President/ Chief Operating Officer (COO)- Tampa, FL

President/ Chief Operating Officer (COO)- Tampa, FL

Build the operation. Lead the people. Scale the vision.

The President/ Chief Operating Officer (COO) is a senior executive role responsible for overseeing all operational functions of Kai Connected across multiple regions, with current operations in Florida and imminent expansion into Texas and additional growth markets.

Kai Connected is a growing community management company delivering HOA, CDD, and Lifestyle services under one roof. Our mission is simple but ambitious: maximize happiness for residents, boards, and our teams. We believe in a people-first culture, high standards, and moving fast without losing heart.

This is a rare opportunity for a seasoned operator to step into a true run-the-business role. As President/ COO, you will own operations end to end, from strategy through execution, partnering closely with the Founder to scale Kai Connected across markets while preserving our culture, standards, and soul.

Operational Leadership

- Oversee day-to-day operations across HOA, CDD, Lifestyle, and corporate departments

- Ensure consistency, compliance, and operational excellence across all regions

- Design, implement, and refine scalable systems, SOPs, and workflows

- Identify gaps, solve problems, and continuously improve service delivery and efficiency

- Own operational KPIs and performance outcomes

Regional Oversight & Expansion

- Provide executive oversight for multi-region operations and future market expansion

- Lead and support Regional Directors, Department Heads, and senior managers

- Build repeatable operating models that support growth without sacrificing quality

- Monitor performance metrics and proactively address risks or challenges

HOA & CDD Operations

- Ensure compliance with governing documents, state statutes, and contractual obligations

- Partner with legal, compliance, and finance teams to mitigate risk and ensure sound financial practices

- Support boards through strong governance, education, and transparent operations

Lifestyle Operations

- Oversee Lifestyle programs that drive engagement, connection, and happiness

- Ensure Lifestyle Directors are trained, supported, and aligned with Kai Connected’s values

- Collaborate with marketing and communications for cohesive messaging

Leadership & Culture

- Lead, mentor, and develop senior leaders and management teams

- Foster a people-first, accountability-driven culture

- Partner with HR on organizational design and succession planning

WHAT WE’RE LOOKING FOR

- Bachelor’s degree required; MBA preferred

- 10+ years senior leadership experience

- Multi-region operational experience

- Deep understanding of HOA and CDD operations

- Proven ability to scale

- Strong decision-making and leadership skills

Why Kai Connected

Real autonomy. High standards. People-first. Build something meaningful.

Why This Role Matters

The President/ COO is central to Kai Connected’s success. You are the bridge between vision and reality, ensuring that as we grow, we remain aligned, operationally excellent, and deeply human.

If you have led operational turnarounds, built scalable teams, and are energized by ownership, accountability, and impact, we would love to hear from you.

• Kai Connected is an equal opportunity employer. We value leadership, integrity, and kindness. We are building something special together. Check us out: