177 Best 1099 Jobs in Tampa, Florida (May 2026)

Director of HRIS and Payroll

19 hours ago

Tampa

About Rocket Youth Rocket Youth owns and operates a growing portfolio of youth sports, enrichment, and after-school activity businesses across the United States. Our company is intentionally multi-brand and multi-location, with each business maintaining its unique identity and local market focus. We are highly acquisitive, completing approximately 10–15 acquisitions per year. Most of our companies are founder-led, with experienced local operators managing day-to-day operations. Rocket Youth provides operational leadership, tools, and support services to improve performance at our local businesses. These services span technology, marketing, CRM, analytics, M&A and de novo expansion, accounting, finance, HR, capital, and more. Position Overview The Director of HRIS & Payroll owns Rocket Youth's HCM/HRIS system, UKG, end-to-end and is accountable for accurate, timely, and compliant payroll execution across our multi-entity, multi-state portfolio. The Director is the lead UKG practitioner — designing system configuration and architecture, building SOPs, deploying new modules, optimizing existing ones including through workflow automation, producing reports and dashboards, and serving as the escalation point for manager-level help-desk questions. The Director also serves as the source of truth on UKG and payroll best practices for downstream HR partners — including the Director of Integrations and HRBPs — producing the SOPs, training materials, and process documentation they rely on. Additionally, the Director is the primary owner of payroll: hands-on directly for the first six months in role, then transitioning transactional execution to offshore payroll specialists in India while retaining ultimate accountability and final sign-off authority on every pay cycle. Given Rocket Youth's acquisition pace, the Director maintains a clean, auditable, and scalable UKG environment that absorbs newly integrated PartnerCos without configuration sprawl. The role partners cross-functionally with HR, Finance, IT, Legal, and M&A leadership. Key Responsibilities: HCM/HRIS Ownership – UKG Strategy, Architecture & Transformation • Serve as system owner and primary practitioner for UKG Pro (HCM and Payroll) and UKG Pro Workforce Management (timekeeping and scheduling), • Lead enterprise configuration strategy: earnings codes, pay rules, work rules, business rules, org structure, security roles, workflows, and integrations, • Design and deploy new UKG modules and system enhancements; evaluate and adopt platform releases, • Produce SOPs, training materials, and rollout communications for managers, employees, and downstream HR partners (Director of Integrations, HRBPs), • Manage manager-level UKG help-desk and serve as the escalation point for system issues, • Define and execute the 12-month UKG roadmap, balancing optimization work, new module deployment, and acquisition integration, • Maintain configuration governance and change-control standards to prevent sprawl as the portfolio grows Payroll Execution & Team Leadership • Personally execute multi-state, multi-entity bi-weekly payroll for the first six months in role, • Transition transactional payroll execution to payroll specialists based in India over a structured 90-day plan, retaining final sign-off authority on every cycle, • Onboard, train, manage, and oversee the offshore payroll team; design the control structure, KPIs, and escalation thresholds that govern the function, • Resolve escalated payroll issues, exceptions, and off-cycle items requiring judgment, • Manage payroll tax accounts and ensure timely, accurate filings (federal, state, local) Multi-State Compliance & Payroll Tax • Ensure multi-state payroll compliance across 40 active states, including SUI, SIT, local taxes, garnishments, ACA, multi-state withholding, and reciprocity rules, • Oversee quarterly and year-end processing (W-2s, 941s, state filings, ACA 1095-C) and any required amendments, • Partner with VP, HR, Legal and Finance on worker classification matters (W-2 vs. 1099) and lead remediation as needed, • Lead internal and external payroll audits; maintain audit readiness year-round, • Design and build proactive compliance monitoring within UKG — configuration controls, automated audit reports, and exception alerts that surface multi-state tax, classification, and wage-and-hour issues before they become liabilities Reporting, Data Integrity & Analytics • Build and maintain reporting infrastructure in UKG Pro BI, including operational dashboards and KPI metric reporting on payroll accuracy, integration health, compliance status, and headcount, • Establish and enforce data integrity standards across UKG Pro and WFM, • Deliver reporting to the VP of HR, VP Finance, Business Operations leaders, and PartnerCo leadership — including dashboards that give individual business operators visibility into their own headcount, payroll, and HR metrics Acquisition Integration & System Scalability • Partner with the Director of Integrations on each new PartnerCo's UKG onboarding, ensuring data, configuration, and processes are migrated cleanly and that newly acquired employees are set up correctly for HR and payroll, • Design configuration patterns that scale to 10–15 acquisitions per year without creating earnings code, pay rule, or org structure sprawl, • Maintain a clean, auditable system of record as the portfolio grows Education and Experience • 5+ years of direct, hands-on UKG Pro and Workforce Management experience (configuration, administration, integrations, and BI reporting) — non-negotiable prerequisite for this role, • 10+ years of progressive payroll and HRIS experience, • Bachelor's degree in Human Resources, Business Administration, Finance, Information Systems, or related field required, • Proven experience operating in multi-state, multi-entity environments, • Experience operating in high-growth and/or acquisition-driven organizations, regularly onboarding and training large numbers of new employees Skills and Knowledge • Multi-state payroll tax compliance fluency, including SUI, SIT, local taxes, garnishments, multi-state withholding, reciprocity, and ACA, • Comfort with hands-on payroll execution — someone who runs cycles personally, not just oversees others running them, • Strong process and SOP discipline; able to produce documentation that an offshore team can execute against without supervision, • Working knowledge of worker classification standards (ABC test, IRS common-law test, multi-state implications), • Direct, clear communication with executives, business partners, and frontline payroll staff alike, • Comfort with ambiguity and rapid change in an acquisition-driven environment, • High integrity and discretion handling sensitive employee and financial data Preferred Qualifications • Experience leading UKG implementations, transformations, major module builds, • Experience managing offshore or distributed payroll teams, • Experience in private equity-backed, roll-up, or acquisition-driven environments, including integrating acquired companies' payroll and HR data into UKG, • Experience supporting seasonal and 1099-heavy workforce populations, • CPP (Certified Payroll Professional) or equivalent certification RY is an equal opportunity employer, considering all applicants for employment regardless of race, color, religion, sex, gender identity, pregnancy, national origin, ancestry, citizenship, age, marital status, physical disability, sexual orientation, genetic information, or any other characteristic protected by state or federal law.

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