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.
- 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.
- 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.
Requirements
- 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).
- Strong generalist with analytical depth, including comfort with financial models, metrics, and data-informed decision-making.
- 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.
- Operations and systems builder at heart: You don't just execute—you build the scaffolding that makes execution repeatable.
- 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 Have
- Previous Chief of Staff experience
Benefits
- Meaningful Impact
- Autonomy & Ownership
- Growth & Learning
- Competitive Compensation & Equity
- Be Your Best Self
Additional Information
- NYC-based who can be in the office ~3 days per week.
- Comprehensive healthcare benefits, unlimited PTO (with a minimum of 10 days off a year), and flexibility so you can take care of yourself.
- Regular team off-sites and events to ensure that even as we tackle big problems we enjoy the journey.
