Chief of Staff - CEO

Iterative Health • New York City, NY

2d • Hybrid

About The Position

Iterative Health is a healthcare technology and services company that accelerates clinical research to improve patient outcomes. The Chief of Staff will serve as a trusted advisor, strategic partner, and problem solver to the CEO, helping shape and execute strategies that advance the company’s mission and drive business impact. As a member of the Executive Team, the role provides broad organizational visibility and an opportunity to grow toward an executive leadership position.

The Chief of Staff will lead high-impact, cross-functional initiatives and drive alignment across company operations, communications, and strategic priorities. The role calls for someone who can navigate complex situations, manage competing priorities, and balance long-term strategic work with immediate business needs. The Chief of Staff will identify organizational challenges, develop actionable solutions, and drive execution of critical initiatives. Areas of focus may change with business needs and in coordination with other Chiefs of Staff.

The position is hybrid, with work from either the New York City or Cambridge office at least two days per week, and approximately 15% travel for customer, partner, or conference engagements.

Requirements

• 6–8 years of experience in management consulting, strategy, business operations, or a comparable high-performance environment.
• Strong business acumen.
• Ability to structure problems, build analytical frameworks, and generate concise, insight-rich recommendations.
• Exceptional project management skills, including the ability to run multiple initiatives, align stakeholders, and drive outcomes independently.
• Strong executive presence and the ability to earn trust quickly and communicate with clarity and influence.
• Experience thriving in fast-paced, high-growth, ambiguous environments.
• Willingness to work from the New York City or Cambridge office at least two days per week.
• Willingness to travel approximately 15% for customer, partner, or conference engagements.

Nice To Haves

• Familiarity with healthcare, life sciences, digital health, or tech-enabled services.
• Experience in health tech, clinical research, or AI-driven healthcare solutions.
• Experience in external-facing roles representing a company and building relationships with investors, strategic partners, and customers.
• Exposure to C-suite advising, Board engagement, or executive-level decision support.
• Prior experience at partner level in management consulting, in an operator role, or at a high-growth startup scaling its operations and business.
• Experience leading or developing a small team.

Responsibilities

• Serve as a trusted advisor and strategic thought partner to the CEO, helping prioritize, sequence, and execute critical decisions and initiatives.
• Extend the CEO’s capacity by synthesizing information, anticipating challenges, and focusing attention on high-impact opportunities.
• Develop executive communications, Board narratives, leadership offsites, and strategic briefings.
• Support the CEO’s engagement with employees, Board members, investors, partners, and key customers through clear messaging, alignment, and preparation.
• Translate company strategy into actionable plans, aligning teams on priorities, success metrics, timelines, and accountability.
• Drive clarity and coordination across the organization to accelerate execution against business objectives.
• Lead and project-manage complex initiatives across areas including clinical operations, site network growth, product development, commercial strategy, and people operations.
• Drive collaboration, resolve dependencies, and maintain momentum across multiple workstreams.
• Structure complex analyses and conduct strategic research to turn business, market, and operational data into actionable insights.
• Provide decision support for strategic opportunities, including market assessments, product expansion, partnership evaluations, and financial modeling.
• Identify opportunities to improve organizational effectiveness, streamline workflows, and strengthen operating processes.
• Develop frameworks, workflows, and playbooks that promote accountability, improve performance, and support growth.
• Ensure information flows across teams and leadership; identify gaps, surface risks, and facilitate timely decisions.
• Establish coordination to keep the CEO and leadership team informed, aligned, and prepared for emerging business needs.
• Adapt to changing priorities, shifting between strategic initiatives, hands-on operational execution, and emerging needs, and take ownership where organizational impact is greatest.
• Perform related responsibilities as requested.

Benefits

• Hybrid work environment with in-office collaboration two days per week in either the New York City or Cambridge office.
• Comprehensive medical, dental, and vision coverage, with up to 80% of premiums covered by Iterative Health.
• Mental health and wellness support through Spring Health.
• HSA or FSA options and supported commuter FSA contributions.
• Unlimited PTO, 12 company holidays, and a company-wide shutdown between Christmas and New Year’s.
• 401(k) program with a company match of up to 3% (up to $3,000 annually).
• Weekly in-office lunch benefit every Tuesday.
• 100% company-paid short-term and long-term disability coverage.
• Annual wellness and professional development stipend.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed