Rise of the machines: 5 Chicago startups breaking new ground with chatbots

by Michael Hines
October 6, 2017

Chatbots are quickly becoming a valuable business tool, helping companies reduce the time spent fielding routine inquiries and collecting valuable user data from the conversations they have.

Chicago’s B2B startup culture and status as a leader in artificial intelligence make it an ideal place to launch and grow a chatbot company. Here are a few of the startups helping establish the Windy City as an emerging leader in the field.



Trying to navigate a health plan can be confusing at best and soul-crushing at worst. HealthJoy knows this, which is why it built a chatbot-powered mobile app to help employees better understand their coverage. Joy can access benefit information, schedule appointments and provide information on wellness programs. Joy also works to keep costs down, whether that’s through helping users negotiate medical bills or by finding coupons for medications.




In hiring, building a relationship with a candidate is as important as verifying their background. Hire Abby’s chatbot automates both processes. Abby texts with applicants to learn about their work histories, allowing companies to engage with candidates while simultaneously vetting them. The chatbot also answers applicant questions, such as where they are in the hiring process and what company culture is like.




For personal trainers, getting clients to work out between sessions is a never-ending battle. Frequent reminders of fitness goals help, but finding time to send motivational messages is tough because trainers don’t spend a lot of time behind a desk. That’s where GOtivation comes in. Its Facebook Messenger chatbot lets trainers send user-specific motivational quotes, images and videos to keep clients inspired and active between appointments.




Truss wants to make it easier for small and medium-sized businesses to find office space. Landlords post offices for rent directly to the platform, and renters work with a chatbot named Vera to find a space that fits their needs. Vera knows the fair market value of an office and can even set up a tour to help close the deal.




NativeMSG wants to ensure companies never miss an opportunity to engage with customers. Its platform lets businesses deploy and manage chatbots across a variety of channels, including Facebook, Twitter, SMS and Amazon Alexa. NativeMSG’s chatbots field general customer service issues and inquiries. They also glean conversation data to help companies get a better idea of who their users are and what platforms to engage them on.


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