AI Product Manager – Business Enablement (Remote) at Progressive Leasing

You're a skilled Product Manager with at least 3 years of experience managing business-facing AI products, including vendor relationships and adoption. A bachel

Work type: remote

Location: Ohio

Type: Full-time

Summary

You're a skilled Product Manager with at least 3 years of experience managing business-facing AI products, including vendor relationships and adoption. A bachelor's degree or equivalent experience is required. **What makes it worth a look...** Progressive Leasing, a FinTech company, is hiring for this fully remote role. They offer competitive compensation and a comprehensive benefits package, including health insurance, a 401k match, and tuition reimbursement. **You might be a good fit if you...** * Have proven experience managing Microsoft 365 and Copilot licensing, governance, and enterprise rollouts. * Possess working knowledge of AI tools like Microsoft Copilot, Copilot Studio, Power Platform, ChatGPT, and Anthropic Claude. * Have experience designing AI adoption programs, change management, and end-user training, with the ability to track adoption metrics. * Are familiar with SaaS vendor management, including contracts and renewals.

Job Description

Progressive Leasingis a leading provider of in-store and e-commerce lease-to-own solutions. With more than 20 years in FinTech, we’ve grown from start-up to industry leader by innovating, simplifying, and valuing people. We are a subsidiary of PROG Holdings (NYSE: PRG), a FinTech holding company with three business segments: Progressive Leasing, Purchasing Power (a leading employee purchase program for consumer products and services using payroll deduction), and Four, a Buy Now Pay Later (BNPL) platform.

We are currently hiring a Principal R&D AI Software Engineer to help grow our company and ensure our mission is achieved!     

This role is a work from home position and can be performed remotely anywhere in the continental US or in our corporate location in Utah.Employee Value Proposition (EVP): PROG is dedicated to providing people with opportunity; opportunity for inclusive collaboration, opportunity for innovation, and opportunity for development.WE ARE: Prog Tech embodies the modernity and transformational vision that is core to our business evolution. As passionate and hungry technical experts, we join together on the mission of progressing through technology. We believe in taking pride in our engineering, in the relentless pursuit of daily progress, and to bring others with you in your march to the future. We continuously experiment, fail fast, and constantly deliver. 

YOU ARE:a Skilled Product Manger who owns the business-facing AI product surface at Progressive Leasing, managing tool licensing, vendor relationships, and adoption governance across the organization. You will partner directly with business unit leaders to identify and prioritize agent use cases, translate business requirements into actionable backlogs, and ensure the teams you serve have the training, best practices, and support structures to use AI tools effectively. You will own the intake and triage process between business stakeholders and the technical enablement team, and serve as the accountability owner for business AI outcomes — tracking adoption metrics, measuring impact, and making prioritization decisions that maximize value across the portfolio.

YOUR DAY-TO-DAY:

• Architect, design, and develop proof-of-concepts and early-stage production systems leveraging LLMs, agentic workflows, vector databases, and emerging AI


• Own the AI tool portfolio for business units — managing licensing, vendor relationships, renewal cycles, and feature roadmap engagement for Microsoft Copilot, Copilot Studio, and Power Platform


• Partner directly with business unit leaders to identify, evaluate, and prioritize AI agent use cases that deliver measurable operational value


• Translate ambiguous business needs into structured requirements, user stories, and actionable backlogs that the technical enablement team can execute against


• Own the intake and triage process between business stakeholders and the AI Agent Developer, ensuring work is scoped, prioritized, and sequenced for maximum impact


• Design and deliver AI adoption programs — including training curricula, best practice guides, and change management plans — that drive sustained usage across business teams


• Define and track adoption metrics, usage analytics, and outcome-based KPIs for every AI tool in the portfolio, and use that data to make prioritization decisions


• Manage stakeholder expectations and communicate timelines, progress, blockers, and outcomes in a clear, data-informed manner to audiences at every level of the organization


• Establish and maintain governance frameworks for AI tool usage across business units, ensuring compliance with organizational policies and security requirements


• Serve as the accountability owner for business AI outcomes — if a tool isn’t delivering value, you’re the one who flags it, fixes it, or kills it

• Product & Program Leadership: 3+ years of experience in product management, IT program management, or technology‑driven business operations, operating effectively between business and technical teams.


• Microsoft 365 & Copilot Ownership: Proven experience managing Microsoft 365 and Copilot licensing, governance, and enterprise rollouts, including coordination with technical partners.


• AI Platforms & Use‑Case Evaluation: Working knowledge of Microsoft Copilot, Copilot Studio, and Power Platform, with broader awareness of AI tools such as ChatGPT and Anthropic Claude to assess fit‑for‑purpose solutions.


• AI Adoption & Measurement: Experience designing or delivering AI adoption programs, change management, and end‑user training, with the ability to define and track adoption metrics, usage analytics, and outcome‑based KPIs.


• Enterprise Communication & Vendor Management: Strong communication and presentation skills, familiarity with SaaS vendor management (contracts, renewals, roadmaps), and a high‑integrity, results‑driven mindset backed by a bachelor’s degree or equivalent experience.


• AI‑enabled tools are already part of how work gets done across our organization, and their use will continue to expand over time. We value people who are curious, adaptable, and open to learning as roles and workflows evolve. 

• Competitive Compensation 

• Full Health Benefits; Medical/Dental/Vision/Life Insurance + Paid Parental Leave 

• Company Matched 401k 

• Paid Time Off + Paid Holidays + Paid Volunteer Hours 

• Employee Resource Groups (Black Inclusion Group, Women in Leadership, PRIDE, Adelante) 

• Employee Stock Purchase Program 

• Tuition Reimbursement 

• Charitable Gift Matching 

• Job required equipment and services 

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