P&C insurance technology, from inside the program - not the deck.
I lead General Insurance Core Technology at TD Insurance - overseeing policy and billing platforms, cloud modernization, and the partner ecosystems powering them. Having worked across core P&C transformation from both the vendor side and the carrier chair, I focus on system resilience, execution realities, and AI governance in regulated environments.
What I write about is narrower than modernization. It is the question of where judgment sits once software starts making the decisions insurers used to make themselves, and what it costs a carrier to get that boundary wrong. The recurring failures in that space have names, and the definitions are collected in the AI Vocabulary. Angles is my weekly digest on where P&C insurance meets AI.
Both sides of the table
For over two decades, I've operated at the intersection of Property & Casualty insurance and enterprise technology - navigating core modernizations, cloud platform migrations, and system architecture across North America. Today that work spans a platform group of around 200 people and a $50M+ multi-year core modernization program, one of the largest of its kind at any Canadian P&C carrier.
My approach is shaped by a rare vantage point: having led enterprise technology from both sides of the ecosystem. I spent years on the core software side, embedded across more than ten P&C carriers - handling platform architecture, integration stability, and operational leadership when mission-critical systems hit production limits. Later, I transitioned fully to the carrier chair, directing large-scale core policy, billing, and cloud transformation programs.
That sequence - ten carriers, then one - fundamentally changes how you view the work. Most people in this industry spend their entire career on one side of the table. Navigating both reveals the real delta: what gets promised in slide decks versus what it actually takes to land resilient systems inside complex, regulated insurance operations with distributed teams and legacy entanglements no demo ever shows.
What I think about most
Most cloud migrations don't fail on technology. They fail on the operating model nobody negotiated upfront. The biggest budget overruns I've seen had nothing to do with code.
Multi-year alignment isn't a kickoff problem - it's a funding-cycle problem. If your program has to re-justify itself every twelve months, you don't have a multi-year program. You have a series of annual ones pretending to be one.
Most enterprise AI pilots in insurance fail one of two tests: they can't survive a regulator's first question, or they solve a problem the business never had. The defensible work rules both out before you build.
Engineering excellence is what platform stability gets called when nobody's funding it. Real excellence shows up in three numbers - deployment frequency, change failure rate, and on-call load. If your leadership team can't tell you what those numbers were last quarter, the excellence isn't real yet.
I write and speak about these because the gap between how transformation is talked about in this industry and how it actually gets done inside large carriers is wider than anyone wants to admit.
Outside the work
Wildlife advocate and expedition planner, happiest when off-grid in remote ecosystems. Hands-on hardware maker and home tech tinkerer. Reader of too many books simultaneously - usually spanning science, history, and leadership.
Selected work.
Publications and engagements - the things that have made it past the company firewall.
PublicationsHow to Solve the IT Backlog (and How Not to) PDF
On why P&C carriers lose millions a quarter when underwriting changes wait in IT backlogs, why ungoverned self-service only trades slow delivery for production instability, and how a risk-tiered Configuration Center gives business teams autonomy without giving up stability or audit compliance.
Companion white paper: Configuration Center - A Blueprint for Core System Agility PDF
The AI Override Nobody Writes Down
On why claims adjusters' overrides of AI reserve estimates are judgment the company is already paying for and losing - and why the fix is a structured reason field feeding back into training, not a free-text box or a "human in the loop" bolted on after the fact.
A Blueprint for Document Management in Insurance
Co-authored ebook published by Guidewire on document management strategy and architecture for Property & Casualty carriers.
Unlocking the World Insurance: Hirak's Top P&C Definitions
A foundational guide breaking down essential Property and Casualty (P&C) insurance concepts and industry terminology into clear, accessible definitions.
Guidewire Connections
Speaking again at Guidewire's annual customer conference.
Guidewire Connections
Spoke at Guidewire's annual customer conference on implementing production observability via mbeans.
Writing.
I write in four places: a weekly digest on where P&C insurance meets AI, shorter takes on LinkedIn, the AI Vocabulary, a glossary of terms for the structural liabilities of AI deployment in P&C insurance, and P&C Definitions, a glossary of core insurance terminology.
The AI VocabularyTwelve named terms for the structural liabilities of AI deployment at P&C carriers, with canonical definitions and the mechanism behind each one.
P&C DefinitionsTwenty core Property and Casualty insurance terms across five categories, with plain definitions, worked examples, and where each concept lives inside a Guidewire InsuranceSuite implementation.
AnglesA weekly digest on where P&C insurance meets AI - read it at angles.hirakonline.com.
LinkedInShorter-form posts on P&C platform modernization, and AI in regulated industries etc - follow along on LinkedIn.
Let's talk.
Best way to reach me is email or LinkedIn. I read everything, even if responses sometimes take a few days.
- mail@hirakchatterjee.com
- linkedin.com/in/hirakchatterjee
- Based in
- Greater Toronto Area, Canada
Available for
- Board & Strategic Advisory - InsurTech governance, P&C platform modernization, and AI safety in financial services.
- Keynote Speaking & Executive Roundtables - Core transformation realities, platform engineering, and operational risk.
- Select Co-Authoring & Research - Technical publications and ecosystem strategy.
Filtering early
I'll generally pass on cold sales pitches, vendor demos disguised as conversations, and "quick chats" that don't have a clear topic. If you can tell me in two lines what you'd like to discuss and why my background is relevant, you'll get a much faster response.