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Jay Signorello

Entrepreneur | Product-Obsessed Technical Leader | Startup CTO & Founder (Acquired by Zillow) | Former VP Engineering @ Zillow | Investor | Advisor & Builder

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Latest posts

What Strength Training Taught Me About Using AI Too Much

A founder's lesson from years of sedentary neglect—and how the same pattern is now showing up in AI overuse: less recall, less creativity, less depth.

Your Calendar Is Lying to You

Digital calendars copied paper ones and stopped. We don't need apps that show us events, we need tools that show us what those events actually require.

AI Didn’t Change the Strategy Game

Everyone is rushing to build apps with AI. But building was never the hard part. Strategy and distribution still are.

The Invisible Toggle

The hardest part of juggling parenting and building software isn't the work itself.

Authoritarian Leaders Are Toxic

My first management job was a disaster. Here's what changed.

The Talk I Wasn’t Ready For

When my project failed, the hardest part wasn't starting over — it was telling my kids. But that conversation turned into one of the most important we've ever had about failure, resilience, and what entrepreneurship really looks like.

Two Moments that Changed My Career

A bus ride home and a few words from Zillow's co-founder helped me realize what I was missing. This is the story of why I walked away from tech management to be there for my kids.

Principles for Managing a Remote Team

These are the lessons I've learned from the experiences of over a decade of managing remote teams, compiled into a list of core principles.

15 Essential Tips to Support New and Junior Employees in Remote Work

Background Through trial and error, I learned some hard lessons in supporting new and junior employees while building my first company, Naked Apartments, in 2009. It was also my first time taking the plunge with managing an all-remote company, along with my fellow co-founders. Turns out, many of the lessons we learned can and should be applied to any work environment. They’re just that more…

Building Strong Team Relationships While Working From Home

Working from home during the COVID-19 pandemic is a rather stressful and anxious time, even for someone like me, who has spent a good portion of my career working from home and managing distributed teams.