Chief of Staff

About Flybridge

Flybridge is the early-stage venture capital firm backing the next wave of our AI-powered future—from developer platforms to agentic applications to transformative ideas that 10x how humans work, create, and relate. With 20+ years operating as a first-check fund and a portfolio of 200+ companies, we give founders unmatched access to enterprise customers, technical talent, and our founder-first platform that accelerates growth from day one. In it for the long haul, we invested early in Arcee.ai, BetterCloud, Chief, Codecademy, Crashlytics, MongoDB, Noetica, NS1, and Splice—proving that East Coast advantage creates lasting value.

The Opportunity

Think 80% Chief of Staff / 20% Investment Associate. You’ll operate as the right hand to Jesse Middleton, a General Partner at Flybridge: magnifying his impact across deal flow, portfolio support, LP relations, firm management, and firm‑wide initiatives, while reporting directly to the GP (with a dotted‑line to the broader partnership) as an extension of him in nearly every setting. Expect to sit in (physically) on nearly every meeting, turn scattered insights into crisp follow‑ups, and ensure nothing—and no one—falls through the cracks.

You Might Be…

• A former founder or early startup COO who thrives on ruthless prioritization.
• A junior VC/consultant with an uncanny relationship‑building chops itching for more operator time.
• A systems geek who loves turning chaos into elegant processes—while still closing the loop personally.

Must‑Haves

• NYC‑based, in‑office 5 days/week.
• In‑office whenever Jesse is in NYC (typically Mon–Fri)
• Daily driver of our tech stack: Slack, Notion, Google Docs, Airtable, Affinity, Superhuman, ChatGPT/Perplexity, and Dynamo (or eager to learn).
• Exceptional organizational rigor; to‑do lists fear you.
• Natural community‑builder and clear writer.
• Fluency (or fierce curiosity) in AI/automation tools.
• Eager to spend some evenings or mornings each week at founder mixers, hackathons, and demo nights.
• Zero ego, high integrity, and comfort hustling at New York speed without cracking under pressure.

Nice‑to‑Haves

• Prior board‑room or startup exposure.
• Familiarity with venture technology platforms (Affinity, Airtable).
• Mastery of data‑driven storytelling—decks, memos, Substack‑style posts.

Compensation & Logistics

• Salary: $100k – $150k (no bonus or carry for initial 2–3‑year tour of duty).
• Travel: Monthly day‑trip to Boston, 1–2 West Coast trips per year, and select conferences/LP events each year—generally accompanying the GP whenever he’s on the road.
• Start: ASAP (flexible for the right candidate).
• Benefits & Perks: Full health / dental / vision, 401(k), paid parental leave, flexible PTO, and a culture that respects evenings & weekends.

Why Flybridge & Why Now

You’ll gain an unprecedented 360º apprenticeship in venture—fund strategy, LP relations, deal execution, and portfolio support—while shaping the operating system of a firm on the front lines of New York’s AI renaissance. If you crave impact, ownership, and a front‑row seat to the city’s next wave of iconic startups, we’d love to meet you.

How to Apply

Apply on LinkedIn by submitting your profile here.

Flybridge is an equal‑opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

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