Senior Director of Product Design · San Francisco

I lead design at Checkr, and I design and ship code myself.

Now: Checkr, 2019–now. Head of product design, research, and content design, reporting to the CPO. Led design as Checkr grew past $700M in revenue.
Team: Grew the design org from 5 to 18 people, including managers for design, research, and content, and promoted 7 people along the way. Today I lead a team of 10 directly, and I’m hiring.
Tools: Claude Code, Claude Design, Cursor, Lovable, Figma

I aim my work at big societal problems, using design and behavioral science to change what people actually do.

At , that means one of the most important decisions an employer makes: who gets access to work. Employers need to hire safely, and people deserve a fair shot even if they’ve made a mistake in the past. Getting it right means working within regulation, weighing hard tradeoffs, and holding a high bar for fairness.

That’s been true throughout my career. At , I co-invented a patented way of coaching households to shift their energy use. Before that, I designed a green jobs program in the Bronx that placed more than 100 people in jobs.

At heart, I’m endlessly curious, a designer who thinks like a researcher and a strategist. I studied social psychology and art history, then business, and I still use all three: understanding why people act the way they do, finding the incentives that bring everyone together, and making the result clear and beautiful.

Selected work

Full walkthroughs available on request.

AI agent design

I originated the design for Checkr Assistant, an AI agent for the small businesses that use Checkr. My early designs and prototype got the team behind it, and the first version launched in September 2026. The prototype went further than ordering a check, imagining help with reviewing results, explaining delays like a court being down, and comparing a report to how a company and its peers have decided in the past. I worked closely with our machine learning engineer to shape its training data, evals, and tone, and my team took it to launch.

Watch the demo
SMB growth and self-serve

For smaller companies that sign up on our website, my team and I redesigned the core flows, from sign-up and onboarding to ordering, checkout, and payment, and we run a steady stream of experiments, including pricing and packaging. Self-serve has grown into a significant, fast-growing part of Checkr’s business.

When I noticed billing confusion in support tickets, I redesigned our billing email and invoice myself. Billing tickets dropped 35% in two months.
Zero-to-one product

In 2019, I designed Assess, Checkr’s hiring rules engine. It gives employers clear, consistent rules for reviewing background checks. Today it’s used on 90% of Checkr’s background checks. It cut review workload 50%, grew fair-chance hiring 10%, and won a 2021 Fast Company World Changing Ideas Award.

I also demoed Assess to criminal justice reform advocates and U.S. Department of Labor staff as a model for fair-chance hiring.

While designing it, I did research on site with enterprise customers and gave many of the sales demos. A major grocery delivery company said they couldn’t have scaled through Covid without it. Another customer told us:

“After this demo I can see that we’re at a strategic disadvantage in the gig economy because we aren’t using this product yet.”
A leading rideshare company
Complex enterprise tooling

Large employers hire across many teams, locations, and roles, each with its own permissions and requirements. I’m leading my team’s work on information architecture, settings, and user management, and I’ve proposed a new navigation structure for where the product goes next.

I’m also writing the code. Our account management area had grown piece by piece, so I rebuilt the whole thing to make it clearer for customers, with a new information architecture, one consistent visual system across every page, and accessibility fixes throughout. It rebuilds every page in the area, with tests throughout, and goes live this month.
API products and integrations

Many of our largest customers build Checkr into their own onboarding flows through our API, so developers are a core audience for us. I work closely with engineering on the developer experience, including docs, webhooks, and logs. We also design our integrations with ATS and HRIS partners, so employers can start a check from the HR tools they already use.

How I work

I keep asking why. I’m still the kid who asks “why” one more time than anyone expects, about how people decide and how systems work. It’s what drew me to psychology, research, and data.

I start with the right questions. Hard problems have open questions in the technology, the policy, the business model, and the org chart. I help my team name them and answer the most important one first. With AI, that matters even more: it builds the right idea much faster, and the wrong one too.

I bring my team with me. I moved our team from static mockups to designing in code, all the way to merge requests in production. I focus on the environment around it, making it safe to try new things, sharing best practices, and celebrating what we do well.

I work at every altitude. I recently presented our executive team with a 2030 vision for an agentic Checkr, where the interface bends to what each person needs. I also built the dashboard the company uses to track our mission impact.

Contact

Happy to talk design, AI tools, and building products that work fairly for people.

rrabison@gmail.com LinkedIn ↗

Selected work

AI agent design

SMB growth and self-serve

Zero-to-one product

Complex enterprise tooling

API products and integrations

How I work

Contact