Job description

Company Overview

At Carrum Health, we are committed to revolutionizing the healthcare system to provide an unparalleled experience for patients, eliminating surprise bills, improving quality, and reducing costs. Founded in 2014, Carrum has redefined the Centers of Excellence category in digital health, with providers ranking in the top 10% nationally and significant venture capital backing. Our impact is validated by studies such as the RAND Corporation's and featured as a Harvard Business School case study.

Role Summary

The Chief of Staff (CoS) reports directly to the CEO and is integral to driving company-wide execution and strategic integration. This role acts as the CEO’s multiplier, ensuring alignment across teams and transforming strategic plans into measurable results. The position involves orchestrating the executive operating rhythm, managing key projects, and leading strategic initiatives, including broad AI adoption.

Key Responsibilities

Distill complex business data and updates into succinct executive briefings to enable rapid CEO decision-making.
Develop and disseminate company-wide messaging on behalf of the CEO to ensure consistent strategic communication.
Serve as a proxy for the CEO to drive cross-functional alignment and unblock priority initiatives.
Lead critical, multi-departmental projects requiring senior leadership coordination.
Design and facilitate the company’s operational cadence including leadership meetings, board preparations, and offsites.
Create repeatable frameworks for strategic decision-making to foster clarity and speed.
Collaborate with data teams to build clear, actionable dashboards representing company performance.
Address organizational conflicts and miscommunications through diplomatic and tactical engagement.
Manage the company-wide OKR lifecycle, from goal-setting to progress reporting and departmental alignment.
Monitor accountability across teams to proactively identify and resolve issues threatening commitments.
Lead the scaling of AI-driven workflows, transitioning pilots into full company-wide implementation.
Promote tech literacy and cultural adoption of AI across the organization to empower effective usage.

Candidate Profile

Minimum of 10 years of experience, ideally including growth-stage startup and consulting firm environments.
Proven leadership skills with the ability to influence without formal authority and build trust across teams.
Expertise in designing operational systems and executive frameworks for high-growth companies.
Strong project management capabilities with diplomacy to manage complex, cross-functional initiatives.
Passion for AI technology, with experience in strategic AI workflow implementation and organizational change management.

Why Join Carrum Health?

Work alongside a talented and supportive team committed to solving healthcare challenges.
Collaborate with nationally recognized hospitals and major employers through the platform.
Enjoy a remote-first culture with flexible hours, generous time off, parental leave, and supportive policies.
Participate in a diverse, inclusive work environment with active employee resource groups and DEIJ initiatives.
Experience the impact of your work on improving lives and transforming healthcare delivery.

Compensation and Benefits

Salary range of $225,000 to $275,000, varying by location and experience.
Equity participation and an annual performance bonus.
Stock option program.
Flexible schedules and remote work opportunities.
Office locations in Chicago and San Francisco available.
Self-managed vacation policy within reason.
Paid parental leave.
Health, dental, and vision insurance.
401(k) retirement plan.

Chief of Staff