Vouch
Hiring
What they do:
Insurance and risk management tools for startups and growth-stage…
Quick facts:
HQ: Chicago, IL, United States
Top Fintech Startups in Chicago
This list has 8 startups and was last updated on Oct 15, 2026. 3 of them are hiring right now. Largest teams: Vouch, Obie, and Inkling.
8 startups
AviaryAI
Hiring
What they do:
Outbound AI voice agents for the financial services industry
Quick facts:
HQ: Chicago, IL, United States
What they do:
Buy flights for only a fraction upfront and pay off the rest in…
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
Obie
Acquired
What they do:
Moving Investment Property Insurance Forward
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
Debteye
Acquired
What they do:
Automate credit counseling.
Quick facts:
HQ: Chicago, IL, United States
Questions and answers
How many startups are on this list?
There are 8 startups on this list, last updated on Oct 15, 2026.
Which of them are hiring?
3 of them are hiring right now, including Vouch, AviaryAI, and BlueHill Payments.
Which of them have the largest teams?
By team size: Vouch (190 employees), Obie (120 employees), and Inkling (11 employees).