chicago-tech
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Sprout Social Built a $457 Million Business on Social Chaos. Now It’s Cutting 20% to Bet on AI.
The Chicago software company made order out of feeds, comments and customer complaints. Its next act is harder: prove that social data is enterprise intelligence - and that the premium price, acquisitions and painful reset are worth it.
Motorola Lost the Smartphone Race. Then It Learned to Sell the Fold.
The company that put a radio in the car and a phone in the hand spent years being bought, sold and outpaced. Its comeback offers a sharper lesson: heritage works only when it is attached to a product people can recognize across the room.
Cars Commerce Wants to Be the Operating System Behind Every Car Sale
Cars.com built the audience. Now its parent is connecting that traffic to dealer websites, appraisals, advertising and wholesale auctions - a bid to own more of the messy journey from search box to showroom.
G2
G2 is the world's largest software marketplace and peer-review platform, where business buyers research, compare, and choose B2B software based on millions of verified user reviews. Founded in 2012 by a team of BigMachines alumni led by Godard Abel, G2 turned the messy, vendor-dominated software buying process into something closer to checking restaurant reviews before dinner. Today the platform hosts millions of reviews across thousands of categories, sells buyer-intent data and marketing services to software vendors, and after its 2026 acquisition of Capterra, Software Advice, and GetApp reaches more than 200 million annual software buyers.