It’s been a big 18 months for startups and software companies in Chicago.

In 2015, local startups raised more than $1.7 billion in funding, Built In Chicago reports, and the tech industry has kept its momentum rolling through the first half of 2016.

“The city’s tech scene is breaking out as investment in local companies now routinely exceeds over a billion dollars each year, and recent billion dollar exits have come from local companies like, Grubhub and Orbitz,” local reporter Mike Ewing wrote for Thrillist at the end of April.

Against that backdrop, here are 20 software companies in Chicago we recommend keeping an eye on for the rest of 2016 and beyond. They’re all poised to do big things.


4D Healthware

4D Healthware has built a platform that lets patients manage chronic conditions online. It can collect a person’s health data from more than 200 devices, deliver that data to care management teams in real time, and use AI to identify the best ways to nudge patients toward more proactive management of their own conditions.

Built in Chicago reported in February that 4D Healthware completed a seed round worth $710,000 in funding.



AddStructure offers a trio of products that are perfect for helping customers find products on major retailers’ websites more effectively. This product suite includes

  • a plugin “to automatically improve relevance for subjective, thematic, and semantic search queries” for on-site searches;
  • a landing page builder that restructures product pages to better fit customer searches;
  • and an API that turns unstructured content such as user reviews “into structured data that is readable and actionable by both machines and humans.”

The Chicago Tribune’s Ally Marotti reported in June that the AddStructure team was one of 10 startups selected for the Techstars Retail accelerator program, which is hosted in collaboration with Target.



Another company participating in a tech accelerator program this year is Akouba, which creates software that makes it easier for local banks to offer small business loans. Akouba is a 2016 cohort of the VC FinTech Accelerator in Little Rock, Arkansas, where founders get a crash course in rapid growth and customer acquisition, reports.



Schaumburg’s benefitexpress builds software for small companies and HR departments so they can easily manage employee benefits. The Daily Herald’s Anna Marie Kukec reported in March that benefitexpress had closed a “sizable” funding round and had brought on Michael Sternklar, a veteran executive in the employee benefits space, as the company’s new CEO.



A member of the Techstars Chicago 2016 class, Bright has built an analytics platform for SaaS providers. “While I realize there’s no shortage of dashboards and BI tools in the market, there’s a gaping hole in visibility,” founder Jeff Judge writes on the company blog.

“SaaS and subscription-based companies need tools that will help them see how growth translates to revenue, and how that revenue translates to making decisions. We see an opportunity to help companies grow faster by giving them context, insights and recommendations.”

startup business people group working everyday job at modern office


Green Key Technologies

Green Key, which has built a platform that allows any financial market participants to communicate via digital voice, has already had a busy 2016. This spring alone, Green Key announced



HealthJoy announced a $3 million funding round in March to grow its platform, which connects patients, healthcare providers and other participants in the healthcare marketplace to help consumers save money on healthcare expenses.

“This investment will allow us to continue to work hard on our healthcare decision platform and advance the development of JOY, our human supported machine intelligence, that is already helping thousands of people every day,” HealthJoy CEO Justin Holland says.



Hearken is building a platform that will allow journalists and news outlets to tap directly into their readership to get real feedback on what stories readers want to see covered. It’s a novel and engaging way to tap into readers’ collective insights — but Hearken pushes back on the use of the E word in this context.

“The word ‘engagement’ to me feels like another way of saying ‘people give a shit and you can tell,'” CEO and co-founder Jennifer Brandel told TheMediaBriefing in June, a few months after the company announced it had raised $700,000 in seed funding.


Motion AI

In late June, VentureBeat’s John Brandon had a great column on why he’s bullish on chatbots. “The tech gets better the more we speak, and here we are using Siri and Alexa as a result,” he writes.

“Chatbots will someday be able to remind me about appointments, let me know that there’s a good deal on the pizza I always order, prompt me when there’s a new Bryson book, and even banter away about Brexit, possibly using correct British grammar.”

Enter Motion AI, which has built a platform that makes creating chatbots incredibly easy. Its service even has a free option that lets companies experiment with chatbot technology for support or concierge services.

Investors seem to be bullish on the technology, too, because the Tribune’s Amina Elahi reported last December that Motion AI had raised $700,000 to hire more engineers to build out its platform.



Opternative has had a busy 2016 already because of pressure from legislators.

The company, whose app lets you conduct eye exams at home with your phone, came under scrutiny from lawmakers in Georgia, who passed House Bill 775 to restrict the ability of residents to use Opternative’s technology (or any other company’s) to perform eye exams at home and get a prescription. Other states are looking to follow suit.

But Opternative has its proponents, including former House Speaker Newt Gingrich and the investors who put in $6 million for a Series A funding round in February. And all of this pushback from lobbyists and entrenched interests just serves to reveal the larger point: Opternative’s team has built a disruptive, awesome product.

downtown chicago, illinois usa



Pearachute has built a platform that will let parents and their children find classes around the city that matches their interests (and the family’s schedule). As Connie Loizos at TechCrunch reported in February, Pearachute has raised $1.2 million and has begun working with three dozen activity centers and 1,200 parents around Chicago for its launch.


Procured Health

Healthcare analytics provider Procured Health announced in June that the company had raised $10 million in a Series B round. Procured’s team says healthcare providers will waste an estimated $35 billion this year just in making poor decisions on what supplies they purchase, and getting data-driven intelligence to these providers to fix that inefficiency will be a big focus of the company’s growth.


Regroup Therapy

Regroup Therapy is another Chicago company working in the telehealth space. The company’s specific focus is on delivering mental health consultations remotely. “There’s just this really deep shortage of providers,” founder and CEO David Cohn told the Tribune’s Meg Graham in May, when Regroup announced it had closed a $1.8 million funding round.

“Fifty-five percent of counties (nationwide) don’t have any behavioral health providers in them. Not a social worker, not a psychiatrist, nothing. It’s a huge problem.”



SpringCM makes software that helps businesses manage contracts and other documents, and the company announced earlier this year it had raised $17.5 million from investors. The company says it expects to release six new products before the end of 2016.



“Most people have a general idea of how many visits their site gets every month, and some could tell me what drove traffic to their site, but almost no one could tell me exactly how well their marketing tactics did at driving customers,” Tend co-founder Ryan Evans writes on the company’s newly-launched blog.

“Having something in place to track what is working should be the foundation of any marketing effort. And, yet, so few people have this in place. Why? Well the answer is actually pretty simple: Most web analytics tools really suck.”

That’s why he and co-founder Marty Thomas built a platform that lets companies see exactly how their website visitors become customers. Tend shows who your website visitors are, where they came from, what pages they went to and if they’re paid traffic what specific ads they clicked on.

startup business people group working everyday job at modern office



Restaurant reservation management system Tock launched in 2015 as a platform for diners to book experiences at the world’s top destination restaurants — like Alinea, for example, which is owned by Tock co-founder Nick Kokonas.

Tock CTO Brian Fitzpatrick tells ChicagoInno that it already is being used by more than 80 restaurants around the world. All told, those restaurants’ bookings through Tock amounted to a half million diners and $30 million in restaurant revenues in the company’s first year.



Industry-agnostic analytics platform Uptake is growing quickly. A little more than years ago, Uptake was a team of four. At the time of writing, it has more than 40 open positions listed on its Jobs page.

Last October, Uptake announced a $45 million round of funding, and that Ray Lane, former president of Oracle, had joined the company’s board of directors. We’re excited to see what Uptake does with all of these resources.



Relocation management software company UrbanBound announced it had raised $8.5 million in a Series B round in April, and the company has its eyes on rapid growth.

“Now, with a team of over 40, we have a stronger understanding than ever before of where UrbanBound is headed and how it fits into the relocation industry,” UrbanBound’s Aria Solar writes on the company’s blog. “We know exactly what challenges we’re aiming to solve and the voids our software is continuing to fill.”



VillageMD‘s platform is designed to help primary care physicians grow their practices through analytics-driven decision-making, access to capital and automation of many administrative tasks.

Fortune mentioned VillageMD in March as part of a piece on Obamacare’s effects on healthcare startups, and reporter Ezekiel J. Emanuel noted the company had shown it has been able to raise primary care physicians’ salaries, which gives those physicians the freedom to move into communities where quality care had previously been harder to access.


We Are Mammoth

We Are Mammoth celebrated a decade in business earlier this year, and what’s notable about that milestone is how the company built slowly toward that occasion with sustainable, deliberate growth.

Over the last decade, the We Are Mammoth team has built two companies — Kin and DoneDone — and the company’s recent projects have included an app for workers’ compensation company AF Group and customer service software for HR tech company Little Bird.

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Eric Barrier