Chief of Staff

Job Details

Position: Chief of Staff

Base Salary Range : $80-200k

Location: Chicago, IL

Work Style: In-Person

Headquartered in Chicago and founded in August 2023, we're redefining revenue cycle management with our AI‑driven Cofactor Denial Suite —a platform trained on millions of claims denial datapoints to automatically surface root-cause discrepancies, craft evidence-backed appeals, integrate with EHRs, and dramatically boost overturn rates while slashing hours of manual work per claim. Facing a 20.2% surge in denials (costing hospitals ~$20B/year in administrative waste) , our solution empowers providers to reclaim lost revenue, protect patients from surprise bills, and improve financial resilience. Backed by a $4M seed round led by Drive Capital —the Ohio-based firm founded by two ex‑Sequoia partners and known for backing Duolingo, Root, Olive, Greenlight, and others —Cofactor is scaling rapidly as the Midwest’s go‑to healthtech breakout.

You’ll join as Chief of Staff / Founding Operator / Executive Ops , functioning as the strategic co‑pilot to the CEO and leadership team. This is a high‑trust , high‑ownership role spanning strategic planning, operational cadences (leadership-syncs, functional stand-ups, KPI tracking), investor relations (board updates, fundraising prep), culture shaping, and embedded special projects—from standing up new functions to evaluating business lines. If ambiguity excites you, execution energizes you, and you’re eager to dive across GTM, People, Compliance, Ops, and Strategy in a lean, fast-moving startup, you’ll be driving conversion of vision into impact from day one—with Cofactor at the center of healthcare’s AI transformation.

Requirements

• Currently working in management consulting or venture
• Exceptional written and verbal communication skills with the ability to translate complex ideas across different audiences
• High "clock speed" - ability to think and execute quickly
• Organized, reliable, and proactive with a high ownership mindset
• Strong systems thinker with curiosity, a bias toward action, and meticulous attention to detail
• Strong judgment and discretion when handling sensitive information
• Proven ability to manage multiple competing priorities in a fast-paced environment and comfortable balancing strategic work with hands-on execution
• Self-starter who can identify and solve problems independently without constant direction
• Ability to build trust quickly with technical and business stakeholders
• Adaptability to a fast-paced startup environment
• Excellent meeting facilitation and project management skills
• Bonus: experience in AI or healthcare, high-compliance industries, and/or managing and training people

Benefits

• Health Care Plan (Medical, Dental & Vision)

• Retirement Plan (401k, IRA)
• Paid Time Off (Vacation, Sick & Public Holidays)
• Stock Option Plan