Director of Sales & Marketing

Named a Top Workplace by the Chicago Tribune and recognized as Best Senior Independent Living by U.S. News & World Report, Chestnut Square at The Glen is a premier independent living community for adults 62+ offering a secure, maintenance-free lifestyle in a vibrant and engaging environment.

At Chestnut Square, you’ll be part of a workplace where people truly matter. Our team members enjoy work-life balance while doing meaningful work that positively impacts the lives of seniors. We foster a supportive, team-oriented environment with approachable leadership and a culture that recognizes and appreciates employees. If you’re seeking a purpose-driven leadership role in a positive and professional setting, we invite you to apply.

We are seeking a dynamic and experienced Director of Sales & Marketing to lead occupancy growth and community outreach efforts. This leadership role is responsible for developing and executing strategic sales and marketing initiatives, cultivating referral relationships, and guiding prospective residents and families through the move‑in process.

The ideal candidate will be an energetic relationship‑builder with strong sales experience, excellent communication skills, and a passion for serving older adults.

This is an incentive-based position that includes a competitive base salary, commission opportunities, and the possibility of additional performance-based rewards.

• Serve as the primary Sales Counselor, conducting community tours and presentations for prospective residents and families
• Develop and implement all aspects of the sales and marketing plan in collaboration with leadership
• Manage lead generation, follow‑up, and conversion efforts to achieve or exceed occupancy goals
• Conduct sales presentations, complete sales closings, and oversee contract execution and related paperwork
• Build and maintain strong relationships with referral sources, community organizations, and professional partners
• Coordinate and participate in networking events, outreach initiatives, and marketing programs
• Oversee advertising, media, and community outreach strategies to enhance visibility and drive inquiries
• Manage resident transfer and refund requests according to company policy under the direction of the CEO
• Maintain accurate and timely documentation of all prospect interactions within CRM software
• Collaborate with operations and leadership teams to ensure a smooth and welcoming move‑in experience for new residents

• Bachelor’s Degree in a related field or equivalent professional experience
• Minimum of three years of proven sales and marketing success; senior living experience preferred
• Strong business development, networking, and relationship‑building skills
• Excellent verbal and written communication skills with the ability to engage a wide range of audiences
• Outstanding organizational, leadership, and problem‑solving abilities
• Professional demeanor with a genuine passion for working with older adults
• Proficiency in Microsoft Office and CRM/database systems
• Ability to work occasional evenings and weekends for events and community outreach activities
• Medical, dental, and vision insurance
• 403(b) retirement plan with employer match
• Generous paid time off (PTO)
• Complimentary lunch meal
• Employee recognition programs and events

Join a team dedicated to providing exceptional service, driving occupancy, and creating a welcoming senior living community where residents thrive. We look forward to reviewing your application.