Director of Sales and Marketing

Why You’ll Love Working at Milestone

Milestone is one of the fastest-growing senior living operators, with 100+ years of combined industry and hospitality experience. We focus on teamwork, creativity, and making a real impact for our residents and staff.

Perks & Benefits

• Medical, Dental, Vision (full-time employees)


• 401(k) with employer match


• Generous PTO


• Pet insurance


• Perks at Work


• Employee Assistance Program


• Voluntary benefits options

About the Role

We’re seeking a Transitions Specialist to guide prospective residents and their families through the move-in process while supporting the community’s occupancy and growth goals. In this role, you’ll combine consultative sales expertise with compassionate guidance, helping families make informed decisions and ensuring a seamless transition into community life. You’ll also develop community partnerships, host engaging events, and serve as a trusted resource for prospects, families, and referral sources.

What You’ll Do

• Guide prospective residents and families through discovery, apartment selection, and move-in processes


• Maintain and grow occupancy in line with community goals and business plan


• Build and maintain a prospect pipeline with detailed CRM records, tracking interactions, follow-ups, and conversions


• Market community services and programs to prospects, families, and advisors, tailoring presentations to their needs


• Plan, execute, and follow up on strategic events that highlight community lifestyle and generate leads


• Represent the community at outside events, professional groups, and local organizations


• Build and maintain relationships with referral sources, including legal and financial professionals, senior organizations, hospital discharge planners, and healthcare providers


• Coordinate with internal teams for smooth resident transitions, including care assessments, apartment preparations, and welcome programs


• Conduct engaging community tours that showcase amenities, programs, and lifestyle benefits


• Identify opportunities to increase revenue and optimize community inventory


• Perform other duties as assigned to support community goals

What We’re Looking For

• Bachelor’s Degree in Business, Marketing, or related field preferred, or equivalent experience


• 2–5 years of sales experience, ideally in senior living, healthcare, or pharmaceutical sales, with a proven track record of closing leads


• Knowledge of sales and marketing principles, strategies, and techniques


• Understanding of state regulations affecting service delivery and familiarity with Medicare/Medicaid processes


• Strong communication, interpersonal, and presentation skills


• Ability to build trust, assess customer needs, and guide families through complex decisions


• Proficient with smartphones, computers, and related software


• Valid driver’s license and willingness to travel frequently


• Self-motivated, organized, and able to manage multiple priorities independently


• Compassionate, professional, and personable demeanor

Join Milestone to help families navigate one of life’s biggest transitions while contributing to a welcoming, vibrant community.

Milestone is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

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