Investment Banker

Investment banking hasn't fundamentally changed in decades — until now. At Off Deal, we're building the world's first AI-native investment bank. Instead of selling software to Goldman Sachs, we're building what Goldman itself would look like if it launched in 2025.

Wall Street's playbook works for billion-dollar deals, but it breaks where most businesses actually exist. Traditional firms run oversized teams on outdated processes, making lower middle market transactions uneconomical. This leaves millions of founders with nowhere to turn for the most important sale of their lives.

We're changing that. We focus exclusively on the lower middle market ($1–10M EBITDA) — founder-led businesses where relationships and judgment matter more than financial engineering. Our platform is a force multiplier: proprietary intelligence, AI-generated first drafts, automated buyer sourcing, and real-time deal insights — so you can deliver more value to clients and close more deals than any traditional banker could alone.

Off Deal has raised $17M from Y Combinator, Radical Ventures, and others. We've generated millions in fees with a lean but mighty team.

Read more about our story:

• Financial Times
  - Behold the first AI-native investment bank

• CNBC
  - Wall Street's new AI era

• Blog
  - The Bull Case for an AI-native investment bank

At a traditional bank, junior bankers often spend years waiting for meaningful exposure to clients, buyers, and real deal decision-making. At Off Deal, you will get those reps much earlier.

As an Investment Banker I, you will work directly with senior bankers across live deal execution and origination support. You will participate in client meetings, work directly with private equity and strategic buyers, manage transaction diligence work streams, as well as keep deal processes moving.

You will also work closely with our Product & Engineering teams. You will be a power user of the Off Deal platform, using AI to move faster across research, materials, diligence, and execution — and helping our engineers understand where the product needs to get better.

This is a rare opportunity for a junior banker to get real deal exposure, direct interaction with middle market private equity buyers, and a front-row seat to building a new model for investment banking.

Support Live Deals. Help senior bankers run active transaction processes. Field diligence requests, coordinate with buyers, and broadly make sure nothing falls through the cracks, getting exposure to every phase of a live transaction – not just the model.

Work With Buyers. Build and manage relationships with middle market private equity firms, independent sponsors, family offices, and strategic acquirers. Help identify relevant buyers, coordinate outreach, track feedback, and join buyer calls.

Prepare High-Quality Materials. Create client‑facing decks, buyer materials, financial analyses, valuation support, business summaries, and process updates. Our AI Agent Archie will give you a strong headstart, but you will need to bring your commercial judgement and polish.

Support Origination. Help senior bankers evaluate new opportunities, prepare for founder conversations, follow up with prospects, and support the work that turns relationships into signed engagements.

Leverage the Platform. Use Off Deal’s AI tools across research, outreach, diligence, materials, and execution. When a workflow is manual or painful, help our engineering team turn it into product.

Grow Into a Closer. You’ve spent a year building the technical foundation. Here, you’ll learn how to talk to a seller, how to read a buyer, how to move a deal forward. Learn how deals are sourced, pitched, executed, negotiated, and closed. Over time, take on more external calls, own more work streams, and build toward running deals end to end on your own.

• Build a buyer list for a founder‑owned landscaping business, coordinate outreach to middle market private equity firms and strategic acquirers and get on the phone with them yourself.

• Prepare a client deck summarizing buyer appetite, likely valuation drivers, and strategic exit alternatives across ESOP and sale to a PE…