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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Richard Branson is leading a campaign to end the death penalty, along with other key business figures. The Virgin Group founder said there is an urgent need to abolish the practice.

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Virgin Group founder, Sir Richard Branson, is spearheading the campaign.

  • Sir Richard Branson spoke to Insider about his ongoing campaign to eradicate capital punishment.
  • The Virgin Group founder called the practice “barbaric” and “inhumane.”
  • He has teamed up with several other business leaders to help spread the message.
  • See more stories on Insider’s business page.

Virgin Group founder Sir Richard Branson has joined forces with other business leaders to launch a campaign to abolish capital punishment in the US and other countries.

The 70-year-old billionaire announced the Business Leaders Against the Death Penalty Declaration in a virtual SXSW event in Austin, Texas, last month.

The declaration was coordinated by the UK-based organization, Responsible Business Initiative for Justice, and has gained 21 signatories. They include Ben Cohen and Jerry Greenfield, co-founders of Ben & Jerry Ice cream, Arianna Huffington, co-founder of The Huffington Post, Helene Gayle, a director at the Coca-Cola Company, and telecom tycoon, Dr. Mo Ibrahim.

The push to end the death penalty comes amid a global focus on racial and economic justice, exemplified by the Black Lives Matter protests last summer.

In an interview with Insider, Branson described the death penalty as “barbaric” and “inhumane.” He explained his involvement in several cases throughout the years where innocent people were sent to death row, in the US and elsewhere. This led him to realize capital punishment is arbitrary and flawed, he said.

Branson gave an example of a case he took up, which involved Anthony Ray Hinton, a man who spent 28 years on Alabama’s death row before being exonerated in 2015. “He was framed for a double murder he didn’t commit, only because the police and prosecutors needed a Black man to convict,” Branson said.

For every eight people executed in the US, one person is freed from death row – often after decades, as was the case with Hinton, Branson added.

This case, among others, highlighted another problem for Branson – that the death penalty is also a symbol of oppression, as well as racial and social inequality.

“Look at people on death row. In most US cases, it’s people of colour and the poor that are sent to death row,” he said. “Some in the US have called it a ‘direct descendant of lynching’, and I’d say there is much evidence of that. In some countries, it’s become a tool of political control and oppression,” Branson said.

Branson believes it is even more crucial to end capital punishment, given it is a wasteful and ineffective misallocation of public funds. Now more than ever, governments must be responsible with public finances given the hard hit on countries’ economies due to the pandemic, he said. “Public funding could be spent on schools, healthcare, infrastructure instead,” he added.

The involvement of so many notable business leaders in the campaign demonstrates an increasing willingness to speak up on issues of inequality, the danger of executing innocent people, and the need for fiscal responsibility.

“We have to ask ourselves: does the death penalty serve a real purpose for us as caring human beings?” Gayle said in a statement. She noted how it felt even more urgent to focus attention on preventable deaths in the wake of the COVID-19 pandemic, and its terrible loss of life.

Cohen and Greenfield wanted to ensure they played their part, too. They told Insider: “We have some of the world’s loudest voices – and we have a responsibility to use them to fight injustice wherever we see it.”

Businesses need to do more than just say Black Lives Matter, they added: “We need to walk our talk and help tear down symbols of structural racism.”

Jason Flom, chief executive of multimedia company Lava Media, is also involved with the campaign. When asked about the main objectives he hoped to achieve, he told Insider: “Goals include changing hearts and minds in the general public, as well as educating the next generation of prosecutors, judges, defense attorneys, and prospective jurors.”

There are 56 countries that still retain death-penalty laws as of 2019, according to Amnesty International. Since 2013, 33 countries have carried out at least one execution, the BBC reported. More than 170 UN member states, out of 194, have abolished capital punishment in law or declared a moratorium.

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In a rare show of solidarity, Republicans and Democrats are working together to pass sweeping criminal justice reform in Michigan as the state’s jail population grows

Michigan's Electors Meet
Michigan Lt. Gov. Garlin Gilchrist opens a session at the state Capitol

  • Michigan lawmakers will have advanced more than two dozen criminal justice reform bills when they close the current session this week.
  • Governor Whitmer created a bipartisan commission in 2019 to look at jails across the state to better understand the problem. Much of the reform effort is modeled on its recommendations.
  • The overhaul aim to reduce the state’s jail population, which has tripled over the past 3 decades even as crime rates have fallen to a 50-year low. 
  • Supporters spanned grassroots racial justice organizations to Amway co-chairman Doug DeVos, the brother-in-law of education secretary Betsy DeVos and a major conservative force in Michigan.
  • Visit Business Insider’s homepage for more stories.

For years, Michigan courts have been taking away peoples’ drivers licenses for reasons that have nothing to do with their behavior behind the wheel.

Instead, suspending the right to drive has been used as a cudgel to get people to pay traffic tickets, court fines, or child support. But because people need to work in order to afford to pay these fees, thousands thousands of them have been driving on suspended licenses in order to get to work. And if they got caught, they wind up in jail. 

Today, driving on a suspended license is one of the leading reasons Michiganders wind up in jail, and the system often appears more designed to squeeze money out of the state’s poorest citizens rather than as a tool to ensure public safety. It’s part of the reason the state’s jail population has tripled over the past 30 years even as crime rates have fallen to a 50-year low.

No one knew how seriously out of whack the jail system had become until earlier this year, when a first-of-its-kind commission took a look at who was going to jail and why. And now, when Michigan has become emblematic of just how broken our political system has become – with right-wing terrorists plotting to kidnap the state’s Democratic governor and some Republicans working to overturn President-elect Joe Biden’s victory in the state – lawmakers who are often at each others’ throats are determined to make big change before they adjourn for the year. By the time the state legislature wraps up this week, it will have advanced more than two dozen criminal justice reform bills.

“Right now, America is kind of at a reckoning,” said Pastor Kevin Harris, who served 14 years in prison for drug-related offenses and is now a community organizer who chairs the board of the group Michigan Liberation. “Even the most corrupt system has to recognize that we went overboard.” 

Detroit BLM
Detroit Activists March, Nov. 7th, 2020.

This session, Michigan lawmakers have already enacted legislation that automatically wipes people’s criminal records clean of most misdemeanors – and some felonies – after several years. It is the most progressive law of its kind in the US. They’ve also passed legislation that makes it easier for those with a criminal record to get an occupational license to work as a barber, roofer, or cosmetologist. 

This week, lawmakers are scrambling to pass a package of 20 more reform bills before their session ends, including one that will stop courts from suspending people’s licenses for reasons unrelated to their driving records. That alone could lift the risk of arrest from over the heads of hundreds of thousands – more than 350,000 people had their licenses suspended because they failed to appear in court for other reasons or because they had unpaid fees or fines in 2018 alone, according to a recent audit. That’s equal to around 1 in 20 drivers in the state.

House Judiciary Chair Graham Filler, a Republican from just north of Lansing whose website describes him as “pro-law enforcement” and “not politically correct,” coordinated the effort in the House. 

Even if lawmakers “start at different places, [we] end at the same place,” Filler told Insider. “Can we have a justice system that is proportional and fair and at the same time does not impact public safety?”

NOT A “PARTISAN ISSUE”

In a month where some Republican politicians attempted to overturn Biden’s election victory in the state, criminal justice is one of the only issues where both parties have been able to work together. The coalition that has advanced criminal justice reform in Michigan spanned the progressive ACLU to the right-wing, Koch-funded Americans for Prosperity. A similar alliance of strange bedfellows was also instrumental in passing national legislation signed by President Donald Trump in 2018, which overhauled mandatory minimum sentencing laws and made other changes to the federal prison system.

“We need to reject the idea that this is a partisan issue,” Democratic Lieutenant Governor Garlin Gilchrist, who co-chaired a bipartisan commission on criminal justice reform, said in an interview. 

Michigan Lt. Gov. Garlin Gilchrist
Lt. Gov. Garlin Gilchrist with Supreme Court Chief Justice Bridget McCormack, right, April 17, 2019.

In Michigan, supporters of this legislation spanned grassroots racial justice organizations to Amway co-chairman Doug DeVos, the brother-in-law of education secretary Betsy DeVos and a major conservative force in Michigan. The politics are good for both the right and left: Progressive ss can tout the reforms package as a win for racial justice, while conservatives can say they managed to shrink the reach of government and bring savings for tax-payers. The state jails cost Michigan’s counties around half a billion dollars each year, eating up around one-quarter of their public safety budgets.

The system “is not actually promoting public safety,” Gilchrist said. “It’s just disrupting people’s lives in dangerous ways.”

Donald Talley knows this cycle first hand. Talley, a 65-year-old who lives west of Detroit in the city of Inkster, first lost his license in 1985 because he had unpaid traffic tickets and child support. He was homeless at the time, earning some money here and there as a mechanic, so he had little choice but to keep driving. 

He was arrested repeatedly over the next 20 years as his fees continued to mount. The arrests became so predictable he even figured out how to use them to his advantage: getting put away in the winter meant he could have a warm place to sleep. Then, through a chance encounter at a soup kitchen, Talley connected with pro bono attorneys who helped him get his fees set aside. By that time, Talley said, he owed well over $180,000 in child support, traffic tickets, and other fees and fines.

Getting out from under the threat of arrest turned his life around, Talley said, and he hoped this legislation would do the same for thousands of others.

“Once you get a smell of victory, you can see the light as far as your life getting better,” Talley said. 

Whitmer jail task force
Michigan Gov. Gretchen Whitmer, left, announces the creation of the bipartisan task force, April 17, 2019.

No one had really conducted a comprehensive study of who was in jail and why until February 2019, when Governor Whitmer created a bipartisan commission to look at jails across the state co-chaired by Lieutenant Governor Gilchrist and Chief Justice Bridget Mary McCormack. This week, lawmakers are working on a package of 20 bills modeled on the report recommendations, including the one that reins in drivers license suspensions. If passed, Chief Justice McCormack told Insider, “it would really make Michigan a national leader.”

The commission took aim at the state’s jails. On average, Michigan’s jails hold more than 16,000 people, usually for stays of less than one week. Jails are often described as the “front door” of the criminal justice system, since people go there to await trial or to serve short sentences. But far more people spend time in jails than go to prison – nationwide, seventeen times more people cycle through jails than prison.  Even a short stay in jail can mean lost jobs, lost custody of children, and fees that can prove hard to escape.

The commission’s work was supported by the Pew Charitable Trusts, which provided a team of technical advisors who have staffed lawmakers as they turned the panel’s recommendations into legislation.

“There are not [other] states, as far as we know, that have tried to understand statewide what’s driving jail populations and what’s contributing to jail growth. This is new and pretty exciting,” said Pew’s Terry Schuster. “With increasing partisanship, criminal justice issues remain one of the few areas where we see continued bipartisan consensus.”

A “KUMBAYA MOMENT”

It took a lot of work to get to this point, especially on the right, said Joe Haveman, a Republican from the Western Michigan city of Holland who tried to advance criminal justice reforms while serving as a state representative between 2009 and 2014. Haveman said his efforts to reform the state’s criminal justice system ran into “brick walls” from “old-school Republicans” during the administration of the Republican Governor Rick Snyder. 

But Michigan has strict term limits, sweeping in a younger crop of lawmakers who look at criminal justice reform through a more libertarian lens. And the opioid epidemic, which hit rural and white communities hard, have also changed attitudes about the role of law enforcement in Republican areas. 

“When I was growing up, I wouldn’t have known anybody who had a problem with the law – I think that was true for a lot of Americans,” Haveman said. “When the opioid epidemic exploded it became somebody we knew… It’s not just a ‘bad person’ – that stereotype that I may see on TV, somebody from a big city.”

Several lawmakers also credited the evangelical community for building support for criminal justice reform among Republicans. Judiciary Committee Chairman Filler said this was an issue of special importance to Speaker Lee Chatfield, son of an evangelical minister who was involved in a prison ministry. (Chatfield declined to be interviewed for this story.)

Lawmakers don’t plan to stop working on criminal justice reform after this session ends. The commission co-chaired by Gilchrist and McCormack made recommendations that the legislature did not act on this year, including provisions to divert people with mental illness away from jail. Lawmakers from rural areas also want to make it easier to wipe arrests for driving under the influence, a common offense outside major cities, from criminal records.

“You’ve had this left-and-right Kumbaya moment on criminal justice reform for the past couple years,” said David Guenthner with the conservative think tank the Mackinac Center for Public Policy. “The objective should be to use prison for those we are scared of, not those we are mad at. And when someone’s coming out of prison, they should have sufficient training and opportunity to earn a living and be a success.”

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