About DiligenceSquared

DiligenceSquared (YC F25) is rebuilding how private equity firms, hedge funds, private credit, and corporates conduct commercial due diligence. We deploy AI agents to automate expert interviews at scale, synthesize findings, and deliver fully traceable CDD reports – at a fraction of the cost and timeline of traditional consulting. Backed by Y Combinator and Relentless, we're a small, high-output team working on some of the most intellectually demanding problems in private equity research.

The Role

We're looking for a sharp, client-facing Founding Business Lead to own the delivery of commercial due diligence for leading private equity funds.

You'll be the human-in-the-loop at the heart of our AI-powered research process: translating client needs into precise guidelines for our AI agents, overseeing the quality of their outputs, and ensuring every engagement is delivered with white-glove service.

This is a highly visible, client-facing role. You'll work directly with partners and deal teams at top-tier PE funds, have real ownership over your work, and help shape how we build and scale the product – without the layers of process that come with larger organizations.

What You'll Do

Own project delivery across multiple simultaneous CDD engagements, from kickoff through final report
Manage client relationships day-to-day
Coordinate expert sourcing across expert networks
Work closely with our AI systems to oversee interviews, analysis and synthesis to ensure coverage against client briefs
Partner with our engineering team to translate client and operational insights into product improvements
Build and refine internal processes and templates that improve delivery quality and speed
Collaborate with the founding team on product feedback

What We're Looking For

3–6 years of experience at an MBB firm, in private equity, or in investment banking
• Experience with commercial due diligence — you understand the methodology, the client expectations, and what separates a good CDD from a great one
Track record of managing complex, deadline-driven workstreams with multiple stakeholders
Exceptional written and verbal communication
High attention to detail — you catch errors others miss and hold your work to an exceptionally high bar
High ownership mentality: you spot problems early and solve them independently
Genuine curiosity about AI and its implications for knowledge work — you should be excited about working at the cutting edge of how AI is transforming research and analysis
Start-up mentality — you're energized by ownership, speed, and variety; equally comfortable shaping strategy and handling the unglamorous work that comes with building something from the ground up
Comfortable operating in ambiguity and building structure where there isn't any

Why DiligenceSquared

Early-stage equity at a YC-backed company with strong investor conviction and active deal flow
Work at the cutting edge of applied AI — you'll use and shape tools that don't exist anywhere else in the industry
Work directly with the founding team — high ownership and real impact from day one
Intellectually demanding work: complex industries, sophisticated clients, high stakes
A front-row seat to how AI is transforming the multi-billion dollar commercial due diligence market
Competitive compensation and a collaborative, no-bureaucracy culture

DiligenceSquared

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