Chief of Staff to the CEO

Unless otherwise noted, all positions are fully remote with work permitted from the following states: CA, CO, IL, MA, MD, NJ, NY, OR, and WA.

We are living through a pivotal moment for reproductive and sexual health---and Hey Jane is uniquely positioned to help.

From day one, we've been committed to providing safe, discreet medication abortion treatment---and have helped more than 100,000 people get the care they need. Today, we offer a range of reproductive and sexual health care services from the comfort and convenience of your phone. Our in-house clinical care team, composed of board certified doctors, advanced practice clinicians, nurses, and patient care advocates, is just a text message away. We're committed to helping our patients get safe, discreet, judgment-free virtual health care, from a team that truly cares.

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.

Other Info

Reports to: CEO, Kiki Freedman

Compensation: $160-230K generous equity

Location: Remote from approved states

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.