Cheryl Contee and the Art of Paying Attention

Cheryl Contee’s technology career began with a calculation about washing dishes. At Yale, her scholarship required a campus job. The kitchens paid better. The computer assistant job paid less. She chose the computers. A sink full of plates had, inadvertently, helped recruit a future software founder.

It is a pleasingly unceremonious beginning for someone whose working life has included political blogging, a digital agency, a software acquisition and books about entrepreneurship and artificial intelligence. There was a student choosing work she could bear, then discovering that helping other people use computers was an education of its own.

Contee studied ethics, politics and economics. Technology became a second, practical curriculum. The combination helps explain her subsequent choices: she keeps returning to places where an organization has something urgent to say, people it needs to reach, and tools that could make the conversation work better.

A political education before the keyboard

She grew up in Washington, D.C., watching the evening news with her family. Her father taught history at Howard University. Politics arrived at home as a regular appointment, long before it became something to discuss with strangers on a screen. Years later, she described continuing the news-watching tradition with her own son.

That background matters because Contee’s interest in digital communication has never depended on the novelty of a device. The political questions were already there. Who gets heard? Who is represented? What happens when a community can speak for itself? The internet supplied another place to pursue them, with fewer people standing between a writer and a reader.

In 2006, she and Baratunde Thurston co-founded Jack and Jill Politics. Contee wrote as Jill Tubman. Its description, “a black bourgeoisie perspective on U.S. politics,” announced a point of view with an eyebrow raised. The blog made room for political commentary from a Black middle-class perspective that she felt was being overlooked.

Satire was part of its vocabulary. So was participation. A blog could answer the day’s news while readers were still arguing about it. It offered a form of political publishing in which the conversation did not have to wait for an editor’s invitation. Contee had found a way to join public argument on her own terms.

“Women need to see that there are many different ways to find your niche in technology.”

Cheryl Contee, 2010

The audience was already on its phone

In 2008, Contee and Rosalyn Lemieux co-founded Fission Strategy, serving nonprofits and foundations. The work took the questions behind the blog into organizations: how do you reach people, persuade them to participate, and give that participation somewhere useful to go?

By 2010, Fission’s work included Oxfam, Greenpeace, the ACLU and MomsRising. One campaign offered a particularly concrete lesson. Working with Reform Immigration for America, the team helped build a mobile action network of more than 150,000 people. Potential rally and march participants were reported to be six times more responsive to text messages than email.

A text message is an unglamorous object on which to hang a technology story. It lacks the theatrical appeal of a new machine. But the result captures Contee’s approach. The relevant question was where people would actually respond. Choosing a channel had consequences for organizing, rather than merely for the appearance of a campaign.

Her advice to women interested in technology was similarly expansive. Programming was one route, but there were others. She had studied society and learned computers by helping people use them. That experience gave her a useful vantage point for clients whose expertise lay in a cause, rather than in software.

Listening became a company

Contee and Lemieux’s next venture, Attentive.ly, began operating in the nonprofit sector in 2012. Its software helped organizations listen to social conversations, identify influential supporters and turn that knowledge into engagement. The supporter already had a voice and a network. An organization could pay attention to both.

The product put a specific problem into software: supporters could be talking about an issue without the organization noticing. Finding those conversations created an opportunity to respond with something relevant. For a nonprofit, that might mean an invitation to take action, rather than another general appeal. The appeal of listening is straightforward. It gives the next message a reason to exist, and gives the person receiving it a reason to pay attention.

The distinction is easy to miss in a world full of broadcast buttons. A mailing list tells you where a message can go. Social listening can reveal what people are discussing before the organization speaks. Attentive.ly gave nonprofits a way to connect those conversations with their outreach, advocacy and fundraising.

In July 2016, Blackbaud announced that it had acquired the company. Lemieux and the employees joined the buyer; Contee continued leading Fission and became a strategic adviser to Blackbaud. The announcement described a practical commercial outcome: social listening and engagement capabilities could reach a broader nonprofit market through an established software provider.

The exit also became a milestone in accounts of Black women’s participation in technology entrepreneurship. Contee has described Attentive.ly as the first technology startup with a Black woman founder acquired by a Nasdaq-listed company. She has also said the historical significance only became clear to the founders when they got there.

There is a temptation to let the acquisition finish the story. A buyer arrives, the entrepreneurial plot resolves, everyone takes a photograph. Contee’s subsequent work suggests that the more interesting question was what experience she could pass on. An exit gives a founder a result; explaining the route can give someone else a starting point.

Who gets judged on the ride?

In 2018, Fission joined with the digital work of 270 Strategies to create Do Big Things. Contee led the agency as CEO. The following year, she published Mechanical Bull: How You Can Achieve Startup Success, a guide built around the experience of founding a company while falling outside Silicon Valley’s familiar expectations.

The title supplies its own miniature scene. Contee has ridden a mechanical bull. In explaining the metaphor, she observed that an audience watches a man’s strength and stamina, while a woman attracts a different kind of scrutiny. The rider still has to stay aboard. The spectators have changed the terms of the performance.

Her book approached entrepreneurship with that unequal attention in mind. A founder needs advice about investors, teams, money and an eventual exit. Yet advice can quietly assume access to resources that a reader does not have. The cheerful suggestion to raise a friends-and-family round becomes less helpful when friends and family cannot write startup checks.

There is humor in Contee’s telling, and something practical beneath it. A useful guide should acknowledge the reader’s circumstances. Otherwise, the instruction manual begins halfway through the job, after someone else has already supplied the tools.

She also worked with founders through Higher Ground Labs, advising on investors and exit strategy. With Barbara Clarke, she co-founded The Impact Seat Foundation to encourage investment in historically excluded entrepreneurs. The recurring concern was access: to capital, to advice, and to people who could help a business move forward.

Another technology, the same human questions

Her current work includes BrightWorks AI, where she is a co-founder and chief innovation officer. Hilary Cherner and Ashley Boyd are her fellow co-founders. The consultancy helps nonprofits and foundations with AI strategy, governance and adoption. Contee also co-founded Change Agent AI and advises PosterChild.AI.

With Darian Rodriguez Heyman, she co-authored AI for Nonprofits: Putting Artificial Intelligence to Work for Your Cause, published in 2025. The book draws on interviews with 57 experts. Its terrain includes fundraising, communications, operations and the organizational work required to introduce unfamiliar tools responsibly.

This is a revealing choice of audience. Nonprofits have missions that can exceed their staffing and budgets. A tool that saves time might matter considerably. So do questions about data, trust and whether the tool serves the people an organization exists to help. Contee’s work places those considerations inside the adoption conversation.

In a 2026 conversation, she told an audience to begin with a task the team puts off until late on Friday. Try improving that workflow. See what happens. It is advice with a useful lack of ceremony: the first experiment can be small enough to evaluate, and ordinary enough that staff recognize the problem immediately.

“Innovation dies in cultures that punish curiosity.”

Cheryl Contee, 2026

Her own example is agreeably domestic. After using AI to prepare a presentation much faster than expected, she found herself with unexpected free time. She went to a yoga class and took a nap. The anecdote is funny because the promised productivity dividend actually arrived, leaving a productive person briefly unsure how to spend it.

The story also supplies a measure of success that a software demo rarely includes. What did the tool let a person do with the hours it returned? Work can expand to consume any spare minute. Contee’s example leaves room for the person who did the work to enjoy the saving.

From a political blog to nonprofit software, she has repeatedly worked on the space between an institution and the people it hopes to reach. The tools have changed; the need for attention has endured. A faster message still needs someone worth hearing from. A larger audience still consists of individual people.

That is where her career becomes particularly legible. She helped people recover files, helped communities publish, helped organizations listen, and now helps teams decide what to do with AI. The student who chose computers over dishes found a durable line of work: making technology useful to somebody else.