Public Sector IT · Ontario Public Service

Chirag Kashyap

IT Senior Manager & Tech Strategist

Justice Technology · Enterprise Modernization · AI Strategy

I lead technology portfolios supporting justice and public-sector delivery in Ontario — modernizing critical platforms, guiding strategic change, and working out where AI genuinely fits in government.

CHIRAG KASHYAP IT SENIOR MANAGER — TECH STRATEGIST
Core Mandate

Where I operate

Three areas I focus on — each one affects real people, so I treat it that way.

DOM·01

Justice Technology & Public Sector IT

Leading the technology portfolio behind criminal law and vulnerable victims applications — steering modernization and change while protecting operational continuity, governance, and risk. These are systems that need to just work, every time, for the people who rely on them.

DOM·02

Enterprise Modernization

Setting the roadmap to replace legacy systems and rebuild platforms so they can scale, stay secure, and be sustained — bringing executive stakeholders along and working within the governance, privacy, and compliance requirements of government.

DOM·03

AI Strategy & Operations

Evaluating where AI can responsibly fit into public-sector workflows and guiding adoption where it does, including CrownAI, an AI assistant for criminal law Crowns — and being honest about where it can't.

Career Record

Experience

Eighteen-plus years, from hands-on technology delivery to leading complex portfolios, modernization, and strategic change.

01

Senior Manager, Business Solutions

Ontario Government · Mar 2021 — Present · Toronto, ON

Lead technology portfolio strategy and modernization for business-critical justice platforms — accountable for governance and risk, cybersecurity and privacy coordination, vendor management, financial and investment planning, executive reporting, and responsible AI evaluation and adoption.

Province-wide portfolio · ~$3M annual budget · 14 employees + up to 6 consultants
02

Senior Project Manager

OMERS · Nov 2013 — Mar 2021 · Toronto, ON

Progressed through Agile delivery and senior project management roles, leading enterprise program portfolios and stakeholder governance across a major pension fund.

03

Quality Assurance Lead (Consultant)

TD Bank Financial Group · May 2011 — Nov 2013 · Toronto, ON

Led quality assurance and release readiness for credit card and core banking platforms, managing production risk across high-volume financial systems.

04

Business Systems Analyst

OMERS · Mar 2010 — May 2011 · Toronto, ON

Translated pension system requirements into functional specifications, bridging stakeholder needs and technical delivery.

05

IT Quality Assurance Analyst

Royal Bank of Canada · Jan 2007 — Mar 2010 · Toronto, ON

Provided QA support for payments and wealth management systems in a large enterprise environment — where I got my start.

Competencies

Leadership & Technology

Leadership & Relationships

Team Leadership Executive Stakeholder Management Vendor Management Change Leadership Cross-Functional Leadership

Strategy & Governance

Technology Portfolio Strategy Modernization Roadmaps Governance & Risk Financial & Investment Planning Privacy & Security Oversight

Technology & AI

Applied AI Strategy Agentic AI Cloud Modernization Systems Integration Automation & Workflow Design
Off the Org Chart

Beyond the Build

A few things I spend time on outside of work.

AI-Assisted Web Creation

In my personal time, I experiment with AI-assisted website design and development — taking ideas from concept and content through implementation and launch. It's a practical way to explore how AI can accelerate creative and technical work.

AI Tools · Web Design · Concept to Launch

Smart Home & Property Systems

Running the systems behind the home: Nest cameras, pool automation, water treatment, tankless heating, and plumbing. The yard gets the same attention, with the tools to match.

Smart Home · Pool & Water · Plumbing · Grounds

Golf & the Sports Calendar

Golf when the weather allows, and a sports calendar that runs from the Raptors and Blue Jays to soccer and the IPL. Something is always in season.

Golf · Raptors · Blue Jays · Soccer · IPL

Travel & Itinerary Planning

Researching and booking trips for family and friends — cruises through the Caribbean and Mediterranean, island escapes, and land tours across South and Southeast Asia, Europe, and North America.

Cruises · Island Escapes · Asia · Europe
Get in Touch

Let's talk

My background spans both private and public sector — RBC, TD, OMERS, and now the Ontario Public Service — across technology delivery, modernization, and AI strategy. I'm always glad to connect. Reach out directly or send a note below.

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