Chief of Staff

Carrum Health•,

17d•$225,000 - $275,000•Remote

About The Position

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. 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.

Requirements

10+ years experience, preferably with prior experience at a growth-stage startup and at a consulting firm, deep experience in stakeholder and project management
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.
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.
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.
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.

Responsibilities

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.
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.
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.
Direct mission-critical, "no-man's-land" initiatives that require a neutral, senior leader to orchestrate success across multiple complex functions.
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.
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.
Serve as the "connective tissue" between the leadership and the rest of the org, identify any organizational miscommunications and conflicts and address them head-on through, diplomatic, tactical, and empathetic approach.
Lead the annual end-to-end process for company-wide OKRs —from inception to regular reporting and 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 never fall through the cracks.
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.
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.