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AI Enablement Specialist

Job

Heartland Business Systems

Little Chute, WI (In Person)

Full-Time

Posted 4 days ago (Updated 2 days ago) • Actively hiring

Expires 6/28/2026

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Job Description

Position Summary:
The AI Enablement Specialist owns user adoption and team-member upskilling for AI at HBS. The role leads HBS's expansion of Microsoft 365 Copilot Cowork through the Microsoft Frontier Program and drives day-to-day adoption and tier-1/2 user support for Microsoft 365 Copilot and Claude-based agents across HBS business units. The analyst owns the HBS AI Champion Pilot Program end-to-end - Champion cohort recruitment and coaching, baseline measurement, prompt and skill library curation, role-based training delivery, peer-coaching coordination, adoption analytics, and synthesizing candid pilot feedback into insights for the Director of AI and ELT. The role serves as the connective tissue between the Director of AI, the broader AI delivery team, and end users, and is explicitly accountable for investing in HBS team members' long-term AI skill growth. Success looks like a growing population of confident, skilled AI users at HBS, measurable productivity lift per role per cohort, a maturing library of prompts and custom Cowork skills, and a Champion network that scales both adoption and career growth across the company.
Roles and Responsibilities/ Essential Functions:
Own the HBS AI Champion Pilot Program and the Microsoft 365 Copilot Cowork Program rollout end-to-end. Deliver role-based enablement and career-development upskilling for Microsoft 365 Copilot, Microsoft Copilot Cowork, and Claude agents through training sessions, certifications, prompt clinics, peer coaching, and ongoing reinforcement. Recruit and support each Champion cohort in partnership with department leaders: produce the Champion Commitment Guide and Manager Fact Sheet, coach champions through 1:1 sessions and group office hours, and run structured peer-coaching sessions with their teammates. Drive cross-department engagement through use-case challenges and visible recognition. Track adoption analytics (daily active users, license utilization, prompt library usage, certification completions) and publish a monthly one-page dashboard against documented baselines. Capture candid pilot feedback from Cowork participants and synthesize it into actionable adoption, governance, and product insights for the Director of AI and the Executive Leadership. Curate and version-control role-based prompt libraries, custom Cowork skills, and agent templates; maintain a searchable internal knowledge base of resolved issues, prompt patterns, and best practices; embed Microsoft 365 Copilot learning paths and Copilot Cowork modules into the HBS internal training site. Act as the strategic bridge between business stakeholders and the technical AI delivery team by contributing business context, prompt design input, and adoption-readiness review on custom solution work, and pilot new Microsoft and Claude AI capabilities internally before they reach client engagements. Operate the AI Helpdesk tier-1 and tier-2 queue, contribute to the refinement of internal AI delivery methods and certification curricula, and apply the AI Use Policy in daily work while flagging exceptions to the Director of AI.