Chief of Staff to the CEO

Role Description

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.

• 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.

Requirements

• Reports to: CEO, Kiki Freedman
• Compensation: $160-230K + generous equity
• Location: Remote from approved states

Benefits

• $160,000 - $230,000 a year

Company Description

At Hey Jane, we work towards the vision of having equitable healthcare, changing the status quo, and rebuilding the way people experience healthcare—and bring that same vision to our workplace. We’re an equal opportunity employer committed to building an inclusive environment, and encourage all applicants from every background and life experience.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.