---
title: 'Investment Banker II at OffDeal'
canonical: 'https://feeny.ai/job/investment-banker-ii-offdeal-new-york-k8c1t3wc17hh'
type: 'job'
last_seen: '2026-09-14'
---

# Investment Banker II at OffDeal

- **Company:** OffDeal
- **Location:** New York, NY
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-01-23
- **Last confirmed live:** 2026-09-14
- **Apply:** https://jobs.ashbyhq.com/offdeal/42ed092e-ef8f-4df2-ba05-3993a1183937

## Job description

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 Traditional firms run oversized teams on outdated processes, making lower middle market transactions uneconomical.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](https://www.ft.com/content/9daf5c7e-e301-4b7d-809a-ff9fb336bdbc)
- [CNBC - Wall Street's new AI era](https://www.cnbc.com/video/2025/08/04/wall-streets-new-ai-era-offdeal-ceo-on-using-ai-to-disrupt-investment-banking.html)
- [Blog - The Bull Case for an AI-native investment bank](https://www.fullydistributed.co/p/the-bull-case-for-an-ai-native-investment)

## 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.

## About OffDeal

## Company Overview
- **One-liner**: OffDeal is an AI-native investment bank that helps small business owners sell their companies at premium prices through a technology-driven M&A advisory process.
- **Entity Type**: Private (Series A)
- **Headquarters**: New York, United States
- **Founded**: 2023
- **Founders**: Ori Eldarov (CEO) and Alston Lin (CTO)

## Core Business
- Primary industry: Investment Banking / M&A Advisory
- Target customers: Small business owners with $5M–$100M in sales, and strategic/financial buyers
- Mission or purpose statement: To modernize dealmaking and help small businesses thrive by building the world’s first AI investment bank

## Products & Services
- **Full-Service M&A Advisory**: End-to-end support from a dedicated M&A advisor, including business valuation, buyer matching, competitive auction process, and deal execution — all with $0 upfront fees.
- **AI Buyer Match**: Proprietary AI technology that maps every strategic and financial buyer in minutes, generating 1,000+ strategic matches on average per deal.
- **Buy-Side Services**: Proprietary deal origination (typically add-ons) and comprehensive market mapping / market research to support due diligence or portfolio value creation.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Total Funding**: $16.8M across 3 rounds (Pre-Seed, Seed, Series A)
- **Key Metric**: $12M Series A raised in August 2025
- **Notable Investors/Partners**: Radical Ventures (lead), Y Combinator, and other institutional investors
- **Growth Signals**: Headcount grew +220% YoY to 15 employees; active job postings for Full Stack Engineer ($240K–$375K) and Investment Banker II ($500K–$1M); NYC relocation allowance offered

## Competitive Advantages
- **AI-Native Core**: Custom-built proprietary AI automates manual analyst grunt work (buyer mapping, data analysis, process transparency), allowing bankers to focus on strategic judgment and client relationships.
- **Full-Service Model**: Unlike DIY listing sites, OffDeal provides end-to-end advisory with seasoned bankers — combining technology with human expertise.
- **Proven Outcomes**: Claims 30% higher offers, 15x more buyers, and initial offers in <45 days (vs. 4 months at traditional firms).
- **No Upfront Fees**: Aligns incentives with sellers — only paid upon successful deal closure.

## Strategic Focus
- Scaling the AI-powered M&A platform to serve more small businesses across multiple sectors (healthcare, business services, industrials, consumer, home services).
- Expanding the buy-side and market research services to support both buyers and portfolio companies.
- Continuing to build out the engineering and investment banking teams to deepen the technology moat and deal capacity.

## Why Work Here
- **Compensation**: Highly competitive — Full Stack Engineer roles range $240K–$375K; Investment Banker II roles range $500K–$1M.
- **Culture & Values**: Relentless focus on a few high-impact priorities; first-principles thinking; data-driven decision-making; AI-first mindset where everyone considers how AI can enhance their work.
- **Perks**: Private medical and dental insurance, Equinox gym membership, unlimited PTO, free lunch/snacks/coffee, NYC relocation allowance.
- **Team & Environment**: Small but rapidly growing team (15 people) with a flat structure; hybrid/office presence in New York; founded by ex-Meta/Google engineers and Harvard MBA.

## Sources
1. [offdeal.io](https://offdeal.io/)
2. [offdeal.io/careers](https://offdeal.io/careers)
3. [offdeal.io/about-us](https://offdeal.io/about-us)
4. [linkedin.com/company/offdeal](https://www.linkedin.com/company/offdeal)
5. [ycombinator.com/companies/offdeal](https://www.ycombinator.com/companies/offdeal)

## Other roles at OffDeal

- [Founding Content Lead](https://feeny.ai/job/founding-content-lead-offdeal-new-york-zgnrgzf1smvp) — New York, NY
- [Director of Sales Development](https://feeny.ai/job/director-of-sales-development-offdeal-new-york-574k99zaxbgq) — New York, NY
- [Investment Banker I](https://feeny.ai/job/investment-banker-i-offdeal-new-york-p9xtvtwpdsqj) — New York, NY
- [Member of Technical Staff](https://feeny.ai/job/member-of-technical-staff-offdeal-new-york-2mt7c5j1kcty) — New York, NY