Technology Leadership
Head of IT and CTO-level ownership: strategy, roadmap, vendor wrangling, budget sanity, and a steady hand on the day-to-day. Twenty-five years of it.
// where it startsI'm Chris Bennett. For twenty-five years I've led IT and security for Bermuda's insurers, reinsurers and law firms: board-level governance, regulatory engagement, and disaster recovery that has actually been tested. The whole time, I've been building production software, now a studio of products under dot.bm. Leadership from someone who still ships.
Operator by day, builder by night, for twenty-five years. I answer my own emails.
I've spent twenty-five years making sure technology never lets a regulated business down. The instinct that keeps a law firm audit-ready is the same one that ships a product people rely on: understand the real problem, respect the constraints, build something that holds.
Head of IT and CTO-level ownership: strategy, roadmap, vendor wrangling, budget sanity, and a steady hand on the day-to-day. Twenty-five years of it.
// where it startsCustom software, integrations, and internal tools, actually built and shipped, not outsourced and forgotten. Web apps, data platforms, and the automation that quietly saves your team hours.
// hands on keyboardAn Authorize.net partner getting Bermuda businesses processing payments, and connecting the systems you depend on so they finally talk to each other.
// live in productionDR and business-continuity plans you've actually tested: end-to-end recovery exercises, not backup logs you hope you'll never have to read.
// find the gaps firstPolicy suites, risk registers, and ISO 27001 / NIST mapping with evidence packs that hold up when the BMA, or your board, comes asking. Proportionate, defensible, done.
// regulator-testedTranslating technology risk into decisions your board can actually make, with reporting they'll actually read. No fear, no FUD, just clear trade-offs.
// plain englishRebuilt disaster-recovery assurance from "the backups ran" into full end-to-end recovery tests, and found the gaps before a real outage could.
Wrote the AI usage policy that let a regulated firm adopt AI safely and deliberately, instead of banning it and pretending nobody was using it.
Sat across from the Bermuda Monetary Authority, explained and defended the policy and the risk calls, and left with them onside.
Led IT consolidation through the Catlin–XL merger, aligning systems and risk across multiple jurisdictions.
Replaced ineffective security-awareness training with something people actually completed, at no added cost.
I don't just manage technology. I build it. Through dot.bm, my Bermuda technology studio, I design, build, and run production software for the island. This is what "still writes the code" actually looks like.
Weather intelligence built for Atlantic subtropical conditions, not a generic forecast bolted onto an island.
wopnin.fyi ↗Civic reporting for Bermuda: flag the pothole, the light, the problem, and route it where it goes.
fix.bm ↗Contact your MPs, mapped to Bermuda's real parish and constituency system.
writethem.bm ↗Authorize.net payment processing set up and supported for Bermuda businesses: a local partner, not a call centre.
Authorize.net partnerBermuda's economy, read weekly: an economic pulse over public sources and sector watchlists.
coming soonGrocery price comparison across the island's stores: optimise a whole shopping list, not one item.
grocr.fyi ↗Planning-application tracker mapping the Official Gazette, with alerts inside the objection window.
coming soonWeather broadcasting for Bermuda: the forecast, made watchable.
islecast.live ↗STACK · Astro · SvelteKit · Next.js · Python · Postgres · Docker · self-hosted and self-run on my own infrastructure. Nine products, four verticals, one two-person studio.
Own security governance, risk, and regulatory alignment across the firm. Set the AI usage policy, lead BMA engagement, report to the board, and rebuilt DR assurance around real end-to-end recovery testing.
Security governance, risk advisory and regulatory support for professional-services and reinsurance clients, plus a growing studio of Bermuda software products, all designed, built and operated in-house.
IT and security oversight across Bermuda and South American offices; accountable for compliance, cyber posture and continuity, and led consolidation through the Catlin–XL merger.
Ran IT and security across three jurisdictions, built the business-continuity and security policy programme, and led incident response and risk mitigation.
// EARLIER · Started in IT at 16, at Logic Communications. MCSA (91%), MCSE. Served in the Bermuda Regiment. Recognised in the 2012 Bermuda TechAwards. Building software on the side ever since: postit.bm (2016), PayApp (2019), and everything that followed.
Whether you're a Bermuda business with a technology problem, a team looking for someone senior, or you just want to compare notes, my inbox is open.
Hamilton, Bermuda · I answer my own emails.