Strategy
Connecting technology direction to business priorities, tradeoffs, and long-term outcomes.
Strategy. Advisor. Builder. → CTO
Sean Canady
I bridge the gap between where a business is going and what its teams are building, using software, AI, data, and automation to drive real outcomes.
What I do is...
10+
Major Transformations Led
$40M+
Active Technology Portfolio
150+
Technology Team
Core
Insurance, Financial Services & Regulated Environments
How I work
Connect strategy to delivery. Make the tradeoffs clear. Build what lasts.
I have spent my career working across technology strategy, architecture, delivery, infrastructure, data, and AI. The throughline has stayed consistent: connect technology direction to the business, modernize and transform with discipline, and help teams turn change into results.
Perspectives
Selected perspectives on technology and leadership.
A curated collection of thoughts on technology, AI, leadership, and transformation in complex organizations.
Browse the perspectivesAIBuilding
The 'Ship Monthly' Challenge
I set a goal to create something meaningful each month because shipping small, real projects teaches me more than keeping ambitious ideas on a backlog.
Published July 2026
AIQuantified Self
Building the Annual Report I Had Put Off for Years
Nicholas Felton inspired me to document a year through data, but AI finally made the years of integration, analysis, and design work practical enough to begin.
Published July 2026
AILearning
Keeping Up With AI: A Curated List
The sources I actually use to (attempt to) keep up with AI, plus the ones I share with people who want to get up to speed. Opinionated on purpose.
Published June 2026
AILife Insurance
Beyond AI Pilots: The Transformation Imperative
Agentic AI, machine learning, and integrated analytics cannot coexist with 2015-era process design. Insurance leaders must choose: optimize old models or redesign fundamentally.
Published June 2026
Experience
Built for enterprise scale, change, and delivery.
Strategy & ExecutionChange LeadershipTalent DevelopmentAI-EnablementCritical ThinkingAdaptability
Architecture
Building standards, platforms, and integration patterns that keep change coherent.
Delivery
Turning direction into execution with teams, tooling, and practical operating discipline.
Innovation
Putting AI and modernization to work in ways the business can actually use.
1995-2000
The Foundation Years
Director of IT in early twenties
2000-2009
Enterprise Technical Depth
Middleware to architecture leadership
2010-2024
Architecture & Data Leadership
CVP leading architecture and data management for Fortune 100 insurer
2024-Present
Technology Officer
Unified technology direction across AI, architecture, infrastructure, and modernization
An open-source take on life insurance administration, built to explore what a modern core platform could look like without decades of legacy assumptions.
Next.jsJavaDockerAWS
A brewing dataset and toolset I use for experiments, recipe decisions, and brewing analytics.
Next.jsPythonData ScienceData Analysis
Fermentation as a systems problem: process control, repeatable execution, and data-informed iteration applied to beer, cider, and experimental ferments.
HomebrewingFermentation ScienceRecipe Development
A machine-readable career profile schema I built after running into the limits of standard resume formats. It also powers this site.
JSON SchemaTypeScriptAINext.js
A data-informed portrait of a year, built from health, activity, travel, listening, work, and other personal records without letting AI invent the answers.
PythonPersonal DataData VisualizationAI
Artifacts
Things I have built and explored.
Active builds and experiments: data tooling, career infrastructure, fermentation analytics, and more in progress.
These artifacts make the thinking tangible: working systems, experiments, and tools built to test ideas in practice.
Browse the artifactsStart the conversation
If something here resonates, let's connect.
Open to conversations about technology strategy, modernization decisions, AI adoption, or building something new. If the site sparked a question or a possible fit, reach out directly.