Business Lead

About Diligence Squared

Diligence Squared (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.

We’re looking for a sharp, client-facing 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.

• 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

• 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 work streams 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

• 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