Lisa McLaughlin and the hat that stayed in the bookstore

The hat said “analog.” Lisa McLaughlin spotted it beneath the register at Literati, the Ann Arbor bookstore, while shopping for books about artificial intelligence. A technology founder buying books about the digital future had found herself coveting a hat advertising the opposite. Retail occasionally develops a sense of humor.

She left it behind. She and a friend had agreed to buy no new clothes for five months. The promise held; the hat stayed at the shop. In her March 2025 writing, McLaughlin remembered the moment with affection. After years of building a company, she was paying attention to what could be found close by: a bookstore, a friendship, a promise small enough to keep.

It is an appealing place to begin the story of Workit Health’s co-founder and former co-CEO. The venture rounds and awards belong here, too. But the hat introduces a person whose relationship with technology has always involved looking beyond the screen. What does a tool ask of someone? Whose time does it consume? And what happens when an organization mistakes collecting information for understanding it?

The question that didn’t fit the form

Years earlier, while studying social work, McLaughlin helped with the response to Hurricane Katrina. She was gathering information from people who had lost their homes. The survey asked them to estimate the damage. Some had lost everything. The distance between the question and the person answering it stayed with her.

A community information seminar gave her somewhere to take that unease. Here were people examining the social consequences of gathering information. She asked her adviser how she could get involved in information science. She completed master’s degrees in both information and social work at the University of Michigan in 2008.

After graduating, she worked with Daniel Atkins, a founding dean of the School of Information. Her assignment involved interviewing 30 people from his professional network and preparing a report about the future of community informatics. Listening became a way to investigate how institutions might work differently. The project also introduced her to people she otherwise would not have met.

Before the startup, the shared bookshelf

By 2010, McLaughlin was managing OER Commons at the Institute for the Study of Knowledge Management in Education, known as ISKME. Open educational resources presented a deceptively simple proposition: make useful teaching materials available for others to use and adapt. Putting material online was only the beginning. People still had to find it, judge it, and understand how it might fit their work.

In an international online discussion that October, she described a collection of roughly 30,000 resources. The problem under discussion was quality versus quantity. Her response described curated collections organized around subjects, including a planned collection of agricultural materials. A large digital library, it turns out, still needs someone to think about the shelves.

In November 2011, Achieve and ISKME announced an evaluation tool on OER Commons. Educators could assess resources and their alignment with Common Core standards. McLaughlin was ISKME’s named contact on the announcement. It was practical work on a familiar internet problem: abundance helps only when people can make useful choices within it.

Her career moved through open knowledge networks, product innovation, and a partnerships role at Gooru. These jobs gave her experience with the connective work behind a product: relationships, organization, and the routes by which something useful reaches the people who might use it. The eventual founder had spent years around the machinery before putting her name on a company.

Michigan was part of the plan

McLaughlin and Robin McIntosh brought different professional backgrounds to their partnership. McIntosh came from design; McLaughlin brought information science, social work, and experience in education technology. They had become friends and worked together in startup settings before starting their own company. Workit was incorporated at the beginning of 2015, following conversations late the previous year.

McLaughlin had worked in Silicon Valley. Establishing a presence in Michigan nevertheless made sense to her. She knew people in Ann Arbor’s growing technology community and believed the region could support the team she wanted to build. Familiarity was an asset, even if some people elsewhere regarded it as an eccentric attachment.

The objections were blunt. She recalled being told she could not grow a large company there and should return to the Bay Area. Michigan was dismissed as a flyover state. The response she remembered feeling was personal as well as commercial: her home state deserved a more serious hearing.

Her argument rested on hiring, existing institutions, and the cost of living. A company needs people who can afford to stay and do the work. Geography affects that calculation. By 2021, Workit’s $118 million Series C, led by Insight Partners, supplied a fairly substantial answer to the earlier skepticism. Michigan had not prevented the company from attracting capital.

A company with two people at the top

The co-CEO title made their partnership visible on the organization chart. McIntosh described the arrangement as a way to support one another and divide difficult challenges. The two women could share responsibility in an industry where they often found themselves among men. Their friendship preceded the title, giving the arrangement a foundation beyond a division of duties.

In 2019, both received Schwab Foundation recognition as social entrepreneurs. McLaughlin later named that moment among the memorable experiences of her career. It placed their work alongside projects from other countries addressing social and environmental problems. For a founder committed to using business for a public purpose, the company had acquired a wider set of peers.

Her advice to younger women emphasized the capacity to learn. Skills, she argued, could develop; difficult experiences could teach. She described challenging assumptions within the company and approaching problems with curiosity. That is demanding advice for anyone in charge. It leaves room for an employee, a colleague, or a customer to notice something the founder missed.

“Make accessibility a priority.”

Lisa McLaughlin

She also connected accessibility to particular product choices, including software standards and video that would work on older devices. Those are decisions a team can actually discuss and test. A founder can announce that a product is for everyone; an older phone has a brisk way of examining the claim.

The twelve-person company and the paperwork

Some of McLaughlin’s clearest descriptions of leadership concern the less glamorous business of setting rules. Workit began pursuing B Corp certification when it had about twelve employees. The process took roughly six months alongside other priorities, with Venture for America fellows helping. It required the young company to examine practices it had not yet fully developed.

She valued the assessment as a guide to gaps in areas such as employment practices and environmental responsibility. It gave the team something concrete to work against while the business was growing. The exercise also influenced thinking about remote work and helped communicate the company’s purpose to prospective employees.

This is a useful detail in a founder story because it brings ambition down to working height. Someone has to decide how employees will be treated. Someone has to write the policy, discover the missing procedure, and return to a question the team thought it had settled. McLaughlin spoke about certification as assistance with building the organization itself. The badge came with homework.

Returning the introductions

Her own experience gave her reason to take professional networks seriously. Over time, she became involved with organizations that help other founders: Desai Accelerator, Endeavor Detroit, and Michigan Founders Fund. She also served on the investment advisory board of the University of Michigan’s Accelerate Blue Fund from March 2021 to September 2024.

Accelerate Blue invests in startups based on technology licensed from the university. The connection fits a career spent moving between academic work and the practical demands of building organizations. Research can produce an idea; developing a company around it requires another set of conversations. Advice and an introduction can be useful pieces of that work.

Recognition had accumulated along the way: a Detroit technology award in 2017, New Enterprise Forum’s Rising Star award for 2018, and later its Entrepreneur of the Year award for 2020. These were local milestones as well as entries on a résumé. Her career had become part of the Michigan entrepreneurial community she had once needed investors to take seriously.

The next venture had a subscribe button

In February 2024, McLaughlin introduced Every Grain of Sand, her Substack publication. She presented the newsletter as the venture for that moment and described herself as a lifelong learner. The format gave her a place to pursue questions in writing, with readers able to follow along.

There is a pleasing connection to something she had shared with University of Michigan students back in 2015: a question about whether someone wants to be a poet or wants to write poetry. It directs attention to the activity behind an identity. Starting a publication is one way to put that distinction to work. You need to produce the next piece.

Then comes the bookstore, the AI books, and the hat she declined to buy. McLaughlin’s career contains substantial rounds of funding, international recognition, and years of shared executive responsibility. It also contains a continuing interest in how people learn and what they owe one another. At Literati, the immediate obligation was straightforward. She had made a promise to a friend. The hat could wait.