AI Enablement Specialist

Heartland Business Systems

AI Enablement Specialist at Heartland Business Systems leading Microsoft 365 Copilot adoption. Responsible for user training and support across business units.

Posted 6/2/2026full-timeWest Des Moines • Iowa • 🇺🇸 United StatesMid-LevelSeniorWebsite

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

3 to 5 years of professional experience in IT operations, technology consulting, end-user enablement, learning and development, or AI/automation operations.
Demonstrated hands-on experience using Microsoft Copilot Cowork as a daily working tool - delegating outcome-based, long-running, multi-step tasks across Microsoft 365 apps and building reusable custom Cowork skills; practical experience supporting Microsoft 365 Copilot rollouts, including training delivery, prompt design, governance configuration, and end-user support.
Experience designing and delivering training, certification programs, or structured change-enablement content for software adoption, including running a Microsoft 365 Copilot Champion program or equivalent peer-driven adoption program.
Experience producing adoption analytics and ROI-style reporting against documented baselines.
Preferred Experience: Experience with Anthropic Claude and Claude Cowork for cross-tool AI workflows; familiarity with Microsoft 365 Copilot Studio agents, Power Platform, or other automation platforms such as Rewst is a plus. Experience operating a tiered helpdesk model with SLAs, ticket analytics, and knowledge-base curation. Prior experience at a Microsoft Solutions Partner, Managed Service Provider, VAR, or AI/digital transformation consultancy, with familiarity in governance, data classification, and DLP practices for AI tools in an enterprise environment.

Benefits

Comp & perks

Equal Opportunity Employer – Including Disabled and Veterans

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Microsoft 365 CopilotMicrosoft Copilot CoworkClaude agentstraining deliveryprompt designgovernance configurationadoption analyticsROI reportingknowledge base curationAI Use Policy

Soft Skills

coachingcross-department engagementcommunicationcollaborationleadershiporganizational skillsfeedback synthesisstrategic thinkingpeer coachingchange enablement