Technical Chief of Staff Cassidy | NYC, In-Office

Cassidy is an AI agent and automation platform that connects to the tools and knowledge a company already uses, turning repetitive work into automated workflows so people can focus on what actually matters. We're Series A and scaling fast.

The Role

The Technical Chief of Staff is our CTO's operational right hand — an owner, not a coordinator. Someone who picks up hard, ambiguous problems and independently solves them.

The Responsibilities

Operational leverage for the CTO. Own technical operations functions end-to-end. As the company grows, the scope grows with it.

• Manage technical vendor relationships and negotiations
• Own bug triage and engineering prioritization so nothing critical falls through the cracks
• Run our engineering hiring process

Technical credibility in commercial contexts. You'll represent Cassidy in commercial conversations where we need a technical voice, such as with enterprise buyers, security teams, and compliance auditors.

• Own security reviews and technical evaluations with enterprise customers
• Show up on sales calls as the technical voice when deals need one
• Lead compliance programs

Real product ownership. You'll PM product areas that sit at the core of how we operate and scale, working directly with engineers and owning outcomes.

• Own the internal admin dashboard and compliance tooling
• PM our pricing infrastructure
• Scope and spec features across these areas end-to-end

Who You Are

You have a technical foundation, like a CS background or enough engineering exposure that you're comfortable in the room and credible with the team. You don't need to write production code, but you need to think like someone who could have.

You're probably a few years into your career and you've been in a role where the problem space was ambiguous and the job was to figure it out anyway. Early-stage startup experience, product management, or technical operations would all translate well.

You're exceptionally organized and effective. You don’t build systems for their own sake, but nothing falls through cracks, decisions turn into outcomes, and the right people always have what they need.

If you're thinking about being a founder, a technical exec, or a product leader someday, this role is good preparation for that. You'll see how a technical org actually scales commercially, operationally, and structurally.