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

We’re living through a turning point for reproductive and sexual health—and Hey Jane is uniquely positioned to help. Since day one, we’ve been committed to providing safe, discreet medication abortion care, and we’ve helped more than 100,000 people access the treatment they need. Today, we deliver a range of reproductive and sexual health services right from your phone. Our in-house clinical team—board-certified physicians, advanced practice clinicians, nurses, and patient care advocates—is available just a text away. We’re dedicated to helping patients receive safe, discreet, judgment-free virtual care from a team that genuinely cares.

Role Overview
The Chief of Staff to the CEO will be an essential member of Hey Jane’s leadership team. You will own the company’s operating rhythm—planning cadence, leadership meeting flow, and all-hands coordination—and lead a small number of high-impact strategic initiatives. 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, either as a function head or as Chief of Staff.
– A clear, credible communicator: You translate complexity into alignment across functions and levels, from frontline teams to senior leaders and external stakeholders.
– High-EQ and adaptable: You quickly read the room, build trust, and hold multiple perspectives at once.
– Comfortable challenging the CEO: Especially on priorities, strategy, how time is allocated, org design, and execution quality.
– A systems thinker who can execute: You can move smoothly from high-level strategy to hands-on work.
– Committed to abortion access: Passionate about making healthcare radically accessible, even in a politically complex environment.
– Experienced: 6–12+ years total, including time as a function head or a senior operator at a high-growth company. Healthcare experience is a plus, but not required.

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.
– Lead high-stakes, cross-functional projects, including AI operations.
– Share information across the company and keep the CEO, leadership team, and broader organization aligned.
– Support investor communications and fundraising materials.
– Identify operational bottlenecks and recommend solutions to improve efficiency and workflows.
– Push back when necessary—challenging priorities, strategic direction, organizational 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 per year

At Hey Jane, we work toward equitable healthcare, changing the status quo, and improving how people experience healthcare—and we bring the same vision to our workplace. We’re an equal opportunity employer committed to building an inclusive environment, and we encourage applicants from all backgrounds and life experiences.