Onsite Managing Director

Job Details: Job Location: Kissimmee, FL

• Kissimmee, FL 34741, Position Type: Full Time, Salary Range: $140000.00 - $140000.00Salary/year, Job Category: ORLONS, Company Summary Real. Manage is a leading national community association management company serving homeowners' associations (HOAs), condominium associations, cooperatives, luxury high-rises, municipal utility districts, master-planned communities, and nationally recognized developer and builder clients. Real. Manage is proud to be recognized on the Inc. 5000 list of America's fastest-growing private companies and ranked among the top firms in the community management industry. We combine experienced people, innovative technology, and proven practices to help communities thrive. At Real. Manage, The RM Way is our service identity - something we live every day. It provides a shared definition of what great looks like, a common language for coaching and recognition, and a standard every associate can own. It guides how we serve our clients, how we serve each other, and how we grow. Our commitment to an exceptional associate experience is reflected in Real. Manage being Great Place to Work® Certified™. We believe exceptional client experiences start with our associates, and we foster a workplace where people are supported, encouraged to grow, and empowered to deliver outstanding service. Join Real. Manage and be part of a values-based organization where The RM Way shapes how we serve, work, grow, coach, and recognize one another every day - while making the communities we manage stronger because Real. Manage is there. Our Guiding Values Real. Manage is a values-based company with the following values as our guiding principles: Integrity: we always do the right thing. Respect: for our customers, employees and company; mutual respect is the cornerstone for every Real. Manage relationship. Selflessness: more than teamwork; we are part of something special and much larger than any of us. Personal Relationships: we are a professional services company; people do business with people they like. Always Improving: never satisfied, always learning, and always growing. At Real. Manage, we are always getting better. Community Summary This position supports a premier, large-scale community in the greater Kissimmee area. The community was developed around the concept of creating an engaging, connected, and high-quality residential lifestyle. The community includes a substantial residential portfolio and an extensive collection of recreational, wellness, lifestyle, and community amenities. The Association oversees a broad range of community infrastructure and services, which may include gated entrances, private roads, rights-of-way, sidewalks, golf cart paths, common areas, lakes, irrigation systems, landscaping, and other community assets and services. Given the scale of the community, breadth of amenities, and complexity of its operations, the Association requires a highly collaborative, service-oriented, and experienced onsite management team. Team members play an essential role in maintaining the Association's financial and operational integrity, preserving community assets, supporting the Board of Directors, and delivering a high standard of service to residents. This role offers an opportunity for an experienced executive to lead a sophisticated, large-scale community through organizational integration, operational excellence, financial stewardship, and resident-focused service. All onsite team members are expected to embrace a unified approach to community management by fostering collaboration across departments, maintaining clear and professional communication, demonstrating accountability, and supporting the shared goal of delivering exceptional service to residents and the Board of Directors.

Role Summary

The Managing Director serves as the senior executive responsible for integrating two management organizations into one cohesive, high-performing operation, establishing unified standards, policies, financial discipline, and consistent resident experience. This position requires a seasoned operational leader with demonstrated experience navigating organizational transitions, aligning diverse teams, and fostering a shared culture of accountability, collaboration, and service excellence.

The Managing Director provides strategic direction, establishes performance expectations, and develops a strong leadership structure that empowers department managers to effectively oversee their respective operations. With a system-oriented approach and a commitment to continuous improvement, this leader ensures that organizational success is supported by sustainable processes, clear accountability, and consistent service standards.

Reporting to the Board of Directors, the Managing Director directly oversees the General Manager (LCAM), Manager Finance, Manager Fit. Well, Manager Events, Manager Facilities, and Manager Grounds and Landscape. The Managing Director and all reporting leaders work collaboratively with established Board committees, recognizing their important role in strategic planning, policy development, recommendations, and organizational initiatives.

The position serves as a trusted strategic partner to the Board, providing informed recommendations, transparent communication, and sound operational judgment while maintaining appropriate boundaries between governance and management. The Board establishes policy and strategic direction, while management is responsible for executing operations within approved authority.

Real. Manage provides employment administration and management support, subject to the final governance arrangement. Through approachable leadership, operational expertise, and a resident-focused mindset, the Managing Director cultivates a unified organization where departments work toward shared objectives, leaders are empowered and accountable, and decisions support the community's long-term sustainability and continued success.

Strategic Leadership & Board Governance Lead integration of the two management organizations into one structure, culture, and set of operating standards; finalize leadership roles, decision rights, and accountability between the Managing Director, department managers, and Board. Translate the Board’s and Strategic Planning Committee’s long-term vision into annual operating plans, budgets, and measurable priorities; collaborate with established committees in developing strategies and recommendations.

Provide the Board with decision-ready options, analysis, recommendations, and timely follow-through, allowing directors to focus on governance rather than routine operations. Serve as a trusted liaison among the Board, committees, Real. Manage leadership, and relevant governing entities; maintain transparent, professional communication.

Provide informed recommendations on service delivery, operational risks, long-term planning, and matters requiring Board consideration. Financial Stewardship & Business Operations Own the operating and capital budget process in partnership with Manager Finance; support disciplined, justified assessments and long-term financial sustainability.

Ensure reliable financial reporting, sound internal controls, clean audits, effective cost management, and clear explanations of budget variances. Oversee compliance with approved purchasing, contract administration, invoice approval, and financial control procedures within delegated authority. Evaluate operational processes and implement policies, procedures, and controls that improve effectiveness, consistency, and stewardship of Association resources.

Coordinate with Real. Manage and Cira. Connect shared services to resolve financial and operational service issues. Department Leadership, People Development & Accountability Set direction, expectations, and standards for six direct reports: General Manager (LCAM), Manager Finance, Manager Fit. Well, Manager Events, Manager Facilities, and Manager Grounds and Landscape.

Managers are accountable for running their respective departments. Recruit, onboard, coach, mentor, and evaluate managers; ensure timely performance reviews, staff development plans, and appropriate documentation. Set clear expectations, establish department goals and service standards, and hold leaders accountable for deadlines, quality, staffing, and resident experience.

Promote effective workforce planning, succession development, interdepartmental coordination, and constructive resolution of operational challenges. Partner with Human Resources and Real. Manage leadership on employee relations, policy implementation, and escalated personnel matters. Community Operations, Facilities & Risk Management Establish community-wide resident service standards and coordinate department leaders to ensure services reflect resident needs and consistent operational quality.

Oversee major contracts, including resident landscaping services through the General Manager (LCAM), and monitor service agreements, vendor performance, capital projects, and asset preservation. Work with department leaders to identify safety concerns, emergency preparedness needs, insurance-related issues, and other operational risks; escalate appropriately.

Review recurring service concerns and establish corrective action plans, follow-up mechanisms, and quality-assurance practices. Support asset preservation, capital planning, and coordinated responses to urgent community conditions. Board, Resident & Stakeholder Relationships Build credibility and constructive working relationships with Board members, residents, committees, vendors, and community partners.

Respond to sensitive or escalated concerns with professionalism, sound judgment, appropriate confidentiality, and timely follow-through. Coordinate communication across departments so residents and Board representatives receive clear, accurate, and consistent information. Establish structured resident feedback loops, including an annual survey, town halls, and service-level reporting; use resident input, utilization, and cost data to guide improvements.

Represent the Association professionally in appropriate civic, business, and community activities. Reporting, Continuous Improvement & Service Excellence Implement a consistent operating management system with departmental scorecards, monthly performance reviews, quarterly performance conversations, documented standard operating procedures, and accountability checkpoints.

Provide a monthly operating report to Real. Manage leadership and/or the Board covering department KPIs, budget-to-actual performance, staffing and overtime, resident concerns, vendor performance, safety incidents, projects, risks, and upcoming 30–60-day priorities. Participate in recurring leadership meetings, track action items, and resolve cross-functional issues or escalate matters requiring executive or Board direction.

Promote continuous improvement through the adoption of best practices and preferred methodologies, such as Kaizen and 5S, to enhance service delivery, operational consistency, efficiency, and cross-departmental collaboration. Champion unified service excellence through visible leadership, mutual respect, accountability, and collaboration with Real.

Manage shared services. Decision-Making Authority & Governance Exercise executive authority within Board-approved policies and delegated limits, while maintaining clear separation between Board governance and day-to-day operational management. Approve expenditures only within Board-approved budgets, established purchasing procedures, and expressly delegated authority limits.

Recommend and prioritize capital and operational projects in partnership with the Board and onsite leadership team. Establish departmental goals, performance expectations, and operating procedures consistent with Board direction and Real. Manage policies. Direct vendor performance, contract administration, and service standards within approved agreements and delegated authority.

Resolve cross-department operational issues and recommend organizational changes, staffing models, and strategic initiatives for appropriate approval. Partner with the General Manager (LCAM) to ensure operational compliance with applicable Florida Chapter 720 requirements and governing documents; maintain community-owned, consistent, enforceable policies and procedures.

Leadership & Technical Expertise Systems-oriented executive capable of designing effective operating rhythms, scorecards, budgets, documented procedures, and continuous-improvement practices, including familiarity with Kaizen and 5S. Resident-first and data-driven leader who uses surveys, participation, service levels, and cost information to make sound decisions and communicate financial performance clearly.

Trusted Board and committee partner who respectfully maintains governance and management boundaries, builds consensus, and offers actionable recommendations. Supportive but accountable coach who develops managers, resolves cross-functional issues, delivers commitments, and plans for evolving resident demographics and future community needs.

Success at 12 Months Within 12 months, the Managing Director will have established one integrated, accountable organization with unified financial reporting, policies, standards, and a stable leadership team, demonstrated through: Integration & Standards: One coordinated organization, a consolidated set of books in partnership with Manager Finance, documented operating procedures, and clear decision rights.

Resident Experience: Resident survey results improve against a documented pre-integration baseline, with visible service standards and responsive feedback mechanisms. Board Governance & Strategy: Board meetings increasingly focus on decisions, policy, and long-term strategy instead of routine operational issues; committee partnerships are effective and well defined.

Leadership & Accountability: All six direct-report functions have empowered leaders, clear responsibilities, department scorecards, and consistent performance reviews. Disclaimer This description is not intended to be an exhaustive list of duties.

Responsibilities

may evolve based on Board direction and community needs. Reasonable accommodation may be made to enable qualified individuals to perform the essential functions of this position.

Qualifications

Bachelor’s degree in business administration, Management, or a related field preferred; MBA, MPA, or similar advanced degree a plus. Preferably 5–10 years of senior leadership experience overseeing multiple departments or operational functions in a large-scale community, resort, hospitality, municipal, club, or related environment.

Demonstrated experience leading organizational integration, change management, or the unification of distinct teams, processes, and organizational cultures; community association management experience strongly preferred. Florida Community Association Manager (CAM) license preferred but not required; professional designations such as CMCA, AMS, PCAM, or LSM are highly desirable.

Demonstrated business acumen, financial management expertise, budget analysis, strategic planning, and sound operational decision-making. Proven experience overseeing service delivery, contracts, vendor relationships, major projects, personnel development, and complex stakeholder relationships. Strong leadership, organizational, written and verbal communication, conflict resolution, and Board presentation skills, with the ability to build consensus and maintain productive relationships with diverse stakeholders.

Physical Requirements Ability to sit for prolonged periods at a desk and work on a computer. Ability to occasionally stand, walk, bend, or reach as needed. Ability to lift or move objects up to 10–15 pounds (e.g., files, office supplies). Manual dexterity to operate a computer keyboard, mouse, telephone, and other office equipment.

Visual acuity to read printed materials, spreadsheets, and computer screens. Hearing and speech ability to communicate effectively in person, by phone, and in virtual meetings. Ability to work in a standard office environment with moderate noise levels. Ability to work a standard schedule, with occasional extended hours as required.

Pay and Benefits $140,000 annually.

Benefits

include Medical Insurance Dental Insurance Vision Insurance Life and Disability Insurance HSA (Required High Deductible Medical Plan to be eligible) FSA Education Reimbursement 401K matching Employee Assistance Program (EAP) 11 paid Holidays EEO & Values Statement Real. Manage is a values-based, equal opportunity employer.

We celebrate diversity and are committed to creating an inclusive environment for all employees. ADA Statement Real. Manage is committed to providing reasonable accommodation to individuals with disabilities. If you need an accommodation to apply for this position or perform essential job functions, please contact Human Resources at hr@ciramail.

com.