Remote Pilot Operator Jobs in Massachusetts (NOW HIRING)

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.

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. 

• 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.

• 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-native organizational model (leveraging team "brains," autonomous agents, and a shared data graph). 
• Master of Structured Communication: You have exceptional writing and thinking skills. You can take a chaotic, multi-variable problem and distill it into a crystal-clear, actionable memo or deck. • Comfortable in the Storm: You thrive in a fast-moving, shifting environment. You have a massive bias to action and are comfortable "rebuilding the plane while it\'s in flight." 
• Industry Knowledge: A background in Healthcare, regulated industries, or B2B SaaS is a massive plus.

Benefits

• Medical, Dental, and Vision Coverage: Comprehensive plans with options for low-to-no-cost premiums.
• Employer HSA Contribution: Company-funded contributions to your Health Savings Account.
• 401(k) Retirement Plan
• Equity Incentive Plan
• Annual Company-Wide Bonus: Opportunity for up to 15% bonus based on company performance.
• Remote-First Culture: We are remote-first with a dedicated NYC office and reimbursement options for co-working spaces.
• Flexible Vacation Policy
• Summer Fridays: 5 additional Fridays off during the summer (separate from PTO).
• Home Office and Wellness Stipend
• Monthly Internet Stipend
• Annual Learning and Development Stipend

Base Salary Band (based on experience and level)

$200,000-$275,000

California job applicants may access the Notice of Collection of Personal Information and Privacy Policy with information and rights required by the California Privacy Rights Act (CPRA) the link here.

We are proud to be an equal opportunity employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth related medical conditions and lactation), gender identity or gender expression (including transgender status), sexual orientation, marital status, military service and veteran status, disability, genetic information, or any other characteristic protected by applicable federal, state, or local laws and ordinances.

This role is not eligible for employer visa sponsorship. Applicants must be legally authorized to work in the United States at the time of application and for the duration of employment. The Company does not sponsor employment authorization for this position.