Round one of Minne Inno’s Tech Madness received more than 2,500 votes and featured upsets where some startups beat out Twin Cities tech giants like Jamf and Leadpages.

Now, it’s on to the Sweet Sixteen.

Last week we introduced Minne Inno’s Tech Madness, a reader-driven bracket competition in the spirit of March Madness highlighting some of the local startup scene’s biggest, brightest and most exciting technology companies.

In the tightest race of round one, Kipsu beat out number-one seed Jamf by just ONE VOTE. The CRM startup next faces Techstars alum Upsie, which has been getting a lot of buzz since graduating from the accelerator last fall. Upsie landed $1.7 million to ramp up hiring in January.

Round two also brings us an interesting artificial intelligence face off between Structural and Aftercode. Structural took down Minneapolis tech pillar Leadpages to advance. Both Aftercode and Structural were founded by experienced entrepreneurs. Structural CEO Scott Burns sold his last company, GovDelivery, to Vista Equity Partners for $153 million in 2016. Aftercode CEO Mitch Coopet co-founded Code42 and served as its chief technology officer before founding Aftercode around two years ago.

In other contests, Kidizen beat Foodsby; Code42 topped Kaleidoscope; Zipnosis edged out Bind Benefits; 75F beat Equals3; and Branch Messenger topped ilos Video.

Branch Messenger next faces fellow employee scheduling software startup When I Work in round two. The two companies have a lot in common, perhaps more than any other two businesses in the Tech Madness bracket, but who will come out on top when they go head-to-head?

Remember, to determine the outcome of each matchup we want you to ask yourselves this question: Who would you invest in? This can be interpreted a number of different ways. Is this about which startup could deliver the highest return? Who you think is the safest bet? Or is it about supporting a project or mission you’re passionate about? How ever you want to interpret that question is up to you.

Voting for round two closes next Wednesday, March 28, at 11:59 p.m. Once we crown the Elite Eight of round three, things will start to speed up. Vote for your favorite companies then share with friends and colleagues to help us determine a winner.