Investment Banker II

ABOUT US

Pomelo places the best talent with leading brands, startups, and agencies across the globe. We enable hard-working and ambitious talent to work remotely from the comfort of their own homes. 

ABOUT THE ROLE

We’re looking for an experienced NYC-based Investment Banker (with 5-8 years of banking experience) to join a game-changing, fast-growing, YC- and VC-backed tech startup based in New York City. The startup is an AI-native investment bank that helps buyers discover, evaluate, and execute on lower middle market transactions. In this role, 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 AI, 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.

KEY 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.

QUALIFICATIONS

• 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.

A WEEK IN THE LIFE

• 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

COMPENSATION