Chief of Staff

Parachute Health•Boston, MA

9d•$200,000 - $275,000•Remote

About The Position

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.

Requirements

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.
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.
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.
Your attention to detail is legendary.
You 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.
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).
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.
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."
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.

Nice To Haves

A background in Healthcare, regulated industries, or B2B SaaS is a massive plus.

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 his voice.
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.
Dive in, solve it, and scale it.
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 these initiatives before full-scale resource allocation.

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