OffDeal · New York
Investment Banker I
Investment banking hasn't fundamentally changed in decades — until now. At OffDeal, we're building the world's first AI-native investment bank. Instead of selli...
Investment banking hasn't fundamentally changed in decades — until now. At OffDeal, 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oversized teams on outdated processes, making lower middle market transactions uneconomical.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.
OffDeal 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
THE ROLE
At a traditional bank, junior bankers often spend years waiting for meaningful exposure to clients, buyers, and real deal
decision-making. At OffDeal, 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 workstreams,
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 OffDeal 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.
WHAT YOU'LL DO
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 OffDeal’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 workstreams, and build toward running deals end to end on your own.
A WEEK AT OFFDEAL
- 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 sponsor
- Coordinate diligence requests between a seller, buyer, and third-party advisor on an active deal.
- Review financials for a prospective client and prepare a first-pass analysis of revenue, margins, add-backs, valuation and
potential diligence questions.
- Sit with engineering to show where the buyer outreach or NDA workflow still requires too much manual work — and help design the
next version of the platform.
WHO YOU ARE
Classically Trained, Modern Mindset. You likely have 1–3 years of experience in investment banking, M&A advisory, transaction
advisory, corporate development, private equity, or another rigorous deal environment. You know the fundamentals, but you are
excited to work in ways that did not exist five years ago.
A Deal Person. You like businesses, buyers, sellers, process dynamics, and the craft of getting a transaction done. You want more
exposure to the full deal lifecycle, not just isolated modeling or presentation work.
Commercially Curious. You want to understand why buyers care about a business, what drives value, what creates risk, and how
founders think about the biggest decision of their lives.
Strong on the Details. You are trusted because your work is clean and reliable. You catch inconsistencies, manage follow-ups, keep
processes organized, and communicate clearly.
Comfortable Externally. You’re excited to be in front of clients and buyers – not just supporting behind the scenes. You
communicate with care, ask good questions, and represent the firm in a way that builds trust.
Scrappy. We're a startup. When a process is messy, you organize it. When the tech has a gap, you work around it and help us fix
it. When something needs to get done, you take ownership.
WHY JOIN OFFDEAL
OffDeal is growing fast — deal volume is compounding, the platform is improving every week, and we are still early in building the
category-defining AI-native investment bank.
As an Investment Banker I, you will get a level of exposure that is hard to find in a traditional junior banking role: direct work
with senior bankers, live deal responsibility, interaction with middle market private equity buyers, and the opportunity to help
shape the technology that powers the firm.
If you're an ambitious junior finance professional who wants to become a real dealmaker faster — and help reinvent investment
banking while doing it — let's talk.