Peter Reilly
Senior Manager - GTM @ Toast
Boston, Massachusetts, United States
Artifacts
Toast, Inc. · Senior Manager - Revenue GrowthInheriting 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.
Toast, Inc. · Senior Account ExecutiveIn 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.
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Leave a testimonialWork history
Jul 2018 - Present · 8.3 years · Senior Manager - Revenue Growth, District Manager - Revenue Growth, Team Lead - Revenue Growth, Principal Account Executive, Senior Account Executive, Account Executive - Toast Payroll, Experimental Sales Team Lead
Sep 2014 - Apr 2018 · 3.7 years · Campus Ambassador and Social Media Manager
May 2017 - Aug 2017 · 4 months · Digital Asset Management Intern
May 2016 - Sep 2016 · 5 months · Technology Assistant Intern
Jun 2014 - Aug 2015 · 1.3 years · General Laborer
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