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Swooped is a Talent Platform (not a staffing agency). We are not the employer for this role and do not make hiring decisions. Clicking "Apply" takes you to Swooped to review the role and hiring company details. About the Opportunity The organization lives and breathes the mission of transforming the healthcare system to create an unmatched experience for patients. If you are passionate about changing healthcare and want to finally get rid of surprise bills, poor quality, and high prices, while thriving in an entrepreneurial, cutting-edge environment, this role would be a great fit. The organization reinvented the Centers of Excellence (COE) category in digital health. Today, 90% of the US population lives within 50 miles of a COE and providers rank in the top 10% nationally. The team’s execution has been recognized by the venture community and has raised more than $96M in aggregate from investors. The impact has been externally proven in a study and featured as a case study. The Chief of Staff (CoS) to the CEO reports to the CEO and will play a critical role in the organization's success. The company has experienced tremendous growth in the last few years and is looking for someone with exceptional leadership talent and the ability to lead by influencing through respect and trust, rather than formal authority. The Chief of Staff is the strategic integrator of the leadership team, serving as the connective tissue between vision and execution. This role is not just an advisor; it is the architect of the organization's operating rhythm. The mission is to maximize the CEO’s impact and ensure the organization moves as a single, high-velocity unit. By bridging the gap between high-level strategy and daily operations, this role will ensure the organization's most ambitious goals don't just stay on a slide deck—they become reality. The salary range for this role is $225-$275k, depending on geography and level of experience, plus generous equity and annual bonus. Expand CEOs Execution Capacity Focus: Acting as a force multiplier for the CEO. Synthesis & Decision Readiness: Distill complex operational data, business unit updates, and pilot results into clear, executive-level briefings, moving the CEO directly from context-gathering to rapid, high-impact decision-making. Corporate Communication Liaison: Craft internal and external messaging on behalf of the CEO, ranging from company-wide alignment memos, All Hand Meeting messaging to key commercial updates, ensuring the CEO’s strategic voice is consistently broadcasted across the organization without draining their time. Force Multiplication & Execution: On an as-needed basis, act as a high-leverage proxy for the CEO, driving cross-functional alignment and unblocking high-priority initiatives to ensure leadership decisions are executed without requiring the CEO's day-to-day oversight. Lead High-Stakes Special Projects: Direct mission-critical, "no-man's-land" initiatives that require a neutral, senior leader to orchestrate success across multiple complex functions. Strategic Operations & Governance Focus: Architecting the systems, decision frameworks, and executive rhythm that allow the company to scale. Design the Operating Cadence: Architect and facilitate the rhythm of the business, from board prep and leadership offsites to bi-weekly C-team meetings, ensuring the team stays focused on the right priorities. Codify Decision-Making: Establish repeatable frameworks for how strategic decisions are made, documented, and communicated to ensure organizational clarity and speed. Maturity of Metrics: Work with the Data and other teams to evolve ambiguous business needs into nuanced, data-driven dashboards that provide a "single source of truth" for company health and performance. Drive Organizational Diplomacy: Serve as the "connective tissue" between the leadership and the rest of the organization, identify any organizational miscommunications and conflicts and address them head-on through a diplomatic, tactical, and empathetic approach. Strategy Execution & Accountability Focus: Owning the process for the North Star metrics and leading AI adoption company-wide. Own the Goal-Setting Lifecycle: Lead the annual end-to-end process for company-wide OKRs —from inception to regular reporting and ensuring alignment at the department level. Hold the Line on Accountability: Act as the primary "pulse-checker" for the business, identifying red flags in key initiatives early and working with department heads to ensure commitments never fall through the cracks. Disciplined AI Adoption & Operationalization: Partner with the leadership team to scale AI-driven workflows across the enterprise; help the organization ‘innovate and learn fast’ by graduating experimental pilots into structured, company-wide rollouts to unlock measurable ROI across all business units. Build Internal AI Capabilities: Partner with the leadership team to drive company-wide AI adoption by building hands-on technical literacy and leading the cultural change management needed to turn skepticism into empowered execution. You’re excited about this opportunity because you will... Hold the Line on Accountability: You’ll act as the "conscience" of the leadership team, keeping them honest about OKR progress and ensuring commitments never fall through the cracks. Facilitate High-Level Execution: You’ll design the forums where the organization's biggest decisions happen, ensuring the leadership team is focused on the right priorities at the right time. Solve the Hardest Puzzles: You’ll dive into complex, "no-man's-land" projects that touch every corner of the company—from Product to Finance to Sales—and see them through to the finish line. The organization is excited about you because… You have 10+ years of experience, preferably with prior experience at a growth-stage startup and at a consulting firm, with deep experience in stakeholder and project management. You are a leader who can influence without positional authority: You excel at building deep trust and serving as the "connective tissue" between a CEO’s vision and daily operations, ensuring ambitious goals are translated into measurable reality. You are a systems thinker: You have a proven track record of designing executive operating rhythms and repeatable decision-making frameworks that allow high-growth organizations to scale with clarity and speed. You are a high-velocity execution partner: You possess the "organizational diplomacy" to lead complex, cross-functional projects and the grit to hold leadership teams accountable for the full lifecycle of their OKRs and North Star metrics. You are an AI Evangelist: You don't just use AI; you can architect a strategic roadmap to scale AI-driven workflows across an entire company while fostering a culture of technical fluency and psychological safety. Why you’ll love working with this organization... The team is a hard-working, humble, and compassionate group motivated to solve the hard problems in healthcare today. You’ll work with talented, experienced co-workers from companies like Booz & Company, Livongo, 98point6, Google, and Optum. The organization believes in using data to inform decisions, technology to make jobs easier, and creative thinking to pave the future. The organization is working with some of the most recognized and esteemed names in the country. Top hospitals like Johns Hopkins, Mayo Clinic, Stanford Health Care, Scripps Health, and Rush Health have joined the platform. Employers who use the benefit include US Foods, United Airlines, and large public sector organizations like the self-insured schools of California, and the State of Maine. Team members are empowered to be autonomous and provided a collaborative environment where they receive support and healthy feedback. You can bring your authentic self to work every day and are encouraged to help others do the same. Time is carved out to let go of work to celebrate successes and have fun. This is a remote-first company with employees all over the United States and two office locations. The organization supports employees during the work day and beyond with flexible working hours, generous time off, paid parental leave, and opportunities to connect with coworkers both virtually and in-person. The organization embraces the team’s diversity of thought, experience, and interests and knows that doing so makes the company stronger. The organization has an active employee-led Diversity, Equity, Inclusion, and Justice (DEIJ) committee and several employee resource groups (ERGs). ERGs help employees build stronger connections through social, educational, and community activities. You’ll feel proud that the work you do each day directly impacts people’s lives in big and meaningful ways. Other benefits: Stock option plan Flexible schedules and remote work Chicago and San Francisco offices available Self-managed vacation days, within reason Paid parental leave Health, vision, and dental insurance 401K retirement plan About the Organization This is a health tech company that brings value-based care to the masses. It helps employers deliver a memorable patient experience, immediately lower healthcare costs, and drive better outcomes through the power of technology and human-centered design. Since launching, the organization has partnered with Fortune 500 employers and top hospitals across the nation. It has been recognized by Harvard Business School and featured in TechCrunch, The Los Angeles Times, Washington Post, and Modern Healthcare. The organization believes it's only scratching the surface of its opportunity and is looking for incredible people to help realize its full impact. The organization is an equal opportunity employer and encourages all applicants from every background and life experience.