Best Customer Service Software Companies in Chicago, United States
The 32 best Customer Service Software companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Mattersight.
Ranked: Best Customer Service Software companies in Chicago
| # | Company | Disclosed funding | Last round | Stage | Founder | Founded | Tech stack | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Mattersight SaaS based Enterprise Analytics Solutions | $63M | 115 mo ago | Acquired | — | 2006 | — | 132 patents AI-driven analytics and personalization for contact‑center communications and coaching | — |
| 2 | Tagado Provider of SaaS-based ML and NLP technology for data collection and analytics platform for marketing | $4M | 48 mo ago | Seed | — | 2021 | — | — | — |
| 3 | Telnyx Provider of voice AI platform with global telecommunications infrastructure | $2M | 143 mo ago | Seed | — | 2009 | DocusaurusZendeskApple iCloud Mail+34 | 16 patents Cloud-based secure virtual private mobile and IP networking | — |
| 4 | Synap Customer interactions in one place for B2B companies | $2M | 134 mo ago | Acquired | — | 2015 | PHPRed HatZURB Foundation+12 | — | — |
| 5 | AviaryAI AI based outbound voice agents for enterprises | — | — | Unfunded | Blesson Abraham CEO | 2024 | WebflowMicrosoft ClarityMatomo Analytics+12 | — | — |
| 6 | BetterSession Co-browsing and live chat solutions | — | — | Deadpooled | Kyle Ramirez Founder | 2018 | — | — | — |
| 7 | Bot Penguin AI enabled chatbot development platform for enterprises | — | — | Unfunded | — | 2018 | UptimeRobotTypeScriptNode.js+20 | — | — |
| 8 | Call Center Studio Provider of cloud-native contact center software with AI-powered omnichannel communication | — | — | Unfunded | — | 2018 | WordPressMySQLZoho+37 | — | — |
Top 4 Customer Service Software companies in Chicago
#1
Seed · Chicago, Illinois · founded 2021 · 10 employees$4Mraised▾
Provider of SaaS-based ML and NLP technology for data collection and analytics platform for marketing. It turns unstructured data into actionable insights through automatic tagging and topic classification, feedback sentiment mapping, identifying interesting insights, and more.
- Nov 2022Seed$4M
#2
Acquired · Chicago, Illinois · founded 2006 · 157 employees$62.5Mraised▾
Mattersight provides enterprise analytics solutions focused on customer and employee interactions and behaviors. It uses behavior analytics to capture and analyze customer and employee interactions, employee desktop data and other contextual information to optimally route customers to the best available employee, improve operational performance, and predict future customer and employee outcomes. It's analytics is based on millions of proprietary algorithms and the application of unique behavioral models. The company's SaaS delivery model combines analytics in the cloud with deep customer partnerships. For Call Centers, it offers services like analytics driven call routing, predicting customer action, improving call quality and call recording for training and evaluation purpose. It's solutions are used by leading companies in Healthcare, Insurance, Financial Services, Telecommunications, Cable, Utilities, Education, Hospitality and Government.
- Mar 2017Post IPO$16M
- Aug 2016Venture Debt$22.5M
- Jul 2014Post IPO$12M
- Dec 2013Post IPO$6M
#3
Seed · Chicago, Illinois · founded 2009 · 106 employees$2.2Mraised▾
Provider of voice AI platform with global telecommunications infrastructure. The platform offers tools for building conversational AI agents. It provides voice, messaging, and connectivity solutions. The platform supports speech-to-text, text-to-speech, SIP trunking, and SMS capabilities. It offers APIs and SDKs for developers to integrate voice AI. The platform facilitates real-time audio streaming and contextual memory.
- Nov 2014Seed$1.1M
- Sep 2014Seed$1M
- Aug 2014Seed$118K
#4
Acquired · Chicago, Illinois · founded 2015 · 6 employees$2Mraised▾
Synap automatically organizes your customer communication at every stage in the relationship, creating a single coherent story and data stream that allows for quick learning, advanced analytics, and delightfully easy collaboration both for the organizations employees and customers. Angels include Devin Mathews, Chris Hill. In private beta as of Oct 15.
- Aug 2015Seed$2M
Funding & investor landscape
Market landscape — 10 sub-themes by coverage
Share of Customer Service Software coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
Common questions
Rohit lives in the feed. He covers what's moving right now — the funding rounds, launches and shifts breaking across the trade press — and ties them back to where the sector is heading.