From Convict to Corporate: How Ken Oliver is Supporting the Fair Chance Hiring Movement

Ken Oliver, Vice President of Corporate Social Responsibility at HR tech company Checkr, has taken a long journey of life experiences to make it to his current role and career path.

After being released from a 24 year incarceration, nine of which were served in solitary confinement due to reading a book by former Black Panther Party member George Jackson, Ken re-entered the workforce and discovered how hard it is for justice-impacted people to do so.  So, he made it his mission to change that. I was able to speak with Mr. Oliver to learn more about his story and Beyond the Bars, an interactive escape room exhibit that debuted during the SXSW Creative Industries Expo.

We could say that this part of your life’s story started with that joyride many years ago. When going for sentencing, what did you expect, and what was your reaction when you heard life imprisonment?

I knew I had broken the law and was prepared to take accountability. That offense usually carries probation or 60 days in jail, but the 3 strikes law had just passed. I was a passenger in a stolen vehicle. The judge said a case just came down that determined whether he could give life in prison or not. He decided to offer me a 24-year plea bargain. So, I asked if I could think about it, and the judge gave me 5 minutes.

I turned it down. So the judge gave me 52 years to life. At first, it was a surreal feeling—not thinking I’d have to do that time. I still ended up serving the 24 years before being paroled. Looking back, though, I wouldn’t change it due to the new trajectory my life took.

You sued the state of California for your unjust sentencing, then later secured a $28.5 million investment from the state. How did that feel?

I filed the suit while in solitary confinement. I sued the state for that because it was unconstitutional to have me in solitary for years. I ended up being released in June 2019 and being hired as a paralegal. 2 months later, I was appointed as a speaker to advocate for people wrongfully sentenced.

After getting the idea for something like a college for justice-impacted people, I used my new connections to seek funding for it.

It was a bittersweet irony that the state that wanted me to die in prison was now giving me nearly $30 million to aid justice-impacted men and women with re-entry into the workplace. 

If you give someone off the streets a chance to earn $75,000 a year, they become model citizens.

After that victory, Checkr wanted someone who could lead their social responsibility department and wanted the candidate to have some experience with that life. So I was courted for that position and eventually accepted it.

If you give someone off the streets a chance to earn $75,000 a year, they become model citizens. Checkr is also working to help get the “ban the box” law passed, which will make it illegal to ask applicants if they have been previously incarcerated.

As far as Beyond the Bars, I think it’s a great way to keep people engaged while also being able to grasp the true level of difficulty that justice-impacted people face when trying to re-enter the workforce. How did you come up with the idea?

I’ve always been an entrepreneur at heart, though I sometimes went about that the wrong way. The re-entry simulation was started by the state, just going from table to table, using Monopoly money to try and re-establish themselves. I decided that since we’re (Checkr) a tech company, we should make it more interactive. I know that escape rooms are very popular right now. So I wanted to incorporate that too.

Beyond the Bars is a gamified experience that puts participants in the shoes of someone coming out of prison, showing them how difficult it can be to re-enter the workforce. In this app-enabled, multi-room experience, attendees will attempt to overcome the many barriers faced by formerly incarcerated people as they seek to access employment and re-enter society. Room-by-room, participants will be presented with various choices related to employment, housing, parole, and more to see if they can weather the challenges and stigma that come with being justice-impacted.