Chief of Staff

Our mission is to enable the best builders in the world to build in the U.S., no matter where they were born. We build technology that helps Silicon Valley's fastest-growing companies, incubators, and investors navigate immigration. More than half of Silicon Valley startups have at least one immigrant founder – and only by bridging the gap between talent and opportunity can we power innovation. Read more here, here, and here.

As Chief of Staff, you'll work directly with Lisa, CEO and founder, to run and scale Plymouth. You'll own major operational initiatives from day one, helping grow the business while building the systems that enable the company to scale.

Your two mandates are simple: grow our portfolio of exceptional clients and make the company run better every week. You'll operate strategically with customers and investors while also owning the operational details that determine whether the business succeeds.

This is an operating leadership role – not executive support. You'll be measured above all by what actually gets done.

Operational Leadership

• Take on major operational projects and own them end-to-end, reliably and independently.

• Build and run the company's operating rhythm: leadership meetings, planning cycles, goal-setting, and the follow-through that turns decisions into execution.

• Spot bottlenecks early and build systems that scale.

Growth & Thought Partnership

• Build relationships with top customers and investors while helping grow the business.

• Be the founder's thought partner – pressure-test ideas, challenge assumptions, and help make better decisions.

• Prepare the founder investor conversations, all-hands, and other high-stakes moments.

Execution & Special Projects

• Lead the company's highest-priority cross-functional initiatives, turning ambiguous problems into shipped outcomes across technology and operations functions.

• Build the analysis behind major decisions, including pricing, hiring, fundraising, and build-vs-buy.

• 2+ years in roles that reward ownership – operations, consulting, finance, startup leadership, or Chief of Staff.

• Equally comfortable thinking strategically and doing the operational work that keeps a business moving.

• A strong generalist who earns trust quickly with founders, customers, investors, and teammates.

• Detail-oriented and exceptionally reliable; when you own something, it gets done.

• Comfortable debating ideas with senior leaders and building the analysis that informs important decisions.

First 90 days: our planning and meeting rhythm runs with less of the founder's involvement, operational details stop slipping, you've delivered at least one project that changed a decision, and you've started to own a top-customer relationship.

First 6 months: you're a trusted operating partner the founder relies on daily, the go-to person across the team for getting hard things done, and clearly on track for broader functional or business leadership.

Plymouth is still small enough that one person can fundamentally shape the trajectory of the company, but established enough to work with many of Silicon Valley's fastest-growing startups from day one. You'll work directly alongside the founder, influence nearly every major decision, and help define how the company operates as it scales.