About the role

Role Overview

Chief of Staff to the CEO at Parachute Health. You will act as the CEO’s strategic co-pilot and executive proxy, running the leadership operating cadence and ensuring execution velocity during an AI-native transformation.

Responsibilities

Architect the Executive Operating System: Own executive rhythm (e.g., leadership cadence), maintain a master execution tracker, and enforce accountability.
CEO Decision Facilitation: Prepare decisions with framed options and recommendations; manage information flow to/from the CEO; represent the CEO in appropriate forums; draft key communications in the CEO’s voice.
Influence & Alignment: Bridge CEO, executive leadership, and board members; unblock friction, build consensus, and align teams on critical initiatives without formal authority.
Special Ops & Crisis Management: Take ownership of urgent, high-stakes, or ambiguous problems (market pivots, partnerships, operational fires); solve and scale.
Enterprise-Grade Preparedness: Ensure leadership is perfectly briefed and strategically aligned for high-value enterprise client/partner meetings.
Internal Product & Vertical Incubation: Translate new product concepts and vertical strategies into structured testing frameworks; lead internal tiger-team efforts to prototype, test hypotheses, and run micro-pilots.

Requirements

Entrepreneurial DNA: Think like an owner; experience as a founder, foundational hyper-growth hire, or operator at a major business unit.
Experience: 10+ years across operating, strategy, and execution roles (e.g., prior Chief of Staff, business operations, top-tier consulting, or growth-stage operating leadership).
Leadership & EQ: Executive presence with high emotional intelligence; ability to build fast trust and coach senior leaders.
Operational Discipline: Exceptional organization and attention to detail; manage many moving pieces while preventing gaps and bottlenecks.
AI-Native Mindset: Strong fluency with AI tools and comfort operating in a modern, AI-native environment.

Nice-to-haves

Background incubating products/verticals and running fast experimentation frameworks (prototype → pilot → validate).

About Parachute Health

Parachute Health is transforming post-acute care with a digital ordering platform for medical equipment and supplies. The company connects health systems, health plans, and suppliers to help patients receive life-saving products at home, scaling nationally across the U.S.