Investment Banker II
About this role
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 Traditional firms run oversized teams on outdated processes, making lower middle market transactions uneconomical.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:
The Role
At a traditional bank, you might wait a decade before developing real sector expertise or becoming a thought leader in a vertical. At OffDeal, that starts day one. You'll develop deep coverage in sectors you care about, become the banker that founders in your space know by name, and build a reputation as the person who owns your market.
You'll run full transaction processes supported by our platform, a junior banking partner, and world-class software engineers. But execution is only part of the job. The other part — arguably, the more fun one — is origination: meeting American entrepreneurs and cultivating the relationships that become tomorrow's deals.
What You'll Do
Build Your Practice. Own a sector. Become the banker that business owners call first.
Own the Full Deal. Drive transactions from kick-off to close. Manage timelines, anticipate bottlenecks, and guide founders through the emotional complexity of selling their life's work.
Leverage the Platform. The AI handles the first 80%. You bring the judgment, empathy, and negotiation instincts that win.
Shape the Product. You're not just using cutting-edge AI tools — you're building them. When something doesn't exist yet, you do it manually and then work with engineering to automate it.
A Week at OffDeal
Meet with four family-owned businesses — calls and in-person — building relationships with founders targeting exits in 2026 and beyond
Fly to Philadelphia for an in-person buyer diligence session on an active deal
Prepare for an upcoming asphalt and paving conference in Las Vegas where you'll meet dozens of potential clients
Review an AI-generated CIM and add the final polish — sharpening the narrative, pressure-testing the story
Analyze five competing LOIs and deliver negotiation strategy to your client
Sit down with engineering to turn your manual buyer outreach process into the next platform feature
Who You Are
Classically Trained, Modern Mindset. 5–8 years of experience. You've mastered the fundamentals, but you're excited to work in ways that didn't exist five years ago. You see AI and technology as leverage and the ultimate force multiplier.
A Deal Junkie. You're not in banking for the Excel reps. Execution has been the job, but you're ready to originate. Not in ten years — now.
Scrappy. We're a startup. When the tech has a bug, you build the model yourself. When a situation is messy, you organize it and drive to resolution without waiting for backup.
Why Join OffDeal
OffDeal is growing fast — deal volume is compounding every quarter. Build your own M&A practice with uncapped upside, shape the product that's redefining the industry, and be a foundational team member at a well-funded, high-growth company.
If you're an ambitious mid-career finance pro who'd rather shape the future of dealmaking than polish logos in Appendix K, let's talk.
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You'll be redirected to offdeal's official application page on Ashby ATS.