Chief of Staff

At Carrum, we live and breathe 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, we would love to connect with you. Chief of Staff (CoS) to the CEO The Chief of Staff is the strategic integrator of our leadership team, serving as the connective tissue between vision and execution. You aren't just an advisor; you are the architect of our operating rhythm. Your mission is to maximize the CEO's impact and ensure the organization moves as a single, high‑velocity unit. Expand CEOs Execution Capacity 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‑leveraged 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 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 our 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 miscommunications and conflicts and address them head‑on through a diplomatic, tactical, and empathetic approach. Strategy Execution & Accountability 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 us “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 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. Salary $225‑$275k, depending on geography and level of experience, plus generous equity and annual bonus. Why You’ll Love Working With Us We’re a hard‑working, humble, and compassionate group motivated to solve the hard problems in healthcare today. We are working with some of the most recognized and esteemed names in the country. We empower team members to be autonomous and provide a collaborative environment where you get support and healthy feedback. We carve out time to let go of work to celebrate our successes and have fun. We’re a remote‑first company with employees all over the United States and two office locations in San Francisco and Chicago. We embrace our team’s diversity of thought, experience, and interests. 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 Equal Opportunity Statement Carrum Health is an equal opportunity employer and encourages all applicants from every background and life experience. #J-18808-Ljbffr