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

President/ Chief Operating Officer (COO)- Tampa, FLBuild 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 LeadershipOversee day-to-day operations across HOA, CDD, Lifestyle, and corporate departmentsEnsure consistency, compliance, and operational excellence across all regionsDesign, implement, and refine scalable systems, SOPs, and workflowsIdentify gaps, solve problems, and continuously improve service delivery and efficiencyOwn operational KPIs and performance outcomesRegional Oversight & ExpansionProvide executive oversight for multi-region operations and future market expansionLead and support Regional Directors, Department Heads, and senior managersBuild repeatable operating models that support growth without sacrificing qualityMonitor performance metrics and proactively address risks or challengesHOA & CDD OperationsEnsure compliance with governing documents, state statutes, and contractual obligationsPartner with legal, compliance, and finance teams to mitigate risk and ensure sound financial practicesSupport boards through strong governance, education, and transparent operationsLifestyle OperationsOversee Lifestyle programs that drive engagement, connection, and happinessEnsure Lifestyle Directors are trained, supported, and aligned with Kai Connected's valuesCollaborate with marketing and communications for cohesive messagingLeadership & CultureLead, mentor, and develop senior leaders and management teamsFoster a people-first, accountability-driven culturePartner with HR on organizational design and succession planningWHAT WE'RE LOOKING FORBachelor's degree required; MBA preferred10+ years senior leadership experienceMulti-region operational experienceDeep understanding of HOA and CDD operationsProven ability to scaleStrong decision-making and leadership skillsWhy Kai ConnectedReal autonomy. High standards. People-first. Build something meaningful.Why This Role MattersThe 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: https://hikai.com/