Chief of Staff to the CEO

Role Overview

The Chief of Staff to the CEO will be a critical member of Hey Jane's leadership team. You'll own the company's operating system — planning rhythm, leadership cadence, all-hands — and drive a small number of high-stakes strategic projects. You report directly to Kiki Freedman, Hey Jane's CEO.

You are

A builder. You've designed and run an operating system at a company before as a function head or Chief of Staff. 

A crisp, credible communicator: You turn complexity into clear alignment across functions and levels, from frontline teams to senior leaders to external stakeholders.

High-EQ and adaptable: You read the room, build trust fast, and hold competing points of view at once.

Willing to challenge the CEO: On prioritization, strategic direction, time allocation, org design, and execution quality.

A systems thinker who executes. You can move from high-level strategy to rolling up your sleeves seamlessly.

Committed to abortion access: Passionate about creating radically accessible healthcare, even in a politically complex environment

Experienced: 6–12+ years total, with time as head of a function, or senior operator at a high-growth company. Healthcare experience is a plus but not a requirement.

You will

• Own quarterly and annual planning end-to-end and keep the team focused on what matters.
• Organize and prioritize leadership meetings, agendas, and follow-up actions.
• Drive high-stakes, cross-functional projects including AI operations.
• Move information across the company. Keep the CEO, leadership, and the broader team aligned.
• Contribute to investor communications and fundraising materials.
• Identify operational bottlenecks and propose solutions to improve efficiency and workflow.
• Push back when it matters. You're expected to challenge prioritization, strategic direction, org decisions, and execution quality.