Chief of Staff to the CEO - Remote

22h22 hours ago

Hey Jane

Remote · Full-time · $160,000 – $230,000

About this role

The Chief of Staff to the CEO is a critical leadership role at Hey Jane, owning the company's operating system — planning rhythm, leadership cadence, and all-hands meetings. Reporting directly to CEO Kiki Freedman, you will drive a small number of high-stakes strategic projects while keeping the organization aligned and focused.

Day-to-day, you will own quarterly and annual planning end-to-end, organize leadership meeting agendas and follow-ups, and drive cross-functional projects including AI operations. You will move information across the company, ensuring the CEO, leadership, and broader team stay aligned.

You will work alongside an in-house clinical care team of board certified doctors, advanced practice clinicians, and patient care advocates dedicated to safe, discreet virtual healthcare. Hey Jane is fully remote for approved states and deeply committed to expanding reproductive and sexual health access.

This role offers the opportunity to shape strategic direction, challenge the CEO on prioritization and org design, and contribute to investor communications and fundraising materials. You will be a key partner in building the future of accessible healthcare.

Requirements

A builder who has designed and run an operating system at a company as a function head or Chief of Staff.
A crisp, credible communicator who turns complexity into clear alignment across functions and levels.
High-EQ and adaptable: reads the room, builds trust fast, and holds competing points of view.
Willing to challenge the CEO on prioritization, strategic direction, time allocation, org design, and execution quality.
A systems thinker who executes, moving from high-level strategy to rolling up sleeves seamlessly.
Committed to abortion access and creating radically accessible healthcare 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.

Responsibilities

Own quarterly and annual planning end-to-end, keeping 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 to keep the CEO, leadership, and broader team aligned.
Contribute to investor communications and fundraising materials.
Identify operational bottlenecks and propose solutions to improve efficiency and workflow.
Push back on prioritization, strategic direction, org decisions, and execution quality when it matters.

Benefits

Remote work permitted from approved states: CA, CO, IL, MA, MD, NJ, NY, OR, WA.
Generous equity package.
Competitive compensation range of $160,000–$230,000.
Opportunity to work with a passionate team advancing equitable reproductive and sexual healthcare.
Mission-driven culture committed to inclusivity and equal opportunity.