Investment Banker II

OffDeal • New York, NY

8d

About The Position

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 Traditional firms run oversized teams on outdated processes, making lower middle market transactions uneconomical.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, 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.

Requirements

• 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.

Responsibilities

• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1-10 employees