AI Coach for Employee Onboarding

Toast R&D onboarding included a huge amount of knowledge distributed across Confluence, team documentation, tools, and different onboarding platforms. In their first weeks, new hires often had to work out which source was current, what applied to their role, and what to do next.

As the Confluence knowledge base grew, finding an answer quickly became harder. The experience depended too heavily on each new hire knowing what to search for before they had enough context to ask the right question.

The organization already had rich onboarding content. What new hires lacked was a clear path through it: what matters now, what can wait, where an answer lives, and who can help when documentation is not enough.

This reframed the opportunity from building another knowledge destination to creating a contextual onboarding layer that connects people to the right next step.

The R&D Onboarding Manager brought the domain expertise and created the original product structure using Claude. I built on that foundation as Lead Designer, translating the initial structure into a clear experience architecture and leading the UX direction across the product.

My ownership included the AI conversation experience, New Hire and Manager journeys, interaction patterns, glance-able information design, design iteration, and Buffet implementation.

I designed two primary areas of the product. The New Hire experience helps employees understand priorities, ask questions, find knowledge, and move through their first weeks. The Manager experience gives managers visibility into progress and creates timely opportunities to support each person.

The Admin experience is still under development, so this case study focuses on the two areas I have designed and the relationship between them.

A conversational interface can easily reproduce the same problem as a dense knowledge base by returning a long block of text. I proposed a response structure that lets new hires understand the answer at a glance before deciding whether they need more detail.

Responses prioritize the direct answer, organize supporting information into clear sections, and surface the most relevant next actions. This turns the conversation from passive reading into guided progress.

Managers needed to understand how new hires were progressing, remember when to follow up, and offer support at the right moment. Existing information was scattered across documents and informal check-ins, making it easy to lose track.

I designed the Manager experience to make progress visible and follow-up manageable without creating another administrative burden. The goal is a smoother workflow for managers and a more thoughtful, connected experience for every new hire.

Rather than creating a separate visual language for onboarding, I applied Toast’s existing Buffet Design System across the platform. I defined how its components and patterns should support onboarding-specific needs such as content hierarchy, task guidance, knowledge retrieval, progress, and contextual support.

This implementation keeps the experience consistent with the broader Toast product ecosystem as new roles, teams, tasks, and knowledge sources are added. The onboarding platform feels like part of Toast, not a disconnected internal tool.