PayIt gains $25M follow-on investment from early backer Weatherford Capital
May 31, 2019 | Tommy Felts
A Tampa-based venture capital firm run by three brothers sees investing in Kansas City’s PayIt as part of its long-term strategy.
Weatherford Capital first backed PayIt in 2016, through a $4.5 million Series A round led by New York-based Advantage Capital Partners, and followed by Weatherford, Royal Street Ventures, the Missouri Technology Corporation and Five Elms Capital.
The firm confirmed to Startland this week a follow-on investment of $25 million for the Kansas City GovTech innovator, which is led by co-founders John Thomson and Michael Plunkett.
Specializing in GovTech applications that better connect government to its constituents, PayIt made news in 2018 thanks to major partnerships with the State of Kansas and the Unified Government of Kansas City, Kansas. Its iKan app notably allows Kansas to skip the line at the Department of Motor Vehicles.
PayIt was named one of Startland’s 10 Kansas City Startups to Watch in 2017 and 2018.
“As investors, we seek out quality teams, leaders, and healthy cultures, not just assets and good ideas,” reads the investment firm’s website. “We believe that through long-term partnerships with purposeful capital and high-quality companies we will produce outcomes that promote human flourishing.”
Driven by Will, Sam, and Drew Weatherford, the firm has a nationwide focus on middle market firms with enterprise value of $50 million or more.
In March, PayIt made headlines with a more than $100 million investment by New York-based Insight Partners, which provided an exit for investors within the KCRise Fund.
Click here to read about the game-changing investment for PayIt and Kansas City.
“The company [PayIt] happens to be in Kansas City — Investors expect a return. They’re looking for big, scalable, durable businesses,” PayIt’s Thomson said at Startland’s May Innovation Exchange event. “You’ll hear the phrase ‘escape velocity’ — those that can turn into the next Fortune 500 company in a market or a category. It’s all about the execution of the business, the growth trajectory and how investable is that team and business.”
Meeting with more than 85 firms in its most recent funding push, however, PayIt saw rising interest not only in its GovTech offering, but in its hometown backing, he acknowledged.
“There’s a broad awareness of Kansas City, this ecosystem and this environment — and that it’s been on the rise,” Thomson said.
Featured Business

2019 Startups to Watch
stats here
Related Posts on Startland News
Small Biz to Watch: Matchless Cabinet throws ‘BBQ nerds’ onto national spotlight’s grill
Editor’s note: Startland News is showcasing five Kansas City small businesses this week through the newsroom’s first-ever Small Biz to Watch series, presented by Bank of America. The following highlights one of the 2025 honorees, curated by editors from Kansas City’s wide array of hard-working entrepreneurs and business owners. Selection criteria is based on factors…
KC-built creator marketplace expands to connect small businesses to influencers of all sizes
When Wes Elder and Caleb Vetter launched CreatorSpace more than a year ago, they set out to carve their own path through the blended world of entertainment and technology, Elder shared. Now their startup — what they bill as the world’s first creator marketplace — is taking a new turn. The co-founders plan to release…
Tiger 21 expands its invite-only peer network in KC as number of ultra-wealthy leaders rises
A prestigious — and relatively new-to-Kansas City — resource for high-net-worth C-suite leaders and successful entrepreneurs and founders is expanding: Tiger 21, a premier peer membership organization for ultra-wealth creators and preservers, is adding a second group. The launch is being orchestrated by Heidi Lehmann, a seasoned investor, board member and five-time startup founder leading…
Small Biz to Watch: Deposit The Work builds mass with tech-enabled consistency — no excuses, all grit
Editor’s note: Startland News is showcasing five Kansas City small businesses this week through the newsroom’s first-ever Small Biz to Watch series, presented by Bank of America. The following highlights one of the 2025 honorees, curated by editors from Kansas City’s wide array of hard-working entrepreneurs and business owners. Selection criteria is based on factors…

