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- AI Automation will play a key role in shaping the future of AI and automation at Peoplease. This individual will manage initiatives from concept to completion; defining needs and success criteria, coordinating across business and technology teams, ensuring seamless implementation, and tracking impact and ROI. 

This is a hands-on, fast-paced role suited for an early-to-mid career professional eager to take ownership, grow rapidly, and make visible contributions to high-impact innovation efforts within the company.  

Essential Duties and Responsibilities

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

• Program Ownership – Define scope, success criteria, and roadmaps for AI/automation initiatives; develop project/resource plans and lead execution to completion. 
• Business & Technology Alignment – Translate business needs into actionable requirements for developers, vendors, and internal stakeholders through interviews, workshops, and documentation. 
• Cross-Functional Leadership – Drive collaboration between Operations, IT, and business teams; proactively remove roadblocks and ensure alignment. 
• Value Delivery & ROI – Establish success metrics, track performance, and report on business impact to leadership. 
• Change & Adoption – Lead rollout, training, and change management to ensure solutions are adopted and sustained. 
• Vendor & Technology Evaluation – Assess, select, and manage vendor solutions; identify emerging AI/automation opportunities relevant to Peoplease. 

Minimum Qualifications (Knowledge, Skills, & Abilities)

Minimum: 

• 3–5+ years in product, project, or program management (PMP/ACP/CSM a plus). 
• 2+ years hands-on with Artificial Intelligence, or workflow technology implementations. 
• Proven success leading cross-functional initiatives and vendor integrations. 
• Strong ability to drive change and influence adoption across diverse teams. 
• Business-first mindset; skilled at linking technical solutions to measurable outcomes. 

Preferred: 

• Experience in HR services, payroll, or the PEO industry. 
• Familiarity with workflow automation platforms (e.g., Zapier, UiPath, Power Automate, or similar). 
• Exposure to product ownership practices (road mapping, backlog management). 
• Demonstrated ability to evaluate and prioritize emerging technologies. 

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. 
• Occasional lifting (up to 25 lbs) may be required. 

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.