Remote Director Jobs in Springfield, MA (NOW HIRING)

Milestone Funeral Partners is seeking an experienced and proactive Director of Facilities & Fleet to oversee the care, maintenance, and long-term management of our growing portfolio of facilities, properties, and fleet assets across the Northeast. This leadership opportunity offers competitive compensation, comprehensive benefits, and the opportunity to build a rewarding career with one of the Northeast's leading funeral service organizations.

Why Join Milestone?

When you join Milestone, you're becoming part of a team that is deeply connected to the communities we serve. Every day, your work helps families navigate some of life's most difficult moments with compassion, dignity, and exceptional care. We value your expertise, invest in your growth, and help you build a career with purpose.

About the Role

The Director of Facilities & Fleet plays a critical role in managing and growing the value of Milestone Funeral Partners' physical footprint, including company-owned vehicles, funeral homes, cemeteries, crematories, offices, and other real estate holdings within the New England & Tri State area. You'll oversee the full lifecycle of these assets—from preventative maintenance and repairs to capital improvements, replacement planning, and the disposition of surplus properties.

As the central point of contact for facilities and fleet management, you'll build trusted relationships with vendors, contractors, brokers, and service providers while partnering closely with Finance, Operations, and market leadership to ensure our assets are safe, well maintained, operationally effective, and positioned to maximize long-term value.

This is a full-time, remote opportunity based in the Northeast with approximately 40–60% travel required. Preference given to candidates residing along the Massachusetts/Connecticut corridor for central access across Milestone's portfolio. 

What You'll Do

• Oversee the maintenance and full lifecycle management of Milestone's fleet, funeral homes, cemeteries, crematories, corporate facilities, and other real estate assets spanning Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, Connecticut, and New York
• Develop and manage preventative maintenance programs, conduct facility inspections, and prioritize maintenance needs to support safe, reliable, and well-maintained properties
• Coordinate repairs, emergency maintenance, capital improvements, and renovation projects from initial scoping through completion while minimizing disruption to operations
• Support acquisitions by reviewing property inspection findings and integrating identified maintenance, facility, and fleet needs into long-term plans
• Manage the sale or disposition of surplus real estate assets and oversee property tax matters in partnership with brokers, legal counsel, Finance, and third-party consultants
• Manage fleet operations, including preventative maintenance, inspections, registrations, repairs, warranty claims, utilization, replacement planning, and applicable regulatory compliance
• Build and manage relationships with preferred contractors, vendors, and service providers, including soliciting bids, negotiating agreements, and evaluating performance
• Develop and maintain multi-year capital improvement and asset management plans using condition data, lifecycle costs, and ROI analysis to guide investment decisions
• Maintain accurate asset records and reporting while evaluating and implementing asset management or CMMS tools to improve visibility, planning, and operational efficiency
• Partner closely with Finance, Operations, and market leadership to align maintenance, capital, and fleet priorities with business needs and travel throughout the Northeast to support company locations

What You'll Bring

Required Qualifications

• 7+ years of experience in facilities management, fleet management, property management, construction management, asset management, or a related field
• Strong project management skills with the ability to manage multiple projects, priorities, and locations simultaneously
• Working knowledge of building systems, including HVAC, electrical, and plumbing
• Experience managing vendors, contractors, and service agreements
• Experience with budget management and capital expenditure (CapEx) forecasting
• Excellent organizational, communication, and problem-solving skills
• Ability to travel throughout the Northeast approximately 40–60%, including occasional overnight travel
• Ability to travel independently by automobile and occasionally by air

Preferred Qualifications

• Experience managing geographically dispersed properties or multi-site operations
• Experience supporting