President / Chief Operating Officer (COO)
Location: Candidates located outside of Florida are encouraged to apply. Relocation assistance may be available for highly qualified candidates. Candidates who do not relocate should expect periodic travel to the Tampa office and other business locations as required.
Employment Type: Full-Time/Salaried/Exempt
Travel Expectations: Ability to travel periodically throughout Florida and other growth markets as business needs require.
Build the Operation. Lead the People. Scale the Vision.
This role is designed for an experienced executive who can serve as the operational counterpart to the Founder, ensuring strategy is translated into execution while supporting the company's continued growth and expansion.
Kai Connected is a growth-stage community management company providing HOA, CDD, Lifestyle, and Community Services throughout Florida, with expansion plans into Texas and additional markets.
Our mission is simple: maximize happiness for residents, board members, clients, and our team.
We are seeking a highly accomplished President / Chief Operating Officer (COO) to serve as the operational leader of the organization and partner directly with the Founder. This executive will oversee all day-to-day operations, lead department heads and senior leaders, drive accountability, strengthen culture, improve operational efficiency, and help scale the company for long-term growth.
This is not a traditional executive role. This is a hands-on leadership position for someone who enjoys building systems, developing leaders, solving complex operational challenges, and creating organizational excellence.
Position Overview
The President / COO will provide leadership and oversight to multiple operational departments and senior leaders across the organization. This role is responsible for ensuring alignment, accountability, and operational excellence throughout all functions of the company while serving as the primary operational partner to the Founder.
Areas of responsibility include, but are not limited to:
- HOA Management Operations
- Community Development District (CDD) Operations
- Lifestyle Operations
- Accounting & Financial Operations
- Human Resources
- Resident Support Services
- Communications & Marketing
- Field Operations
- Administrative Services
Areas of Responsibilities
Executive Leadership & Strategic Execution
- Partner directly with the Founder to execute the company's strategic vision
- Translate business goals into operational plans and measurable objectives
- Drive organizational alignment across all departments
- Lead operational planning, forecasting, and execution initiatives
- Identify opportunities to improve efficiency, scalability, and profitability
- Serve as a key advisor to executive leadership
Operational Leadership
- Oversee all day-to-day business operations
- Establish and maintain company-wide operational standards
- Develop, implement, and improve policies, procedures, and workflows
- Create scalable systems that support continued growth
- Monitor operational performance and drive continuous improvement
- Ensure service excellence across all communities and departments
Leadership & Talent Development
- Lead, coach, mentor, and develop Vice Presidents, Directors, and senior leaders
- Build accountability throughout the organization
- Create leadership development initiatives and succession planning strategies
- Partner with Human Resources on workforce planning and organizational design
- Foster a culture of professionalism, collaboration, and continuous improvement
HOA & CDD Operations
- Ensure compliance with governing documents, contracts, and applicable regulations
- Support operational consistency across all managed communities
- Partner with department leaders to improve board and resident experiences
- Identify and address operational risks proactively
- Ensure communities receive exceptional service delivery
Growth & Scalability
- Develop infrastructure to support future growth and expansion
- Evaluate organizational structure and recommend improvements
- Identify operational bottlenecks and implement solutions
- Support acquisitions, integrations, and new market expansion initiatives
- Create repeatable processes that can scale with company growth
Financial & Business Performance
- Partner with Accounting and Finance leadership to monitor business performance
- Review operational metrics, KPIs, budgets, and forecasts
- Improve operational efficiency while maintaining service quality
- Drive accountability for departmental performance and outcomes
- Utilize data to guide decision-making and business strategy
Required Qualifications
- Bachelor's Degree required
- Minimum 10 years of progressive leadership experience
- Minimum 5 years in a senior executive, COO, President, Vice President, Regional Director, or equivalent leadership role
- Experience leading multiple departments and functions simultaneously
- Proven track record of scaling organizations and leading growth initiatives
- Experience managing senior leaders and leadership teams
- Strong operational, strategic, and financial acumen
- Exceptional communication and leadership skills
Preferred Qualifications
- CAM License
- MBA
- Texas market experience
- CDD experience
- Multi-state HOA portfolio experience
Required Experience
- HOA Management leadership experience, Community Association Management leadership experience, Property Management leadership experience, CDD Operations leadership experience, or a closely related residential community services leadership background.
- Experience leading multi-community, multi-property, or multi-region operations.
- Experience working directly with Boards of Directors and executive leadership teams.
Candidates without direct HOA, Community Association Management, Property Management, CDD Operations, or closely related residential community services leadership experience may not be considered.
Who You Are
- You thrive in fast-growing organizations.
- You enjoy building systems, developing leaders, and solving complex challenges.
- You are comfortable making difficult decisions while maintaining a people-first approach.
- You are comfortable leading leaders and holding teams accountable while maintaining a positive, people-first culture.
- You balance strategic thinking with operational execution.
- You lead with accountability, integrity, and transparency.
- You are energized by growth and continuous improvement.
Compensation & Benefits
- Medical, Dental, and Vision Insurance
- 401(k)
- Paid Time Off and Company Holidays
- Relocation Assistance Available for Qualified Candidates
- Opportunity to partner directly with executive leadership and influence company strategy
- Additional incentive opportunities may be available based on performance, company growth objectives, and business development contributions
What Success Looks Like
Within your first 12 months, you will:
- Develop strong partnerships with Vice Presidents, Directors, and department leaders while creating a culture of accountability and operational excellence.
- Establish clear operational accountability across departments
- Improve organizational efficiency and communication
- Strengthen leadership development and performance management
- Implement scalable systems and processes
- Support successful company growth and expansion initiatives
- Help create a best-in-class culture focused on service, accountability, and results
Why Join Kai Connected?
- Opportunity to help shape the future of a growing organization
- Direct partnership with executive leadership
- High-impact role with meaningful influence
- Ability to build and improve systems from the ground up
- Strong company culture focused on people and performance
- Growth-oriented environment with expansion opportunities
Application Requirements
To be considered, applicants should submit:
- Current Resume
- LinkedIn Profile
Application Questions
Please be prepared to answer the following during the application process:
- Why does this opportunity interest you?
- Describe your executive leadership experience.
- Describe your experience leading organizational growth and operational scalability.
- What size teams and budgets have you been responsible for overseeing?
- Describe a time you led an organization through significant growth, change, or operational transformation.
Kai Connected is an equal opportunity employer. We value leadership, integrity, and kindness. We are building something special together. Check us out: https://hikai.com/
Benefits:
- 401(k)
- Dental insurance
- Health insurance
- Life insurance
- Paid time off
- Vision insurance
Application Question(s):
- Describe your direct HOA, Community Association Management, CDD, or Property Management leadership experience, including portfolio size and leadership responsibilities.
- Have you directly managed Community Managers, Portfolio Managers, Regional Managers, or Property Management leadership teams? If yes, please describe.
- What is the largest portfolio of communities, associations, or properties you have overseen?
- Describe your experience working directly with HOA Boards, Condominium Boards, Master Associations, or governing boards.
Education:
Experience:
- HOA/Community Association Management/CDD Leadership: 6 years (Preferred)
License/Certification:
- CAM (Community Association Manager) license (Preferred)
Ability to Relocate:
- Tampa, FL 33607: Relocate before starting work (Preferred)
Work Location: In person
