Chief of Staff

Building the financial operating system for healthcare, and bringing the joy back to healthcare by fixing the financial chaos behind it.

The healthcare payment system is a complex and inefficient maze - healthcare practices leave $125 billion in revenue uncollected each year, lost in the chaos of fragmented financial data, manual workflows, and opaque payer systems. This financial uncertainty leaves practices struggling to stay afloat, while valuable revenue slips through the cracks.

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 closed a funding round led by world-class investors and angels 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.

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. 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.

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. 
• 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. 

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. 

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.

The base pay range for this role is $175,000 – $210,000 per year.

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. 
• 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. 

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. 
• Bring a low-ego, high-ownership mindset to everything you touch. 

We’d love to hear from you if…

• 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. 
• 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’re 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. 

Working at Joyful

At Joyful Health, we’re on a mission to fix one of the most broken systems in healthcare.

Learn more about our culture and how we do work at Joyful here!

Joining us means having the opportunity to make a direct, meaningful impact on the lives of clinicians and the financial health of their practices.

👉 Read more about our values and how we operate here! [Public] How We Work Guide

Here’s what you can expect from working with us:

🚀 Meaningful Impact You’ll be tackling one of the most complex challenges in healthcare—helping practices thrive in a chaotic financial landscape. Your work will directly contribute to solving one of the most hair on fire problems for providers, ensuring that they can focus on what they do best: caring for patients.

🔑 Autonomy & Ownership As an early team member, you’ll have significant autonomy and the chance to shape our company from the ground up. You’ll have ownership over your work and the freedom to challenge the status quo in an environment that values initiative and creativity.

📈 Growth & Learning We’re a small, ambitious team with big goals, which means you’ll be constantly learning and growing. You’ll take on new challenges, expand your skill set, and have direct access to experienced founders and advisors who are invested in your development. We also offer stipends for professional development courses & books (that we often will partake in together!) so we can all continuously grow.

💰 Competitive Compensation & Equity We believe that our team is our most valuable asset. We offer competitive compensation packages, strong equity, and the opportunity to share in the success of Joyful Health. We want you to feel supported, both financially and professionally, as we grow together.

❤️ Be Your Best Self We provide the benefits you need to stay happy and healthy, including comprehensive healthcare benefits, unlimited PTO (with a minimum of 10 days off a year), and flexibility so you can take care of yourself. We also organize regular team off-sites and events to ensure that even as we tackle big problems we enjoy the journey.

 If you’re passionate about empowering practices and excited to tackle one of the most important (& challenging!) problems in healthcare, we’d love to meet you.

Please apply even if you don't meet 100% of the criteria. Nobody checks every box every time and we'd love to talk to you about how and why you can see yourself growing into this role. We're also very open to candidates with non-traditional experience.