Chief of Staff to the CEO

    Up to $230,000/year
    Remote
    Full-Time
    Senior (7+ yrs)
    Operations & Project Management
    Leadership
    First posted 118 days ago

    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: Chief of Staff experience strongly preferred

    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.

    Company:  Hey Jane

    Virtual reproductive and sexual health clinic offering telemedicine abortion care and related services.
    11-50 employees
    Healthcare & Life Sciences
    HQ: United States