Cheryl Contee is the award-winning CEO and co-founder of Fission Strategy, which helps the world’s leading non-profits, foundations and social enterprises design digital ecosystems that create change globally. She is also the co-founder of groundbreaking social marketing software Attentive.ly at Blackbaud, the first tech startup with a black female founder on board in history to be acquired by a NASDAQ-traded company and one of the few to have raised over $1mm in venture funding. Cheryl is proud to be a co-founder of #YesWeCode, which represents the movement to help low opportunity youth achieve high quality tech careers.
She was also the co-founder of Jack and Jill Politics writing as “Jill Tubman” on the leading top black audience targeted blog during the 2008 and 2012 election cycles. Cheryl has been listed among The Influencers 50 in Campaigns and Elections magazine. Cheryl was named as an Affiliate of Harvard University’s Berkman Center for Internet & Society. She was inducted into the first The Root 100 list of established and emerging African-American leaders. Huffington Post included her as one of the Top 27 Female Founders in Tech to Follow on Twitter in 2011, as did Black Enterprise. Fast Company named her one of their 2010 Most Influential Women in Tech.
This is the first conversation in The Flex Company’s series Living Black History with The Flex Company cofounder Panpan Wang.
Panpan: Thank you, Cheryl, for being our first guest as part of our Living Black History series, where we highlight leaders in the black community. I’m curious what was your childhood like? How did you succeed so early in life, and what was important to your success?
Cheryl: My father fell ill early in my childhood. He went from being an incredibly articulate and dynamic professor to being someone who really struggled even just to say our names for some years, after a debilitating heart attack and stroke, so, seeing his courage and perseverance really shaped my character. In terms of my career, if you look back at the 70s, the 80s, 90s, the careers that a lot of people have now in digital didn’t exist then, and I think that’s probably true of a lot of the millennials and Generation Z: the careers that they have or will have don’t exist now. There are incredible forces shaping the future, you have to navigate and create your own opportunities and designs and your own career.
Panpan: Did you know where you wanted to head professionally, then?
Cheryl: I went to Yale for undergrad, and the highest paying job there was working in the kitchens in the Reunion House. They made $17 an hour, which was a lot then, I mean, it’s still a lot now, it’s certainly way more than minimum wage. However, I hate washing dishes. I’d rather scrub 20 toilets than wash a dish, actually. But more than that an inner voice told me you’re just not going to learn that much washing dishes day in and day out. You’re here to learn. Is there a job here that you can do that will make you some cash and still help you learn for the future?
So, I ended up working at the second highest paying job, which was called a computer assistant. That meant helping students and professors with their computers and laptops that were in the student centers. I worked in the main library in the basement in the computer center. I did the same when the dot com happened around 2000, that was a moment when I said to myself, “Wow. Is this still a viable career option?” and I said, “Yeah, this is a tough time for people doing interactive work, but the internet’s not going anywhere.” I mean, I still believe that the internet is going to reshape our society and our commerce, so I doubled back, and I’m glad I did it.
Panpan: Well, that was very forward-thinking, and I’m sure you helped a lot of professors with their printer drivers along the way.
Cheryl: Yeah, I sure did. And printer jams. And sort of “Hidden Figures” style. People would walk by and say, “Hey, you can’t work in there. That’s where the computer assistant sits.” I was like, “I AM the computer assistant.”
Panpan: I would say that I’m surprised, but I’m not. You used a word to describe your father: “articulate”. That word is often used to describe black people as a backhanded compliment. You obviously did not use it that way, but I wanted to get your take, both on that word, as well as just the general state of political correctness and the importance of those kinds of words.
Cheryl: Way to go all the way in there, Panpan.
Panpan: Surprise: We’re going to talk about race.
Cheryl: Here’s the thing about political correctness. It’s not always about the word itself, and it usually depends on the context of it and how is it being used, and what it’s achieving, right? To talk about someone as an illegal immigrant versus an undocumented immigrant, there’s nothing wrong with the word “illegal” used in its right context, but along with the word undocumented hook it onto immigrant and things really makes a difference in how you might perceive a person and their motivations and even their very humanity.
A word like “articulate” before I forget the context in which it became an eroded term, but before it was fine, but people would use it to talk about educated black people, like, “Look, a talking monkey! How articulate. You can say words like people do!” and that was where articulate is a perfectly good word to describe someone who is eloquent, someone who not only knows language, but can use it very effectively.
Panpan: In the context of centuries of injustice and today’s current events, how important is Black History Month?
Cheryl: I think it’s incredibly important. It was considered radical and inflammatory when it was first proposed, and of course now it’s become very much integrated into our society, and importantly so.
You can’t separate the history of America from Black history, and yet extreme measures were taken in the past to do so.
I have actually been pleased to see is the development of other history months: Latino/Hispanic History Month has become a pretty big deal, Asian-Pacific American Heritage Month: those are starting to gain more traction, and that’s important.
The role of Chinese immigrants in America is usually overlooked, and yet incredibly important. Railroads wouldn’t exist! There’s so much that wouldn’t have happened, or certainly wouldn’t have happened the same way without Chinese culture in America.
We should celebrate. If it takes a moment out of a month, to focus on that, to get people’s attention, I’m okay with that, because otherwise, it may go from us.
Panpan: Who are your heroes?
Cheryl: I have a lot of heroes, but right now, I think about the work of someone like Shirley Chisholm. I mean, given that there are people who have admitted that they weren’t able to vote for Hillary Clinton because she’s a woman, the concept that someone like Shirley Chisholm could become the first black woman elected to congress and then actually run for president and have people take that seriously. It’s just incredible. I can’t even — I’m sad that I did not live through her heyday, because she must have been the biggest badass ever.
Here’s a quote from Shirley that I like:
“Tremendous amounts of talent are not brought to our society just because our talent wears a skirt.”
Panpan: So, you have been involved in politics from the digital media side. You wrote under a pseudonym, Jill Tubman, for your blog, “Jack and Jill Politics,” along with your Co-Founder Baratunde Thurston, and I was curious about that pseudonym. I’m guessing that’s a reference to Harriet Tubman?
Cheryl: I chose “Jill Tubman” to commemorate Harriet Tubman and Baratunde chose “Jack Turner” to give a reference to Nat Turner. We both chose the names of people who attempted to lead other people to freedom. Harriet Tubman continues to be incredibly inspirational. You think about all of the things that she went through, that people don’t — people of course know her as an abolitionist, but she was also a scout and a spy for the army during the Civil War, she was an incredibly persuasive spokeswoman for feminism, abolitionism, she was incredibly brave.
The fact that she will replace Andrew Jackson on the $20 bill speaks to the kind of society that we should aspire to become.
Panpan: And like a certain computer assistant at Yale, as a spy I’m sure Ms. Tubman was also often overlooked by folks.
Cheryl: I have a feeling people were just like, “She’s a random black woman, just wandering by, minding her own business,” yeah.
Panpan: In a 2010 article you wrote, “We may not be able to use the internet to fix politics overnight or ever, but the nature is surely changing the game we play with our government to expand and defend our precious freedoms.”
Do you still feel the same way?
Cheryl: I do. But I’ve actually been on a panel with speakers who warned of the other side, the dark side of this. That the internet could be used against those working for freedom and human potential. I think we’re seeing that. There are lots of ways in which it seems clear that something happened during the election in terms of fake news, I know that is very disturbing. There are things that say China is doing in terms of trying to create a “walled garden” in which little comes in or out, they’re able to filter, but that’s just not human.
Knowledge wants to travel.
Things want to be known.
People want to connect and speak with each other.
That’s just the way that human beings work. So, I do think that even though governments are attempting to use the internet to consolidate or control, again, much like Trump, I see it as somewhat of a last gasp.
I don’t know how much you know about the history of the creation of the internet, but it was essentially created as an “un-killable” communications form — that in the event of a nuclear holocaust, there needed to be some way in which people could communicate with each other fairly securely and pretty easily no matter what, right?
So, that’s the internet. I mean, you can’t kill it. You can’t kill it.
There’s always some way in, out, around, down, up.
Panpan: An optimist to the end.
Cheryl: An optimist to the end! I believe in peace and people. It’s true that things can go sideways, and things can go sideways for a while, okay? You only have to look at things like Ceaușescu, Stalin, or Hitler or who knows where Trump is going to end up in that ranking, but things can go sideways for a while. It can take years, but the people have always come back. You can’t keep people down forever.
Panpan: I believe some guy somewhere said, “the long arc of history bends towards justice.”
Cheryl: Yeah, who was that dude? Some dude, I don’t know, ha!
Panpan: Voting rights. If I were to play devil’s advocate on the issue of voting rights, I would ask: Why do we need to make it so easy? Voting is a very sacred right of citizens and it is incumbent on those citizens to be educated on who they’re voting for. I don’t understand why a voter ID law, which everyone can get a voter ID for free in their states, if they are a citizen or allowed to vote, or even a reading test, is so bad.
Why shouldn’t we place some sort of bar on the level on competence of the voter themselves?
Cheryl: Well, I had that feeling first, but then when I understood who that was really impacting, when you talk about something like a voter ID law, you’re talking about seniors, the disabled, younger people, who may not have an ID, and to say, “Oh, well it’s easy to go and get one.” You try that! You’re a single mom, you’re 19, you work at Walmart, you’ve got these crazy shifts, and you’re asking me now to go and get some ID? Who has time for that? Who has time to wait at the DMV? It lowers the ability for people to participate and the desire to participate if you make it even harder to vote. I mean, right, in theory, right, it shouldn’t be a big deal. But, it’s asking more of people at a time when we already make voting fairly difficult in this country.
Cheryl: And asking for a reading test, in the past, that was directly used to discriminate against African-Americans.
The entire purpose of that — just to be clear — the entire purpose of that law is to discriminate against a group of people who had been prevented by law from learning to read. It’s not that they weren’t interested or engaged in the politics of the day, they couldn’t read. And that’s still true. Sadly, there are people who fall between the cracks here of our system, who may have learning disabilities, like Tom Cruise.
Panpan: I want to get a little bit back to your role as a black leader, a leader in general in the tech community. Do you take on that role of being a “black leader” in the tech community?
It’s not like I roll in a room and people are like, “Oh, just another white guy.”
That’s never going to happen, right? I’m always going to stand out, and I’m always going to — at least for now, until we successfully bring more diversity to the tech space, I’m going to stand out at a networking thing or at a tech conference.
I embrace being a black leader in tech. I love what I do. I hope that people look at me and see me and say, “Well, if Cheryl can do it, I can do it too.”
You don’t have to look a certain way, or be a certain way. You can just be you and be smart and be willing to work hard and be creative and resourceful and innovative. It doesn’t matter what you look like, where you come from in technology, to a certain extent. That’s one of the things I like about what I do.
Panpan: This gets a little bit at diversity in tech. Are there other examples or other industries, either at the macro-industry level or the micro-organizational level that have done a really good job of increasing diversity?
Cheryl: Most orchestras, say 20 years ago, were all male. They had to bring in females.
Part of how they did it was having people audition behind screens so you couldn’t see the gender and color of that person; you could just hear the music, right?
It was just a way to screen for implicit bias. When you hear people talk about diversity in tech, people often take the moralizing, ethical approach to it, which, sure, okay, but it’s ultimately about the future of our economy. Don’t do it because you think it’s a “good” thing to do that’s going to make you feel good. Do it because this is the future of how people are going to work.
Panpan: Henry Ford didn’t pay people five dollars a day to work in his factories because he was a good humanitarian. He did so because then his people could buy Model-Ts.
Cheryl: Right. He understood the role that he was playing in the economy. The President’s promise that he’s going to bring back certain types of jobs…that’s just not going to happen. Anyone who understands how economic forces are shaping our globe today, certain types of jobs just aren’t coming back. But, there are hundreds of thousands, millions of jobs that are going unfilled, because people aren’t transitioning, or they don’t realize that they’re there. That’s what I want to see, i.e., the conversation shift in terms of diversity in tech. Obviously, the moral and the ethical parts are important, but there’s a whole business bottom line that people aren’t really paying attention to.
Panpan: Last question: how would you like to be remembered?
Cheryl: Oh boy. Are you asking me to write my epitaph?
Panpan: I’m asking you to write the summary in your son’s history books.
Cheryl: You know, Van Jones is a friend of mine, and he actually once said something — it was an offhand comment at a party — but it really struck me. He said,
“Wherever there is a struggle for social justice, Cheryl is there.”
And I hope that’s what people say about me. I endeavor to make a difference.
Follow Cheryl and her work @ch3ryl