Best Digital Transformation Services Companies in Chicago, United States
The 57 best Digital Transformation Services companies in Chicago, United States in 2026, ranked by funding and momentum. Funding, investors, founders, valuation, tech stack and live signals. Top: Thoughtworks.
Ranked: Best Digital Transformation Services companies in Chicago
| # | Company | Disclosed funding | Last round | Stage | Founder | Founded | Tech stack | Patents & IP focus | Recent signals |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Thoughtworks Leading global technology consultancy integrating strategy, design, and software engineering to enable… | $748M | 65 mo ago | Public | Mike Sutcliff CEO | 1993 | Adobe Experience ManagerSentryZendesk+44 | — | — |
| 2 | Rightpoint Provider of web & mobile application development and IT consulting services | $55M | 133 mo ago | Acquired | Ron Shamah CEO | 2007 | ContentfulApple iCloud MailMicrosoft 365+23 | — | — |
| 3 | CCC AI and cloud-driven insurance claims solution for the insurance and automotive industry | $14M | 75 mo ago | Public | — | 1980 | WebflowMarkerApple iCloud Mail+28 | 3 patents Passive dust suppression systems for bulk material transfer chutes and conveyors | — |
| 4 | Ashling Partners Provider of digital transformation services | $10M | 37 mo ago | Unfunded | Marshall Sied Co-Founder | 2017 | — | — | — |
| 5 | Fanisko AI-powered solutions transforming experiences and empowering enterprises through technology consulting | — | 24 mo ago | Seed | Aravind Sampath Co-Founder & COO | 2014 | Wix eCommerceWixSentry+13 | — | — |
| 6 | One Six Solutions Provider of software & data analytics, cloud development, and digital transformation services | — | 44 mo ago | Seed | Ajit Monteiro Co-Founder | 2013 | WordPressMySQLPHP+27 | — | 1 partnership · 1 award |
| 7 | e-Zest Provider of IT suite & digital transformation services | — | 63 mo ago | Seed | Jaywant Deshpande Founder & Director | 2000 | HubSpot CMS HubApple iCloud MailMicrosoft 365+26 | 215 patents Dental restorative and whitening materials, attachment devices, and related dental kits | — |
| 8 | Bounteous Provider of digital transformation services | — | 115 mo ago | Acquired | Leela Kaza Founder & Co-CEO | 2003 | Apple iCloud MailMicrosoft 365Salesforce+27 | — | — |
Top 8 Digital Transformation Services companies in Chicago
#1
Public · Chicago, Illinois · founded 1993 · 10500 employees$748Mraised▾
Thoughtworks is a leading global technology consultancy that specializes in integrating strategy, design, and software engineering to help enterprises and technology disruptors achieve their goals. They offer a range of services and solutions to drive innovation and create extraordinary impact.
- Jan 2021Series B$720M
- Dec 2016Grant (prize money)$1M
- Apr 2000Series A$28M
#2
Unfunded · Chicago, Illinois · founded 2017 · 181 employees$10.2Mraised▾
Provider of digital transformation services
#3
Public · Chicago, Illinois · founded 1980 · 6 employees$14.1Mraised▾
AI and cloud-driven insurance claims solution for the insurance and automotive industry. It also provides workflow software and enabling technologies to automotive collision repairers, parts suppliers, property and casualty insurance carriers. It provides marketing solutions for users.
- Mar 2020Unattributed$14.1M
- Jul 2013PE—
- Dec 2011Unattributed$1.8M
- Sep 2011Unattributed$1M
#4
Acquired · Chicago, Illinois · founded 2007 · 437 employees$55Mraised▾
Provider of web & mobile application development and IT consulting services . Its other services include UX design, business intelligence, system integration, customer experience, content & creative, digital transformation, and CRM.
- May 2015Series B$55M
#5
Seed · Chicago, Illinois · founded 2014 · 61 employees—raised▾
AI-powered solutions transforming experiences and empowering enterprises through technology consulting. The company reimagines enterprise technology stacks using advanced AI approaches and high-end consulting. It delivers intelligent automation, creative solutions, content generation, predictive analytics, and personalized experiences through Generative AI. The company offers proactive protection, threat detection, and intelligent defense through comprehensive cybersecurity solutions. It transforms raw business information streams into powerful actionable insights that strategically drive measurable sustainable growth. The company enhances customer and workforce experiences through innovation, offering solutions that revolutionize engagement, foster deeper connections, and support continuous learning. The company provides services like GenAI & ML, Cybersecurity, Data Engineering, Cloud Computing, and Extended Reality. It focuses on delivering tangible results, offering end-to-end solutions, and staying at the forefront of technology advancements. The company's mission is to enable brands to convert casual fans into digital enthusiasts and create new revenue opportunities through di
- Jun 2024Angel—
#6
Seed · Chicago, Illinois · founded 2013 · 29 employees—raised▾
Provider of software & data analytics, cloud development, and digital transformation services
- Oct 2022Seed—
#7
Seed · Chicago, Illinois · founded 2000 · 680 employees—raised▾
Provider of IT suite & digital transformation services
- Apr 2021Seed—
#8
Acquired · Chicago, Illinois · founded 2003 · 794 employees—raised▾
Provider of digital transformation services. It delivers end‑to‑end digital solutions including AI & Data Strategy & Engineering, Experience Innovation & Design, Digital Product & Platform Engineering, Digital Commerce, Marketing Activation & Loyalty, Cloud Enablement & Modernization, and Enterprise Digital Transformation.
- Nov 2016PE—
Funding & investor landscape
Notable founders
Market landscape — 10 sub-themes by coverage
Share of Digital Transformation Services coverage by sub-theme.
Regulatory-risk over time rising
Funding & growth over time
funding rising · growth rising
Common questions
Riya reads income statements for fun. She covers the real money in a sector — revenue, growth, who actually earns — and never met a vague claim she didn't want a number for.