Chief of Staff

About the role

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 eliminate surprise bills, poor quality, and high prices, while thriving in an entrepreneurial, cutting-edge environment, we would love to connect with you.

In 2014, Carrum reinvented the Centers of Excellence (COE) category in digital health. Today, 90% of the US population lives within 50 miles of a Carrum COE, and our providers rank in the top 10% nationally. Our team’s execution has been recognized by the venture community, with over $96M raised from investors like OMERS, Tiger Global Management, and Wildcat Ventures. Our impact has been externally proven in a 2021 RAND Corporation study and featured as a Harvard Business School case study.

The Chief of Staff (CoS) to the CEO reports directly to the CEO and will play a critical role in our success. As the strategic integrator of our leadership team, you will serve as the connective tissue between vision and execution. You are not just an advisor; you are the architect of our operating rhythm, maximizing the CEO’s impact and ensuring the organization moves as a single, high-velocity unit.

Responsibilities

• Expand CEO’s Execution Capacity
  • Act as a force multiplier for the CEO by distilling complex operational data, business unit updates, and pilot results into clear, executive-level briefings, enabling rapid, high-impact decision-making.
  • Serve as the internal liaison, crafting messaging on behalf of the CEO—from company-wide alignment memos to key commercial updates—ensuring the CEO’s strategic voice is consistently broadcasted without draining their time.
  • Act as a high-leverage proxy for the CEO on an as-needed basis, driving cross-functional alignment and unblocking high-priority initiatives to ensure leadership decisions are executed without requiring day-to-day oversight.
  • Lead high-stakes, cross-functional "no-man's-land" initiatives that require a neutral, senior leader to orchestrate success.
• Strategic Operations & Governance
  • 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.
  • Establish repeatable frameworks for how strategic decisions are made, documented, and communicated to ensure organizational clarity and speed.
  • Evolve ambiguous business needs into nuanced, data-driven dashboards that provide a "single source of truth" for company health and performance.
  • Serve as the "connective tissue" between leadership and the rest of the organization, identifying and addressing miscommunications and conflicts through a diplomatic, tactical, and empathetic approach.
• Strategy Execution & Accountability
  • Own the end-to-end process for company-wide OKRs, from inception to regular reporting, ensuring alignment at the department level.
  • Act as the primary "pulse-checker" for the business, identifying red flags in key initiatives early and working with department heads to ensure commitments are met.
  • Partner with the leadership team to scale AI-driven workflows across the enterprise, helping to "innovate and learn fast" by graduating experimental pilots into structured, company-wide rollouts to unlock measurable ROI.
  • Build internal AI capabilities by driving company-wide AI adoption, fostering technical literacy, and leading cultural change management to turn skepticism into empowered execution.

What excites you about this opportunity

• Hold the line on accountability by acting as the "conscience" of the leadership team, ensuring OKR progress and commitments never fall through the cracks.
• Facilitate high-level execution by designing the forums where our biggest decisions happen, ensuring the leadership team focuses on the right priorities at the right time.
• Solve the hardest puzzles by diving into complex, cross-functional projects that touch every corner of the company—from Product to Finance to Sales—and seeing them through to completion.

Requirements

• 10+ years of experience, preferably with prior experience at a growth-stage startup and at a consulting firm, with deep expertise in stakeholder and project management.
• A leader who can influence without positional authority, building deep trust and serving as the "connective tissue" between a CEO’s vision and daily operations.
• A systems thinker with 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.
• A high-velocity execution partner with 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.
• An AI evangelist who can architect a strategic roadmap to scale AI-driven workflows across an entire company while fostering a culture of technical fluency and psychological safety.

Benefits

• Stock option plan.
• Flexible schedules and remote work options, with offices available in Chicago and San Francisco.
• Self-managed vacation days, within reason.
• Paid parental leave.
• Health, vision, and dental insurance.
• 401K retirement plan.
• Collaborative and autonomous work environment with a focus on diversity, equity, inclusion, and justice (DEIJ), including active employee resource groups (ERGs).
• Opportunities to connect with coworkers both virtually and in-person, including social, educational, and community activities.

Pay

The salary range for this role is $225,000–$275,000, depending on geography and level of experience, plus generous equity and an annual bonus.

About Carrum

We’re a health tech company that brings value-based care to the masses. We help 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 in 2014, we’ve partnered with Fortune 500 employers and top hospitals across the nation. We’ve been recognized by Harvard Business School and featured in TechCrunch, The Los Angeles Times, Washington Post, and Modern Healthcare.