Josh Olsen

Giving new users a clear path to protect their digital lives.

Company1PasswordRoleLead DesignerTimeline2024–2025

Password managers put stronger security within reach, but setup can be concept-heavy. When trying 1Password, everyday people were abandoning in frustration.

Over two years, I led the vision and roadmap that clarified why users struggled and aligned the org around getting new users to the moment they actually feel value: autofill. That direction led 1Password to staff two cross-platform engineering crews, where I led design and oversaw end-to-end execution.

Impact

Trial-to-paid conversion+36%Support traffic from early adoption friction-50% YoYExtension adoption+15%User satisfaction85%

“I thought like everything from the email up until I was in was very straightforward, super easy. Like I knew where to click every time.”

— Research Participant, New User

Before

The legacy experience dropped users in product with little context, leaving them to choose their own adventure. Spoiler: many left.

After

I resequenced the entire first-run around one insight: get users to autofill as fast as possible. That's the moment they feel 1Password's value. Every step is designed to earn the next.

Extension first, account second. Without the browser extension, 1Password can't deliver its core value, so I moved it to step one.

1Password's dual-key security model is genuinely complex. This screen makes it graspable in seconds and prevents lockouts down the road.

A deliberate pause. You just created an account, that's real progress. Celebrate it before asking for more.

Users practice autofill on a simulated site with the real extension. They feel the product's core value before they've saved a single real password.

The extension meets users where they already are, browsing the web. Contextual prompts and a persistent step counter keep momentum without pulling them back to a setup wizard.

One question: "How do you manage your passwords today?" From there, step-by-step guidance tailored to exactly where your passwords live.

The same thoughtful sequencing, adapted for mobile: a prompt, a guided flow, a clear payoff.

The strategic artifact behind the work. A 9-stage lifecycle model with real user questions at every stage that I used to align the org on where to invest across a multi-year roadmap.