Innovating Technology: Chocolatey Software Inc.

Photos by Emma Highfill, Rose Wheat Photography

Technology Automating

A sweet technology for managing software delivery for Microsoft Windows began in Topeka and is now being used all over the world by hundreds of organizations and thousands of IT professionals. Chocolatey automates the management of third party and internal software on Windows computers and servers and is installed on machines at a rate of 70 installations per minute.

A corporate software developer, Rob Reynolds was curious about how to better automate Microsoft Windows operating systems and expedite computer configurations and deployment on a global scale. As a side project from his day job, he developed the necessary expertise to create the Chocolatey so ware code in 2011 that later became the basis for a company he launched in 2016.

The company’s name play is derived from NuGet, the packaging framework used for Windows development.

“We joked that if it also managed software and system-level tools, then those packages would not be vanilla NuGet packages, they would be chocolatey,” he said.

Reynolds made the technology available through open source networks and continues to support an open source edition.

Technology Bootstrapping

After a successful kickstarter campaign in 2014, Rob Reynolds released Chocolatey for Business (C4B) in mid-2016, then converted all assets and operations into Chocolatey Software Inc. in January 2017. The software company decided to grow organically rather than seek funding from venture capitalists.

“Bootstrapping is definitely harder but at the end of the day, we only have to serve one master and that’s our customers,” said Reynolds. “Going the traditional route allows us to concentrate on solving our customers’ needs rather than also trying to make sure we have marketable releases or ensuring a valuation looks great for VC firms.”

The community software repository, a free offering Chocolatey Software manages, contains more than 7,000
software automation packages, receives nearly 60 million daily requests (twice as many as last } year), and transfers between five to 10 terabytes of data each day.

Technology Efficiencies

Rob Reynolds earned a business management degree with an emphasis in management information systems and a minor in leadership studies from Kansas State University. He began his career at the Kansas Department of Transportation where he discovered he had an aptitude and affinity for software development. In subsequent positions with other companies, he faced the same issues at each employer and began wondering about the applicability of a global solution that could be used across industries.

Reynolds, who always had entrepreneurial aspirations, said, “I created Chocolatey because I was solving a problem for myself and making my own work life easier, but the solution I came up with resonated with a wider community of IT professionals because it allows for quicker installation and more modern, automated testing approaches to be applied to the infrastructure.”

The software, designed to improve reliability, productivity and security, has also provided users with unexpected perks beyond making their daily work more efficient and operationally sound.

“IT professionals were doing a lot of manual work that the Chocolatey software automated to make them more proficient,” said Reynolds. “People approach us at conferences or send us thank you notes saying that they got raises and better jobs because Chocolatey allowed them to go home earlier and spend time with their loved ones doing things they enjoy instead of managing deployments manually or fighting systems that were not designed for current modern automation needs.”

We decided to pursue physical office space in 2018 when we realized we were going to expand, and not everyone wants to or is well suited to work from home,” said Reynolds, who plans to bring the entire team to the capital city once or twice a year for week-long strategy, team building, and compliance training sessions.

“We see each other on screens every day, but it doesn’t quite meet the same level of interaction as being able to chat face to face over a cup of coffee,” he said.

Technology Team

Chocolatey is a team of 12 individuals, including Reynolds and co-founder Mukesh Sharma, chief operating officer, based in Kent, England, whom he met while both were employed by Puppet. Three employees work at the Topeka office, and five more are spread out across North America. Sharma and three others are based in the United Kingdom. Reynolds anticipates employing 20 or more people in 2020 as the company continues to grow, although he intends to keep total staff count under 50.

Being located in Topeka and in the center of the country also offers advantages for the company.

“Not spending hours each day stuck in traffic gives us a competitive edge,” Reynolds said, noting that he’s eager to see how Google Fiber’s expansion will draw new talent to the area.

Reynolds said his team continually focuses on the user experience, gleaning input from users and prospects about what they like and what they want for future iterations through five to 10 product demonstration meetings each week.

Technology Enhancement

Cultivating strong relationships and gleaning feedback is an integral part of Chocolatey’s business model, especially since the bulk of the company’s users are accessing the open source edition.

One of those serendipitous relationships involved a community user working for Net ix who had contributed code two years ago to set up Chocolatey in a Linux Docker image. Although it wasn’t an application in mainstream use, Reynolds entertained the option and accepted the contribution. In August 2019, the user and a coworker wrote an article,” Applying Netflix DevOps Patterns to Windows,” highlighting Chocolatey’s attributes.

Chocolatey has many household-name customers worldwide, including Hulu and Yelp.

“Watching the growth curve over the past nine years has been amazing, and it’s humbling and exciting to hear about places where it’s used,” said Reynolds.

Growing up in Neodesha, Kansas, Reynolds said, “I always wanted to be famous or make a difference in the world. While I didn’t get fame, at least we’ve built something that’s changing folks’ lives for the better. It’s a really exciting time and we are just on the cusp of where we plan to take the industry in terms of what is possible.”