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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The US ranks below average on women’s equality in the workplace, The Economist found

business woman looking at phone in office
  • The US ranked 18th out of 29 countries in an assessment of the best and worst countries for working women.
  • Women in the US have less parental leave and political representation than other countries.
  • The pandemic has had a significant impact on female representation in the workforce.
  • Visit the Business section of Insider for more stories.

The US ranked 18th out of 29 countries in a yearly analysis by The Economist on the best and worst countries for working women.

The US lagged behind many other countries when it came to parental leave and political representation for women, according to the report. 

During the pandemic, US women have been disproportionately impacted by the economic downturn.

US women have lost 5.3 million jobs since the pandemic started. In 2020, a report from the International Labour Organization found women had seen the greatest employment losses during the pandemic, as remote school work and work-from-home put extra pressure on women who often had to give up job opportunities to take care of their families.

The Economist’s Glass Ceiling Index is a yearly assessment of countries where women have the best and worst chances of equal treatment in the workplace. The report analyzes a group of affluent countries that make up the Organization for Economic Co-operation and Development (OECD).

The analysis takes into account several indicators: higher education, labor-force participation, pay, child-care costs, maternity and paternity rights, business-school applications and representation in senior jobs.

The report found that over the past year the US has seen some improvement in female representation in management positions, moving the country up four spots from the previous year. 

In September, Citigroup named Wall Street’s first female CEO, Jane Fraser. Several other women, including Rosalind Brewer, who became the first black woman ever to run a Fortune 500 company, and Carol Tomé, who was named CEO of the UPS, also increased representation for women in the C-suite.

Across the OECD, women account for about than one-third of leadership roles, according to The Economist. The analysis also found progress to the top of companies is slow for women in most OECD countries.

The report ranked Scandinavia as the top country for working women, while South Korea and Japan ranked last.

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