Gabriel Guenette
Turning AI Strategy Into Measurable Business Results
Proven leader who transforms enterprise challenges into competitive advantages. I've delivered $30M+ in strategic value through AI innovation, scaled global teams of 400+, and successfully integrated $15.7B+ in acquisitions across Fortune 500 companies.
Career Snapshot
Leading digital transformation and AI innovation across Fortune 500 companies
My Value & Impact
Principal Program Manager
Okta
•San Francisco, CA- Pioneered enterprise AI strategy as founding member of AI Innovation Council
- Partnered with C-suite executives on digital transformation initiatives
- Led enterprise-wide programs including unified customer/partner training platform
- Championed Agile best practices across IT delivery teams
Senior Director Strategy and Operations
Block
•San Francisco, CA- Charter Member of Block's AI Council, driving financial use case exploration
- Orchestrated end-to-end Afterpay acquisition integration ($30M+ value)
- Established global Finance Transformation PMO
- Architected hybrid global workforce model (200+ resources)
Senior Technical Program Manager (M&A)
Salesforce
•San Francisco, CA- Spearheaded integration of multi-billion dollar acquisitions (Tableau $15.7B)
- Led 400+ cross-functional team members with $30M+ budgets
- Implemented enterprise-wide security transformations
- Developed executive dashboards and analytics tools
Principal, Strategy and Transformation
Shift Business Services
•San Francisco, CA- Led strategic implementations of Gainsight and Salesforce
- Architected scalable cloud-computing infrastructure
- Pioneered program management best practices and Agile methodologies
- Developed optimized operating models for SMBs
Director Product Management
Ubisoft
•San Francisco, CA- Directed distributed global engineering teams (Montreal, Paris, Bucharest)
- Managed project budgets up to $490K using Agile methodologies
- Spearheaded organizational project management transformation
- Enhanced executive visibility through automated portfolio dashboards
PMO Director
TIO Networks Corporation
•Vancouver, BC- Established and scaled PMO for 2,000+ North American ATM deployments
- Achieved 20% reduction in deployment costs
- Led enterprise-wide PCI-DSS compliance initiative
- Architected business intelligence infrastructure
Core Competencies
Expert-level proficiency across AI strategy, program management, and digital transformation
AI & Automation Strategy
Program & Portfolio Management
Enterprise Systems & Operations
Business Intelligence & Analytics
Change & Transformation Leadership
Leadership & Innovation
Typical Projects
Strategic initiatives that drove measurable business impact and innovation
Enterprise AI Strategy & Governance
Pioneered AI innovation councils at both Okta and Block, establishing governance frameworks and driving AI-driven programs across security, identity transformation, and financial use cases.
Afterpay M&A Integration
Orchestrated end-to-end systems and process integration for Block's Afterpay acquisition, migrating Finance (Oracle Cloud), IT, and HR platforms.
Tableau Acquisition ($15.7B)
Spearheaded the integration of Salesforce's largest acquisition, leading 400+ cross-functional team members and managing $30M+ budgets.
Global Finance Transformation PMO
Established and scaled a global PMO delivering a $30M+ strategic roadmap, implementing OKR and ROI-based portfolio prioritization.
Hybrid Global Workforce Architecture
Designed and operationalized a hybrid workforce model integrating 22 FTEs, 40 offshore MSP resources, and 130 contingent workers alongside an Automation COE.
Enterprise Security Transformation
Led enterprise-wide security transformations implementing single customer identity solutions across Salesforce applications.
Thought Leadership
Insights on AI's transformative impact on work, society, and the future
Featured Articles
The Accidental Developer: How AI Is Turning Everyone Into Software Creators
How AI collaboration is democratizing software development, enabling anyone to build custom solutions by orchestrating rather than coding.
Leveraging Project Management Principles to Enhance AI Prompt Engineering
Learn how structured planning, task prioritization, and iterative refinement can transform your AI prompts into consistent, high-quality outputs.
Upcoming Publications
The AI Job Displacement Wave: Developers, Analysts, and Designers on the Chopping Block
AI is rapidly replacing not just software developers, but also data analysts, QA testers, technical writers, UI/UX designers, and junior-level roles across the tech industry, fundamentally reshaping the workforce landscape.
Raising an AI First Child
Exploring how parents can prepare children for a world where AI collaboration is as fundamental as reading and writing, teaching them to become solution orchestrators rather than passive technology consumers.
Building Enterprise AI Governance: Lessons from the Trenches
Real-world insights from establishing AI governance frameworks at Okta and Block. What works, what doesn't, and how to get executive buy-in for AI initiatives.
Follow My Writing Journey
I regularly share insights on AI's transformative impact on work, society, and the future through LinkedIn articles and Medium posts. Connect with me to get notified when new content is published.
New articles published monthly • Cross-posted on LinkedIn and Medium
Education & Certifications
Continuous learning in AI, leadership, and emerging technologies
Education
Master of Business Administration (MBA)
IT Management
Specialized in enterprise technology strategy, digital transformation, and IT governance with capstone focused on technology-driven business innovation.
Bachelor of Science
Genetics
Foundation in analytical thinking, data interpretation, and scientific methodologies with strong quantitative analysis and research skills.
Recent AI & Leadership Certifications (2024-2025)
Generative AI Leadership & Strategy Specialization
AI for Business
ChatGPT + Excel: AI-Enhanced Data Analysis
Google AI Essentials
AI Foundations for Everyone
Agentic AI and AI Agents for Leaders
Generative AI Assistants Specialization
Prompt Engineering Specialization
AI for Product Management
Generative AI for Project Managers
Mergers and Acquisitions
Project Management Professional (PMP)
About Gabriel
As a seasoned executive with over 15 years of experience leading complex technical programs and enterprise transformations, I specialize in bridging the gap between cutting-edge technology and strategic business objectives. My passion lies in pioneering AI strategy and driving digital innovation that creates measurable impact.
Leadership Philosophy
I believe in data-driven decision making, continuous improvement, and fostering cultures of innovation. My approach combines strategic thinking with hands-on execution, always focusing on scalable solutions that drive sustainable growth and operational excellence.
Core Expertise
My experience spans AI strategy development, large-scale M&A integrations, global PMO establishment, and enterprise system implementations. I've successfully led teams of 400+ members, managed multi-million dollar budgets, and delivered transformational initiatives across diverse industries including technology, finance, and healthcare.
AI Innovation Leadership
As a founding member of AI Innovation Councils at both Okta and Block, I've been at the forefront of enterprise AI adoption, establishing governance frameworks and driving practical AI implementations that enhance security, identity transformation, and business operations.
Recognition & Impact
Achieved 22% improvement in project delivery capacity through enhanced resource utilization
Successfully integrated $15.7B+ in acquisitions (Tableau, Afterpay)
Established and scaled global PMOs managing $30M+ strategic portfolios
Led digital transformation initiatives across Fortune 500 companies
Let's Drive Innovation Together
Ready to transform your organization with AI strategy, lead complex digital transformations, or scale your enterprise operations? I partner with forward-thinking leaders to deliver measurable results.
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