Jonathan
Tushman

CTO / CAIO at Hi Marley

Building at the intersection of artificial intelligence, insurance, and the teams that make it all work.

About

Harvard Business School grad, serial founder and CTO who's spent twenty-plus years building technology companies from the ground up. Currently leading technology and AI strategy at Hi Marley, where we're transforming how insurance companies communicate with the people they serve. I'm endlessly drawn to the space where AI amplifies human connection rather than replacing it.

Thinking & Writing

The Integrated Operating System

I believe AI isn't a feature you bolt on — it's an operating system you build into. At Hi Marley, we're proving that when you weave intelligence into every layer of how a company communicates, you don't just make things faster. You make them more human.

Coming Soon

The Integrated Operating System

2026

Why AI strategy isn't about adding features — it's about rethinking how your entire organization operates.

Coming Soon

AI Strategy for Insurance

2026

Lessons from building conversational AI in one of the world's most complex, regulated industries.

Coming Soon

Building Engineering Culture

2026

What twenty years of founding and leading engineering teams has taught me about hiring, shipping, and staying curious.

The Collection

On the Turntable

Twenty records I keep coming back to. Not a "best of" list — just the albums that have shaped how I hear everything else.

Blue by Joni Mitchell
Blue
Joni Mitchell
Tommy by The Who
Tommy
The Who
#1 Record by Big Star
#1 Record
Big Star
Eat a Peach by Allman Brothers Band
Eat a Peach
Allman Brothers Band
Doolittle by Pixies
Doolittle
Pixies
Physical Graffiti by Led Zeppelin
Physical Graffiti
Led Zeppelin
Lawn Boy by Phish
Lawn Boy
Phish
OK Computer by Radiohead
OK Computer
Radiohead
I'm Wide Awake, It's Morning by Bright Eyes
I'm Wide Awake, It's Morning
Bright Eyes
The Southern Harmony and Musical Companion by Black Crowes
Southern Harmony
Black Crowes
Highway 61 Revisited by Bob Dylan
Highway 61 Revisited
Bob Dylan
Greetings from Asbury Park, N.J. by Bruce Springsteen
Greetings from Asbury Park
Bruce Springsteen
XO by Elliott Smith
XO
Elliott Smith
Weezer (The Blue Album) by Weezer
The Blue Album
Weezer
The Band by The Band
The Band
The Band
Paul's Boutique by Beastie Boys
Paul's Boutique
Beastie Boys
Can't Buy a Thrill by Steely Dan
Can't Buy a Thrill
Steely Dan
Layla and Other Assorted Love Songs by Derek and the Dominos
Layla
Derek and the Dominos
Europe '72 by Grateful Dead
Europe '72
Grateful Dead
Yankee Hotel Foxtrot by Wilco
Yankee Hotel Foxtrot
Wilco

Beyond the Screen

Off the Clock

When I'm not building software, I'm usually running — a Boston Marathon finisher and Pan-Mass Challenge rider, raising money for Dana-Farber Cancer Institute. The rest of the time you'll find me in the kitchen, experimenting with whatever's in season, or digging through crates for the next record to add to the collection.