Moments of impact from Peter Reilly's career
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.
Entering FY25, my team faced a challenging reset: my three top performers were still ramping, two tenured reps were coming off a career-best year but starting FY25 slow, and two others had inconsistent performance against increasingly difficult org-wide goals. Compounding this, we experienced attrition among our most tenured reps just as leadership rolled out new, more demanding targets—all against an org backdrop where average rep attainment was hovering around 40%. To turn this around, I restructured how the team generated pipeline, shifting emphasis toward self-sourced opportunities. I built personalized, data-driven goals for each rep based on their historical deal size and conversion rates, so everyone understood exactly how many opportunities they needed to create monthly, and I tied our core top-of-funnel metrics directly to self-sourced generation. I also overhauled my coaching approach: rather than reactively parachuting into deal cycles as the team scaled to 7-8 reps, I instituted mandatory weekly coaching blocks for every rep, regardless of performance level. These sessions were distinct from standard 1:1 business reviews—each one identified a specific development area, built a continuous action plan around it, and ended with clear next steps and "homework" before the following session. This doubled the time I spent coaching and made that time far more productive and targeted. The results were the best of my career leading a team: we finished FY25 at 80% team attainment versus roughly 40% org-wide, ranking #1 out of 18 teams. The team generated $5 million in self-sourced pipeline, and all 7 of my reps earned Presidents' Club designation. Three of my reps finished in the top 6 across the entire organization—all three of whom I personally hired and ramped from the ground up.
Toast, Inc. · District Manager - Revenue GrowthIn 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