Investment Banker , US - Investment Banker

Off Deal 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 Traditional firms run oversized teams on outdated software, making smaller M&A transactions uneconomical.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:

As an Investment Banker at Off Deal, you’ll focus on what matters most: earning owners’ trust and closing deals. Unlike traditional roles where 70 % of time is spent prospecting and creating documents, our AI does the heavy lifting. You step in once qualified owners are engaged – enabling you to work on 20‑30 deals per year versus the industry norm of 3‑5.

• High‑Value Advisory: Build rapport with owners, provide strategic guidance, and structure optimal deals while AI drafts the core materials.

• Efficient Deal Execution: Operate in a two‑person pod: a dedicated BD banker fills your pipeline with pre‑qualified sellers and you do the closing.

• AI‑Enhanced Deal Preparation: Refine AI‑generated teasers, CIMs, and buyer lists; weeks of work collapse into hours.

• Product Innovation: Feed real‑time feedback to engineers and help shape the future of tech‑enabled M&A.

A typical month as an Off Deal Investment Banker:

• Engage with 50‑100 qualified business owners

• Manage 5‑10 active sell‑side mandates

• Close 1‑2 deals

• M&A
  
  Experience:
  
  2‑4+ years in investment banking or private equity from a top firm

• Financial Acumen: Strong financial literacy (statements, multiples, diligence flows)

• Communication & Empathy: Elite communicator who can translate complexity for first‑time sellers

• Entrepreneurial Spirit: Self‑starter who excels in a fast‑moving, ambiguous environment.

• Educational Background: Bachelor’s in Finance, Business, Economics, or related field

• Off Deal is growing exceptionally fast and is a leader in AI‑enabled services—deal volume is compounding every quarter

• Top‑tier benefits, including medical, dental, vision, and unlimited PTO

• 401K Matching

• Perks like free food, Equinox membership, and NYC relocation allowance

• Opportunity to be a foundational team member at a well‑funded, high‑growth startup

• Be part of a mission to shape the future of small business ownership and to promote American entrepreneurship

If you’re an ambitious early‑ or mid‑career finance pro who’d rather shape the future of deal making than polish logos in Appendix K, let’s talk.