Onsite Managing Director (KFL11326)

RealManage•Kissimmee, FL

3d•$140,000 - $140,000•Onsite

About The Position

The Managing Director is the senior executive responsible for integrating two management organizations into one cohesive, high-performing operation, with unified standards, policies, financial discipline, and a consistent resident experience. The role provides strategic direction, establishes performance expectations, and develops a leadership structure that enables department managers to oversee their operations effectively. It emphasizes sustainable processes, clear accountability, continuous improvement, and resident-focused service. Reporting to the Board of Directors, the Managing Director directly oversees the General Manager (LCAM), Manager Finance, Manager FitWell, Manager Events, Manager Facilities, and Manager Grounds and Landscape. The role works with Board committees and serves as a strategic partner to the Board, providing recommendations, transparent communication, and operational judgment while preserving the distinction between Board governance and management. RealManage provides employment administration and management support, subject to the final governance arrangement. The position leads strategic planning and organizational integration; financial stewardship and business operations; department leadership and employee development; community operations, facilities, and risk management; Board, resident, and stakeholder relationships; and reporting, continuous improvement, and service excellence. The Managing Director exercises executive authority within Board-approved policies and delegated limits, and partners with the General Manager (LCAM) on compliance with applicable Florida Chapter 720 requirements and governing documents. Within 12 months, the Managing Director is expected to establish an integrated and accountable organization with unified financial reporting, policies, standards, documented procedures, clear decision rights, a stable leadership team, department scorecards, and consistent performance reviews. Success also includes improved resident survey results against a documented baseline, effective committee partnerships, and Board meetings increasingly focused on policy, decisions, and long-term strategy. The role is based onsite in Kissimmee, Florida, and supports a large-scale community with extensive residential, recreational, wellness, lifestyle, and community amenities and infrastructure. The position follows a standard schedule, with occasional extended hours as required. The job description notes that responsibilities may evolve based on Board direction and community needs, and reasonable accommodation may be made for qualified individuals to perform essential functions.

Requirements

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.
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.
Ability to sit for prolonged periods at a desk and work on a computer; occasionally stand, walk, bend, or reach; and lift or move objects up to 10–15 pounds.
Manual dexterity to operate a computer keyboard, mouse, telephone, and other office equipment; visual acuity to read printed materials, spreadsheets, and computer screens; and 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 and a standard schedule, with occasional extended hours as required.

Nice To Haves

Bachelor’s degree in business administration, Management, or a related field preferred.
MBA, MPA, or similar advanced degree is a plus.
Community association management experience is strongly preferred.
Florida Community Association Manager (CAM) license is preferred but not required.
Professional designations such as CMCA, AMS, PCAM, or LSM are highly desirable.

Responsibilities

Lead integration of two management organizations into one structure, culture, and set of operating standards; clarify leadership roles, decision rights, and accountability.
Translate the Board’s and Strategic Planning Committee’s long-term vision into annual operating plans, budgets, and measurable priorities; collaborate with committees on strategies and recommendations.
Provide the Board with decision-ready options, analysis, recommendations, and timely follow-through, and serve as a liaison among the Board, committees, RealManage leadership, and relevant governing entities.
Own the operating and capital budget process in partnership with Manager Finance; support disciplined 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 RealManage and CiraConnect shared services to resolve financial and operational service issues.
Set direction, expectations, and standards for six direct reports: General Manager (LCAM), Manager Finance, Manager FitWell, Manager Events, Manager Facilities, and Manager Grounds and Landscape.
Recruit, onboard, coach, mentor, and evaluate managers; ensure timely performance reviews, staff development plans, and appropriate documentation.
Establish department goals and service standards and hold leaders accountable for deadlines, quality, staffing, and resident experience.
Promote workforce planning, succession development, interdepartmental coordination, and constructive resolution of operational challenges; partner with Human Resources and RealManage leadership on employee relations and escalated personnel matters.
Establish community-wide resident service standards and coordinate department leaders to provide consistent operational quality responsive to resident needs.
Oversee major contracts, vendor performance, service agreements, capital projects, and asset preservation, including resident landscaping services through the General Manager (LCAM).
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 urgent community responses.
Build constructive relationships with Board members, residents, committees, vendors, and community partners; handle sensitive or escalated concerns with professionalism, confidentiality, and timely follow-through.
Coordinate communication across departments and establish resident feedback mechanisms, 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.
Implement an 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 RealManage 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 using best practices and methodologies such as Kaizen and 5S, and champion unified service excellence through visible leadership, respect, accountability, and collaboration.
Exercise executive authority within Board-approved policies and delegated limits; approve expenditures only within approved budgets, purchasing procedures, and expressly delegated authority.
Recommend and prioritize capital and operational projects with the Board and onsite leadership team; establish departmental goals, performance expectations, and procedures consistent with Board direction and RealManage policies.
Direct vendor performance, contract administration, and service standards within approved agreements and delegated authority; 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, and maintain consistent, enforceable community-owned policies and procedures.