Executive Director - Assisted Living

Executive Director - Allegro Winter Park

Winter Park, FL - CORE Required

Lead with vision. Inspire a team. Run a community that sets the standard.

Allegro Winter Park is seeking an experienced, dynamic Executive Director to lead one of our premier Independent and Assisted Living communities in the heart of Winter Park, Florida. This is a role for a proven senior living leader who is ready to take full ownership of community operations - driving census, developing teams, delivering exceptional resident experiences, and upholding the Allegro standard of excellence every single day.

If you're a licensed, experienced IL/AL leader who thrives in a high-expectation, high-reward environment, we want to talk to you.

What You Bring:

• Florida CORE License (Executive Director License) - required
• Proven experience as a senior living Executive Director or senior operations leader with both Independent and Assisted Living settings.
• Strong track record of census growth, team development, and regulatory compliance
• Financial acumen and experience managing community budgets
• Exceptional communication, relationship-building, and leadership skills
• A genuine passion for seniors and a commitment to delivering an exceptional quality of life

Why Allegro Winter Park?

Allegro is one of the most respected senior living brands in Florida, and Winter Park is one of its crown jewel communities. You'll lead in a market known for its charm, culture, and discerning residents and families - backed by a strong operational team and a company that invests in its leaders. This is a career-defining opportunity for the right executive.

Allegro Winter Park | 2701 Howell Branch Road, Winter Park, FL 32792
Executive Leadership Role | Premier Senior Living Community

Apply today and lead at the highest level.

The primary responsibility of the Executive Director (ED) is the overall success of Community. This includes all phases of operation, general administration, resident care, resident and associate satisfaction, sales & marketing efforts, protection of physical assets, capital improvement, and achievement of all financial goals and key performance indicators (KPIs).


Ongoing communication between the ED and all other associates is critical to the welfare of the Community, keeping in mind that maintaining excellent service quality, high occupancy and high resident and associate satisfaction is always the goal.

Areas of Responsibility

• Serves as the most senior role in the entire Community, with responsibility for all sales, capital, and operations.
• Responsible for quality, care, resident satisfaction, associate satisfaction, maintaining compliance with regulatory requirements and Company policies and procedures, adhere to Company parameters, KPIs and financial responsibility, property goals, and protection of assets across the entire campus.
• Manage, educate, and develop all associates under direct and indirect supervision.
• Focus on financial objectives through budgeting, analytical tracking of trends, rate optimization, and intervention with teams that need support to achieve desired results.
• Direct the recruiting, hiring, and training of all Community personnel as well as motivating, supervising, and evaluating personnel. Establish both individual and team reward programs and continue to monitor associate satisfaction.
• Ensure Community complies with all State/Federal/City/County requirements and regulations.
• Some travel required.
• Other duties as assigned - see full job description.

Required Qualifications

• Must be a minimum of 18 years of age.
• Minimum associates degree or equivalent.
• Minimum two (2) years experience in assisted living, memory care, and/or skilled nursing management if a Community with assisted living/memory care. For an independent living Community, minimum three (3) years experience in retirement community management. Must have proven supervisory experience.
• Must have a positive Criminal Background Screening.
• The Community is a drug free workplace, associates are subject to adherence to the Company Drug Free Workplace policy.

Preferred Qualifications

• Four (4) year college degree preferred.
• Licensed nurse is a plus if the Community has assisted living.
• Previous experience in sales and marketing highly desired.

Allegro Living, LLC serves as the parent company of Allegro Management Company and Spring Arbor Management Company, uniting decades of senior living expertise under one trusted name. Formed through the 2025 merger of two well-established brands, Allegro Living is building a premier senior living platform defined by inspired lifestyles, compassionate care, and meaningful regional reach. The only thing we're missing is YOU!

Equal Employment Opportunity & Non-Discrimination

Allegro Living provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

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