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 complex data flows between HRIS, payroll, benefits, and insurance platforms
- Simplify the leave of absence experience for employees
- Reduce the operational burden for employers, carriers, and TPAs
We are backed by Diagram Ventures and are working alongside insurance carriers to launch our MVP.
We are now looking for a senior technical leader to join as VP of Engineering, owning the technical foundation of the platform and helping shape its evolution from early product to scalable infrastructure.
Note: This is not an employment opportunity at Diagram, but a role within a new company launched through the Diagram venture studio.
What You’ll Do
As VP of Engineering, you will own technology and engineering from day one. Expect to:
- Technical accountability — Owning technology and engineering (architecture, reliability, security, and delivery, etc.).
- 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 are a senior technical leader who is comfortable owning both systems and teams.
- Proven builder — you’ve taken a product from 0→10 with full technical ownership.
- Data Management Expert — data management, ETL pipelines, data transformation, normalization, and synchronization across systems
- 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 VP of Engineering 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 — Work alongside other high-caliber founders with a validated roadmap.
- De-risked startup ride — traction already in place:
- Already established partners, investors and clients
- Product roadmap validated through extensive research during Diagram incubation
- Other strong co-founders already on board
- Unfair advantage — leverage a 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.