OVERVIEWThe Senior Director of Florida Operations is responsible for leading, coaching, and strengthening regional executive directors across Florida to ensure healthy teams, operational excellence, and measurable impact. This leader ensures Better Together's mission, vision, and strategic priorities are effectively executed across all regions.
This role focuses on leadership development, regional performance, strategic execution, and proactive problem solving. The Senior Director works closely with executive directors to build strong teams, increase capacity, improve program quality, and achieve meaningful outcomes for the children, families, and job seekers we serve.
The ideal candidate is an experienced, relational, and results-oriented leader who knows how to develop people, build healthy teams, analyze performance, and solve complex problems. This individual leads with humility, exercises sound judgment, and brings both strategic thinking and operational discipline to the role.
ROLES AND RESPONSIBILITIESThe Senior Director of Florida Operations has four primary areas of responsibility:
LEADERSHIP DEVELOPMENT AND TEAM HEALTHBuild strong executive directors who lead healthy, high-performing teams and translate Better Together's vision into action.
- Directly supervise, coach, and develop regional executive directors, strengthening their leadership, people management, and decision-making capabilities.
- Ensure executive directors understand, embrace, and effectively communicate Better Together's mission, vision, values, and strategic priorities.
- Establish clear expectations, performance benchmarks, and accountability through Leadership, Management, and Accountability (LMA) practices.
- Support executive directors in recruiting, hiring, retaining, and developing excellent team members, ensuring the right people are in the right seats.
- Equip executive directors to strengthen team performance, increase individual capacity, and build a culture of coaching, ownership, and continuous improvement.
- Foster healthy, mission-aligned teams characterized by trust, collaboration, accountability, and professional growth.
REGIONAL IMPACT, PERFORMANCE, AND DATAEnsure every region achieves measurable results while maintaining program quality, consistency, and integrity.
- Hold executive directors accountable for achieving regional goals, organizational KPIs, and meaningful outcomes.
- Regularly review performance data, scorecards, forecasts, and trends to identify gaps, opportunities, and areas for improvement.
- Ensure regional staff have clear performance benchmarks and understand their individual contributions to organizational goals.
- Evaluate both the quantity and quality of program outcomes, ensuring increased impact without compromising safety, service, or program fidelity.
- Partner with executive directors to address performance gaps, strengthen accountability, and implement measurable improvement plans.
- Collaborate with Training and Quality Assurance teams to strengthen program delivery, reinforce best practices, and ensure consistent execution of Better Families and Better Jobs.
STRATEGIC EXECUTION AND CAPACITY BUILDING
Help executive directors execute strategic priorities, strengthen partnerships, and increase regional capacity and impact.
- Partner with executive directors to develop and execute regional strategic plans aligned with organizational goals and priorities.
- Coach executive directors in strategic thinking, prioritization, creative problem solving, and effective decision-making.
- Identify opportunities to increase regional capacity through stronger leadership, improved productivity, and effective use of resources.
- Support executive directors in developing strategic relationships with churches, donors, employers, volunteers, and community partners.
- Equip executive directors to serve as effective ambassadors who communicate Better Together's mission, mobilize stakeholders, and strengthen community engagement.
- Oversee regional budgeting, forecasting, and resource allocation to ensure responsible financial stewardship and sustainable growth.
PROACTIVE PROBLEM SOLVING AND ISSUE RESOLUTIONEquip executive directors to anticipate challenges, resolve issues effectively, and protect relationships, program quality, and organizational integrity.
- Proactively coach executive directors to identify and address operational, personnel, and program challenges before they escalate.
- Strengthen executive directors' skills in conflict resolution, difficult conversations, customer service, and sound decision-making.
- Serve as a trusted resource and thought partner in navigating complex leadership and operational situations.
- Step in when necessary to de-escalate sensitive situations involving families, volunteers, partners, or team members, preventing further escalation.
- Ensure concerns are resolved promptly, professionally, and in accordance with organizational policies and safeguarding standards.
- Identify recurring issues and partner with appropriate departments to improve training, systems, and preventive practices.
REQUIREMENTS- Minimum of seven years of progressive leadership experience, including at least three years directly supervising and developing managers or senior leaders.
- Demonstrated success leading multiple teams, departments, or geographically distributed operations.
- Proven ability to coach leaders, build healthy teams, manage performance, and establish accountability.
- Strong experience in operational management, strategic planning, performance measurement, budgeting, and organizational growth.
- Ability to analyze data, evaluate performance trends, and translate insights into actionable improvements.
- Strong communication, interpersonal, organizational, conflict resolution, and problem-solving skills.
- Ability to balance strategic leadership with practical execution, sound judgment, and attention to detail.
- Bachelor's degree required. Advanced degree in business, nonprofit management, public administration, social work, or a related field preferred.
- Experience in nonprofit leadership, child welfare, human services, or workforce development preferred.
- Proficiency with technology and performance management systems, with experience using Salesforce, Basecamp, or similar platforms preferred.
- Alignment with Better Together's mission, vision, and core values.
- Ability to travel regularly throughout Florida.
TIMING, LOCATION AND COMPENSATIONBetter Together seeks to fill this position as soon as possible. The organization's headquarters are in Naples, Florida. This position is based in Florida, with regular statewide travel required.
Better Together has built a highly successful work culture over the past decade with systems and structures designed for clarity, flexibility, accountability, and great communication. This is a full-time, exempt position reporting to the Chief Operating Officer.
Key elements of the environment include:
- Weekly team meetings with clear accountability and opportunities to solve issues collaboratively.
- Quarterly in-person team meetings to build deeper relationships, set clear goals aligned with the Better Together vision, and identify new opportunities.
- 90-day orientation to familiarize new team members with Better Together's mission, programs, policies, systems, and operations.
- Home office setup, including equipment and communication tools needed to succeed in a hybrid, remote-within-Florida environment.
Compensation and Benefits:
Annual Salary: Commensurate with experience.
Better Together also offers a generous benefits package, including:
- Medical insurance (99% employer paid, employee-only coverage)
- Dental insurance
- Vision insurance
- Life insurance
- Paid holidays
- Paid time off
- Retirement savings plan with 50/50 employer match up to 6%
QUESTIONSPlease direct all questions to [email protected].
