Chicago is home to 52 SaaS and AI products actively bought by companies on Cledara, led by G2 (0.22% market share). This ranking is built from real purchasing data — what companies actually pay for, not funding announcements — and updates monthly. Data as of 17 August 2026, 17:36 UTC.
| # | Product | Category | Description | Founded | Employees | Funding | 12-mo rank |
|---|---|---|---|---|---|---|---|
| 1 | G2 | Marketing & Growth | G2.com is a platform offering a collection of software solutions and user reviews to assist businesses in making decisions about the tools they use. Users can access software categories, including productivity, collaboration, marketing, sales, customer service, and more. Through user reviews and ratings, businesses can evaluate the performance and suitability of different software products for the | 2,012 | 501-1,000 employees | $100M - $250M | +142 |
| 2 | ActiveCampaign | Marketing & Growth | ActiveCampaign is a platform that offers email marketing, automation, and CRM capabilities. It provides solutions to various business problems by allowing users to create and manage email marketing campaigns, automate tasks and workflows, and track customer interactions. | 2,003 | 1,001-5,000 employees | $100M - $250M | -88 |
| 3 | Sprout Social | Marketing & Growth | Sprout Social helps businesses transform their social media marketing strategy and improve their overall organization. The platform streamlines and scales monitoring and engagement efforts, enabling businesses to manage and respond to social conversations through a unified social inbox. It also offers publishing and scheduling capabilities, access to comprehensive social data and analytics, and li | 2,010 | 1,001-5,000 employees | $25M - $50M | -113 |
| 4 | Postmark | Marketing & Growth | Postmark is a platform that securely delivers transactional emails, like password reset notifications and purchase confirmations, to recipients' inboxes. | 2,009 | 1,001-5,000 employees | $100M - $250M | -6 |
| 5 | Pricelabs | Sales & Revenue | PriceLabs is a dynamic pricing tool for vacation rentals that analyzes market data and booking patterns to optimize pricing strategies, integrating with 110+ PMS and Airbnb. | 2,014 | 201-500 employees | $25M - $50M | +385 |
| 6 | Keeper Security | IT & Security | Keeper Security is a platform that provides password and secrets management solutions to protect individuals and organizations from cybersecurity threats. Their main product, the Password Manager, offers different versions tailored to the needs of enterprise, business, managed service providers (MSPs), public sector, personal, and family users. | 2,011 | 501-1,000 employees | -409 | |
| 7 | Basecamp | Collaboration & Productivity | Basecamp is a project management software and online collaboration tool that is designed to help small teams move faster and make more progress. It aims to solve the struggles of juggling people, projects, clients, deadlines, and expectations, especially for underdog teams competing against larger companies. | 1,999 | -197 | ||
| 8 | Fingerprint | IT & Security | Fingerprint is a device intelligence platform that identifies up to 99.5% of visitors to web and mobile applications, including anonymous ones. It provides actionable real-time insights about user behavior and intent, enabling detection of fraudulent activities like payment fraud and account takeover. | 2,020 | 51-200 employees | $25M - $50M | -473 |
| 9 | Litera | Legal, Risk & Compliance | Litera is a software company that offers a suite of legal technology solutions. Its main product is Litera Draft, a comprehensive document drafting software for legal professionals that streamlines the creation, review, and management of contracts and documents within MS Word. It includes features for proofreading, styling, document repair, and secure document sharing. | 2,001 | 501-1,000 employees | +306 | |
| 10 | Scrapfly | Data & Analytics | Scrapfly provides APIs for web scraping, data extraction, and screenshot capture, solving issues with anti-scraping measures, data format conversion, and automation. | 2,017 | 51-200 employees | +572 | |
| 11 | Visible | Finance & Accounting | Visible is a platform designed to provide businesses with tools for managing their investments and portfolios. It offers features that allow users to track key performance indicators, analyze financial data, and generate reports to gain insights into their investment activities. Additionally, Visible offers collaboration tools that enable teams to work together on investment analysis, portfolio ma | 2,016 | 11-50 employees | $1M - $5M | -992 |
| 12 | GMass | Marketing & Growth | GMass is a platform that enables email marketing and mass email campaigns through Gmail. | 2,014 | 11-50 employees | +4 | |
| 13 | DocuSeal | Legal, Risk & Compliance | DocuSeal provides a secure platform for electronic signatures and document management. It allows users to electronically sign, manage, and share documents while ensuring compliance with legal and security standards. The platform offers features such as document tracking, automated workflows, and integration with other business tools to streamline the signing process and document handling. | 2,023 | 2-10 employees | +248 | |
| 14 | Xverify | Marketing & Growth | Xverify is a real-time data validation platform that offers services such as email, phone, postal address, name, IP, and reverse phone verification. These services integrate via JavaScript, REST API, or batch upload to support fraud prevention, deliverability, and hygiene workflows. | 2,011 | 2-10 employees | ||
| 15 | QuillBot | Marketing & Growth | QuillBot is an AI-powered paraphrasing tool that enhances your writing by providing various ways to rephrase your text. It aims to improve your fluency, vocabulary, tone, and style, allowing you to use the right words for any occasion. The tool offers unlimited Custom modes and 8 predefined modes, giving you the flexibility to customize the amount of vocabulary change you want. It also utilizes an | 2,017 | 201-500 employees | $1M - $5M | +572 |
| 16 | Jungle Scout | Operations & Supply Chain | Jungle Scout is a platform designed for Amazon sellers, providing tools and resources for product research, keyword research, sales analytics, and inventory management. | 2,015 | 51-200 employees | $100M - $250M | |
| 17 | Highrise | People Ops & Talent | Highrise is a CRM (customer relationship management) platform designed for small business use. It offers contact and task management, enabling tracking of client communications and deal statuses. The software supports contact importation from sources like Outlook, Gmail, and Excel, and allows for contact organization and searching. Additional features include note-adding, task creation and reminde | 2,007 | 2-10 employees | ||
| 18 | Logikcull | Legal, Risk & Compliance | Logikcull is an instant eDiscovery solution that provides a legal software for processing, reviewing, and producing data. | 2,008 | 501-1,000 employees | $100M - $250M | |
| 19 | Source Elements | Collaboration & Productivity | Source Elements provides solutions for real-time remote audio and video collaboration, enabling professionals to record, review, and approve media content. | 2,005 | 51-200 employees | ||
| 20 | BigMarker | Marketing & Growth | BigMarker is a platform for hosting webinars, virtual, hybrid, and in-person events. The platform supports various types of events, from small webinars to large conferences, and integrates with CRM systems for data management. | 2,010 | 51-200 employees | ||
| 21 | Peoplevine | Sales & Revenue | Peoplevine is a Member Experience + CRM Platform to facilitate digital member experiences with self-service tools to collect & connect data. | 2,013 | 11-50 employees | ||
| 22 | ChangeTower | Marketing & Growth | ChangeTower is a platform that monitors and tracks changes on websites, providing real-time alerts and notifications to users. | 2,016 | 2-10 employees | ||
| 23 | Soundslice | Collaboration & Productivity | Soundslice is a web-based platform designed for interactive music learning. It synchronizes sheet music with audio and video recordings, allowing users to practice, transcribe, and teach music. | 2,012 | |||
| 24 | ShowingTime | ShowingTime+ is a real estate technology suite that automates showing scheduling, transaction management, and market reporting for agents and MLSs. | 1,999 | 201-500 employees | |||
| 25 | Copado | Engineering & DevOps | A DevOps platform for Salesforce that automates CI/CD pipelines, manages deployments, and ensures compliance with built-in testing and analytics, requiring Salesforce integration. | 2,013 | 501-1,000 employees | ||
| 26 | Pushover | Engineering & DevOps | Pushover is a platform that offers a straightforward API for sending real-time push notifications to devices. It allows developers to integrate push notification functionality into their applications or services, enabling the delivery of alerts, messages, or updates directly to users' devices. Compatible with various platforms, including iOS, Android, and desktop browsers, Pushover provides a vers | 2,012 | |||
| 27 | Appiphony | Sales & Revenue | Appiphony's Drive Connect integrates Salesforce with Google Drive, enabling document generation using Salesforce data, storage of files in Google Drive, and synchronization of file updates between both platforms. | 2,009 | 11-50 employees | ||
| 28 | Tegus | Finance & Accounting | Tegus is a platform that provides expert call transcripts, financial models, company filings, and benchmarking tools to support investment research. The platform allows institutional users to access expert insights, analyze financial data, and request custom expert calls through a unified interface. | 2,017 | 501-1,000 employees | $10M - $25M | |
| 29 | RSVPify | Marketing & Growth | RSVPify is an online platform that enables users to create customized event registration forms, manage guest lists, and handle ticket sales. It offers tools for sending email invitations, collecting RSVPs, and facilitating event check-ins. | 2,013 | 11-50 employees | ||
| 30 | Hologram | IT & Security | Hologram provides a global IoT SIM and connectivity platform that enables devices to switch carriers automatically, ensuring 99.95% uptime and supporting 2G to 5G networks. | 2,013 | 51-200 employees | ||
| 31 | CloudForecast | Sales & Revenue | CloudForecast is a SaaS platform that provides daily AWS cost management reports and an AWS cost dashboard. It helps users track their spending, forecast end-of-month costs, and identify cost anomalies, with integration options for Slack, Teams, and more. | 2,017 | 2-10 employees | ||
| 32 | Betterteam | People Ops & Talent | Betterteam is an applicant tracking system that distributes job postings to 100+ job boards, collects candidate applications, and manages hiring processes. | 2,016 | 11-50 employees | ||
| 33 | Screencastify | Marketing & Growth | Screencastify is a video creation platform that enables users to record, edit, and share videos up to 10 minutes long, with features for interactive questions and Google Drive integration. | 2,013 | 51-200 employees | ||
| 34 | Mailivery | Marketing & Growth | Mailivery is a tool that enhances email sender reputation through AI-generated email conversations in inboxes, aiming to bypass spam filters and improve email deliverability by ensuring emails reach recipients' inboxes. | 2,020 | 11-50 employees | ||
| 35 | Sovren | People Ops & Talent | Sovren develops Resume/CV Parsing and Semantic Matching / Artificial Intelligence Matching (AIM) components. | 1,996 | 11-50 employees | ||
| 36 | DYNO Mapper | Marketing & Growth | DYNO Mapper streamlines the discovery, analysis, and planning phase of web development. | 2,014 | 2-10 employees | ||
| 37 | ReviewTrackers | Customer Success & Support | ReviewTrackers is a customer feedback software used to measure and analyze customer experience. | 2,012 | 51-200 employees | ||
| 38 | Certiverse | People Ops & Talent | Certiverse is an online platform that enables organisations to create, manage, schedule and deliver professional exams and certification tests. The platform supports the full exam lifecycle from content development through delivery and reporting. | 2,019 | 51-200 employees | $10M - $25M | |
| 39 | FigPii | Marketing & Growth | FigPii is a platform for conversion rate optimization and website user research. The tool provides heatmaps, session recordings, and A/B testing features through a single interface to identify visitor behavior patterns. | 2,016 | 11-50 employees | ||
| 40 | Vuplex | Engineering & DevOps | 2,018 | Self-employed | |||
| 41 | Phenix | Engineering & DevOps | 2,013 | 51-200 employees | $10M - $25M | ||
| 42 | Deep.ad | Marketing & Growth | 2,017 | 2-10 employees | |||
| 43 | Iron Software | Engineering & DevOps | 2,016 | 11-50 employees | |||
| 44 | Cision | Marketing & Growth | 1,001-5,000 employees | $250M+ | |||
| 45 | Greyscalegorilla | Marketing & Growth | 11-50 employees | ||||
| 46 | Rocket Travel by Agoda | Operations & Supply Chain | 201-500 employees | $5M - $10M | |||
| 47 | TrueOps | Finance & Accounting | 2,023 | 2-10 employees | |||
| 48 | 123RF | Marketing & Growth | 2,005 | 201-500 employees | |||
| 49 | SDR Nation | Sales & Revenue | 2,020 | 11-50 employees | |||
| 50 | Grubhub | Operations & Supply Chain | 1,001-5,000 employees | ||||
| 51 | Puttshack Bank | 2,017 | 1,001-5,000 employees | $100M - $250M | |||
| 52 | VeryGoodCopy | Marketing & Growth | 2,014 | Self-employed |
The complete list is available as <a href="/api/export/startups/united-states/chicago.csv">CSV</a> or <a href="/api/export/startups/united-states/chicago.json">JSON</a>.
The largest SaaS company from Chicago by headcount is Grubhub (1,001-5,000 employees).
16 of 52 have disclosed funding, topped by Cision ($250M+).
The newest entrant is DocuSeal (founded 2023).
The oldest is Sovren (founded 1996); the newest, DocuSeal (2023).
| Category | Products |
|---|---|
| Marketing & Growth | 19 |
| Sales & Revenue | 5 |
| Engineering & DevOps | 5 |
| People Ops & Talent | 4 |
| IT & Security | 3 |
| Collaboration & Productivity | 3 |
| Legal, Risk & Compliance | 3 |
| Finance & Accounting | 3 |
| Operations & Supply Chain | 3 |
| Data & Analytics | 1 |
| Customer Success & Support | 1 |
| Other | 1 |
Chicago's SaaS scene skews toward Marketing & Growth — 19 of its 52 tracked companies build marketing & growth software.
Chicago accounts for 1% of the 3,476 ranked SaaS products founded in the United States.
G2, ActiveCampaign and Sprout Social are the most-used SaaS products founded in Chicago, based on real purchasing data from companies on Cledara. Last updated 17 August 2026, 17:36 UTC.
52 SaaS and AI products founded in Chicago are actively bought by companies tracked on Cledara. Aggregators list more registered startups; this ranking counts only products with real, current usage.
Xverify and Scrapfly show the strongest rank gains among Chicago-founded products over the last 90 days.
Most lists rank Chicago startups by funding raised or valuation. This one ranks them by adoption — how many companies actually pay for each product — measured monthly from Cledara's purchasing data.