OffDeal · 2 days ago
Investment Banker II
New York
Full-time
Onsite
Mid, Senior Level
5+ years expOffDeal is building the world's first AI-native investment bank, focusing on lower middle market transactions. The Investment Banker II will develop deep sector expertise, manage full transaction processes, and cultivate relationships with American entrepreneurs.
Artificial Intelligence (AI)Information TechnologySoftware
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
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
Qualification
Required
5–8 years of experience in investment banking or related field
Mastered the fundamentals of investment banking
Excited to work with AI and technology as leverage
Ready to originate deals immediately
Ability to drive transactions from kick-off to close
Strong judgment, empathy, and negotiation instincts
Experience in building relationships with business owners
Ability to manage timelines and anticipate bottlenecks
Scrappy and resourceful in a startup environment
Company
OffDeal
AI-native investment bank for buying and selling small businesses
11-50 employees
Funding
Current Stage
Early StageTotal Funding
$16.82MKey Investors
Radical VenturesY Combinator
2025-07-29Series A· $12M
2024-05-31Seed· $4.7M
2024-02-27Pre Seed· $0.12M
Recent News
Business Insider
2025-10-13
2025-10-02
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2025-08-31
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