Chief of Staff

OffDeal is the world’s first AI-native investment bank for small businesses. Instead of selling AI to Goldman Sachs, we’re building what Goldman itself would have looked like if it launched in 2025.

Wall Street's playbook works well, but only for billion-dollar deals - it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical. This leaves millions of small business owners with nowhere to turn for the most important sale of their lives… Until now.

Our engineers built software to automate 80%+ of analyst work with AI, so our in-house bankers can focus where it counts - on earning owners’ trust and closing deals.

We recently closed a $12M Series A ($17M in total funding) from Radical Ventures and Y Combinator and are scaling really fast. In less than a year, our team has already launched over 30 sell-side M&A transactions and has delivered numerous life-changing exits to our clients - and we’re just getting started.

Read more about our story:

• https://www.ft.com/content/9daf5c7e-e301-4b7d-809a-ff9fb336bdbc

• https://www.cnbc.com/video/2025/08/04/wall-streets-new-ai-era-offdeal-ceo-on-using-ai-to-disrupt-investment-banking.html

• https://www.fullydistributed.co/p/the-bull-case-for-an-ai-native-investment

The Role

Be the bandwidth‑multiplier for the CEO and the connective tissue across banking, BD, marketing, and product. Your North Star: surface the right problems, drive the right decisions, and ship the right projects - fast.

If you’re a force of nature - slightly obsessed, high‑agency, and wired to bend reality in a startup’s favor—this seat is built for you.

What You’ll Do

• Own the Operating Rhythm – Design and run quarterly planning, exec meetings, all‑hands, and board prep so everyone rows in the same direction.

• Make Metrics Meaningful – Decide which numbers truly move the needle, build dashboards, and keep the score visible company‑wide.

• Hunt Bottlenecks – Spot friction in workflows, tooling, or org design and drive the fix—process tweak, product change, or new hire.

• Run Special Projects – Spin up cross‑functional sprints with Sales, Marketing, Investment Banking, and Product to attack “CEO‑level” problems from idea to launch.

• Partner on Talent & Org Design – Shape head‑count plans, screen key candidates, and keep the culture tight as we double in size.

Who We’re Looking For

• 4–8 years in top‑tier consulting, investment banking, BizOps, or prior CoS / operator role at a high‑growth startup.

• High-agency builder. You thrive in chaos, see ambiguity as opportunity, and execute without waiting for instructions.

• Elite communicator. Clear writer, concise speaker - comfortable from boardroom to hallway whiteboard.

• Low ego, high ownership. Happy to write strategy memos in the morning and comb through the data that afternoon.

• Hustle x IQ x EQ. Relentless drive, sharp analytical chops, and the empathy to bring others along.

• Data‑literate. Fluent in financial statements and funnel metrics; you believe arguments beat opinions when numbers back them up.

• Launch‑pad ambition. You view this role as a fast track to GM, COO, or founder.

Why Join OffDeal

• Scope without ceilings. If it’s mission‑critical and unowned, it’s yours.

• Front‑row seat to company building. Shape strategy, org design, GTM motions, and investor narratives—simultaneously.

• Top‑tier benefits: medical, dental, vision, unlimited PTO, free meals, Equinox membership, 401K matching, and NYC relocation allowance.

• In‑person in NYC. Work side‑by‑side with founders and a team rewriting the playbook for a trillion‑dollar industry.