Technology Executive · CIO / CTO Leadership
Sean Canady
Technology executive focused on CIO/CTO leadership. Over 30 years I've led technology across strategy, architecture, AI, data, engineering, and security. Focused on business and customer outcomes, building teams that deliver, and technology-enabled transformation.
What I do is...
22%
Year-over-Year Delivery Improvement
70%+
Platforms Migrated to Cloud
$43M
Active Technology Portfolio
157
Technology Team
How I work
Connect strategy to delivery. Make the tradeoffs clear. Build what lasts.
Every role has come back to the same job: tie technology decisions to what the business needs, modernize without breaking what works, and build teams that ship.
AI leadership
Leading AI transformation across the business.
At NYL Direct I lead AI transformation on two fronts: how technology gets built, and how the business runs. I created the business AI transformation program and lead it alongside the shift in engineering.
Engineering
Moving from a traditional SDLC to an agentic development lifecycle (ADLC): governance-first AI adoption for developers across the entire organization, AI-enabled engineering patterns and training, and AI agents delivering real work.
Employee enablement
AI skills and tools for employees, with significant adoption across the organization.
Agentic enablement
Targeted process transformation, with AI agents taking on work inside key business processes.
Domain transformation
Redesigning entire functions end to end to drive growth and efficiency.
The AI and data work I led with my teams earned NYL Direct an Info-Tech Innovator of the Year award.
Experience
A track record of delivery.
From building IT operations at a growing software company to leading technology for New York Life's direct business.
Leaders I've developed
A CIO, a CTO, and several principal architects, plus team members who moved into senior business leadership.
NYL Direct
2024 – Present
Leads architecture, AI, data, business technology transformation, engineering enablement, and technology strategy for the direct-to-consumer business of New York Life, the largest U.S. mutual life insurer: a $43M portfolio and 157 technology professionals. Improved delivery 22% year over year, won an Info-Tech Innovator of the Year award for AI and data work, and moved more than 70% of platforms to the cloud, while the business kept growing efficiently in a level-to-declining market.
New York Life
2010 – 2024
Built the enterprise architecture practice and led data management across warehousing, governance, and analytics through 14 years of platform modernization, while keeping the business running.
AEGON
2000 – 2010
Led enterprise integration strategy and SOA adoption across distributed teams, helping the business modernize without more point-to-point sprawl.
ECI Software Solutions
1996 – 2000
Built IT operations and infrastructure from the ground up and laid the technical foundation behind the company's growth and acquisition.
Outside the day job
2026
Shipped a personal project most months, including a coaching platform, a leadership development platform, and an open-source life insurance platform.
Perspectives
Selected perspectives on technology and leadership.
A curated collection of thoughts on technology, AI, leadership, and transformation in complex organizations.
Browse the perspectivesBeyond 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
What a Consumer Launch Taught Me About Enterprise Delivery
Launching my first consumer app showed me how an AI-native delivery pipeline can turn user feedback into a release the same day, and why the people running it need breadth more than niche specialization.
Published October 2026
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.
Revised September 2026 ·Originally June 2026
New Skills for the New Era
I keep seeing the same pattern: enterprises talk transformation, but many of the skills they reward now create drag in a faster, less forgiving era.
Published June 2026
Projects
Things I have built and explored.
Building hands-on is how I stay connected to what actually works across the technology ecosystem, which matters more than ever in the AI-native era. Each project tests an idea I would otherwise only read about.
Browse the projectsAn open-source take on life insurance administration, built to explore what a modern core platform could look like without decades of legacy assumptions.
A machine-readable career profile schema I built after running into the limits of standard resume formats. It also powers this site.
A brewing dataset and toolset I use for experiments, recipe decisions, and brewing analytics.
A data-informed portrait of a year, built from health, activity, travel, listening, work, and other personal records without letting AI invent the answers.
Fermentation as a systems problem: process control, repeatable execution, and data-informed iteration applied to beer, cider, and experimental ferments.
Start the conversation
Let's talk about technology leadership.
I'm focused on CIO and CTO leadership in organizations where technology drives business and customer outcomes. If you're shaping that kind of role or agenda, I'd welcome the conversation.