They’ve got mad skills: Chicago organization provides training for underrepresented groups

The free program focuses on preparing South and West Side residents for entry-level tech sales jobs.

Happy Friday,

More companies are paying attention to hiring individuals underrepresented in tech, but getting hired isn’t always as easy as just having relevant skills. Some people are at a disadvantage because their backgrounds preclude them from having some of the soft skills and tech industry savviness that are advantageous for landing and succeeding at a job. Chicago-based nonprofit re:work training aims to fill those gaps with specialized training for entry-level tech sales roles.

The organization’s primary mission is to improve employment outcomes for Chicago’s underrepresented communities with its free, eight-week training and job placement program. re:work especially aims to serve individuals from the South and West Sides, which are predominantly black and Latinx. “We help to diversify tech and essentially make our workplaces look more like our neighborhoods,” said Ashley Jordan, re:work operations manager.

The trainers – mostly volunteers – are people currently working in tech sales. They cover skills such as designing resumes to be relevant to the sector, job interviews, dealing with business documents, and personal development. Candidates learn the latest tech sales techniques and go through mock interviews with people who already do the job. re:work then helps to place candidates in an entry-level, full-time tech sales job in Chicago that has a starting salary of $55,000 per year. Some partners include Groupon, LinkedIn, Salesforce, and DocuSign.

The program helps candidates who might not have the traditional pedigree that tech firms seek. Even introductory sales roles at big companies typically have requirements of three to five years’ previous work experience and a four-year college degree, Jordan said.

“I think it’s starting to become common knowledge that those requirements aren’t really necessary and might even be hurting the bottom line,” she said. “A lot of the people who don’t have previous experience or educational experience didn’t have opportunities because of where they come from or what they look like.”

re:work makes an effort not to admit people to the program who don’t truly need help or who are simply looking for an easy reference. It also does not accept candidates who would not be ready to start working in eight weeks.

Another unique aspect is that it tends to attract participants who skew older than many entry-level job training programs. Reasons include changing career directions, taking care of family members, or simply being a so-called “late bloomer.” A lot of candidates are in their late-20s or early-30s. “There are already so many programs and organizations out there for youth development,” Jordan said. “Something I didn’t think about before joining re:work was the service gap with people who are a little older.”

re:work launched in 2016 and has a 72% placement rate, which it hopes to increase as it continues to scale up. The first cohorts had just a handful of people but have grown to more than a dozen candidates each. The three-person team relies heavily on volunteer help, and it aims to expand its footprint to serve more candidates.

“We have more demand than we can keep up with, which is a good and bad thing. We’re happy that our name is out there and people see the value we provide. But we wish we could help everyone,” Jordan said.

(re:work CEO Shelton Banks, center, with cohort 16)

re:work just completed its 17th cohort, which transitioned to an online instead of in-person format because of stay-at-home requirements during the pandemic. It is in the process of creating a more robust online learning environment to accommodate for the circumstances. It added weekly webinars, and into May it will run weekly online trainings. re:work saw the need to expand services to alumni as well because of current job market conditions, and therefore it will offer online continuing education opportunities.

“Our community was hit hard by the economic downturn, and we want to make sure we are supporting those who lost jobs and income, as well as prepare those who are entering/re-entering what will be an oversaturated and competitive job market,” Jordan said.

Being based in Chicago is a fit not only because of the city’s demographics, but also because the kind of tech work that takes place there, Jordan said. Whereas the West Coast has a reputation for being a large engineering hub, tech sales has a prominent presence in Chicago. Most of the candidates remain in the region once they get a job.

“The fact that most of the time they stay in Chicago – and stay in the neighborhoods they grew up in – is really important for our overall impact,” Jordan said. re:work calculates its social return on investment for entire communities, not just for program candidates. In 2019, for every dollar invested in re:work, $3.05 was invested back into the communities because the candidates can invest in and boost their families – such as through health insurance coverage. Improved family situations in turn raise up neighborhood outcomes.

“There aren’t a lot of pipelines for qualified, diverse talent… Our mission is to have companies start to rethink the way they hire,” Jordan said.

What organizations in your communities are helping to level the playing field for tech job seekers from underrepresented groups? Let me know so I can highlight them in a future newsletter. Email or connect on Twitter @centereddottech to share ideas.

Other stories we’re watching:

  • St. Louis Metro Transit employees designed, fabricated, and installed polycarbonate shields to protect bus drivers from exposure to the coronavirus during the pandemic. The team is now working to make the shields for transit partners at Madison County Transit in Illinois and MTA in Nashville, Tennessee. (Mass Transit)
  • Milwaukee-based consortium Mask Force — consisting of more than 50 local manufacturers, healthcare providers, first responders, and educational institutions — has designed, developed, and produced an FDA-authorized reusable N95 face mask. The initial production of 30,000 masks is now underway in Waukesha, Wisconsin. (BizTimes)
  • Chicago-based nonprofit charity Creating IT Futures is launching the CompTIA Tech Career Academy to offer an expanded program to prepare adults for their first IT jobs. All of the training classes will be online indefinitely during the pandemic. (

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