Chief of Staff

Role Description

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.

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. Your mission is to maximize the CEO’s impact and ensure the organization moves as a single, high-velocity unit.

• 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.
• Internal Liaison: Craft messaging on behalf of the CEO, ensuring the CEO’s strategic voice is consistently broadcasted across the organization.
• Force Multiplication & Execution: Act as a high-leverage proxy for the CEO, driving cross-functional alignment.
• Lead High-Stakes Special Projects: Direct mission-critical initiatives that require a neutral, senior leader.
• 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.
• Codify Decision-Making: Establish repeatable frameworks for strategic decisions.
• Maturity of Metrics: Work with teams to evolve ambiguous business needs into data-driven dashboards.
• Drive Organizational Diplomacy: Serve as the "connective tissue" between leadership and the rest of the organization.
• 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.
• Hold the Line on Accountability: Act as the primary "pulse-checker" for the business.
• Disciplined AI Adoption & Operationalization: Partner with the leadership team to scale AI-driven workflows.
• Build Internal AI Capabilities: Drive company-wide AI adoption and cultural change management.

Qualifications

• 10+ years experience, preferably with prior experience at a growth-stage startup and at a consulting firm.
• Ability to influence without positional authority.
• Proven track record of designing executive operating rhythms and repeatable decision-making frameworks.
• Strong organizational diplomacy to lead complex, cross-functional projects.
• Ability to architect a strategic roadmap to scale AI-driven workflows.

Requirements

• Experience in stakeholder and project management.
• Ability to build deep trust and serve as the "connective tissue" between a CEO’s vision and daily operations.
• Grit to hold leadership teams accountable for the full lifecycle of their OKRs and North Star metrics.

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.

Company Description

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 technology and human-centered design.

• Recognized by Harvard Business School.
• Featured in TechCrunch, The Los Angeles Times, Washington Post, and Modern Healthcare.
• Partnered with Fortune 500 employers and top hospitals across the nation.