Investment Banker II

About the Company

OffDeal is building the world's first AI-native investment bank, focusing exclusively on the lower middle market ($1–10M EBITDA). Backed by $17M from Y Combinator and Radical Ventures, the company uses proprietary AI intelligence to automate deal sourcing and documentation, allowing bankers to focus on relationships and judgment.

Responsibilities

• Build and own a specific sector practice to become a trusted advisor to business owners.
• Drive full transaction processes from kick-off to close, managing timelines and founder relationships.
• Leverage the AI platform to handle routine tasks while providing high-level judgment and negotiation.
• Collaborate with engineering teams to shape and automate product features based on manual workflows.
• Conduct origination activities, including meeting entrepreneurs and cultivating long-term relationships.

Requirements

• 5–8 years of experience in investment banking or similar financial services.
• Mastery of banking fundamentals with a modern, tech-forward mindset.
• Strong desire to move from pure execution into deal origination.
• Scrappy, startup-oriented mentality with the ability to solve problems manually when technology is evolving.
• Ability to manage the emotional and complex nature of founder-led business sales.