Chief of Staff - CEO

Iterative Health is a healthcare technology and services company powering the acceleration of clinical research to transform patient outcomes. We built a leading performance-driven network of 100+ sites across the US, Europe, India, and Australia, conducting research directly in the communities where care is delivered across gastrointestinal, hepatology, obesity, and cardiology. By combining deep clinical trial expertise with cutting-edge AI, we connect sponsors' scientific ambitions with high-performing research teams that expedite and expand access to novel therapeutics for patients in need. Today, Iterative Health is headquartered in Cambridge, Massachusetts, and New York City with 250+ employees world-wide. The Chief of Staff (CoS) 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, this role offers a unique, fast-track opportunity to grow into an executive leadership position. The CoS will lead high-impact, cross-functional initiatives and drive alignment across company operations, communications, and strategic business priorities. Success in this role requires the ability to navigate complex situations, manage competing priorities, and balance long-term strategic initiatives with immediate business needs. With broad visibility across the organization, the CoS will identify challenges, develop actionable solutions, and drive the execution of critical initiatives. This is an exceptional opportunity for a high-performing, strategic thinker who thrives in ambiguity, excels at turning strategy into action, and seeks accelerated exposure to executive-level decision-making. This position is hybrid and located in New York City Where You’ll Drive Impact • Serve as a trusted advisor and strategic thought partner to the CEO, helping prioritize, sequence, and execute the company’s most critical decisions and initiatives. Act as an extension of the CEO’s capacity by synthesizing information, anticipating challenges, and ensuring focus on the highest-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, ensuring clear messaging, alignment, and thorough preparation for key interactions. • Translate company strategy into actionable plans, ensuring alignment across teams on priorities, success metrics, timelines, and accountability. • Drive clarity and coordination across the organization to accelerate execution against key business objectives. • Lead and project manage high-impact, complex initiatives spanning clinical operations, site network growth, product development, commercial strategy, people operations, and other critical business functions. • Drive collaboration, resolve dependencies, and maintain momentum across multiple workstreams. • Structure complex analyses and conduct strategic research to distill business, market, and operational data into actionable insights. • Provide decision support for strategic opportunities, including market assessments, product expansion, partnership evaluations, and financial modeling, to improve the quality and speed of executive decision-making. • Identify opportunities to improve organizational effectiveness, streamline critical business workflows, and strengthen operating processes. • Develop frameworks, workflows, and playbooks that drive accountability, improve performance, and support the company’s continued growth and scale. • Ensure information flows seamlessly across teams and leadership, proactively identifying gaps, surfacing risks, and facilitating timely decisions. • Establish the structure and coordination needed to keep the CEO and leadership team informed, aligned, and prepared to address emerging business needs. • Operate effectively in a dynamic, fast-paced environment where priorities and responsibilities evolve with the needs of the business. • Shift seamlessly between long-term strategic initiatives, hands-on operational execution, and emerging priorities, taking ownership wherever the greatest organizational impact can be achieved. Areas of focus may vary over time based on business needs and in coordination with other Chiefs of Staff. • Performs related responsibilities as requested What You Bring to the Team • 6–8 years of experience in management consulting, strategy, business operations, or a comparable high-performance environment. • Strong business acumen required • Familiarity in healthcare, life sciences, digital health, or tech-enabled services is a strong plus • Proven ability to structure problems, build analytical frameworks, and generate concise, insight-rich recommendations. • Exceptional project management skills, with the ability to run multiple initiatives, align stakeholders, and drive outcomes independently. • Strong executive presence, with 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 our NYC or Cambridge office 2+ days per week. • Willingness to travel approximately 15% for customer, partner, or conference engagements. Preferred Qualifications • Experience in health-tech, clinical research, or AI-driven healthcare solution strong plus • Experience in external-facing roles, with the ability to represent the company professionally and build trusted relationships with external stakeholders, including investors, strategic partners, and customers. • Exposure to C-suite advising, board engagement, or executive-level decision support. • candidate or scaling startup or in an operator role. • Prior experience at a partner level in management consulting, in an operator role, or within a high-growth startup scaling its operations and business. • Experience leading or developing a small team. How We Work • Collaborative and low-ego team environment • High ownership and accountability culture • Fast-paced and highly iterative growth environment • Open communication and continuous learning mindset • Mission-driven organization focused on improving patient outcomes • Comfortable navigating evolving business priorities and opportunities Benefits That Support You We believe great teams do their best work when they feel supported — professionally and personally. • Hybrid work environment with in-office collaboration two days per week in either our NYC 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 • Health HSA or FSA options, and commuter FSA contributions supported by Iterative Health • Unlimited PTO, 12 company holidays, and a company-wide shutdown between Christmas and New Years • 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 to support your health and growth • And more! New York pay range $230,000—$270,000 USD At Iterative Health, we’re actively working towards creating an environment that is representative of the diversity of patients our technology serves. We are focused on building an equitable and inclusive culture, and by extension, hiring process. If you require any accommodations to make the application process or interviewing experience more accessible to you, please contact CandidateAccommodations@iterative.health.