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.

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 and we’ve raised more than $96M in aggregate 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 (HBS) case study.

The Chief of Staff (CoS) to the CEO reports to the CEO and will play a critical role in our success. We’ve experienced tremendous growth in the last few years and we’re 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 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. By bridging the gap between high-level strategy and daily operations, you will ensure our most ambitious goals don't just stay on a slide deck—they become our 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 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 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 andthe rest of the org, identify any organizational miscommunications and conflicts and address them head-on through, diplomatic, tactical, and empathetic approach.

Strategy Execution & Accountability

Focus: Owning 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 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

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 us honest about our OKR progress and ensuring commitments never fall through the cracks.

• Facilitate High-Level Execution: You’ll design the forums where our 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.

We’re excited about you because…

• You have 10+ years experience, preferably with prior experience at a growth-stage startup and at a consulting firm, 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 us...

• We’re 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. We believe in using data to inform decisions, technology to make our jobs easier, and creative thinking to pave the future.

• We are 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 our platform. Employers who use our benefit include US Foods, United Airlines, and large public sector organizations like the self-insured schools of California, and the State of Maine.

• We empower team members to be autonomous and provide a collaborative environment where you get support and healthy feedback. You can bring your authentic self to work every day and are encouraged to help others do the same.

• 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 support our 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.

• We embrace our team’s diversity of thought, experience, and interests and know that doing so makes us stronger as a company. Carrum has an active employee-led Diversity, Equity, Inclusion, and Justice (DEIJ) committee and several employee resource groups (ERGs). Our 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 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 and achieve this 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. We believe we’re only scratching the surface of our opportunity and we’re looking for incredible people like you to help us realize our full impact.

Carrum Health is an equal opportunity employer and encourages all applicants from every background and life experience.