Sr. Director, Sales

Parachute Health

19h•$120,000 - $165,000•Remote

About The Position

Parachute Health is transforming post-acute care through the leading digital ordering platform for medical equipment and supplies. We replace the outdated, error-prone paper and fax process, which negatively impacts over 30 million patients annually, with a system that’s 10 times faster. Our platform connects a vast network of Home Medical Equipment (HME) providers, clinicians, and payors across all 50 states, ensuring millions of patients get the life-saving products they need quickly and efficiently. Join our team and make a difference in patient care. About the Role The Sr. Director, Sales of Home Medical Equipment (HME) Sales is responsible for leading and scaling the company’s HME-focused SaaS revenue engine. This role owns sales strategy, execution, and team leadership for a sales organization, driving lead generation, new customer acquisition, and retention across HME providers ranging from small business, mid-market to enterprise. This leader partners closely with Marketing, Customer Success, Product, and Strategic Partnerships to deliver predictable growth, shorten sales cycles, and position the company as a trusted technology partner within the HME ecosystem.

Requirements

5-10+ years of progressive sales leadership experience, preferably in SaaS
Direct experience selling to Home Medical Equipment (HME), DME, or closely related healthcare providers
Proven track record of leading and scaling sales teams with consistent quota attainment
Strong understanding of SaaS metrics (ARR, CAC, churn, expansion)
Experience managing complex, consultative sales cycles

Nice To Haves

Experience selling workflow, revenue cycle, or operational software in healthcare
Familiarity with HME regulatory and reimbursement environments
Experience partnering with channel or technology integration partners
Background working with mid-market and enterprise healthcare customers

Responsibilities

Own and execute the HME sales strategy aligned to company revenue and growth objectives
Lead, coach, and develop a sales professionals (new business, account management, or hybrid, as applicable)
Establish clear performance expectations, KPIs, and accountability across the team
Drive a high-performance, customer-centric sales culture
Achieve and exceed bookings, ARR, and retention targets within the HME segment
Oversee pipeline generation, forecasting accuracy, and deal execution
Actively participate in strategic and enterprise-level deals
Build trusted executive relationships with HME owners, operators, and clinical leaders
Gather market and customer insights to inform product roadmap and go-to-market strategy
Partner with Marketing on demand generation, messaging, and vertical-specific campaigns
Work closely with Customer Success to ensure smooth handoffs, adoption, renewals, and upsell
Coordinate with Strategic Partnerships (e.g., manufacturers, integrated platforms) to drive joint opportunities
Implement and optimize sales processes, playbooks, and CRM discipline

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 Bands (based on experience and level) $120,000 - $165,000