Chief of Staff

Parachute Health is transforming post-acute care as the leading digital ordering platform for medical equipment and supplies. We connect major health systems, health plans, and suppliers to help patients get the life-saving products they need at home. Since launching, we've connected 300,000+ clinicians and 3,000+ supplier locations across all 50 states and helped 15M+ patients. What started as a DME ePrescribing tool has become the order management platform of choice for home medical equipment. Join our team and make a difference in patient care. About the Role As the Chief of Staff at Parachute Health, you will operate as the right hand, strategic co-pilot, and executive proxy to our CEO, David. You will hold the keys to our operational engine—driving the executive agenda, aligning senior leadership, and scaling our execution cadence during a massive, AI-native transformation. This is a high-stakes, high-energy role engineered for a brilliant operator with an entrepreneurial spirit. It requires a rare mix of magnetic charisma to influence without authority, and ruthless organizational discipline to turn visionary chaos into flawless execution. If you have the gravitas to command a room of seasoned executives and the grit to build the future of healthcare infrastructure, this is your next mountain to climb. Responsibilities Architect of the Executive Operating System: Serve as the definitive heartbeat of the leadership team by owning the executive rhythm, managing the master execution tracker, and enforcing relentless accountability. You will translate the CEO’s grand vision into actionable, cross-functional roadmaps, ensuring the executive team hits milestones with absolute velocity. CEO Decision Facilitation: Prepare decisions with framed options and a recommendation, manage the flow of information to and from the CEO, and represent him in forums where appropriate. Draft key communications in his voice. You carry the CEO's voice and authority. Influence & Alignment: Act as a diplomatic bridge between the CEO, the executive leadership team, and external board members. You will unblock friction, build consensus, and rally teams around critical initiatives without needing direct authority. Special Ops & Crisis Management: Take ownership of the "too hard, too urgent, or too ambiguous" problems. Whether it’s an urgent market pivot, a high-value partnership, or a sudden operational fire, you dive in, solve it, and scale it. Enterprise-Grade Preparedness: As Parachute targets massive health systems, payors, and enterprise suppliers, ensure the executive team is perfectly briefed and strategically aligned before critical, high-value client/partner meetings. Internal Product & Vertical Incubation: Translate David’s new product concepts and vertical strategies into structured testing frameworks. Stand up and coordinate internal, cross-functional tiger teams to rapidly build prototypes, test hypotheses, and run micro-pilots to validate these initiatives before full-scale resource allocation. The profile we’re hiring Entrepreneurial DNA: You think like an owner, not an employee. You’ve likely started your own company, been a foundational hire at a hyper-growth startup, or led a major business unit. • Experience: 10+ years across operating, strategy, and execution roles—prior Chief of Staff, business operations, top-tier consulting, or operating-leader experience at a growth-stage company. • Charismatic Leadership & High EQ: You possess the executive presence to challenge, coach, and build fast trust with senior leaders, combined with the humility to celebrate the team's wins while operating behind the scenes. Ruthlessly Organized & Disciplined: Your attention to detail is legendary. You can balance fifty moving pieces, anticipate bottlenecks three moves ahead, and ensure nothing ever drops. • AI-Native Thinker: You don't just use AI; you think in it. You are highly fluent in AI tools and comfortable operating inside a modern, AI-nativ…