Chief of Staff

Joyful Health•New York City, NY

6d•Hybrid

About The Position

Joyful Health is building the AI-powered financial operating system for healthcare practices. Our mission is to bring the joy back to running a private practice by simplifying financial operations so providers can focus on patient care. We spent 10 months working as fractional CFOs for a dozen practices, doing this work side by side with providers as we developed our product. We just announced our $22M Series A led by CRV and world-class investors including the founders of MongoDB & KAYAK. We have an enormous opportunity in front of us. The broken healthcare payment ecosystem impacts practices of all sizes, and the opportunity to make a real difference is massive. We’re looking for a Chief of Staff to partner closely with our CEO and leadership team as Joyful Health scales. This is a senior, high-impact role, ideally for someone with prior Chief of Staff experience or experience operating in similarly broad, high-leverage roles. You’ll act as a force multiplier for the CEO and for the company — helping set direction, drive execution, and ensure that the most important work gets done exceptionally well. You’ll effectively run an “Office of the CEO” — maintaining context across priorities, decisions, hiring, and key initiatives so nothing slips through the cracks. This role has a seat at the table and operates with a high degree of trust and autonomy. Highly versatile: On any given day, this role might involve anything from supporting hiring and leadership planning, pressure-testing product or GTM strategy, helping move an enterprise deal forward, or driving a cross-functional initiative that helps the company function better. This is a leadership role with wide scope and high expectations — and it’s also one of the fastest ways to grow as an operator. You’ll gain a front-row seat and will be an active partner in building and scaling a company: product decisions, hiring, fundraising, GTM, and operational tradeoffs. Externally facing: This role requires high emotional intelligence and strong judgment. You’ll regularly represent Joyful — and the CEO — in internal and external contexts, including with partners, candidates, customers, and investors. We’re looking for someone who can build trust quickly, read the room, and act with the same care and thoughtfulness as the leadership team. This is not an Executive Assistant role, and it’s not a role focused solely on “special projects.” The core of the job is building leverage, operating systems, and alignment as we grow. We’re deeply invested in your growth and will support you in getting where you want to go. This role is especially well-suited for someone who wants to start a company one day or grow into senior leadership and wants to see the full picture — not just one function. This role is full-time. We’re looking for someone NYC-based who can be in the office ~3 days per week.

Requirements

Deeply aligned with Joyful Health’s mission and motivated by fixing broken systems in healthcare.
7–10+ years of experience
Previous Chief of Staff experience preferred, or experience in similarly scoped roles (e.g. strategy & ops, consulting, investing, early-stage operator).
Strong generalist with analytical depth, including comfort with financial models, metrics, and data-informed decision-making.
Thrive in fast-moving, ambiguous environments and enjoy bringing clarity to chaos.
Exceptional capacity for context switching and can move between hiring, strategy, operations, and execution without dropping the ball.
Strong judgment and discretion and are comfortable operating in a high-trust role.
Communicate exceptionally well — clear, thoughtful, and tailored to your audience.
Comfortable communicating well in all mediums, whether it’s an investor update, board deck, sales proposal, customer email, or internal update.
Operations and systems builder at heart: You don't just execute—you build the scaffolding that makes execution repeatable. You see a messy process and instinctively create structure around it.
Ambitious, low-ego, and highly proactive — willing to do whatever helps the company succeed.
High emotional intelligence and strong presence — you can represent the company thoughtfully and credibly in a wide range of settings.
Exercise excellent judgment under ambiguity and know when to move independently vs. when to pull others in.

Nice To Haves

Previous Chief of Staff experience
Experience operating in similarly broad, high-leverage roles (e.g. strategy & ops, consulting, investing, early-stage operator)
Non-traditional experience

Responsibilities

Partner closely with the CEO as a thought partner on company-wide priorities, decision-making, and execution - making sure that their time is focused on the most impactful and highest-leverage priorities.
Maintain full context on what’s in flight across the business — key initiatives, hires, deals, risks — and ensure nothing important slips.
Prepare for board meetings, leadership discussions, and high-stakes external conversations.
Draft internal and external communications on behalf of the CEO with a high bar for clarity and judgment.
Anticipate priorities, surface blockers early, and help the CEO show up prepared and focused.
Own and drive cross-functional initiatives across product, engineering, RCM, GTM, and operations.
Build systems to track, triage, and address important work as we scale the team and add new functions.
Coordinate projects that span across multiple teams and cut operating inefficiencies wherever you find them.
Translate strategy into concrete plans with clear goals, timelines, and owners.
Unblock teams, resolve dependencies, and keep momentum high.
Step into ambiguous problems, diagnose what’s needed, and drive solutions forward.
Help build and refine core operating rhythms (planning, goal-setting, leadership meetings, retros).
Stand up and maintain company-wide goals and metrics, ensuring progress is visible through scorecards, dashboards, and regular reviews.
Identify where the company needs more structure and design lightweight, scalable systems to support growth.
Bring analytical rigor to prioritization and tradeoffs, using data and financial insight to inform decisions.
Jump into whatever is most important for the company that week — whether strategic or executional.
Support on hiring for senior and high-impact roles, and help ensure the organization scales in a healthy, intentional way.
Bring a low-ego, high-ownership mindset to everything you touch.