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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. 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, requiring magnetic charisma to influence without authority and ruthless organizational discipline to turn visionary chaos into flawless execution.
Responsibilities
- Serve as the definitive heartbeat of the leadership team by owning the executive rhythm, managing the master execution tracker, and enforcing relentless accountability.
- Translate the CEO’s grand vision into actionable, cross-functional roadmaps, ensuring the executive team hits milestones with absolute velocity.
- 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 the CEO's voice, carrying his voice and authority.
- Act as a diplomatic bridge between the CEO, the executive leadership team, and external board members.
- Unblock friction, build consensus, and rally teams around critical initiatives without needing direct authority.
- Take ownership of the "too hard, too urgent, or too ambiguous" problems, diving in to solve and scale them.
- Ensure the executive team is perfectly briefed and strategically aligned before critical, high-value client/partner meetings.
- Translate 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 initiatives before full-scale resource allocation.
Requirements
- You think like an owner, not an employee.
- You have likely started your own company, been a foundational hire at a hyper-growth startup, or led a major business unit.
- 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.
- Possess executive presence to challenge, coach, and build fast trust with senior leaders.
- Humility to celebrate the team's wins while operating behind the scenes.
- Attention to detail is legendary.
- Can balance fifty moving pieces, anticipate bottlenecks three moves ahead, and ensure nothing ever drops.
- You don't just use AI; you think in it.
- Highly fluent in AI tools and comfortable operating inside a modern, AI-native organizational model.
- Exceptional writing and thinking skills.
- Can take a chaotic, multi-variable problem and distill it into a crystal-clear, actionable memo or deck.
- Thrive in a fast-moving, shifting environment.
- Have a massive bias to action and are comfortable "rebuilding the plane while it's in flight."
- A background in Healthcare, regulated industries, or B2B SaaS is a massive plus.
- Applicants must be legally authorized to work in the United States at the time of application and for the duration of employment.
- This role is not eligible for employer visa sponsorship.
Skills
- AI-Native Thinking
- Structured Communication
- Influence without Authority
- Organizational Discipline
- Crisis Management
- Strategic Alignment
- Product Incubation
- Team Building
- Problem Solving
Location
- Remote-First
Work Type
- Remote
- Full-Time
Experience Level
- 10+ years
Salary/Compensations
- $200,000-$275,000
Benefits
- Medical, Dental, and Vision Coverage with options for low-to-no-cost premiums.
- Employer HSA Contribution.
- 401(k) Retirement Plan.
- Equity Incentive Plan.
- Annual Company-Wide Bonus (up to 15% based on company performance).
- Remote-First Culture with a dedicated NYC office and reimbursement options for co-working spaces.
- Flexible Vacation Policy.
- Summer Fridays (5 additional Fridays off).
- Home Office and Wellness Stipend.
- Monthly Internet Stipend.
- Annual Learning and Development Stipend.
About the Company
- 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.
Equal Opportunity
- 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.