Episode Summary
One of society’s most complex problems is mass incarceration. And contrary to popular belief, incarcerated people can also be talented, motivated, and capable individuals who are ready for the opportunity for a thriving career — in technology, for example. They need support, inclusion, and a second chance.
But many tech companies don’t hire folks with prison backgrounds, and as a result, they often miss out on really good candidates.
In the new episode of Taking the Lead, Christina Brady welcomes Kate Leidy, the CEO of Strively. Christina and Kate talk about reducing prison recidivism, the similarity between tech salespeople and those in the prison system, and also the importance of making space for the previously incarcerated because they can be an incredible asset to the tech industry.
Guest Profile
- Name: Kate Leidy
- What she does: She is the CEO of Strively.
- Company: Strively
- Noteworthy: Kate has been working in technology for over 17 years and has had the opportunity to support companies from the startup stage to IPO. After volunteering at the Soledad Correctional Facility, she recognized the similarities in personality between tech salespeople and those she worked with within the prison system. Observing their drive, savvy, and focus, it became clear that making space for the previously incarcerated is an incredible asset to the tech industry. Further, preventing recidivism is imperative for the betterment of society.
Key Insights
- Everyone deserves a second chance. There are many talented people around us, but we often don't give them a chance to show it. For example, few people support folks who have been incarcerated or are in the prison system. Kate considers that a mistake. "I got an opportunity to volunteer at Soledad — which is a state prison here in California — and to go with Hartnell College to teach employment skills: how to write a resume, how to present yourself in an interview, and how to talk about your background. I had never been to prison before. I don't know anyone really who’s been to prison, and I just didn't know what to expect. I thought I was going to be walking into what you see in the movies or on TV. And I was terrified. But what happened is I walked into this room, and I just recognized a room full of talent. The guys in this class were very curious. They asked me a ton of questions. They wanted to know how much money I made and how they could get jobs in tech. And I thought, 'Oh my gosh, these guys would make great salespeople.'"
- The easiest way to get into a tech company is through the SDR role. Doing something that we've never done sounds scary. But actual activism and true advocacy can make the world a better place. Kate has done that through her program by reducing prison recidivism and training the incarcerated population for a career in tech sales. "I know from working in tech my entire life that the easiest way to get into a tech company is through the SDR role. And it has the absolute clearest paths for advancement. And it gives you this beautiful window into all the different parts of the business. So if you don't have experience, you get exposure to marketing, or events, or finance, or whatever, and then that gives you ability. Or a person who maybe hasn't had formal life training around technology, or even in school, it gives them exposure to all these different departments so they can understand what their interests may be and what they're good at. And so we chose the SDR role, and that's what we train for. So we trained for that entry-level [position]."
- It's crucial to find the right company for previously incarcerated people. When people come out of prison, they need some time to decompress and organize their life, but they've also got to make money to take care of themselves and their families. And they have a lot of transferable skills; they just need a job. According to Kate, tech companies find it difficult to accept such candidates. "Some of the larger companies — they've got a lot of bureaucracy, they've got a lot of things written into their hiring practices that are out of an overabundance of caution to be transparent. The place where we are finding the most success in getting our candidates hired is in that mid-market to startup world where there's less bureaucracy. That comes with its own challenges because their processes aren't in place, and they've got younger teams usually. And so, finding the right type of company that has a lot of internal support is important. Our candidates are paired with a mentor on day one of the program, and then that lasts through the first year of employment. So not all of our hiring partners are bearing the weight of making sure that people that are coming from diverse backgrounds are able to be successful. They're coming out of our program with a very solid support system."
Episode Highlights
Volunteering in a state prison
“The person I went in with is someone I went to high school with. She is a professor, so I had someone that I knew who talked me through it and assured me that everything was going to be okay. And as I was going through security, I met this little tiny woman. She had to be in her 70s or 80s and maybe five feet tall. She could see that I was really nervous, and she said, ‘You have nothing to worry about. I come here all the time. These guys would give their life to save me if something bad happened.’ And I just went with it.
[…] I didn’t know what to expect. And I don’t mean to say anything bad about my expectations, but I didn’t expect them to completely blow my mind. They were asking me really interesting questions, and I was so impressed with them. So the activities that I brought, we didn’t even do them. We just talked for an hour.”
Create a relationship with support organizations
“I don’t think we do any part of what Strively does on our own. Everything we do is in partnership with either people in the tech industry or support organizations. So we work with organizations like Defy Ventures, which has an entrepreneurship program that starts inside prison and then continues outside. So we have a partnership with them, and we’ve got several graduates that have come through our program and are working in tech now. So that foundation is really important. And this role is a difficult one, and it takes a certain kind of someone. So having those relationships and helping them understand what a good kind of persona is for this role — these are critical to the success of our candidates.”
The data does not support the fear that companies have when hiring
“The data shows that when candidates who are coming from a felony background or some kind of criminal history are given a chance to rebuild their life, they are the hardest working people and the most loyal. They’re not flipping around from company to company; they get their foot in the door, and then they’re hanging on and doing the best they possibly can. So that’s one side; the data just doesn’t support that it’s a risk. And then the other side is that no one has been told ‘no’ more than someone who’s been in the US prison system.”
Strively is an organization with credibility
“A lot of people are contacting us now, which is so great. The first two years have been about just building a name for ourselves and then proving that our model works. And now that we’ve proved that, we’ve got candidates who are working at Demandbase, Gong, U-NICA, and Pilot. Now we’ve got credibility. So it’s making it a lot easier to place people because the people that I’m sending to our hiring partners know what they’re getting because I’ve stress tested them. We’re making sure that we’re sending gold star candidates.”
