Chief of Staff

Role Description

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.

What this role is

• 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.
• Hightly 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.

What this role is not

• 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.

What You’ll Do...

• 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.
• Multiply Execution Across The Company
• 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.
• Cookordination 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.
• Strengthen Joyful’s operating foundations
• 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.
• Do the work that needs doing
• Jump into whatever is most important for the company that week — whether strategic or executional.
• Some work will be high-level and strategic; some will be hands-on and operational.
• 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.
• Support on hiring for senior and high-impact roles, an help ensure the organization scales in a healthy, intentional way.

Qualifications

• You’re deeply aligned with Joyful Health’s mission and motivated by fixing broken systems in healthcare.
• You have 7–10+ years of experience, with previous Chief of Staff experience preferred, or experience in similarly scoped roles (e.g. strategy & ops, consulting, investing, early-stage operator).
• You’re a strong generalist with analytical depth, including comfort with financial models, metrics, and data-informed decision-making.
• You thrive in fast-moving, ambiguous environments and enjoy bringing clarity to chaos.
• You have exceptional capacity for context switching and can move between hiring, strategy, operations, and execution without dropping the ball.
• You have strong judgment and discretion and are comfortable operating in a high-trust role.
• You communicate exceptionally well — clear, thoughtful, and tailored to your audience.
• You feel comfortable communicating well in all mediums, whether it’s an investor update, board deck, sales proposal, customer email, or internal update.
• You are an 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.
• You are ambitious, low-ego, and highly proactive — willing to do whatever helps the company succeed.
• You have high emotional intelligence and strong presence — you can represent the company thoughtfully and credibly in a wide range of settings.
• You exercise excellent judgment under ambiguity and know when to move independently vs. when to pull others in.