Sr. Director, Sales

Parachute Health$155K — $175K *
US-AnywhereRemote in United States
Healthcare
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5-10+ years of progressive sales leadership experience, preferably in SaaS
  • Direct experience selling to Home Medical Equipment (HME) 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

Responsibilities

  • Own and execute the HME sales strategy aligned to company revenue and growth objectives
  • Lead, coach, and develop 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

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
Full Job Description
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.

Responsibilities
  • Own and execute the HME sales strategy aligned to company revenue and growth objectives
  • Lead, coach, and develop 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

Qualifications & Experience

Required Experience
  • 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

Preferred Experience
  • 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

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)

$155,000 - $175,000

About Parachute Health

Parachute Health is a healthcare technology company that provides a platform for ordering and delivering medical equipment. The company's platform enables healthcare providers to order medical equipment and supplies for their patients, and then have those items delivered directly to the patient's home. Parachute Health's platform is designed to streamline the medical equipment ordering process and improve patient outcomes. The company was founded in 2015 and is headquartered in New York, New York.
Learn more about Parachute Health
Size
50 employees
Industry
Net Income
-$5 million
Founded
2015
5 Year Trend
+30%
Revenue
$10 million

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