The Office of Jason James

Jason James is a designer of products, brands, teams, and companies.



Jason James is a design leader, repping Chicago on the West Coast. Currently, he’s Head of Design at Thumbtack and hiring for a lot of roles.

His work and work ethic are both deeply influenced by his blue-collar, modest upbringing in Northern Illinois. When not working, he plays with his two cats, Whiskey and Ringo, and drinks Cabernet with his wife while watching Hulu. If you’d like to say hello, email



5 Myths About Design Management

Jul 2018 – What design management is and isn't in order to help aspiring managers make a more informed decision about their career path

Our Answers to the Most Popular Interview Questions from Product Designers

May 2018 – After running 600+ product design interviews in the last two years, I thought, "Why not just publish the answers?"

Q: What is your biggest, most visible design regret?

Sep 2017 – My biggest, most visible regret: designing failed or failing companies

The Primacy of Shipping

Jun 2017 – To my fellow product designers, you will be judged by what you ship. Shipping is everything and the only thing.

What Makes A Great Product Designer

Mar 2017 – Guidance about the opportunities for career development and personal growth within the Product Designer role

A Framework for Deciding Your Next Job

Dec 2016 – Consider being very methodical about your next job change. Evaluate the opportunities across 16 different factors. Here’s a tool to help.

What traits do you look for when evaluating a product design candidate?

Apr 2016 – For every product designer, they will be evaluated across three areas: technical caliber, diversity, and values.

What Long Hours Really Mean

Nov 2013 – If some place or some job is making you feel like long hours “come with the territory” just know they are misleading you to their benefit.

Culture Matters, Prestige Does Not

Jul 2013 – When you’re faced with a decision between a prestigious job or a non-prestigious job, pick the one with the best culture.

Believing the Best

Jun 2013 – Mistakes happen. But your response to those events sets the tone for your workplace.

You Owe It To Yourself To Move On

May 2013 – Selling off the best hours of the best years of your life is one of the biggest decisions you’ll ever make (and remake).