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. This position has a starting annual salary of $72.8K with a commission plan in place. 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.