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 areA 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.
Skills Required
- 6-12+ years of relevant experience in a senior operational role
- Experience designing and running an operating system
- Ability to challenge the CEO on prioritization and strategic direction
What We Do
Hey Jane is healthcare, on your own terms. As the most-trusted, most-funded virtual clinic offering telemedicine abortion care, we’re proudly putting the power back in people’s hands by providing care that’s private, safe, supportive, accessible, and convenient.
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