minimize surprises, and personally intervened the moment a project fell even 1-2 days behind schedule, opening direct threads with onboarding teams and customers to diagnose issues and get things back on track.
The results validated this live-revenue-first approach: while I finished #2 in the org on bookings with just shy of $1.6 million, I generated the most live revenue of anyone in the organization, totaling $1.45 million. This included over $1 million in payroll bookings translating into more than $900,000 in live payroll revenue, on our most operationally complex product line. This achievement demonstrated that disciplined post-sale execution and cross-functional alignment could outperform pure booking totals in delivering real, realized value to the business.
