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Midwest SaaS Startups & Software Company News

Midwest SaaS startup news and benchmarks — B2B software, growth metrics, design-led development, and how the region's SaaS companies stack up nationally.

Midwest SaaS Startups & Software Company News

Midwest Startup Funding for the week ending September 11 2026

Midwest Startup Funding for the week ending September 11, 2026

September 12, 2026

Founder Stories: Nikhil Teja Kolli of MokSa - AI-powered security for retail

Founder Stories: Nikhil Teja Kolli of MokSa - AI-powered security for retail

September 8, 2026

StartMidwest - Store Front in Middle America during the SaaSpocalypse

The Myth of the SaaSpocalypse

Chicago fintech Vinyl Equity raises a $20M Series A led by Jump Capital

Chicago’s Vinyl Equity raises $20M Series A led by Jump Capital

Chicago's Honeycomb Insurance raises $40M for AI-driven property insurance underwriting

Chicago’s Honeycomb Insurance raises $40M for AI-driven property underwriting

Patron Points loyalty software company secured investment from Straylight Capital

Patron Points secures growth investment from Detroit's Straylight Capital

Chicago-based sponsorship intelligence platform Trajektory announces $8 million funding round

Trajektory Raises $8M in Chicago for Sponsorship Intelligence Platform

StartMidwest - Backing Wonder in Growth Stage Companies by Michelle Erikson of Straylight Capital

Backing Wonder in Growth Stage Companies

StartMidwest Benji universal API for loyalty raises 6 million in seed funding

Benji raises $6.25M for loyalty product; three Midwest funds invest

Chicago’s definity Unveils Agentic Data Engineering Platform with $12M Series A

StartMidwest - Simplify Ventures

Simplify Group Launches Simplify Ventures in Illinois

StartMidwest - Straylight Capital - Michelle Erickson - the case for tech enabled services

Human-Powered Trust is the Real Moat: A Case for Tech-Enabled Services

StartMidwest Letter AI Raises $40M Series B

Letter AI Raises $40M Series B

StartMidwest Founder Stories: Justin Turk of ConStrat AI

Founder Stories: Justin Turk of ConStrat AI

Why More Midwest SaaS Companies Should Embrace Design Earlier

February 6, 2026

Chicago’s When raises $10.2M to expand health coverage platform

February 3, 2026

StartMidwest - Cleveland Ohio CHAMP Titles raises 55 million

Cleveland’s CHAMP Titles raises $55 million in its largest funding round to date

January 7, 2026

StartMidwest Startup Wisconsin Podcast: Shantanu Singh of Obviate.ai

Startup Wisconsin Podcast: Shantanu Singh of Obviate.ai

December 17, 2025

StartMidwest Nebraska startup CompanyCam becomes first unicorn in that state after $415m round

Nebraska startup CompanyCam becomes first unicorn in that state after $415m round

December 12, 2025

How Mike White and Secchi are helping redefine how real work happens

December 5, 2025

StartMidwest 2025 SaaS Benchmarks: Where the Midwest Is Winning (and Where It Lags)

2025 SaaS Benchmarks: Where the Midwest Is Winning (and Where It Lags)

November 19, 2025

StartMidwest Founder Stories: Ryan Rybolt of Payload

Founder Stories: Ryan Rybolt of Payload

November 17, 2025

StartMidwest Ann Arbor-based Scorbit Raises $5 Million for connected gaming

Ann Arbor-based Scorbit Raises $5 Million for connected gaming

November 14, 2025

StartMidwest Luster raises $3 million to help sales teams improve and impact revenue.

Luster raises $3 million to help sales teams improve and impact revenue.

November 4, 2025

StartMidwest Michelle Erikson of Straylight Capital How can we bring creativity back to the boardroom?

How can we bring creativity back to the boardroom?

August 29, 2025

Propel People Raises $3 Million to Speed Up Skilled Trades Hiring

StartMidwest APFusion Raises 6.5m to Digitize Auto Salvage

APFusion Raises $6.5M to Digitize Auto Salvage

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