Head of GTM

About DiligenceSquared

DiligenceSquared is the AI-native consulting firm. We deliver investment-grade market research and commercial due diligence, powered by AI agents and led by experienced consultants. Our founding team brings deep experience from Blackstone and BCG, and we're backed by Y Combinator and Relentless. Our clients include 5 of the 10 largest private equity firms in the world and represent more than $3T in combined AUM.

The Role

We're looking for our first commercial leader to build and lead go-to-market at DiligenceSquared. You'll work directly with the founders to define how we win new private equity clients, grow relationships across existing funds and build a repeatable commercial organization.

We build client relationships through high-value, project-based engagements. Success starts with earning the first mandate, delivering an exceptional client experience and expanding that trust across deal teams, strategies and offices to build a durable fund-wide relationship.

This is a hands-on builder role. You'll personally originate and close business before building the team and systems that make the approach repeatable.

What You Will Do

- Win new clients: Build and execute a targeted outbound strategy, create qualified pipeline and lead opportunities from first conversation through proposal and close.
- Grow existing accounts: Develop relationships across sector teams, strategies and offices within the funds we already serve, turning strong delivery into repeat and expanded revenue.
- Own strategic relationships: Build trust with deal professionals and senior decision-makers through relevant insights, thoughtful follow-up and a strong understanding of their work.
- Shape solutions: Partner with founders and delivery leaders to understand client needs, scope engagements, develop proposals and price work appropriately.
- Build the commercial system: Establish account planning, pipeline management, CRM discipline, forecasting, handoffs and performance measurement.
- Partner with marketing: Turn content, events, partnerships and inbound interest into commercial conversations and measurable pipeline.
- Build the team: Determine the next GTM hires, recruit and coach them, and create clear ownership across new business and account expansion.

What We Are Looking For

- Relevant leadership experience: You have at least eight years of relevant commercial experience, including experience selling to sophisticated institutional clients and leading commercial people.
- Proven revenue ownership: You have personally originated and closed meaningful business and have been accountable for a team or company-level revenue target. Experience in private equity, consulting or investor relations is valuable, but does not substitute for demonstrated commercial results.
- Experience building a commercial function: You have hired and coached commercial talent and established a repeatable approach to account planning, pipeline management, forecasting, CRM discipline, handoffs and performance measurement.
- Private equity fluency: You understand how PE deal teams work, what creates demand for commercial diligence and research, and how buying decisions are made.
- Hands-on leadership: You're excited to originate and close business yourself before and while building the team. You are not looking simply to inherit an established organization.
- Excellent judgment with senior clients: You can lead a substantive conversation with PE professionals, recognize a real opportunity and earn the next step.
- Commercial discipline: You follow through, ask directly for business and know how to balance revenue growth with strong project economics and a high-quality client experience.
- Close founder partnership: You can challenge assumptions, make decisions with incomplete information and work closely with founders and delivery leaders to build the function.

Experience That Would Be a Plus

- Experience in commercial due diligence, private equity or strategy consulting
- Experience selling research, expert-network, advisory or technology-enabled services to investment teams
- A strong network across private equity deal teams
- Previous startup experience

Why DiligenceSquared

- Build the GTM function at a YC-backed company with real revenue and strong client traction
- Work directly with founders who bought this research at Blackstone and delivered it at BCG
- Serve some of the world's leading private equity firms and help turn early relationships into a category-defining business
- Meaningful early-stage equity and the opportunity to build and lead the commercial organization
- Intellectually demanding work across complex industries, sophisticated clients and high-stakes decisions
- A small, senior team that enjoys working together, with regular offsites, team dinners and meals together at the office
- Competitive compensation, high ownership and very little bureaucracy

Compensation

Base Salary $190K – $220K • Offers Equity • Offers Commission • $350,000-$400,000 OTE

$350,000-$400,000 OTE