AI Enablement Program Lead

The AI & Automation team at TRM is responsible for designing and building AI-powered applications and agentic solutions that help our internal teams operate at scale. We partner directly with business leaders across the company to identify high-impact opportunities, then design, build, and own end-to-end solutions that meaningfully move the most critical business metrics.

We are looking for an AI Enablement Program Lead (IC) whose focus will be to drive enterprise-wide enablement, education, and adoption of internal AI tools (Glean, n8n, Cursor, ChatGPT, Zapier, etc.) You will design and deliver trainings/workshops, codify “happy paths,” produce runbooks and short-form content, own vendor liaison and light admin/governance, and publish clear adoption and impact metrics. This is a high-autonomy, stakeholder-facing role that proactively engages teams to accelerate time-to-value of our current and future enterprise-wide AI tools.

• Drive enterprise‑wide AI enablement programs that help every team at TRM (GTM, R&D, CS, Ops, People, etc.) adopt our core AI tools (Glean, n8n, Cursor, ChatGPT, Zapier, Tribble, and future tools) in a structured, measurable way.
• Design and deliver high‑impact learning experiences—persona‑based workshops, onboarding → power‑user learning paths, office hours, and “roadshows”—that move people from curiosity to confident day‑to‑day usage.
• Codify “happy paths” for AI workflows by partnering with teams to identify high‑ROI use cases and turning them into prescriptive templates, playbooks, and reusable blueprints that can be quickly rolled out across the company.
• Own a self‑serve AI enablement hub with concise runbooks, FAQs, “how‑to” guides, short video walkthroughs, and “what’s new” updates so teams can unblock themselves without waiting for 1:1 support.
• Lead vendor and tool relationships for our AI enterprise stack, coordinating roadmaps, betas, feature rollouts, and escalations, while managing light platform administration (org structure, permissions, provisioning workflows, guardrails) in partnership with IT/Sec.
• Define and track success metrics for each AI tool, including adoption (e.g., WAU/MAU, stickiness), depth of use (templates reused, automations per team, feature utilization), and outcome impact (time saved, ticket deflection, workflow cycle‑time reduction).
• Run structured intake and proof‑of‑value sprints for new enablement requests, triaging by impact/effort, validating high‑ROI use cases quickly, and turning successful experiments into standardized programs or templates.
• Lead change‑management and adoption campaigns, including champions networks, internal case studies, release notes, nudges, demo days, and Bot‑camp Wednesday programming that steadily improve team‑level AI fluency.
• Translate data into clear stories for leaders, telling the “so what” behind the numbers and recommending where to double down, where to simplify, and where to experiment next.

• 6+ years of experience in enablement, L&D, customer education, program management, or a closely related role, with a track record of building and running programs that change how people work.
• Hands‑on experience with modern AI tools in a business context, e.g., configuring or administering platforms like Glean, building automations in tools like n8n/Zapier/Make, using AI coding tools like Cursor/GitHub Copilot, or designing AI‑assisted workflows for non‑technical users.
• Enablement pedagogy and curriculum design skills: able to design persona‑based learning paths, workshops, certifications, and short‑form content that drive real behavior change (not just attendance).
• Program‑level ownership: experience owning a roadmap, setting success criteria, scoping and prioritizing work, and driving cross‑functional execution with minimal oversight.
• Analytics fluency: comfortable defining instrumentation, working with SQL and/or Google Sheets to analyze tool usage data, building simple dashboards, and quantifying impact (e.g., time saved, adoption uplift, depth of use).
• Exceptional written and verbal communication: able to create tight, high‑signal documentation and present complex AI concepts and metrics in a way that is accessible to non‑technical audiences and credible to technical ones.
• Change‑management mindset: experience running multi‑touch campaigns (comms, training, champions, nudges) around new tools or processes, and iterating based on data and feedback.
• High ownership and autonomy: comfortable operating in ambiguous spaces, setting your own pace and priorities, and proactively pulling in the right stakeholders to move from idea → pilot → scaled program.
• Strong cross‑functional collaboration skills: history of partnering effectively with teams like Engineering, Product, GTM, Operations, People, and IT/Security, and building trust with stakeholders at multiple levels.

Bonus:

• Experience owning enablement or adoption programs specifically for B2B SaaS or internal enterprise tooling, especially in technical or data‑heavy environments.
• Background in L&D, adult learning, or instructional design with examples of measurable improvements in ramp time, certification completion, or behavioral change.
• Experience building or scaling champions networks, early‑access/beta programs, or internal “bot camps”/demo days.
• Familiarity with evaluating AI tooling (e.g., comparing vendors, building business cases, or running structured pilots with success criteria).

• You’ll sit within TRM’s AI Automation function, working closely with AI/automation engineers, data and analytics partners, People Programs, IT/Security, and leaders across GTM, R&D, CS, and Operations to make TRM one of the most AI‑enabled organizations in our space.
• The team operates in a high‑ownership, high‑velocity environment: we care deeply about measurable impact (time saved, adoption uplift, reliability) and are comfortable iterating quickly based on what the data and teams are telling us.
• We treat AI enablement as a product, not a series of ad‑hoc trainings, maintaining a roadmap, success metrics, and a backlog of experiments across tools and teams.
• Our culture emphasizes psychological safety, candor, and craftsmanship: we expect teammates to give and receive direct feedback, hold a high bar for documentation and programs, and support each other in shipping ambitious work.
• TRM is a distributed, not distant company. For this role, we’re looking for someone with at least 4–6 hours of overlap with US Pacific Time (PST) to collaborate effectively with stakeholders and teammates.
• There is no formal pager‑style on‑call rotation for this role, but you’ll be the primary point of contact for enablement questions and urgent adoption/usage issues during core working hours, partnering with engineering and IT/Sec when issues touch platform reliability or access.