Enterprise Account Executive

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 environment.
• Deep familiarity with hospital and health system buying processes, including procurement, value analysis committees, IT governance, and clinical sign-off.
• Strong understanding of the post-acute care continuum — including HME/DME operations, home health, and supply chain dynamics within integrated delivery networks.
• Executive presence and credibility: you can hold your own in a room with a Chief Supply Chain Officer, VP of Post-Acute Operations, or CIO.
• Excellent business case and ROI development skills — you can quantify value in terms that resonate with healthcare finance and operations leaders.
• Highly disciplined sales process and pipeline management; you use your CRM as a strategic tool, not an afterthought.
• Comfortable operating in a startup or growth-stage environment where playbooks are still being written.
• Bachelor's degree in Business, Healthcare Administration, or a related field — or equivalent professional experience.

Strongly Preferred

• Direct experience selling software or technology platforms into hospital-owned HME departments, post-acute divisions, or health system supply chains.
• Existing relationships with decision-makers at health systems, IDNs, or large regional hospital networks.
• Familiarity with HME/DME-specific workflows: intake and order management, Medicare/Medicaid billing, prior authorization, resupply, and compliance.
• Experience navigating GPO relationships, enterprise contract vehicles, or health system group purchasing dynamics.
• Prior experience at a SaaS company serving the post-acute, home health, or healthcare supply chain market.
• Understanding payer dynamics, CMS reimbursement policies, and how regulatory changes affect HME operations and purchasing decisions.

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)

$80,000-$165,000 Base + Commission

This role carries a competitive on-target earnings structure with uncapped upside. We build compensation plans that reward enterprise sellers who close large, strategic deals — not just volume.

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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.

This role is not eligible for employer visa sponsorship. 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.