About

Hilary Johnson

I study work by designing the systems through which it gets done. My background spans enterprise information architecture, user research, interaction design, and the operation of an AI-native business of one.

I am a principal product designer with a background in enterprise platforms, information architecture, mixed-methods research, and human–computer interaction.

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Work

From enterprise platforms to an AI-native business

From 2016 to 2022, I led user research, information architecture, and interaction design for myLiberty, Liberty Mutual's global employee digital workplace serving 45,000+ employees. I worked across site structure and navigation, search, HR self-service, accessibility, language, audience targeting, and international rollout to make a complex employee system easier to use and maintain.

During the platform rebuild, I led site-structure research with 400+ employee participants and designed accessible navigation across desktop and mobile. After launch, navigation support tickets went from hourly to zero.

That work taught me to look beyond individual screens. Across projects, I used experience architecture maps to show current and future states and trace how employees moved through tasks. The maps made the steps, decisions, and handoffs that shaped employees' experiences visible to teams planning platform changes.

I built and launched Oak Grove as an AI-native business of one: a real operating business and production environment for studying how AI can extend one person's capacity across product, commerce, content, marketing, analytics, and operations.

Running it brought product strategy, production methods, suppliers, pricing and margins, catalog architecture, digital commerce, localization, merchandising, and marketing into one connected set of decisions. AI extended the range of work I could take on; I retained responsibility for direction, quality, and every consequential business decision.

As model capabilities expanded from chat to file generation, image editing, direct Airtable access via MCP, and structured workflows, I adapted the division of work. I decided what to delegate, what required review, and what stayed manual based on quality, provenance, brand integrity, and business risk.

Education

People, technology, and business

My formal training combines human factors, information design, digital media, and business. At Bentley University's McCallum Graduate School of Business, I learned to connect evidence about people with organizational goals and technology decisions. Harvard's Digital Media Design program expanded the creative and technical range to carry those decisions into working digital experiences.

M.S. Human Factors in Information Design
Bentley University — McCallum Graduate School of Business

A.L.M. in Extension Studies, Digital Media Design
Harvard University

B.A. Biology and East Asian Studies
Brown University

That combination shapes how I work: understand people and their context, make the structure of a system visible, and connect design decisions to how an organization succeeds.

Now

Applied AI and complex work

I design products and operating systems for complex work—combining human factors, information architecture, research, interaction design, and applied AI when those disciplines need to work together.

I am particularly interested in helping organizations redesign how work gets done with AI: deciding what the system should handle, what people should control, how quality should be evaluated, and how failure should be made visible.

If that is the kind of problem your team is working on, I would love to hear from you. Email me at hilary.m.johnson+ai@gmail.com.