Chief of Staff

This is a rare opportunity to work hand in hand with the CEO of a fast-growing, mission-driven health tech company.

As Chief of Staff, you will be a central participant in Pearl Health’s most important decisions and a trusted partner to the CEO and Management team, shaping priorities, driving execution, and translating strategy into action. This is not a “watch from the sidelines” role: you’ll have a true seat at the table with real ownership and impact, while also remaining deeply hands-on, building plans, solving problems, and driving initiatives forward.

Backed by world-class investors and tackling one of healthcare’s hardest problems, Pearl offers a unique chance to help build something meaningful and to learn how a company is truly led.

Pearl Health is dedicated to empowering primary care providers, health systems, and physician-led networks to succeed in the shift to value-based care. Our platform delivers the technology, financial tools, and expert services that enable practices to provide more proactive, effective care to their Medicare patients, ultimately lowering costs and improving health outcomes.

Founded in 2020, we are a team of healthcare and technology innovators backed by premier investors like Andreessen Horowitz, Viking Global Investors, and AlleyCorp. We partner with thousands of providers across 44 states to build a more sustainable future for American healthcare.

• Serve as a trusted partner to the CEO, shaping priorities, ensuring focus on the highest-impact work, and preparing him for critical decisions, meetings, and external engagements

• Assist the CEO in managing his direct reports and key initiatives, ensuring strong preparation, clear follow-up on action items, and continuity across regular check-ins

• Plan and run core leadership processes, including planning cycles, OKR development, and key leadership meetings

• At the direction of the CEO, lead or execute on special projects and strategic initiatives across the company, in close partnership with relevant department leaders e.g. fundraising, performance management, executive hiring, public relations, strategic opportunities etc.

• Assist in building and managing relationships with our Board, clients, and colleagues

• Own the end-to-end development of Board and investor materials, coordinating leadership inputs and synthesizing them into a clear, compelling narrative

• Design and run leadership offsites and key in-person moments to ensure time together drives alignment, decisions, and momentum

• Operate as a hands-on leader, stepping in to solve problems, unblock teams, and drive execution where needed

• 4+ years of experience in a high-intensity environment such as top management consulting (MBB), investment banking, private equity, venture-backed technology companies, or similar

• Bachelor's degree required; MBA or other advanced degree a plus

• Low-ego, high-ownership mindset; willing to do whatever moves the business forward

• Strong emotional intelligence, with an intuitive ability to build credibility and relationships

• High judgement and trustworthiness

• Structured thinker who can break down complex problems and drive clarity

• Comfortable operating with incomplete information and navigating evolving priorities

• Highly organized and detail-oriented, able to handle multiple deadlines, projects, and stakeholders simultaneously

• Strong judgment and thoughtful discretion; able to be trusted with sensitive information

• Background in healthcare preferred but not required

This role is based in our NYC office and is intentionally in-person. The Chief of Staff is at the center of how the company operates, and the work is most effective when done side-by-side with the CEO and team.

We’re seeking someone who enjoys being in the office, values real-time collaboration, and wants to be fully immersed in the company’s rhythm. Some travel will be required.

🤝 Collaborate to Innovate: We believe the best solutions arise from intelligent teamwork. We trust the expertise of our teammates and pursue opportunities to learn and grow from each other. By embracing diverse perspectives and encouraging authenticity, we create and evangelize groundbreaking health solutions.

🗣️ Trust Through Transparency: We prioritize transparency in all our interactions, ensuring that employees, patients, clinicians, and partners have access to the information they need to make informed decisions. Integrity is at the core of how we operate.

❤️ Serious Impact, Big Heart: We go above and beyond to empower proactive, patient-centered care — and we celebrate every step forward. Humor and positivity fuel our creativity and strengthen relationships.

We are an Equal Opportunity Employer on a mission to improve lives. Our strength comes from the diverse backgrounds, experiences, and perspectives of our team. We welcome all candidates and are committed to a fair, inclusive hiring process free from discrimination.

The expected offer for this role includes the following components:

• Base Salary Range: $180,000 - $230,000 per year.

• Additional Compensation: This role is eligible for a discretionary performance bonus and equity options.

• Benefits: We offer a competitive benefits package. You can learn more on our benefits page.

Final compensation for this role will be determined by a variety of factors, including a candidate's relevant skills, experience, labor market conditions, and location.

We are not currently working with contingency search firms. If a resume is submitted to any Pearl Health employee by a third party without a valid written and signed search agreement, it will become the property of Pearl Health and no fee will be paid, irrespective of whether the candidate is hired.

While steps may vary by role, you can typically expect:

• Recruiter Screen: Introductory call to discuss background and motivation

• Hiring Manager Interview: Deep-dive conversation with a core member of the team

• Panel Interview: Meetings with teammates and cross-functional partners

• Case Assignment / Presentation: Practical exercise solving a real-world challenge

• Executive Interview: Final conversation(s) with 1–2 members of our leadership team