AI transformation & field CTO advisory

Jerome Short

Enterprise AI transformation leader helping regulated and complex organizations move from experimentation to scaled adoption across Copilot, Azure OpenAI, agents, responsible AI, governance, data, and cloud modernization.

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Executive profile

Turning AI ambition into operating reality.

Enterprise AI transformation leader and executive technology advisor with deep experience helping regulated and complex organizations adopt Microsoft AI, modernize operating models, and move from experimentation to scaled adoption.

Effective as an AI strategy lead, field CTO, or transformation advisor who can connect board-level ambition to executable roadmaps, customer trust, adoption motions, and measurable business outcomes.

Copilot strategy Azure OpenAI Agentic AI Responsible AI Executive advisory Governance & security Cloud modernization

Core strengths

Where strategy, architecture, and adoption meet.

AI operating models

Copilot, Azure OpenAI, agents, model selection, human-agent collaboration, and transformation roadmaps.

Governance and risk

Responsible AI, retention, DLP, identity, collaboration readiness, regulatory concerns, and enterprise controls.

Executive advisory

Business-value framing, stakeholder alignment, adoption planning, change leadership, and trusted technology guidance.

Transformation delivery

Discovery, roadmap creation, blocker removal, readiness planning, and cross-functional execution.

Team enablement

Mentoring, reusable narratives, architecture guidance, and leadership across sales, technical, partner, and customer success teams.

Customer trust

Bridging customer outcomes, technical decisions, and adoption patterns in complex enterprise environments.

Experience

Expandable role highlights.

Account Technology Strategist Microsoft | May 2017 - Present
  • Advise enterprise customers across regulated industries on Microsoft AI, cloud modernization, governance, security, data, collaboration, and business-value-driven adoption.
  • Recognized for high-impact enterprise AI transformation work helping organizations move from AI experimentation toward scaled Copilot, agent, and Azure AI adoption.
  • Shape AI transformation strategies involving Copilot, Azure AI, agents, human-agent collaboration, and new operating models for legal, insurance, financial services, and professional-services organizations.
  • Help organizations evaluate and adopt enterprise AI by addressing governance, security, retention, collaboration, and readiness considerations.
  • Lead executive and technical conversations that connect AI, data, cloud, and security strategy to business outcomes, adoption plans, and measurable transformation priorities.
  • Support Azure OpenAI and advanced AI motions, including adoption planning, deployment readiness, customer education, and model strategy conversations.
  • Create reusable AI transformation narratives and readiness guidance that help account teams frame responsible adoption, governance, and value realization.
Systems Engineer IV Kforce Inc. | May 2007 - Apr. 2017
  • Led engineering and architecture work across Azure, Office 365, Dynamics 365, identity, enterprise applications, security, DevOps adoption, application migration, and architecture governance.
  • Worked directly with business, architecture, and executive stakeholders to connect IT modernization, security, technical debt, cloud adoption, and business-value outcomes.
  • Implemented early Microsoft cloud capabilities, including Office 365 adoption, Azure infrastructure for agile development teams, cloud security governance, and collaboration with Microsoft account teams.
Earlier experience Independent consulting, technology, and customer-experience roles | 1989 - 2006
  • Built marketing websites and customer-facing digital campaigns while developing durable skills in value messaging, audience engagement, and customer communication.
  • Designed and delivered technical training and custom courseware while working with partners on enterprise collaboration, business intelligence, natural language, taxonomy, ontology, and early AI-for-business solutions.
  • Built foundational customer-experience, team leadership, hospitality, event, marketing, and communication skills in a nationally recognized hospitality environment.

Selected recognition

Credibility built through customer impact and team leadership.

Strategic AI transformation

Recognized for contributions to high-impact AI transformation initiatives involving Copilot, agents, and enterprise adoption.

Culture and leadership

Nominated for Microsoft culture recognition for proactive Copilot proposal leadership and customer impact.

Cross-functional impact

Recognized by peers and leadership for trusted advisory work, reusable architecture guidance, and support of customer-facing teams.

Technology and domain areas

AI, cloud, governance, and transformation toolkit.

Microsoft Copilot Azure OpenAI Agents Model strategy Responsible AI AI governance Retention DLP Identity Security Microsoft 365 Azure Data modernization Fabric MLOps Adoption planning Executive advisory Transformation leadership

Interview video

A Short executive introduction video.

Coming soon

A 'Short' discussion on why AI transformation matters, how you advise executive teams, and what makes your Microsoft AI/cloud perspective valuable.