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 $160,000 - $230,000 a year 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.