Remote collaboration
Remote collaboration

Over the past year my team has done what almost every design and research team has had to do — adapt to a fully remote world. As part of that, we had to figure out how to make our design sprints 100% remote.

Prior to COVID, our team was mostly co-located in one office, with a few distributed members and a smaller team at another site, so we had some experience doing hybrid sprints. …


One of the benefits of joining a startup is the ability to have more varied opportunities and larger scope projects, all in a shorter amount of time compared to an established company. But the flip side is that startups don’t normally provide formal career development until they reach a certain level of organizational maturity.

In fact, there’s a tacit acknowledgement about the lack of career development resources at startups — we’re used to thinking that it’s just what comes with the territory and that you have to pull yourself up by your bootstraps when it comes to your own professional…


As a member of the LGBT community who has been out since I was a teenager I’ve long been hyper aware of spaces where I felt both uncomfortable and unsafe. There have been workplaces where I needed to be the “buttoned up” version of myself verses those where I could be the relaxed, creative and authentic me. So it’s no surprise that I think about inclusive team culture a lot as a creative leader and a team manager. Throughout my career I’ve strived to create cultures where diversity and inclusion is celebrated and the norm. And it’s not just because…


I recently spoke at Dribbble’s Hangtime LA conference about how our product (UX) design team created a strategic vision film to inform future product strategy (If you’re interested in learning about our visioning work checkout some posts starting here). Throughout the conference several attendees stopped me to ask how they could make the transition from doing freelance and agency work to moving to an in-house embedded UX / product design team. I shared a few tips I’ve collected over the years based on my own experiences as both a designer who made the jump from agency to in-house, as well…


Communicating vision to make an impact + case studies

A still from a video vision piece we did for our 2018 company kickoff

This is the final article in a 3 part series on design visioning. In the first article I covered the basics of what design visioning is and why it’s important. In the second article I shared some useful visioning tools and techniques, as well as how to make visioning a priority in your daily work. This article will go over how to communicate visioning to make an impact and share a few case studies.

Communicating Vision

During a few of my early visioning projects at MySpace in 2008 and Sony in 2010, I naively thought making the time to do the work…


Great hires start from great interview feedback

These are guidelines we created for the product design team at Thumbtack for writing more consistent, balanced and useful interview feedback. While we’re focused on hiring product designers, user researchers and content strategists, we think these best practices can apply to almost any role.

As a growing product design team at a growth-stage startup, we’ve interviewed hundreds of candidates over the past year for our product design, user research and content strategy roles. Since our candidates meet 6–8 people from our team during an onsite interview, it’s important that our team is consistently calibrated, and that our candidates are evaluated…


This post is about how we Get Sh*t Done (GSD) on the Thumbtack Product Design team. Over the past 2 years we’ve more than tripled the size of our team, pivoted to a new product strategy and shipped a rebrand. Here’s some reflections on how our team has navigated these changes and found a way to stay sane, have fun, and GSD.

Our Team

Who are we? Our team is made up of 3 functions: Product Design, User Research and Content Strategy. 2 years ago we were a small team of 8, and today we’re 25 and growing. Since we don’t have…


Tools & Techniques, and making visioning a priority in your daily process

A week long team visioning sprint at Thumbtack, featuring the Product Design Team Pineapple.

This is the second article in a 3 part series on design visioning. In the first article I covered the basics of what design visioning is and why it’s important. This time I’ll talk about some useful visioning tools and techniques as well as how to make visioning a priority in your daily work. The final article goes over how to communicate visioning to make an impact, and I share a few case studies.

Visioning Tools & Techniques

Visioning can be an incredibly personal process, and varies widely from team-to-team. …


Part 1 of 3: What is visioning + why it’s important

This is the first article in a 3 part series that covers the basics of what design visioning is and why it’s important. In the second article I share some techniques for how to make visioning a realistic priority in your daily work and the third article talks about how to communicate visioning and make an impact.

When I started at Thumbtack in late 2016 one of my personal on-boarding missions was asking everyone I met about their long-term vision for the company. Each person I talked to had a different answer at the time. …


How I found an unexpected career opportunity

Six months ago I started looking for a new design role, and it was the first time I’d actively had to look for a new job in nearly 6 years. Going through the job search process this time around I noticed a pattern in my career choices that lines up with many fellow designers’: when we’re looking for our next career move, we’re drawn to the extremes. It’s either the companies where design is already well established, offering design-first cultures and polished product execution. …

Josh Sassoon

UX lead @ Google Photos. Previously Thumbtack, YouTube, Apple, & Sony.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store