Enterprise Account Executive

About this role

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.

About the Role

As an Enterprise Account Executive, you'll own high-value prospective accounts. Your focus will be on enterprise HMEs, hospital-owned HMEs, and adjacent markets where the complexity and scale of the opportunity demand a sophisticated, consultative sales approach. You'll be responsible for the full sales cycle — from prospecting and discovery through contracting and handoff to Customer Success — and will work closely with leadership to shape how we enter and win new markets.

This is not a volume role. You'll carry a focused pipeline of strategic opportunities and be expected to drive large deals that often involve procurement, IT, clinical leadership, and executive sign-off. You bring the credibility, process discipline, and healthcare domain knowledge to earn a seat at the table with senior decision-makers.

What You'll Do

Pipeline Development & Territory Strategy

• Own a defined territory of enterprise prospects — enterprise HMEs, hospital-owned HMEs, and new markets.

• Develop and execute a territory plan that identifies the highest-value targets, maps the buying landscape, and builds a multi-quarter pipeline.

• Work with BDRs on outbound prospecting efforts into new accounts, leveraging industry relationships, conference presence, referrals, and targeted outreach to build a pipeline from scratch.

• Partner with Marketing and Leadership to identify and pursue new market opportunities — including adjacent verticals, emerging care models, and geographies where our platform can expand.

• Maintain a disciplined, accurate pipeline in HubSpot with clear stage progression, next steps, and deal timelines.

Enterprise Sales Execution

• Run a consultative, solution-oriented sales process tailored to the complexity of hospital and health system buying environments.

• Navigate large, matrixed organizations — building relationships and consensus across supply chain, revenue cycle, clinical operations, IT/informatics, and C-suite stakeholders.

• Lead discovery deeply enough to understand the operational, financial, and strategic problems the customer is trying to solve — and connect those to our platform's capabilities in a compelling, credible way.

• Develop and deliver executive-level presentations, business cases, and ROI analyses that speak the language of health system leadership.

• Manage complex, multi-phase RFP and procurement processes, coordinating internal resources (Solutions Engineering, Implementation, Legal, Finance) to move deals forward.

• Negotiate contracts, pricing structures, and multi-year agreements, balancing deal economics with long-term customer fit.

• Own deal velocity — driving urgency without sacrificing relationship quality, and keeping stakeholders aligned through extended sales cycles.

New Market Development

• Serve as a strategic scout and builder for new markets — identifying patterns in buyer needs, competitive dynamics, and platform fit that inform how we expand beyond our core.

• Bring market intelligence back to Product, Marketing, and Leadership to help shape positioning, packaging, and go-to-market strategy for new segments.

• Build relationships with key industry associations, health system networks, GPOs, and thought leaders that create a long-term pipeline and credibility in new verticals.

• Develop repeatable sales plays and discovery frameworks for new market segments as you learn what works.

Cross-Functional Partnership

• Partner with Enterprise CSMs on seamless post-sale handoffs, ensuring Customer Success has the context and commitments needed to deliver on what was sold.

• Work closely with Solutions Engineering on technical discovery, demo customization, and proof-of-concept engagements for complex accounts.

• Collaborate with Marketing on account-based campaigns, event strategy, and enterprise-specific content that supports pipeline development.

• Contribute to sales process improvement — sharing deal learnings, win/loss insights, and buyer feedback that make the entire team better.

What We're Looking For

Requirements

• 5+ years of enterprise B2B sales experience, with at least 2–3 years selling into health systems, hospital networks, or complex healthcare organizations.

• Demonstrated track record of closing large, multi-stakeholder deals — six-figure ACV and above — with long sales cycles in a healthcare or healthcare technology…