AI & Technology Transformation Executive  |  Enterprise Agility Leader  |  Board Director

I help C-suite executives and boards turn AI ambition into operational reality — with governance, change management, and technology roadmaps that create lasting impact.

Currently accepting 2–3 strategic advisory and board engagements — Q2/Q3 2026

Scottsdale, AZ  |  Dual Citizen: Canada & United States  |  Flexible for travel and hybrid work

Leah C. Jochim — AI & Technology Transformation Executive, Board Director

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About

AI transformation executive and board director with 25+ years partnering with CIOs, CEOs, and PE-backed leadership teams to convert AI strategy into measurable operations — driving productivity gains, accelerating technology adoption, and building governance frameworks that make transformation stick. Proven across Fortune 500 enterprises, 20,000-person engineering organizations, and complex nonprofit institutions.

Trusted for translating technical complexity into strategic clarity and commercial outcomes. Deploys OKR-based governance, enterprise agile frameworks, and human-centered change management to ensure organizations don't just adopt AI — they operationalize it for sustainable, measurable value creation.

Core Values: Servant leader · Compassion in action · Data-driven decision making · Inclusive leadership · Transparent governance · Sustainable impact · Deliver value sooner, safer by happier teams

Signature Technology Stack & Frameworks

Azure | Microsoft 365 & SharePoint | Salesforce & Dynamics CRM | Microsoft & Google Suites  | Prosci & Kotter Change Management | GenAI Workflow Design | Prompt Engineering | AI Readiness Assessment

Core Competencies

AI Transformation
GenAI Adoption
Enterprise AI Strategy
AI Governance
OKR Implementation
Change Management
Digital Transformation
CIO Advisory
Technology Due Diligence
Platform Modernization
Engineering Productivity
PE/VC Strategy
Board Technology Oversight
Nonprofit Governance
Agile at Scale (SAFe)
Data Analytics Strategy

Executive Leadership Experience

Convergence Technology Solutions & L&T Ventures

Scottsdale, AZ

2023 – Present

Co-Founder & Partner — AI & Technology Transformation Advisory

Architected and delivered technology transformation programs for C-suite executives across healthcare, finance, nonprofit, and PE/VC-backed organizations. Designed Product Roadmaps, AI Enablement Playbooks and AI Readiness Assessment frameworks. Developed ARIA, an AI-native platform for venture capital and private equity due diligence, reducing deal assessment cycle time.

  • Designed AI Enablement Playbook adopted across client organizations — accelerating time-to-first-AI-deployment and providing repeatable governance structure for enterprise AI rollouts
  • Architecting ARIA, a proprietary AI-native due diligence platform for PE/VC clients, integrating data analytics, automated assessment workflows, and outcome tracking
  • Led Strategic Planning, prioritization and product roadmap executive workshops as well as advised on product management and engineering best practices to attain key business outcomes
  • Built comprehensive vendor evaluation and technology due diligence frameworks, enabling executive teams to make AI investment decisions with confidence and fiduciary rigor
  • Advise executive teams on AI strategy, infrastructure investment, cloud migration prioritization, and operating model design connecting AI capabilities to measurable business outcomes

Microsoft Corporation — Azure & Windows Engineering

Remote

2020 – 2023

Principal Program Manager, Customer Insights & Transformation

Led 'Our Way of Work' enterprise transformation for 20,000+ Azure and Windows engineers globally. Delivered 10-point increase in employee sentiment, built technology roadmaps, managed two of the world's largest Azure DevOps accounts, and served as trusted advisor to Senior Vice Presidents on multi-million-dollar technology investments.

  • Drove 10-point increase in employee sentiment across 20,000-person engineering organization through strategic community building, tooling improvements, and change management
  • Saved hundreds of hours per engineering team through AI-assisted and automated workflow improvements and optimized engineering practices
  • Managed governance for two of the world's largest Azure DevOps accounts (20,000+ users), achieving 4/5 CSAT; set benchmark for enterprise DevOps at scale
  • Advised C-level executives on multi-million-dollar technology investments and vendor selection decisions, bridging technical complexity with strategic business outcomes

American Express

Phoenix, AZ

2017 – 2020

Vice President, Enterprise Agility — reporting to CIO

Architected company-wide technology transformation strategy reporting directly to the CIO. Increased engineering productivity 25% and shifted the enterprise to outcome-based OKR planning in under one year. Led monthly Technology Working Group with executives from all business units. Managed $10M+ annual vendor portfolio.

  • Increased engineering productivity 25% through formation of four value streams — delivering measurable capacity gains without headcount addition
  • Shifted $10M+ annual vendor portfolio to outcome-based contracts; negotiated strategic technology partnerships while maintaining cost discipline
  • Led automation engineering team that saved 40,000+ hours across 40+ application teams — equivalent to ~20 FTE years of engineering capacity
  • Implemented enterprise OKR framework from zero in <12 months, aligning 15+ technology business units to common outcome measurement

Microsoft Corporation — Microsoft IT

Redmond, WA

2014 – 2017

Principal Program Manager, Agile Adoption & Organizational Transformation

Led enterprise-wide Agile transformation for a 5,000-person division across 3 continents, converting 1,100 individual contributors to Agile ways of working and achieving an 80+ Net Promoter Score from engineering teams.

  • Converted 1,100 ICs to Agile across 3 continents, achieving 80+ NPS — one of Microsoft IT's highest-rated transformation programs
  • Built and scaled PMO governance frameworks connecting team-level agility to divisional OKRs and executive reporting
  • Designed people-process-tool playbooks that became internal reference standards for subsequent Agile adoption programs across Microsoft

Earlier Career — Foundation Roles

OrganizationRoleDates
Microsoft CRM & Office/SharePointSenior Consultant & Principal PM — CRM platform strategy, enterprise content management, collaboration workflow design2000–2017
Government of CanadaFirst Webmaster — pioneered digital government content management and structured data publishing1991–2000

Board & Nonprofit Governance

Tri Delta Fraternity — International Executive Board

Delta Delta Delta

2022 – 2026

Executive Board Director — Technology, Data & Governance Oversight

Provide technology and AI governance oversight for a $200M+ multi-entity international women's organization with 138 collegiate chapters and 250,000 members. One of six global Executive Board Directors — the only Canadian member in organizational history. Responsible for fiduciary oversight, CEO performance management, and technology investment stewardship.

  • Advised CEO and executive leadership on 2025-26 Technology Plan — governing infrastructure modernization, CRM optimization, and data analytics platform selection aligned to organizational OKRs
  • Approved and monitored $13M+ annual operating plans; oversaw technology vendor contracts and capital investments ensuring fiduciary alignment and ROI accountability
  • Authored strategic technology brief for Presidential transition — connecting AI readiness, data governance, and platform investments to 2026-2028 strategic plan outcomes
  • Reviewed and approved enterprise risk management processes including cybersecurity frameworks, data privacy governance, and business continuity planning

Courage to Caregivers

Mental Health Advocacy Nonprofit

2021 – Present

Board Member — Strategy, Technology & Development

Serve on Development Committee and Strategic Planning Committee for mental health advocacy nonprofit supporting caregivers of individuals living with mental illness. Provide strategic technology advisory and AI adoption guidance to amplify mission impact within constrained nonprofit resources.

  • Serve on Development Committee and Strategic Planning Committee
  • Provide strategic technology advisory and AI adoption guidance to amplify mission impact within constrained nonprofit resources

Work & Impact

Transforming organizations through AI governance, enterprise agility, and board technology oversight

Technical Expertise & Strategic Frameworks

AI & Emerging TechGenAI Strategy & Governance, AI Readiness Assessment, AI Workflow Design, Prompt Engineering, AI Enablement Playbook Development, ML/AI Product Management
Cloud & InfrastructureMicrosoft Azure, AWS, Cloud Migration Strategy, DevOps at Scale, Azure DevOps (20K+ users), Platform Modernization
CRM & DataSalesforce, Microsoft Dynamics CRM, Data Analytics Strategy, Impact Measurement Frameworks, Enterprise Content Management
Collaboration & ProductivityMicrosoft 365, SharePoint, Viva Goals, Teams, Workboard OKR Platform, PMO Tools
Strategic MethodologiesOKR (Objectives & Key Results), Kotter's Leading Change, Prosci Change Management, SAFe & SCRUM, Design Thinking
Governance & ComplianceEnterprise Risk Management, Information Security Frameworks, Fiduciary Oversight, Board Governance, Vendor Contract Management ($10M+ portfolios)

AI & Technology Transformation

Architecting and delivering AI-powered transformation programs for C-suite executives across healthcare, finance, nonprofit, and PE/VC-backed organizations. Designed proprietary AI Enablement Playbook and AI Readiness Assessment frameworks. Developing ARIA, an AI-native due diligence platform for PE/VC clients.

  • AI Enablement Playbook deployed across client organizations — accelerating time-to-first-AI-deployment
  • ARIA: AI-native due diligence platform integrating data analytics and automated assessment workflows
  • Vendor evaluation and technology due diligence frameworks enabling fiduciary-grade AI investment decisions

Board Technology Oversight

Providing technology and AI governance oversight for a $200M+ multi-entity international organization. As Executive Board Director for Tri Delta — the only Canadian member in organizational history — responsible for fiduciary oversight, CEO performance management, and technology investment stewardship across 138 chapters and 250,000 members.

  • $13M+ annual operating plan oversight with technology vendor contract governance
  • Cybersecurity frameworks, data privacy governance, and business continuity planning
  • AI readiness and platform investment strategy connected to 2026-2028 organizational outcomes

Enterprise Agility & Engineering Productivity

Architected company-wide technology transformation at a well-known Fortune 10 bank reporting directly to the CIO — increasing engineering productivity 25%, implementing OKR governance across 15+ business units, and leading an automation team that saved 40,000+ hours of engineering capacity.

  • 25% engineering productivity gain through four value streams — measurable capacity without headcount addition
  • 40,000+ hours saved across 40+ application teams — equivalent to ~20 FTE years of engineering capacity
  • $10M+ vendor portfolio shifted to outcome-based contracts with strategic partnership discipline

Agile at Scale & Organizational Transformation

Led enterprise-wide Agile transformation for 20,000+ Microsoft engineers globally and a 5,000-person division across 3 continents — converting 1,100 individual contributors to Agile ways of working and achieving 80+ NPS, one of Microsoft IT's highest-rated transformation programs.

  • 1,100 ICs converted to Agile across 3 continents — 80+ NPS from engineering teams
  • 10-point employee sentiment increase across 20,000-person Azure & Windows engineering organization
  • People-process-tool playbooks adopted as internal reference standards for subsequent Microsoft programs

“Leah is a fantastic leader. She naturally builds deep relationships and partnerships across organization boundaries, is fantastic at creating communities and naturally drives large transformational initiatives. She is very customer and outcome-oriented, and a true servant leader for her team. She has transformed the whole 15,000+ person Azure organization to transform how they track work and collaborate among themselves, all within 6 months, influencing and leveraging several Corporate Vice-Presidents to drive top-down, bottom-up and sideways commitment and adoption. If you ever have a large transformational initiative that might be too hard to pull off, tap her for it.”

Ram Nagasubramani

Leader in Product Management & Development | Cloud Scale Products & Services

Managed Leah directly · May 2023

Proprietary Frameworks & Thought Leadership

Original IP developed from leading transformations at Microsoft, a well-known Fortune 10 bank, and across PE/VC-backed client organizations

AI Enablement Playbook

Proprietary end-to-end framework guiding organizations from AI ambition to operational deployment — covering readiness assessment, use case prioritization, governance design, change management, and adoption measurement.

ARIA Readiness Model

AI-native due diligence platform and assessment methodology for PE/VC firms evaluating technology assets — integrating structured data analysis, AI scoring, and outcome-linked investment frameworks.

The 5-Stage AI Adoption Ladder

Practical adoption methodology for enterprise and nonprofit organizations — mapping from AI awareness through experimental use to operationalized, governance-grade AI deployment with measurable outcome tracking.

Engineering Productivity Playbook

People-process-tools framework developed at Microsoft scale (20,000+ engineers) providing pragmatic best practices for increasing engineering team productivity, DevOps maturity, and cross-team dependency management.

Insights

Original perspectives on AI transformation, enterprise governance, and human-centered change management

Latest — March 13, 2026

More Output Is Easy. More Value Is the Work.

AI can now generate code, documents, prototypes, and analysis faster than ever. But are we creating more value — or just more output? The organizations that win the AI era won't be the ones who produce the most. They'll be the ones who stay relentlessly focused on outcomes that matter.

Read the article

The AI Enablement Playbook: A 5-Stage Framework for Enterprise GenAI Adoption

Most organizations have AI ambition but lack the operational architecture to act on it. The AI Enablement Playbook maps a proven path from readiness assessment through governed, measurable deployment — built from lessons leading transformations at Microsoft, a well-known Fortune 10 bank, and across PE/VC-backed clients. Stage 1 isn't about technology. It's about organizational readiness, data governance, and the change management layer most vendors skip entirely.

Read more

OKR to AI: How Outcome-Based Governance Accelerates Technology Adoption

The fastest-moving AI organizations share one structural trait: they govern AI with outcomes, not outputs. Having implemented OKR frameworks from zero at a well-known Fortune 10 bank (aligning 15+ business units in under 12 months) and at Microsoft scale, the pattern is consistent — organizations that anchor AI investment to measurable outcomes adopt faster, sustain longer, and waste significantly less.

Read more

Governing AI in the Boardroom: What Directors Need to Know in 2026

Board directors are now accountable for AI governance whether they feel ready or not. Drawing on experience providing technology oversight for a $200M+ international organization and advising PE/VC-backed technology investments, this piece maps the six questions every board should be asking — from AI ethics and data privacy to cybersecurity risk, vendor accountability, and ROI measurement frameworks.

Read more

AI for Nonprofits on a Budget: A Practical Prioritization Model

Nonprofits can't afford to experiment broadly with AI — they need a disciplined prioritization model that connects AI use cases directly to mission outcomes. Having advised organizations from Courage to Caregivers to Tri Delta's 250,000-member network, the highest-ROI AI investments in the nonprofit sector follow a consistent pattern: donor engagement, program delivery measurement, and administrative automation — in that order.

Read more

Human-Centered AI: Why Change Management Is the Missing Layer

The most common reason enterprise AI programs underperform isn't the technology — it's the change management layer that was never built. After leading transformations for 20,000+ engineers at Microsoft and driving a 25% productivity gain at a well-known Fortune 10 bank, the consistent differentiator is not the AI tool chosen — it's whether the organization was prepared to adopt it. Prosci ADKAR and Kotter's model, applied to AI rollouts, change the outcome entirely.

Read more

Book a Strategy Conversation

Currently accepting 2–3 strategic advisory and board engagements. Available to discuss AI transformation strategy, technology governance, board director roles, and PE/VC advisory engagements.

Based in Scottsdale, AZ. Dual citizen of Canada & United States.

Available for domestic and international travel. Remote-first with strategic in-person engagement.