The Opportunity

In the past few years, 20+ new state and federal leave laws have emerged in the US. By 2030, US employers are expected to spend over $40B annually on employee leave protection. While this is a win for employees, it creates massive complexity for employers and insurance carriers.

Today’s leave administration processes are fragmented, slow, and painful. We are building the next-generation Data infrastructure for HR and Insurance to:

• Orchestrate data between HR and insurance systems
• Simplify the leave of absence experience for employees
• Reduce the operational burden for employers, carriers, and TPAs

We are backed by Diagram and are working alongside insurance carriers as co-design partners to launch our MVP. We are now looking for an exceptional technology leader to join as CTO & Co-Founder. This is a unique chance to co-found a company with major early traction and the support of one of the world’s most successful venture studios.

Note: This is not an employment opportunity at Diagram, but a co-founding role within a new company launched through the Diagram venture studio.

What You’ll Do

As CTO & Co-Founder, you will own technology and engineering from day one. Expect to:

• Lead as a co-founder — share full accountability with the founding team for growth, scale, and long-term success.

• Build the team — recruit top technical talent and create a strong, high-performance engineering culture.
• Code and ship — roll up your sleeves, architect, and write code in the early stages.
• Move fast — thrive in ambiguity, embrace speed, and focus on outcomes over process.
• Drive AI-native thinking — embed intelligent automation into every layer of the product.

Who You Are

You’re a builder and entrepreneur with the grit to thrive in an early-stage startup.

• Proven builder — you’ve taken a company, product, or major business unit from 0→10 with full technical ownership.

• Integration expert — strong background in connector/integration products, ideally with leading SaaS/cloud players (e.g., MuleSoft, Boomi, Informatica, Zapier, Fivetran, Finch, Merge, etc.).

• Hands-on technologist — you are excited to code, prototype, and push products forward directly.
• Fast mover — comfortable with limited process, high ambiguity, and rapid iteration.
• Talent magnet — experience hiring, developing, and leading world-class technical teams.

What’s In It For You

Joining us as CTO & Co-Founder is a rare chance to step into a high-upside venture without the “starting from scratch in a basement” hassle.

• High equity compensation — meaningful ownership in the company.
• Leadership from day one — co-found alongside other high-caliber founders with a validated roadmap.
• De-risked startup ride — traction already in place:
• • Pipeline of partners, investors and clients
  • Product roadmap validated through extensive research during Diagram incubation
  • Other strong co-founders already on board
• Unfair advantage — leverage Diagram’s deep insurance network and relationships with carriers.
• Proven venture studio model — Diagram has one of the best track records in the industry: out of 25+ ventures launched thus far, 80% make it at least to Series A, with several exits including 1 IPO in less than 10 years.

About Diagram

Diagram’s mission is to build companies that solve meaningful problems. We partner with top entrepreneurs, match them with vetted ideas, and provide capital, resources, and an ecosystem to accelerate success. Since 2016, Diagram has raised $400M+, launched/invested in 25+ companies in Fintech and ClimateTech, and cultivated an ecosystem of 200+ angel investors and a global partner network. Diagram is part of Sagard, a global alternative investment platform with $25B+ AUM.