Remote Director Ancillary Service Jobs in Florida

ABOUT PEOPLEASE

Peoplease is a leading Professional Employer Organization (PEO) providing solutions to small and medium-sized businesses in the blue and gray-collar industries. We enable our clients and partners to achieve their aspirations by offering world-class service and administrative solutions in payroll, human resources, benefits, and risk management. At Peoplease, we foster a culture of inclusion and belonging, driven by our core values: Engagement, Integrity, Tenacity, Curiosity, Happiness, and a Service-obsessed mindset.

POSITION SUMMARY

The Product Manager – Ancillary is responsible for defining, developing, and scaling Peoplease’s ancillary product portfolio, including time & attendance, applicant tracking, and related HR technology solutions. This role owns the end-to-end product lifecycle from vision and roadmap through vendor selection, integration, launch, and optimization - ensuring ancillary offerings are tightly aligned with Peoplease’s core HRIS, operational capabilities, and client needs.

Partnering cross-functionally with Payroll Operations, Sales, Client Services, Implementation, Compliance, and external vendors, the Product Manager ensures solutions are compliant, service-ready, and commercially successful. This role blends strategic product leadership with hands-on execution, using data and customer insights to drive adoption, revenue growth, and client retention across Peoplease’s client base.

This role requires a balance of strategic product leadership and hands-on execution, including vendor management, integration oversight, and go-to-market coordination.

ESSENTIAL DUTIES AND RESPONSIBILITIES

Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.

• Works under the direction of the Director of Program & Product Management on strategic decisions, with primary responsibility for execution and delivery.
• Plays a strategic role in the product vision, roadmap, and lifecycle for ancillary PEO products such as time & attendance, applicant tracking, and related HR technology solutions, with a focus on increased adoption, sales, and client retention.
• Participate in the evaluation and selection of third-party vendors/partners for ancillary systems; serve as the primary owner of associated vendor relationships, and lead integrations to ensure seamless functionality with core HRIS platforms.
• Partner with Finance, Legal, Information Security, and Compliance on vendor contracts, pricing structure, and performance.
• Conduct market, competitive, and customer research to identify unmet needs and opportunities for new product offerings or enhancements, establishing ongoing voice-of-customer feedback loops with clients and internal teams.
• Translate business requirements into clear, prioritized product specifications, user stories, and acceptance criteria for development teams and vendor partners.
• Collaborate closely with Payroll Operations, Sales, Client Services, Implementation, and Compliance teams to ensure product feasibility, operational alignment, clear go-to-market readiness, and service-ready rollout.
• Lead end-to-end product launches, including planning, internal training, documentation, pricing recommendations, and performance tracking.
• Monitor product KPIs (adoption, utilization, revenue, retention, and satisfaction), including attach rates to core PEO offerings, and drive continuous improvement based on insights and feedback.
• Ensure all ancillary solutions remain compliant with federal, state, and industry regulations impacting labor, scheduling, applicant tracking, and workforce management.
• Serve as the subject-matter expert for ancillary products, acting as a resource to internal stakeholders and clients.

MINIMUM QUALIFICATIONS (KNOWLEDGE, SKILLS & ABILITIES)

• 3–5+ years of product management experience, ideally within a PEO, HR tech, payroll, or workforce-management environment.
• Experience with systems such as time & attendance, ATS, HRIS add-ons, or other workforce-management platforms.
• Strong understanding of PEO operations, including HR, payroll, benefits administration, compliance, and client service workflows.
• Demonstrated success working with cross-functional teams and leading complex integrations or vendor-driven, third-party product implementations.
• Data-driven decision maker with experience creating and tracking KPIs and business cases.
• Excellent communication and stakeholder-management skills; able to translate between technical and non-technical audiences.
• Familiarity with the PrismHR marketplace or similar PEO/HRIS ecosystems with third-party integrations.

WORK ENVIRONMENT & PHYSICAL REQUIREMENTS

• This is a remote-first role with occasional travel for meetings, training, or industry events.
• Regular virtual collaboration across distributed teams.
• Frequent computer-based tasks, including data analysis and report generation.

WHY JOIN US?

• Be part of a forward-thinking company in a rapidly growing PEO sector.
• Opportunity to influence strategy and shape operations at an enterprise level.
• Work with a company positioned to be the leading provider of PEO services in the U.S.
• Competitive compensation and benefits package, with opportunities to lead thought leadership initiatives.