Fleet Strategy Jobs (NOW HIRING)

Dragonfly Health is the leading care-at-home data, technology and service platform, and the industry’s first scale durable medical equipment (DME) and pharmacy solution. Built on a 20-year history, Dragonfly Health uses advanced technology and robust analytics to manage DME and pharmaceutical services as part of a single, efficient solution for caregivers, patients, and their families. We serve over 145,000 patients every day in all 50 states.

Here, you are an integral part of a team that is transforming the future of hospice and post-acute healthcare. This is where innovation, collaboration and compassion thrive, allowing us to carry out our work at the highest level to serve our patients at a time in their life when they need us most.

We offer a dynamic and inclusive workplace where you'll have the unique opportunity to shape the future of healthcare alongside a passionate and talented team. We believe in empowering our employees to grow both personally and professionally, providing ample opportunities for career advancement, continuous learning, and skill development.

The dragonfly is symbolic of the transformational impact we’re making on the industry, our people, and the lives we touch. We are a guiding force for what’s ahead, delivering more than equipment and medications, but also comfort and peace of mind. We are agile and adaptable, able to quickly and easily pivot from one point to the next, ready for whatever situation or patient need that arises. 

• Competitive Pay $125,000+ annual salary (depending on experience) + 20% annual bonus opportunity
• Comprehensive Benefits Package (Health, Dental, Vision, PTO, Sick Time, 401k w/match, etc.) 
• Growth Opportunity and Career Advancement
• Agile and Adaptable team culture
• Innovative and revolutionary technology solutions
• A higher calling to provide quality patient care

See how Dragonfly Health is transforming the world of hospice and post-acute care.

• Build and execute the long-term fleet strategy, aligning vehicle assets, replacement cycles, and fleet performance with company growth goals.
• Lead enterprise-wide fleet budgeting, including capital planning, expense forecasting, cost analysis, and financial performance monitoring.
• Oversee asset lifecycle management, including vehicle specification, procurement, leasing decisions, upfitting, deployment, rotation, resale, and replacement planning.
• Establish and maintain fleet policies, procedures, safety standards, and operational expectations across all company locations.
• Ensure fleet compliance with DOT requirements, state regulations, healthcare accreditation standards, insurance requirements, and internal documentation standards.
• Lead preventive maintenance strategy to maximize vehicle uptime, reliability, safety, and operational readiness.
• Manage national and regional vendor partnerships for maintenance, repairs, leasing, upfitting, fleet technology, and vehicle logistics.
• Use fleet performance data, telematics platforms, maintenance trends, safety events, fuel usage, downtime, and capital spend to drive better business decisions.
• Partner with operations, safety, HR, accounting, and leadership teams on accident response, insurance claims, fleet recovery, financial controls, and complex fleet-related decisions.

• 7+ years of progressive fleet management experience, ideally with multi-site or enterprise-level responsibility.
• Proven experience leading fleet strategy, asset planning, maintenance programs, vendor relationships, and operational performance initiatives.
• Strong financial acumen, including experience with budgets, capital planning, expense forecasting, and cost-control decisions.
• Prior leadership experience with the ability to mentor, develop, motivate, and hold teams accountable.
• Strong understanding of DOT requirements, fleet safety, compliance documentation, vehicle risk management, and regulatory standards.
• Experience with fleet management systems, telematics platforms, reporting tools, and data-driven operational decision-making.
• Strong communication, negotiation, and executive-facing presentation skills.
• Ability to manage multiple priorities, deadlines, projects, vendors, and stakeholders in a fast-moving operating environment.
• Bachelor’s degree in business, logistics, supply chain, or a related field required; MBA, fleet certification, healthcare, or durable medical equipment transportation experience preferred.

The Fleet Director is critical because Dragonfly Health’s fleet is not just a support function; it is part of the operating backbone of the business. Vehicles must be safe, compliant, available, cost-effective, and reliable for teams to serve patients, customers, and field operations without disruption.

A strong Fleet Director protects the business from avoidable downtime, compliance exposure, safety risk, uncontrolled costs, and poor asset decisions. This role turns fleet operations into a strategic advantage by ensuring the company has the right vehicles, the right systems, the right vendor partners, and the right long-term plan to support growth at scale, leading to better patient care.