Chief of Staff

About Parachute Health

Parachute Health is revolutionizing post-acute care through its leading digital ordering platform for medical equipment and supplies. Connecting extensive networks of clinicians, health plans, and suppliers nationwide, it enables patients to receive essential medical products at home. Since inception, Parachute Health has engaged over 300,000 clinicians and 3,000 supplier points across all 50 states, assisting over 15 million patients. The platform, initially focused on durable medical equipment ePrescribing, has evolved into the preferred order management system for home healthcare equipment.

Role Summary

The Chief of Staff will serve as the strategic partner and proxy to the CEO, acting as the central operational force facilitating executive agenda progression and leadership alignment amid a significant AI-driven transformation. This prominent role requires exceptional operational acumen, entrepreneurial mindset, persuasive leadership without formal authority, and uncompromising organizational rigor to translate broad vision into seamless execution.

Key Responsibilities

• Lead the Executive Operating System by managing the leadership team’s cadence, maintaining the master execution tracker, and enforcing stringent accountability to ensure timely achievement of strategic milestones.
• Support the CEO in decision-making by preparing clear options with recommendations, managing communication flow, and representing the CEO’s perspectives in various forums, including drafting pivotal communications.
• Serve as a diplomatic liaison among the CEO, executives, and board members, resolving conflicts, securing consensus, and motivating teams without direct control.
• Tackle urgent, complex, or ambiguous challenges, including market pivots, critical partnerships, and operational crises, by personally addressing and scaling solutions.
• Ensure the executive team is comprehensively prepared and strategically aligned for high-stakes meetings with prominent health systems, payors, and suppliers.
• Translate innovative product and vertical strategies into structured experiments by organizing cross-functional tiger teams to prototype, test hypotheses, and pilot initiatives efficiently before resource commitment.

Candidate Profile

• Entrepreneurial mindset with ownership thinking demonstrated by founding startups, being key hires during hyper-growth phases, or leading significant business units.
• Minimum 10 years of professional experience spanning operations, strategy, and execution roles such as Chief of Staff, business operations leadership, top-tier consulting, or operational leadership in growth-stage companies.
• Exceptional leadership presence coupled with emotional intelligence to engage, challenge, and build rapid trust with senior leaders, while valuing team achievements.
• High-level organizational skills with the ability to juggle multiple priorities, foresee obstacles, and maintain flawless execution.
• Expertise in AI-native environments, including fluency with AI tools and comfort in operating within a data-driven, autonomous, and collaborative organizational framework.
• Outstanding written and analytical communication abilities to convert complex, multifaceted problems into clear, actionable documentation and presentations.
• Resilience in fast-paced, dynamic settings with decisive action orientation, comfortable managing evolving priorities and uncertainties.
• Experience in healthcare, regulated sectors, or B2B SaaS environments is highly advantageous.

Benefits

• Comprehensive medical, dental, and vision insurance plans with options for minimal or no premiums.
• Employer contributions to Health Savings Account (HSA).
• 401(k) retirement plan.
• Equity participation opportunities.
• Company-wide annual bonus eligibility of up to 15%, tied to organizational performance.
• Remote-first culture with a designated NYC office and coworking space reimbursement options.
• Flexible vacation policy along with five additional summer Fridays off.
• Home office and wellness stipends.
• Monthly internet reimbursement.
• Annual learning and professional development stipend.

Additional Information

Salary range for this position is approximately $200,000 to $275,000 per year, adjusted based on experience and seniority. This position is not eligible for employer-sponsored visa support; candidates must be authorized to work in the United States throughout employment. The company is committed to equal opportunity employment and prohibits discrimination based on any legally protected characteristics. California applicants will receive information regarding personal data collection and privacy rights as required by applicable law.