Wilson Dos Santos
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AI Evangelist & Transformation Leader

Bridging business strategy and technology execution.

I am Wilson Dos Santos, PMI-ACP®, a highly accomplished Strategic IT Leader with 10+ years of direct leadership experience managing teams and delivering digital transformation initiatives within government and public sector environments, including the City of Mississauga.

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10+
Years Leadership
PMI-ACP
Agile Certified
AI
Evangelist
100+
Digital Projects

The Story

Highly accomplished Strategic IT Leader with 10+ years of direct leadership experience managing teams and delivering digital transformation initiatives within government and public sector environments, including the City of Mississauga.

As Manager of Digital Solutions, I led enterprise-wide technology adoption across multiple municipal departments, driving cultural change and improving staff engagement. I also managed multi-year digital roadmaps, aligning cross-department priorities and delivering transformation initiatives in a structured, sustainable way.

Certified in Agile and Scrum (PMI-ACP®, SFC) with deep expertise in bridging the gap between municipal objectives and technological implementation — translating complex business challenges into scalable, secure, and future-ready solutions.

Professional Experience

A track record of leadership, execution, and technological innovation across diverse sectors.

2020 — Present

AI Evangelist

Techway Solutions
Milton, ON
Current Focus
  • AI Adoption and Use Case Leadership: Translate business needs into practical, high-impact AI opportunities and drive adoption across teams.
  • AI Education and Stakeholder Influence: Deliver workshops, demos, and communications that build AI literacy, trust, and alignment.
  • AI Strategy, Governance, and Responsible AI: Partner with product, engineering, and leadership to shape strategy, standards, and ethical deployment.
  • AI Trends, Tools, and Executive Advisory: Stay current on emerging AI technologies and advise leadership on adoption, risks, and best-fit solutions.
Nov 2018 – Jan 2021

Manager of Digital Solutions

City of Mississauga
Mississauga, ON
  • Strategized & Executed Digital Transformation: Developed and led a comprehensive IT digital modernization project aligned with municipal goals and fiscal constraints, ensuring all initiatives met the municipality's goals, vision, and budget.
  • Strategic Governance: Served as a key member of the Steering Committee for the Digital Modernization Project, guiding high-level decision-making on IT priorities and investments, while ensuring cross-departmental alignment with the City's long-term digital vision.
  • Directed Multi-Year Digital Roadmaps: Managed the evolution of municipal IT systems by integrating Smart City technologies (IoT, AI) and emerging trends to modernize legacy infrastructure and enhance community engagement.
  • Championed Data-Driven Decision Making: Prioritized and championed digital initiatives delivering the greatest organizational value, using data-driven insights, stakeholder input, and industry best practices.
  • Facilitated Stakeholder Consensus: Facilitated engagement sessions with senior leadership and department heads to define technology requirements, bridging the gap between technical teams and business units.
Jan 2013 – Nov 2018

IT Project Manager

City of Mississauga
Mississauga, ON
  • Managed Enterprise Deployment: Oversaw the end-to-end deployment and integration of complex technology solutions across multiple departments, prioritizing business continuity to ensure minimal disruption to critical municipal services.
  • Championed Digital Adoption & Change Management: Designed and implemented comprehensive user training and support frameworks to drive cultural change, ensuring high adoption rates and seamlessly integrating new platforms into daily operations.
  • Enforced Data Governance & Security: Embedded robust security protocols and governance frameworks into all digital deployments, safeguarding municipal data and ensuring full compliance with privacy regulations and standards.
  • Project Portfolio Management: Created and managed the project portfolio, balancing short- and long-term initiatives while prioritizing projects that deliver maximum value to the municipality.
Jul 2008 – Jan 2013

Web Specialist

City of Mississauga
Mississauga, ON
  • Operational Excellence & Service Delivery: Managed all aspects of day-to-day operations for the City's high-performing "eCity" portals, ensuring robust uptime and seamless digital access for citizens.
  • Technical Leadership & Team Enablement: Guided programmers and developers through the full SDLC (design, coding, testing, deployment), fostering a collaborative environment that supported successful client initiatives.
  • Secure Digital Ecosystems: Developed and integrated stable, accessible, and secure digital solutions (web and mobile), ensuring compliance with data governance and security standards.

Core Expertise

Digital Transformation

  • Modernizing legacy systems
  • Optimizing cloud infrastructure
  • Redesigning business processes
  • Digital-first landscape

AI & Innovation

  • Generative AI integration
  • Advanced analytics
  • Automating workflows
  • Unlocking business capabilities

Technology Leadership

  • Cross-functional teams
  • Mentoring
  • Culture of accountability
  • Agility & technical excellence

Product & Strategy

  • Business objectives
  • Product roadmaps
  • Technical specifications
  • Strategic IT plans

Operations & Execution

  • PMI-ACP certified
  • Scrum Fundamentals
  • On-time delivery
  • Budget management

Technology Architecture

  • Software development
  • Python & .NET
  • Enterprise CMS
  • Resilient systems
Key Achievements

Recognized for Excellence

My commitment to innovation and operational excellence has been recognized at the highest levels of municipal government and enterprise organizations.

City Manager's Award of Excellence

City of Mississauga

Recognized for demonstrating outstanding qualities of excellence and performance that best exemplify the vision of the City, specifically for the Canada 150th Anniversary Program.

Award for Innovative Business Solutions

City of Mississauga

Honored for significant achievements and commitment to excellence in delivering the MiWay Real-Time Bus Information Project, setting a standard for municipal innovation.

"An invaluable leader. His personality and experience make him an asset to any organization."

Strategic Thinker

Navigating complex political and technical landscapes to deliver results.

Culture Builder

Cultivating positive, accountable work environments that inspire teams.

AI Visionary

Expertly integrating artificial intelligence to advance organizational capabilities.

Education & Certifications

PMI Agile Certified Practitioner

Project Management Institute · Credential ID: 2758811
Mar 2020

Scrum Fundamentals Certified

SCRUMstudy · Credential ID: 749290
Dec 2019

Bachelor's Degree, Graphic Design

University Tuiuti do Paraná
Brazil · 2000 – 2004