AI Platform Enablement Lead – Engineering & Adoption

Progressive Leasing is 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 AI Platform Enablement Lead – Engineering & Adoption 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: an AI Platform Enablement Lead Engineer who can support an embedded change agent role focused on bringing AI-native ways of working to every development team in the technology organization. You will spend the majority of your time in the field — working alongside engineering teams to stand up new tools, establish platform standards, introduce agentic workflows, and build the habits and practices that make AI assistance stick. You will run enablement programs, collect feedback from the teams you serve, and bring structured requirements and adoption signal back into the platform team's backlog. Equal parts technologist, coach, and internal consultant, this role is the connective tissue between the platform team's capabilities and the 350+ person technology organization that depends on them.

YOUR DAY-TO-DAY:

• Spend the majority of your time embedded with engineering teams — working alongside developers to stand up AI coding tools, establish platform standards, and introduce agentic workflows into their daily delivery process
• Run hands-on enablement programs including workshops, lunch-and-learns, one-on-one coaching sessions, and team-level onboarding for AI development tools like Claude Code and GitHub Copilot
• Assess team-level AI readiness across the 350+ person technology organization — identifying gaps in documentation, coding standards, context files, and workflow design that limit AI effectiveness
• Prescribe and deliver targeted interventions that help teams get more value from the agentic platform — from CLAUDE.md setup and prompt engineering to agentic workflow configuration and best practice adoption
• Collect structured feedback from every team you serve and translate it into actionable requirements and adoption signal for the platform team’s backlog
• Produce playbooks, best practice guides, and enablement materials that help engineering teams integrate AI tools into their existing Git, Jira, Confluence, and GitHub Actions workflows without disrupting delivery
• Define and track adoption indicators across teams — measuring what’s working, what’s stuck, and what needs adjustment — and present clear signal to platform leadership on enablement progress
• Serve as the connective tissue between the platform team’s capabilities and the engineering organization that depends on them — equal parts technologist, coach, and internal consultant

YOU'LL BRING:

• 5+ years’ of experience in software engineering, developer relations, technical enablement, or a role that combines deep technical credibility with organizational change work
• Enough technical depth to credibly work alongside engineering teams — comfortable reading code, understanding repo structure, and evaluating whether AI tooling is configured correctly
• Practical experience with AI coding tools — Claude Code, GitHub Copilot, or equivalent — including context file setup, prompt engineering for development tasks, and agentic workflow basics
• Experience delivering technical enablement, internal training, or developer advocacy programs at a team or organizational scale
• Ability to assess team-level AI readiness and prescribe targeted interventions that move teams from passive tool usage to active, high-leverage AI-assisted development
• Strong written communication skills for producing playbooks, structured feedback reports, and best practice guides that inform platform team priorities
• Experience with developer tooling ecosystems — Git, Jira, Confluence, GitHub Actions — and the ability to help teams integrate AI tools into their existing workflows
• Comfort facilitating workshops and coaching sessions with engineers across varying skill levels and varying degrees of enthusiasm for AI-assisted development
• Metrics orientation: ability to define adoption indicators, track progress, and present clear signal on what’s working and what needs adjustment
• Bachelor’s degree or equivalent work 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.

WE OFFER:    

• 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

Progressive Leasing welcomes and encourages diversity in the workplace. We do not discriminate in any aspect of employment on the basis of race, color, religion, national origin, ancestry, gender, sexual orientation, gender identity and/or expression, age, veteran status, disability, or any other characteristic protected by federal, state, or local employment discrimination laws where Progressive Leasing does business.