Josh Olsen

Built with Cursor

Principal-level IC building trust-critical products used by millions at work and at home.

I thrive in ambiguous spaces across B2C and B2B, aligning cross functional peers from first insight to shipped product. I use AI to accelerate exploration and write code so ideas reach users quickly and course correct faster.

My focus is simple: connect what customers need to what moves the business, and make that connection obvious in the experience.

Complex systemsB2C & B2BCustomer value → ROIAI + code

Work that made an impact

Doubling account conversion with a clear path to value

Doubling account conversion with a clear path to value

I defined the experience architecture and sequencing for 1Password's first-run across platforms, aligning product, design, and engineering on a core user path to value and executing a multi-year roadmap.

Account conversion

2x

Support traffic

-50%
Rebuilding Varsity Tutors' live classroom as an AI-ready, reliable core product.

Rebuilding Varsity Tutors' live classroom as an AI-ready, reliable core product.

I led a rebuild of Varsity Tutors' live classroom, moving from early discovery to a 100% launch on a new stack.

As the sole designer on the project, I owned the experience architecture, grounded decisions in real learner and tutor feedback, and partnered in the production repo to ensure the system behaved the way people actually needed it to during live teaching.

Discovery to launch

<3mo

AV error rate

-50%

Cost per call

-40%
🚧 Case study in progress

Companies I've grown alongside

Nerdy

Principal Product Designer

2025 - Present

1Password

SeniorStaff Product Designer

2020 - 2025

Turo

InternSenior Product Designer

2014 - 2020

Josh with his cat
Josh in cowboy attire at The Avalon Lounge

© 2025 Josh Olsen