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Role Description

We are seeking a high-trust, high-output Chief of Staff to join our team. In this role, you will serve as the "execution engine" for the COO - translating strategic priorities into coordinated action, owning cross-functional project delivery, and ensuring the leadership team is aligned, accountable, and moving at an AI-accelerated pace.

Key Responsibilities

• Executive Operations & Force Multiplication:
  • Serve as the primary operational partner to the COO; manage priorities, prepare decision-ready briefs, and own the executive meeting cadence (agenda architecture, pre-reads, and aggressive action tracking) to ensure no detail falls through the cracks.
• Cross-Functional Project Ownership:
  • Drive the accountability layer across COO-sponsored initiatives—from automation task force workstreams to company-wide operational pivots—identifying blockers and surfacing risks before timelines slip.
• AI & Automation Enablement:
  • Act as an AI-first champion by using tools like Claude and ChatGPT to accelerate workflows, documenting automation decisions, and identifying operational friction points that can be reduced through technology.
• Team Leadership & Internal Communications:
  • Directly manage the Executive Assistant (EA) function and partner with department heads to ensure consistent messaging and operational clarity across all business units.
  • Maintain compliance with company policies and applicable regulations.
  • Perform other duties as assigned.

The Impact You’ll Make

• Strategic Execution: You will own the tracking and accountability for COO-sponsored initiatives, ensuring cross-functional projects across Engineering, Clinical, and Sales stay on trajectory.
• Executive Operations: You’ll manage the COO’s priorities, prepare decision-ready briefs, and act as a proxy in key meetings to ensure momentum never stalls.
• Team Leadership: You will direct our Executive Assistant (EA) function, mentoring the team and ensuring our administrative operations are world-class.
• AI Advocacy: You will identify operational friction points and work with our internal task forces to solve them through automation and AI-driven workflows.

Qualifications

• 5+ years of experience in a Chief of Staff, senior operations, strategy, or executive program management role.
• Demonstrated ability to manage complex, multi-stakeholder initiatives end-to-end with minimal oversight.
• AI Fluency: Genuine enthusiasm for and professional experience using AI tools (ChatGPT, Claude, etc.) as a core productivity multiplier.
• Strong communication and organizational skills, with the ability to write crisp executive memos and detailed project plans.

Preferred Qualifications

• Experience in healthcare SaaS, digital health, or a similarly regulated industry.
• Prior experience supporting a C-suite executive at a growth-stage company.
• Experience managing EA functions or administrative teams.
• MBA or equivalent graduate degree.

Compensation & Benefits

• Competitive base pay: $100,000 – $150,000 annually.
• Performance-Based Bonus: Eligible for an annual bonus based on company and individual performance.
• Benefits Include:
  • Unlimited PTO
  • Medical, Dental, Vision, and supplemental insurance options
  • 401(k) Plan with 3.5% Company Match
  • Company-provided equipment

Company Description

At Nsight Health, you’ll be part of a fast-growing organization that sits at the intersection of healthcare, technology, and compassion. We’re looking for people who care deeply about improving patient lives and building the future of connected care.

Our team culture is collaborative, agile, and purpose-driven. Every role—from clinical operations and customer success to marketing, technology, and leadership—directly contributes to improving how healthcare organizations care for their patients.