Jesse Taylor

Berkeley, California Enterprise AI Sales jt@jessetaylor.info

Seven years selling complex software to skeptical buyers.

I run full-cycle enterprise sales for AI products — outbound to close. Last quarter I closed $670K against a $280K plan, including the largest deal in my company's history. About half of everything I close, I source myself.

Jesse Taylor
Jesse Taylor, Account Executive at Vooma.ai
240%
of plan, Q1 2026
$670K
closed in one quarter
$160K
largest deal — a company record
~50%
of closed revenue self-sourced
How I Sell

Process over charisma. I sell on structured discovery, not demo theater. Before a prospect ever sees the product, I want agreement on the problem, its quantified cost, and who has to say yes. I run mutual action plans on every serious deal — a joint project plan, built backward from the customer's go-live date — so urgency is real rather than manufactured. When the groundwork is right, deals move fast: I've closed a $70K contract in five days.

Pipeline is my responsibility. I started my career doing 100% cold outbound into enterprise companies, and I've never stopped generating my own pipeline. Calls, walk-ins, conferences with pre-booked meetings, and outreach creative enough to get answered. Roughly half of my closed revenue comes from deals I sourced myself.

Sales is a craft, and I study it. I work with an executive sales coach every week — reviewing real calls, deal strategy, and discovery technique the way an athlete reviews film. I've also built my own tooling with Claude: a deal tracker that scores opportunities against my qualification framework, and a daily automation that reports my pipeline metrics every morning.

The sale isn't done at signature. AI products that don't get adopted become shelfware, and shelfware churns. I stay involved through implementation — on-site trainings, stakeholder alignment, change management — because I'm selling an outcome, not a contract.

Jesse Taylor at home in Berkeley, California
Berkeley, California. I moved to the Bay Area because the most important work in AI is happening here.
Experience
2025 — Present
San Francisco

Vooma.aiGTM / Account Executive

AI agents for freight, backed by Y Combinator and Craft Ventures. Full-cycle sales into mid-market and enterprise logistics companies up to $4B in revenue, against well-funded competitors. $260K closed in Q4 2025; $670K in Q1 2026 — 240% of plan — including the largest deal in company history. Run enterprise procurement, security review, and C-suite presentations end to end.

2021 — 2025
Remote

Parade.aiFounding Sales Engineer → Account Executive → Partner Marketing

Joined early and grew with the company. As an AE, top seller in my best quarter — $260K on a $200K plan — averaging $190K per quarter. Later drove AI go-to-market through thought leadership, speaking engagements, and partner channels, beating MQL targets both quarters.

2020 — 2021
Remote

CeligoAccount Executive

Consultative sales across 300 mid-market and enterprise integration-platform accounts. Beat quota both full quarters; top seller on the team in Q4 with its largest deal.

2019 — 2020
Seattle

ConvoySales Development Representative

Built pipeline from zero through 100% cold outbound into enterprises from $50M to $140B in revenue. Where I learned prospecting discipline.

Education: B.A. Economics, Western Washington University, cum laude. Semester abroad in Brazil — fluent in Portuguese.

What's Next

I want to sell for a foundational AI company.

My conviction is simple: foundational model companies are the source the rest of the AI economy is built on. I use these tools every day, I sell AI to skeptical operators for a living, and I moved to the Bay Area to be close to the work that matters. I'm not applying everywhere — I'm pursuing a short list of teams, deliberately.

jt@jessetaylor.info · LinkedIn