Sr. Director M&A Deal Modeler

Leadout Capital; San Francisco (CA); On-site; USD 200,000 - 320,000; Full time

Job summary

Leadout Capital in San Francisco seeks a senior strategic finance leader to own the financial and operating models behind AI Labs acquisitions and investments. You will partner with portfolio CEOs and AI Labs leadership to validate assumptions before investments, translate approved deal models into executable post-close budgets, and track performance against acquisition expectations.

Ideal candidates are CFO/finance leaders in high-growth tech, with deep SaaS/AI economics understanding, and

Qualifications

• Senior finance leader with CFO/strategic finance experience in high-growth tech companies.
• Deep understanding of startup economics, SaaS/AI business models, and growth-stage decisions.
• Exceptional financial modeling and analytical judgment.

Responsibilities

• Own end-to-end operating and financial models for AI Labs acquisitions.
• Build and challenge revenue, headcount, compensation, investments, margins and cash assumptions.

Skills

Strategic finance leadership

Financial modeling

Executive partner with founders

Job description

The Experience

We are looking for a senior strategic finance leader to build and own the financial and operating models behind AI Labs acquisitions and investments.

This role will ensure that acquisition models reflect how AI-native companies actually operate—not simply transaction assumptions—and that the commitments made before close translate into executable post-close plans.

What You'll Actually Be Doing

• Own the end-to-end operating and financial model for AI Labs acquisition opportunities.
• Build and challenge assumptions across revenue, growth, headcount, compensation, investment, margin, and cash requirements.
• Partner directly with portfolio CEOs/founders and AI Labs leadership to validate assumptions before investment decisions are made.
• Work closely with M&A while maintaining independent ownership of the operating model within Finance.
• Translate approved deal models into executable post-close budgets and operating plans.
• Track actual performance against acquisition assumptions and identify material variances early.
• Establish a consistent modeling framework across AI Labs acquisitions while allowing for differences in company stage and business model.
• Incorporate critical talent, founder retention, and other material people investments into acquisition economics.

You're Our Person If...

• Experience as a CFO, strategic finance leader, or senior finance executive in a Series B–D or similarly high-growth technology company.
• Deep understanding of startup economics, SaaS/AI business models, and growth-stage operating decisions.
• Exceptional financial modeling and analytical judgment.
• Experience partnering directly with founders and executive teams.
• Ideally, experience spanning both venture-backed companies and scaled/public-company environments.
• Comfortable challenging assumptions and bringing an operator's perspective to investment decisions.

Hiring preference:

External candidates with meaningful startup operating experience.