AI Platform Enablement Lead – Engineering & Adoption (Remote)

Progressive Leasing is a leading provider of in-store and e-commerce lease-to-own solutions. They are seeking an AI Platform Enablement Lead to support engineering teams in adopting AI-native workflows and tools, enhancing their development processes.

Responsibilities:

• 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

Requirements:

• 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