Community Sales Associate Jobs in Chicago, IL (NOW HIRING)

About Discovery Management Group

Discovery Management Group leads one of the nation’s most purpose-driven and people-centered senior living organizations, managing and enhancing senior living communities across the United States. With a focus on operational excellence, lifestyle personalization, and culture-driven leadership, we proudly serve residents and families with more than 15,000 units nationwide and growing.

As part of one of the largest senior living families in the U.S., our communities have earned Great Place to Work® certifications from 2022–2027. At Discovery Management Group, purpose guides our work, culture fuels our success, and growth defines our future. We continually aspire and invest in learning and development opportunities that support our team members’ professional growth, ensuring every team member has the tools to build a meaningful and rewarding career.

As Senior Director of Sales, you’ll play an essential role in enriching the lives of seniors, creating meaningful connections, and making a difference every single day.

Your Role:

As the Senior Director of Sales, your role includes leading sales operations and strategy to achieve occupancy and revenue goals. You’ll provide coaching and direction to the community’s sales team, analyze performance, and drive a consistent, customer-focused sales process that delivers exceptional experiences for residents and families.

Position Highlights:

• Status: FULL TIME
• Schedule: Traditional leadership workweek with flexibility required based on business and operational needs.
• Rate of Pay: Base pay of 85k - 90k base + Commission
• Travel: 20%

What You’ll Do:

• Provide leadership, coaching, and accountability to the community sales team (Directors of Sales, Sales Associates)
• Execute and ensure compliance with the company’s Sales Playbook and sales systems
• Achieve community sales targets through oversight of inquiries, tours, conversions, and move-ins
• Analyze competitive market conditions and develop tactical strategies to maintain a competitive edge
• Build and maintain referral networks, conduct outreach, and represent the community at professional events
• Partner with the Executive Director and Regional Sales Leaders on sales strategy, pricing, and tactical plans
• Evaluate sales performance weekly, coach sales associates, and drive CRM data integrity and reporting
• Collaborate with executive and regional leadership on competitive analysis, revenue optimization, and NOI contribution
• Oversee the move-in process, ensuring a smooth transition for residents and families
• Track KPIs, prepare forecasts, and present performance updates to leadership

Qualifications:

• Bachelor’s degree in Business Administration, Marketing, or related field
• Minimum 5 years of experience in senior living sales/marketing with at least 2 years in a leadership role
• Proven success in achieving occupancy and revenue targets
• Strong supervisory and coaching skills with ability to manage multiple sales team members
• Excellent communication, presentation, and relationship-building skills
• Proficiency with Microsoft Office and CRM systems
• Strong analytical ability with experience in competitive market analysis

Why Join Us

Discovery Senior Living Earned Coveted Great Place to Work Certification for 2025-2027!

A large part of what makes Discovery different from other companies in this industry is our willingness to embrace change. At Discovery Senior Living, we are constantly challenging how we are doing things to ensure the lifestyle we are offering our residents is absolutely the greatest value proposition in the marketplace. It’s just as important to us that the environment and culture for our team members are constantly refreshed. In addition, embracing and even encouraging change brings a never-ending supply of new energy to our business and our culture. That energy translates to other far-reaching positive impacts on our residents as well as our team members.

Find out what makes working at Discovery unique in the world of senior living. Discover Your Purpose!

Our Culture & Values

So often, what brings people together is deeply rooted in who we are and what we stand for. And at Discovery Senior Living, we’re unified by certain, core values, which we call our “Pillars of Excellence.” They make up the fabric of our company, and include TEAMWORK, INTEGRITY, PERFORMANCE, ACCOUNTABILITY, COMPASSION, HARD WORK and CREATIVITY.

Individually, they are our virtues, and together, they make up a roadmap which helps us foster innovation and success.

Benefits You’ll Enjoy

For eligible employees, we offer a comprehensive benefits package that includes competitive pay, medical, dental, vision, life, and disability insurance, paid time off and holidays, a 401(k) with employer match, paid training and career growth opportunities, wellness-related benefits, and additional support through our Employee Assistance Program (EAP). 

Equal Opportunity Employer

We are proud to be an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all team members. EOE D/V

A Note to Applicants

This job description outlines the general nature and level of responsibilities for this role and is not an exhaustive list of all duties. Qualified individuals with disabilities, as defined by the ADA, must be able to perform the essential job functions with or without reasonable accommodation, as determined on a case-by-case basis.

Agency Policy

We do not accept unsolicited resumes from staffing agencies. Please refrain from contacting hiring managers directly.

Employment Scam Warning

We only post jobs on our official careers site and accept applications through that platform. We do not conduct interviews via text or social media or ask for personal or banking information.

Regulatory Compliance & Background Screening

Discovery Senior Living complies with all applicable federal, state, and local employment laws and regulatory requirements governing hiring practices, background screening, and workforce eligibility. Employment may be contingent upon successful completion of state-mandated and/or federally required background screenings, which may include criminal history checks, fingerprint-based screening, Level 2 background screening, registry verification, and other screenings required for healthcare and senior living roles with direct or indirect resident access.

Certain positions may be subject to additional requirements under federal programs, including CMS, Medicare, and Medicaid regulations, as well as state-specific licensing or regulatory agencies. Screening requirements vary by role and jurisdiction, and candidates must meet all applicable standards as a condition of employment. These measures support regulatory compliance and help maintain a safe, secure environment for residents, families, and team members.

Employment in Florida is contingent upon completion of a Level 2 background screening in accordance with Florida AHCA requirements. Applicants will be required to complete fingerprinting and background screening through the AHCA Clearinghouse. For more information, please visit: https://info.flclearinghouse.com.