Chief Operating Officer

About the Role

As Chief Operating Officer at Parachute Health, you own the company's operating system. We are at a growth inflection, moving from a single core product to a multi-product platform, and executing landmark payor and channel partnerships that multiply our delivery load. The company's strategy, products, and pipeline are strong; the constraint on our next chapter is operational: converting commitments into flawless delivery, running the execution cadence that keeps a scaling organization coherent, and making service quality a competitive weapon rather than a liability.

This is an internal-facing, execution-first executive seat, engineered to complement a specialized leadership team. You do not own field selling (CRO), growth architecture or strategic partnerships (CGO), the revenue-operations and commercial-systems stack (EVP Revenue Operations, reporting to the CFO), or finance (CFO). You own everything that turns their work into delivered, retained customer value: implementations and delivery, customer support and service, program management, platform operations, and the company-wide operating cadence. You are the integrator — the leader who orchestrates across functions so the CEO can stay focused on product, market, and the external agenda.

Responsibilities

Company Operating System

• Operating cadence: Design and run the company's execution rhythm — operating reviews, cross-functional planning, and the accountability system that keeps every function on plan.
• Company scorecard: Drive execution against the company scorecard and KPIs — consuming the commercial source of truth the EVP Revenue Operations maintains, and ensuring every team knows its number and its path.
• Cross-functional orchestration: Break ties, clear blockers, and sequence initiatives across departments; own the seams between functions where execution goes to die.
• Annual operating plan: Translate strategy into the annual operating plan and quarterly commitments, in partnership with the CEO, CFO, and functional leaders.
• Automation-first operations: Partner with our Chief AI officer to embed AI and automation throughout the operating functions — absorbing rising volume with flat or sublinear headcount, and treating automation as the default answer before adding heads.

Delivery, Implementations & Client Operations

• Implementation engine: Own end-to-end customer implementations across suppliers, health systems, and payors — including the surge capacity our 2026 payor go-lives demand — with predictable timelines and quality.
• Delivery economics: Own the economics of delivery — on-time and on-budget performance, implementation cost, and the direct line from go-live velocity to revenue recognition. Implementation speed is revenue at our transaction-based model; you treat it that way.
• Service transformation: Own customer support and service quality end-to-end, with a mandate to materially improve clinician retention, strengthen enterprise escalation management, and build the service operation into a retention weapon. This is the seat's defining first-year deliverable.
• Proactive service model: Move service from reactive to proactive — instrumented client-health scoring, early-warning signals, and playbooks that catch at-risk accounts before they churn, built with the lifecycle instrumentation the EVP Revenue Operations maintains.
• Client operations: Run the operational functions that serve live customers day-to-day, with clean handoffs to the account-management and customer-success organizations that own the relationships.
• Program management: Own company-level program management for the initiatives that cross functional lines.

Organizational Scale & People (Interim)

• Scaling infrastructure: Build the operational infrastructure — processes, systems, capacity planning — for an organization doubling revenue and headcount.
• People bridge: Hold the People function on an interim basis until the Chief People Officer is seated (CPO will report to the CEO), ensuring no drop in hiring velocity or team health during the transition.
• Operational talent & culture: Build, coach, and retain the operations leadership bench — several senior operating leaders will report into this seat — and own the culture and retention of the frontline operations workforce, where attrition quietly destroys service quality.

Executive Partnership

• CEO integrator: Serve as the CEO's primary operating partner — absorbing the internal orchestration load so the CEO focuses on product, market-reading, and the external agenda.
• With the CRO: Deliver the implementation and service quality that protects the number she wins; own the operational side of retention.
• With the CGO: Operationalize landmark partnerships post-signature — the delivery infrastructure that makes channel pull-through real.
• With the CFO & EVP Rev-Ops: Run execution on the instrumentation they build; feed operational reality back into forecasting and planning.

The profile we're hiring

• Execution discipline: Trains run on time under you. You have built operating cadences, delivery engines, and service organizations that perform predictably at scale — and you are personally allergic to slipped commitments.
• Strategic foresight: You see two or three moves ahead and name constraints before they bite — capacity walls, service debt, integration bottlenecks — rather than reporting them after impact.
• Lived scale experience: You have operated through the passage we are in, whether inside a SaaS, network, or healthcare-technology business, and you know which systems break at which milestones because you were there.
• Service & delivery depth: You have owned customer delivery, support, or client operations directly — ideally including a turnaround — and can point to the numbers: churn reduced, NPS moved, on-time delivery raised, while volume grew.
• Automation-first scaler: You have scaled support and delivery volume with flat or sublinear headcount by deploying automation and AI in production — not as pilots, but as the operating model.
• Integrator temperament: High-EQ orchestrator who makes specialized executives better without absorbing their scope; comfortable owning outcomes through leaders you do not control.
• Builder's bias: You build systems before you add heads, and you leave every function more scalable than you found it.

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)

$300,000-$400,000