Program Manager AI Enablement

About the Role:

AI is changing how every team at ShipMonk works—how engineers write code, how CX resolves tickets, how operations route shipments, how finance and analysts find answers. The tools are arriving faster than the organization can absorb them. We are seeking an AI Enablement Program Manager to close that gap: to run the company-wide program that turns AI from scattered experiments into a skill every employee can use well, safely, and with confidence.

In this role, you won't just "schedule training"—you'll run the program that levels up an entire company. You'll curate the curriculum, organize the cohorts, champion the tools, and drive adoption across every department. Your mission is to ensure that every team at ShipMonk knows what AI can do for their work, has the skills and tools to do it, and uses it responsibly—across the whole company.

Desired Experience:

• Program Management Core: 2+ years, project management training, enablement, L&D, or cross-functional programs—you've run a schedule, wrangled stakeholders, and driven something to completion across more than one team.
• Enablement & Education: Experience building or running learning programs (technical training, L&D, developer relations, or sales/CX enablement). You know how adults actually pick up skills—hands-on, in cohorts, against real work—not death by slide deck.
• AI Fluency: Hands-on, current familiarity with modern AI tools—LLMs, AI assistants, prompting. You don't need to build the model; you need to help the marketer, the engineer, and the CX agent get real leverage from it, and you stay current in a field that moves monthly.
• Operating Range: Comfortable working across Engineering, CX, Operations, Product, Finance, and People. You can tailor the same material to very different audiences and earn credibility with each.
• Organized & Measured: You keep a program on the rails—calendars, enrollment, content, follow-through—and you track whether it's actually working.
• Nice to have: Experience in logistics, supply chain, or e-commerce; familiarity with AI responsible-use or data-privacy basics.

Skills & Responsibilities:

• Curriculum Curation (The Backbone): Assemble and maintain a tiered AI curriculum—from "AI for everyone" foundations to role-specific tracks for engineering, CX, ops, and analytics. Keep it current as tools change, sourcing external content where it's faster than building.
• Cohort & Session Delivery (The Engine): Schedule and run recurring cohorts and workshops across both Prague and US time zones. Handle enrollment, logistics, materials, and follow-up so sessions actually happen and actually land.
• Adoption & Champions (The Reach): Drive enrollment and make AI literacy a default expectation rather than an opt-in perk. Stand up a network of embedded "AI champions" in each team so the program scales beyond one person.
• Tooling Coordination: Maintain the catalog of approved AI tools and the sandboxes people learn in, and help people get access and get started.
• Responsible Use: Work with Security, Legal, and Platform to fold practical, safe-use guidance—data handling, approved tools, what not to do—into the curriculum, so the guardrails are taught, not bolted on.
• Stakeholder Coordination: Be the connective tissue between leadership's AI goals and the front line. Work with the department leads to spot high-leverage use cases and turn them into training that sticks.
• Adoption Tracking & Reporting: Track enrollment, completion, active tool usage, and self-reported productivity, and report progress to leadership on a regular cadence—using the data to decide what to double down on and what to drop.