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I started in door-to-door sales, which is where you learn that selling is mostly listening, that rejection is information, and that the only thing separating top performers from average ones is how seriously they treat their reps. Yelp came next — high-volume outbound to local SMBs, where I exceeded quota by 32% in a fast-moving environment built on activity discipline.
WeWork brought a different kind of work. I was part of a core team launching the brand in Phoenix, where we opened our first location at 98% occupancy within six months — a regional record at the time, broken only by the second location we opened. I wore every hat: broker events, hard hat tours, cold calling, account management, and member retention. I learned that go-to-market in a new geography is a contact sport and that customer relationships compound when you treat them like more than transactions.
Flare was the deepest run. I joined as the first AE hire in Phoenix. I was promoted to the first Sales Manager role in the market, eventually progressing to senior client partner before a restructuring layoff in 2023. The Flare years are where I learned what I actually believe about sales leadership: that coaching is a weekly discipline, not an occasional event; that pipeline inspection should surface problems early, not interrogate reps; and that accountability and trust travel together. I led 14 AEs to 110%+ average quota attainment, promoted three reps into leadership, and built the Salesforce dashboards and Gong coaching loops that kept the team's forecasts clean and their performance predictable.
Phoenix Home Cleaning started in 2024 as an experiment. I wanted to know whether I could apply what I'd learned in B2B SaaS sales to a small local services business — the kind of business my Yelp and Flare clients ran. Turns out yes. We grew revenue 157% YoY, lifted conversion from 2.28% to 4.12% through installing the Phoenix Digital Growth playbook, and built employee benefit partnerships, including one with Dutch Bros. The business is currently running on a partner cleaner model, which I'll be writing about as I restructure it through 2026.
Phoenix Digital Growth is the next thing. The thesis is simple: most Phoenix-area home services operators are losing significant revenue not because they don't have enough leads, but because they miss calls, follow up too slowly, never reactivate dead leads, and don't systematically request reviews. PDG installs a system that recovers that revenue first, then layers in lead generation once the foundation is clean. PHC is the in-house case study — every system PDG sells to clients gets installed on PHC first.
—Jesse Gabriellini