In recent years, the Midwest has been a hot spot for emerging tech and software companies. The regions affordability, abundance of Venture Capital and investment opportunities, and access to global resources has turned the Midwest into a catalyst for tech entrepreneurs– something that was only exclusive to big cities like New York and San Francisco. This is why Endeavor Louisville is proud to work among some of the most impactful software and infotech companies in the region, many of which are creating software that is working to revolutionize industries and improve the way we work. As the software industry continues to grow in our great state and region, we are excited to continue to support them. Here are a few of their stories.

midwest tech companies | Endeavor Louisville

Schedule It

Schedule It is a company based in Elizabethtown, Kentucky that is revolutionizing the way adjusting firms and insurance carriers handle routing, calendars, income, and expenses. Co-founded by CEO Rebecca Wheeling, Schedule It was launched in 2013 as a solution to create better workflows for insurance adjusters to improve customer satisfaction and alleviate clients more efficiently after disasters. Schedule It’s intuitive software schedule appointments, creates fuel and time efficient routes for adjusters, and organizes claim data for better metric reporting. Since its launch, Rebecca has worked as the secretary/treasurer for the National Association of Catastrophe Adjusters in addition to overseeing the day-to-day activity of the company. Rebecca was also recently recognized as an emerging entrepreneur by the Kentucky Entrepreneur Hall of Fame.

Schedule It Logo


Cladwell Founder, Blake Smith, is bridging the gap between Cincinnati’s tech and fashion community. After noticing that millennials specifically are buying less clothing but of better quality, he sought out to create a styling app to cater to that buying trend. By taking inventory of the clothes in your closet, Cladwell is able to pare down your closet and provide users with daily outfit recommendations. Cladwell takes into consideration the weather, and how many times a user has worn an article of clothing when making its clothing recommendations. Since 2013 the app has seen wild success. In its first year, Cladwell saw 200,000 accounts created- roughly $4,000 a month in revenue. Today, they’ve closed five successful seed rounds and have raised upwards of $2.8 million.

Cladwell logo


As any entrepreneur knows, building a strategy, let alone an entire company is no easy feat. Between creating an operation business strategy to training and HR procedures, managing all the moving parts of creating a company can be overwhelming without the right tools. The founders of Lessonly created a modern team-leading software that helps companies translate the important knowledge to help teams practice and perform at the highest level. The Indianapolis-based tech company helps HR and Sales teams all over the world learn the ins and outs of support ticket handling, online chat practice, and email composition so that industry best practices are achieved efficiently. In 2017, Lessonly successfully raised $8 million in Series B funding, led by investors including Indianapolis-based High Alpha Capital and edtech VC firm Rethink Education. Today, Lessonly currently works with 400 companies and has over 900,000 learners.


Abre, a Cincinnati software company, is streamlining communication and management between students, teachers, and parents. The education software platform, founded by Chris Rose, Damon Ragusa, and Zach Vander Veen in 2017, was developed to put an end to outdated and inefficient software for schools. Abre is an open source code software that integrates with the Google App ecosystem so schools, students, and staff can build more efficient learning views. In addition to its open source features, Abre offers fully managed solutions that provide SIS Integration, Cloud Hosting, Uptime SLA, and more.



After spending a decade working as a storm-roof contractor, Demetrius Gray saw a need for a better way for homeowners to file damage claims in the event of a natural disaster. That’s why he partnered with CTO Jermaine Watson and launched WeatherCheck, a SaaS product that tracks damaged areas by natural disasters and automatically notifies property managers and homeowners to mitigate damage. After successfully raising a $5.5 million Series A round, the Kentucky tech startup has been able to expand their tracking capabilities to include extreme weather, storm surges, wildfires, and more. The 12-person team has added more than 30,000 rooftops nationwide to its database so far and primarily serve insurance agents and asset managers as their main customer. In 2018 Demetrius Gray was named Forty under 40 by Louisville Business Journal and a leader in Louisville’s entrepreneur ecosystem by the Courier Journal.

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It’s clear these entrepreneurs’ focus on growth and community impact will continue to earn Kentucky and surrounding Midwest states a place on the tech startup map for years to come. We cannot wait to support the next high-impact entrepreneurs and see what endeavors they have to offer this region.

For more on Endeavor’s Impact in the Louisville region and beyond, see our ‘Impact Report: Volume I’, or read more from our blog.