A software CEO reveals how she used the lessons of the pandemic to create a more diverse and inclusive workplace

Panel at Insider's Future of Work virtual event, June 29, 2021, featuring Insider's Rebecca Knight and Jessie Woolley-Wilson, CEO of educational-software firm DreamBox
Insider’s Rebecca Knight (l) interviews Jessie Woolley-Wilson, CEO of educational-software firm, DreamBox

  • DreamBox CEO Jessie Woolley-Wilson says diversity should be leveraged for success.
  • Employers must understand what workers want and need, as they now have the upper hand.
  • This was part of Insider’s event “What’s next: CEOs on How Talent Drives Transformation,” presented by ProEdge, a PwC Product, on June 29.
  • Click here to watch a recording of the full event.

There’s a wealth of evidence that suggests diverse, equal, and inclusive workplaces are more successful – but the pandemic and death of George Floyd forced leaders to truly reckon with this reality.

“Instead of focusing on how to manage diversity, we need to pivot to focus on how to leverage diversity,” Jessie Woolley-Wilson, CEO of educational-software firm DreamBox, said during Insider’s recent virtual event “What’s next: CEOs on How Talent Drives Transformation” presented by ProEdge from PwC, which took place June 29. “If you really believe that diversity is something to be leveraged and it doesn’t feel like just another project or another obligation, it feels like an opportunity.”

The conversation, titled “Diversity and innovation define the future of work,” was between Woolley-Wilson and Rebecca Knight, senior correspondent for careers and the workplace at Insider.

“Starting out as a woman of color in financial services, the expectations for excellence were either really high or really low,” Woolley-Wilson said. “We believe at DreamBox that diversity is required in order to build empathetic and relevant learning experiences.”

At the height of the pandemic, Woolley-Wilson said she took the unusual step of making the DreamBox digital platform free to help families, students, and teachers combat the equity gaps in education exacerbated by COVID-19.

Internally, she also oriented DreamBox to be guided by three simple principles: take care of each other, take care of our customers, and then by definition, we’ll be taking care of the company.

“We’re at an inflection point,” she said, referring to low unemployment and the changing job market. “The pendulum is swinging, and the leverage is swinging more in the employee camp.”

Woolley-Wilson said the last year highlighted that workplaces need to be more adaptive to the needs of women and racial minorities. Some women might need to work from home more, while others might not have a home environment that’s conducive to work and need to spend more time in the office.

“It’s about being intelligently adaptive, it’s about metabolizing new data, new stimuli from the environment, and meeting people where they are – just like we do with the platform and every individual learner,” she said.

DreamBox also hosts a monthly meeting – the most well-attended meeting company-wide, Woolley-Wilson said – to talk about diversity, equity, inclusion, and justice.

“We talked about hard topics like racial bias or white privilege, we talk about things that happen in the current news cycle,” she said. “All those are dealt with in a very open and authentic way.”

She added that MBA programs of the future are going to have to teach leaders how to create “positive gravity” so the best talent chooses them.

“We’re going to have to make sure that organizations are overt and explicit about what they value, because employees now – from the first day of the interview to the first day of onboarding to their first anniversary and beyond – are unapologetic and very courageous and very intentional about what they want and what they need in their professional environment,” she said.

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I helped mint a trio of NFTs with a team of female and BIPOC digital artists. Here’s how NFTs can help more creators earn money with their artwork.

Jenny Wang
Re-inc cofounder Jenny Wang.

  • Jenny Wang is an investor at Neo and cofounder of re-inc, a streetwear apparel company.
  • In April, she helped mint a trio of NFTs for three US Women’s soccer team players and World Cup champions.
  • Wang hopes NFTs will inspire more creators to make and directly profit from their own artwork.
  • See more stories on Insider’s business page.

This past month, I helped mint a trio of Non Fungible Tokens for three of the US Women’s soccer team players and World Cup Champions – the first NFTs to be released by elite female Olympic athletes.

It was an artistic experiment. We did it quickly – wanting to get the set of NFTs out there early to show anyone who has felt left out of the new world of crypto that they are included. We hope that they inspire more underrepresented communities to get into the NFT world as investors or creators.

Tobin Heath
A still capture of Tobin Heath’s rotating NFT card.

The NFT world is ablaze.

An abbreviation that few knew a few months ago is now part of the everyday vernacular. From Beeple’s $69M sale at Christie’s, to the SNL skit on NFTs, to Pizza Hut launching a pizza NFT, to Elon Musk tweeting about it day and night – NFTs are being minted, sold, swapped, and collected.

Celebrities have quickly embraced NFTs with open arms.

From Calvin Harris, Snoop Dogg, and LeBron James, amoung these success stories one trend stood out: The early NFT beneficiaries are all very talented creators, but lack demographic diversity.

Just like in any emerging market, the first adopters become the thought leaders, successful investors, iconic CEOs. With Bitcoin and Ethereum at all time highs, the cryptocurrency bull market hasn’t yet largely benefited underrepresented or underbanked communities, including those who haven’t had sufficient access to mainstream financial services.

Each of the three NFTs, which were drawn by US Women’s National Soccer Team player Tobin Heath and brought to life by a team of female and BIPOC digital artists, are unique in that they are one-of-one cards featuring a pixelated visual of each player and their authentic signatures. The winning bidders will receive personalized cameo videos from the player, as well as signed merchandise. These NFTs are also differentiated in that they include a donation to a nonprofit, in this case to Black Girls Code, and a promise to buy carbon offsets.

Alluding to her team’s ongoing legal battle for equal pay, Tobin told me that for “our entire careers, established organizations have been using our image and likenesses for their benefit, and without valuing it fairly – which is why we have to fight for equal pay. With NFTs, we can directly profit from our own work.” Both of us felt like it was time for more diverse creators to get their foot in the NFT door, and benefit directly from their work.

As a new form of digital art, NFTs are compelling because they empower creators directly.

Jenny Wang/Re-inc nfts
The NFT trio for the US Women’s Soccer Team players and World Cup Champions.

They do this by democratizing access to the art and entertainment industries, which historically have many walled gardens and gatekeepers, and by allowing creators to directly profit off their work in perpetuity. By adding unlockable content, NFT artists can also deepen the relationship with the eventual owner by including physical merchandise or tickets to a live experience – and even hidden premium surprises for those who collect more than one NFT from a collection. Just like buying a share of $BYND is like investing in sustainable meat, buying an NFT is like investing in a piece of culture.

After the launch, I received messages from two close friends who are also well-known creators: the first, a principal ballet dancer at the top of her field and curator of a popular dance account on TikTok, and the other, an entrepreneurial Supermodel with a blossoming YouTube channel and food brand. Both asked how they could also monetize their likenesses as NFTs, but were hesitant because they hadn’t seen anyone who looked or acted like them participate in the crypto world.

I hope these NFTs can be a success story and inspire more women to mint art, start a business, or create content.

Tobin Heath designing the card, brought to life by female and BIPOC digital artists. Jenny Wang
Tobin Heath designing the card, brought to life by female and BIPOC digital artists.

I think a lot about inclusion, from who can enter the art world, to who gets to play in financial markets. I believe that everyone has a talent to offer, can create things of value, and can build a community around them that shares their vision for the change they want to see.

If an NFT sale is able to empower an emerging singer-songwriter to be able to own their masters rights and sell copies of their work independently, without needing the connections or upfront capital to have a seat at a talent agency, then why not enable that? No asset is perfect – any industry has asymmetric power distribution and unintended side effects, including the inconclusive environmental impacts of cryptocurrency. But the beauty of the creator economy is in enabling this access, discovering new talent, and direct creator-fan relationships.

Meghan Klingenberg and Jenny Wang hosted a Clubhouse room on NFTs and startups. Jenny Wang
Meghan Klingenberg and Jenny Wang hosted a Clubhouse room on NFTs and startups.

After a two-week auction, both Tobin’s and Meghan Klingenberg’s NFTs sold in the thousands, and I was excited to celebrate these small wins. These winning bids are an order of magnitude away from the Beeple’s, Jack Dorsey‘s, or Gronk’s of the world, but a step towards increasing the overall franchise value of women’s sports teams and underrepresented communities. And if they are ever resold, I’m happy that the players will be able to receive an eternal commission on every resale.

Just like Robinhood allowed a new wave of consumers to be able to participate more easily in the stock market, participation in the creator economy, whether through NFTs, personal digital tokens, live tips, or other financial products to come, can empower each of us to use our dollars to vote on the talented artists and changemakers we believe in, and be included in their success.

As Megan Rapinoe would say, isn’t that what equity, progress, creativity and art is all about?

Jenny Wang is an investor at Neo and cofounder of re-inc. She is a Harvard computer science alum based in San Francisco. Follow her on Twitter.

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3 Black queer journalists share their advice for breaking into the journalism industry and what publications should do better to recruit minority employees

Daric L Cottingham interview
(L-R) Tre’vell Anderson, Cerise Castle, Femi Redwood.

  • Regardless of any sudden DEI efforts made in 2020, journalist Daric L. Cottingham says the media industry has a long way to go to promote diversity. 
  • Cottingham interviewed three Black LGBTQ journalists on lessons they’ve learned breaking into the media industry.
  • The group also shared their thoughts on how publications can better recruit and retain Black queer journalists.
  • Visit the Business section of Insider for more stories.

As the spike of police brutality targeted at Black people became a constant headline in 2020, the world began to listen to concerns of structural racism and bias, especially in professional settings. 

Daric Cottingham Headshot 2021
Daric L. Cottingham.

Many industries started to examine their racist pasts. Journalism in particular began to reckon with the lack of diversity in newsrooms, and the racist rhetoric it used in coverage of diverse communities.

These “reckonings” felt like an empty PR attempt, since the same behaviors are still present at many publications in 2021 

Despite these “attempts,” we’re left with a lingering question of how can journalism actively change to be as diverse as the communities it reports on. One way is to hire diverse candidates with intersecting identities, such as Black queer journalists who navigate the industry with the added stress of implicit bias rooted in racism and queerphobia.  

I spoke with three Black queer journalists about the lessons they’ve learned navigating the journalism job market.

Cerise Castle .JPG
Cerise Castle.

Cerise Castle (she/her) is a Black lesbian multimedia journalist who’s produced and hosted segments for VICE News Tonight, Los Angeles NPR affiliate KCRW, and Wondery. 

Tre'vell Anderson headshot 2021.JPG
Tre’vell Anderson.

Tre’vell Anderson (they/them) is a Black queer, non-binary person of trans experience, the president of the National Association of Black Journalists of Los Angeles, co-chair of NABJ’s LGBTQ Task Force, and editor-at-large at Xtra Magazine.

Femi Redwood headsshot 2021
Femi Redwood.

Femi Redwood (she/her) is a Black lesbian TV news anchor who most recently reported for VICE News on intersectional issues including race, gender, and LGBTQ identities. She’s a board member of NLGJA: The Association of LGBTQ Journalists and a co-chair NABJ’s LGBTQ Task Force.

Here’s what they had to say, including advice they have for young Black queer journalists trying to break into the industry and advice for publications to better recruit and retain these diverse journalists. 

What was one lesson you learned as a Black, queer journalist? 

Cerise Castle: The hardest lesson I think is the fastest one you learn: that your voice and ideas will probably always be counted last. I think that’s a valuable lesson because I think it’s helpful to go in knowing the reality of most newsrooms and how most outlets work. Unfortunately, I think it’s a reality that you have to accept most of the time.

Tre’vell Anderson: A lesson that I’ve learned as a Black, queer journalist is that, just because my editor doesn’t understand the importance of a particular story, doesn’t mean that story shouldn’t be told. As Black, queer, trans folks, as folks from a marginalized, less represented community in newsrooms, often the stories that we want to tell about our communities don’t hold that same weight. Or don’t seem as necessary or worthy to our editors, who are white folk more often than not.

Femi Redwood: Pay attention to the media group because it may have more control in how the station or the publication handles things than the individual entity you will work for. If it’s a problematic station group, you don’t want to work there.

What advice do you have for young Black, queer journalists trying to break into the industry?

Castle: I would say not to change yourself for the industry. I had a college professor who told me that to be on camera, I had to have shoulder-length hair and couldn’t wear it naturally. I couldn’t have piercings or do my makeup a certain way. And all of that, just … It isn’t true. 

Granted, there will be some news directors that will force you into that box, but you can always be yourself. The first on-camera job that I got picked me because they liked my curly hair and liked that I bleached it. They liked that I had facial piercings. They liked that I didn’t look just like every other reporter from central casting. Playing into your identity can help you out in many situations, to get that job, and to get the story too.

Anderson: My advice to Black queer journalists, emerging and coming into the industry and those that are fairly established, is to remain undaunted as we navigate these spaces. Follow your heart, follow your gut, follow your intense desire to tell your community’s stories, even when the broader media ecosystem, or your editor, or whomever tells you that those stories don’t have any worth. 

It’s important to build an identity outside of the news organizations that we might work for and beyond the work we do because being a journalist is a thankless job in many ways. Still, it’s a very necessary job at the same time.

Redwood: My one piece of advice to queer Black journalists is to go into every situation as if you were a straight white man. It’s been my recent guiding principle. 

Often we are told we need to accept anything, accept any pay, and accept any position. We are told that unless we check off certain boxes – years of experience, education, awards, etc. – we don’t deserve more. Nah. 

Be like straight white men. They are socialized to expect what they believe they deserve. Young queer Black journos need to do that as well. We often see straight white men “fail up” while we tell ourselves, ‘we aren’t ready for a new position, we don’t deserve a raise, or haven’t earned a promotion.’ 

You deserve that job even if you only worked on your college paper; you deserve that pay even if you didn’t go to what’s considered a top j-school, you deserve that promotion even if you haven’t earned any awards, because why not you.

What can publications do to better recruit and retain Black, queer journalists?

Castle: Pay them. That’s all, that’s my answer. Pay them what they’re worth, more than they’re worth.

Anderson: What these people need to do to recruit more Black queer journalists is the same thing they need to do to recruit more Black journalists, right? They have to get out of their own way and get out of our way. 

Many folks hiring and recruiting reporters aren’t doing intentional outreach to groups of color, to 1) Let us know the available opportunities, and 2) Give us the same kind of level playing field that our white counterparts have. 

It also requires you to not only augment and change your recruiting habits, but you also need to change your retention practices because once you hire a Black person, you need to make sure that the work environment is one they will want to stay at your company. 

That might mean that some people on the team need to leave because they’re toxic, or they’re white supremacists, or they’re racist, or they’re homophobic, or transphobic.

Redwood: It’s all a big circle. And all of these things work hand in hand. To recruit Black queer journalists, you have to create a place they want to work. Because if the environment is homophobic or full of racist microaggressions, then Black folks aren’t going to want to work there. 

The next thing is to create paid internships. Expecting journalists to work for free, it’s a form of gatekeeping that unfortunately prevents many Black and brown and queer journalists from getting in. Because statistically speaking, we don’t have the same wealth as white counterparts.

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There’s a key different between ‘equity’ and ‘equality’ – and you need to understand it to help dismantle systemic racism in America

joe biden executive orders
President Joe Biden prepares to sign a series of executive orders at the Resolute Desk in the Oval Office, including multiple on racial equity.

  • Many corporate and government leaders, including President Biden, are talking about racial equity right now.
  • Equity is different from equality. 
  • Equality treats everyone the same regardless of need, while equity achieves fairness by treating people differently dependent on need. 
  • Visit Insider’s homepage for more stories.

Over the past few months, you’ve probably heard the term “racial equity” either in conversation with friends, in a company memo, or in the news. 

JP Morgan, Walmart, Mastercard, and CitiGroup are just a few examples of dozens of companies that have specifically dedicated millions of dollars (or more) to advance racial equity in the wake of the killing of George Floyd. 

In our nation’s capital, President Joe Biden recently signed a number of executive orders to advance racial equity: enacting policies that promote diversity, equity, and inclusion training, ending the Department of Justice’s use of private prisons, and directing the federal government to redress historical racism in federal housing policies, among other measures. 

But what does “equity” really mean? And how is different from “equality”? Well, there’s actually a key difference and it’s important to know.

Read more: An anti-racist’s dictionary: 19 words on race, gender, and diversity you should know

Equality vs. equity

Social Change UK, a social research and campaign company, explained the difference succinctly in a blog post. 

“Although both promote fairness, equality achieves this through treating everyone the same regardless of need, while equity achieves this through treating people differently dependent on need,” their website reads. “This different treatment may be the key to reaching equality.” 

Still, that might be hard to grasp. 

Rosalind Chow, associate professor of organizational behavior and theory at Carnegie Mellon University’s Tepper School of Business, shared a helpful metaphor of two people competing in a track race. 

Both runners are at their starting points, but one is more than half a lap behind the other.  

Equality, she explained, would mean giving both runners the same starting time, treating them equally. But that would not be fair, since one runner is significantly ahead of the other. The playing field, to mix metaphors, is not level. 

“Equity, in this context, would require giving a bit more of a head start to the runner starting from behind to make up for their deficit, so that they can compete on equal footing as the runner who had been ahead,” Chow told Insider. 

Of course, achieving racial equity is not as simple as giving marginalized and oppressed communities more resources. 

In a blog post on Medium, Richard Leong, DEI consultant and leadership coach, wrote that there’s more work to be done. 

“Driving equity and justice isn’t about tinkering with systems that just ended up being imbalanced, it’s about dismantling oppressive systems that are working exactly as they were designed,” he wrote.

For example, Biden’s executive order on federal housing directs leaders to not only advance the inclusion of Black and brown people in federal housing policies, but work to fix decades of racist policies in housing

The order recognizes the historic, systemic problem. Federal, state, and local governments implemented discriminatory policies that contributed to segregated neighborhoods and prevented many Black, Latino, Asian American, Pacific Islander, and Native American families from building wealth. It then calls for action to end discrimination, work with those who have experienced housing discrimination, and promote diverse and inclusive communities. 

“Systemic racism that has plagued our nation for far, far too long,” Biden said, while signing his executive orders advancing racial equity.

“We’re going to continue to make progress to eliminate systemic racism, and every branch of the White House and the federal government is going to be part of that effort,” he added. 

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