ShipBob
Hiring
What they do:
Providing Amazon level logistics to e-commerce businesses.
Quick facts:
HQ: Chicago, IL, United States
Top B2B Software Startups in Chicago
This list has 30 startups and was last updated on Oct 15, 2026. 5 of them are hiring right now. Largest teams: Vouch, Zerocater, and Bluecrew. Latest round: Factron AI raised $250K (Oct 5, 2026).
30 startups
Vouch
Hiring
What they do:
Insurance and risk management tools for startups and growth-stage…
Quick facts:
HQ: Chicago, IL, United States
What they do:
Zerocater is revolutionizing how companies feed their employees
Quick facts:
HQ: Chicago, IL, United States
Letter AI
Hiring
What they do:
End-to-end content, learning, & deal intelligence for B2B sales teams
Quick facts:
HQ: Chicago, IL, United States
What they do:
Run full stack apps close to your users.
Quick facts:
HQ: Chicago, IL, United States
What they do:
SaaS Platform to manage IT and buy business software
Quick facts:
HQ: Chicago, IL, United States
AviaryAI
Hiring
What they do:
Outbound AI voice agents for the financial services industry
Quick facts:
HQ: Chicago, IL, United States
BlueHill Payments
Hiring
What they do:
Client management, communication, and projects in one platform.
Quick facts:
HQ: Chicago, IL, United States
What they do:
AI to run behavioral health programs better
Quick facts:
HQ: Chicago, IL, United States
Quick facts:
HQ: Chicago, IL, United States
Funding:
$56.3M · Equity · Feb 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2022
Funding:
$19.3M · Equity + debt · Jun 2026
Quick facts:
HQ: Chicago, IL, United States
Funding:
$16.6M · Equity · Jun 2026
Quick facts:
HQ: Chicago, IL, United States
Funding:
$10M · Equity · May 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2023
Funding:
$7.23M · Equity · Mar 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2022
Funding:
$4.3M · Equity · Feb 2026
Quick facts:
HQ: Chicago, IL, United States
Funding:
$3.65M · Equity · Mar 2026
Quick facts:
HQ: Chicago, IL, United States
Funding:
$2.59M · Equity · Jan 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2022
Funding:
$2.5M · Equity · Apr 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2026
Funding:
$1.55M · Equity · May 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2024
Funding:
$1.3M · Debt · Jun 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2023
Funding:
$1.2M · Equity · Mar 2026
Quick facts:
HQ: Chicago, IL, United States
Incorporated: 2025
Funding:
$250K · SAFE · Oct 2026
Bluecrew
Acquired
What they do:
Bluecrew is a web based staffing agency.
Quick facts:
HQ: Chicago, IL, United States
Popular Pays
Acquired
What they do:
Software for collaborating with content creators and influencers
Quick facts:
HQ: Chicago, IL, United States
Inkling
Acquired
What they do:
Inkling, based in Chicago, Illinois, offers collective intelligence solutions to help organizations make more informed decisions. Inkling's products have been…
Quick facts:
HQ: Chicago, IL, United States
TaxProper
Acquired
What they do:
TaxProper helps large Real Estate owners manage their property taxes.
Quick facts:
HQ: Chicago, IL, United States
Preflight
Acquired
What they do:
No-code Web Apps testing for everyone
Quick facts:
HQ: Chicago, IL, United States
Charge Running
Shut down
What they do:
Provides live, virtual running classes to runners all around the world
Quick facts:
HQ: Chicago, IL, United States
Draft
Shut down
What they do:
Making Draft. Super simple version control and collaboration for…
Quick facts:
HQ: Chicago, IL, United States
Protobase
Shut down
What they do:
Protobase is a 10x, next-generation spreadsheet.
Quick facts:
HQ: Chicago, IL, United States
Questions and answers
How many startups are on this list?
There are 30 startups on this list, last updated on Oct 15, 2026.
Which of them are hiring?
5 of them are hiring right now, including ShipBob, Vouch, and Letter AI.
Which of them have the largest teams?
By team size: Vouch (190 employees), Zerocater (140 employees), and Bluecrew (100 employees).
Which of them raised money recently?
Latest rounds: Factron AI — $250K SAFE (Oct 2026), Stridekick — $1.3M Debt (Jun 2026), and Architect Financial Technologies — $19.3M Equity + debt (Jun 2026).