Top Chicago, IL Companies With Unlimited PTO (252)

Block, Inc. is a global technology company with a focus on financial services. Made up of Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto, Block, Inc. builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the...

At Braze, we believe in the passion of our people. We seek to ignite that passion by setting high standards, championing teamwork, and creating work-life harmony. We thrive when people add their unique perspectives to our ever-growing teams—and we strive to empower you to make an impact that fuels both you, and our business.

Moov is a payments infrastructure platform making it easy to accept, store, send, and spend money all from a single, elegantly-designed API. Instead of stitching together multiple vendors, software companies simply add Moov to their products to get the latest in payment technology, user onboarding, licensing, compliance, and more.

Adyen (ADYEN:AMS) is the financial technology platform of choice for leading companies. By providing end-to-end payments capabilities, data-driven insights, and financial products in a single global solution, Adyen helps businesses achieve their ambitions faster. With offices around the world, Adyen works with the likes of Meta, Uber, H&M, eBay, and Microsoft.

As the world’s largest asset manager, BlackRock partners with investors around the globe to help them (and those on whose behalf they invest) plan for life’s most important goals – like retirement, home ownership and their children’s education. Our clients range from governments, foundations and other large institutions to those investing on behalf of individuals, including firefighters, nurses, teachers and...

Over the last 15 years, we’ve grown from a startup to a market-leading organization with over 150 team members, and we’ve created an award-winning culture that makes this company an amazing place to work. We've been ranked on multiple best places to work lists including the 2026 BuiltIn Chicago rankings.

Sprout Social is a leading AI-powered social intelligence platform, built on the belief that All Business is Social℠. Powered by Trellis, Sprout’s proprietary AI agent, the platform transforms real-time social media signals into actionable insights that drive business forward. Consistently recognized as a top software by G2, Sprout enables brands to deliver smarter, faster business impact through a suite of...

We contribute to human progress by empowering people to express themselves, live in the moment, learn about the world, and have fun together.

At Vibes, our premier mobile messaging platform helps world-class brands intelligently automate and optimize their mobile marketing outcomes through the power of SMS, MMS, RCS and Mobile Wallet. Industry leaders like Chipotle, Kohl’s, Polo Ralph Lauren, The Children's Place, KFC, Ulta Beauty, and others use Vibes to grow their customer relationships with relevant, high-volume mobile messaging and mobile wallet marketing on...

Basis is a leading global provider of automation software designed specifically for enterprise marketers. Our platform, Basis, is the industry’s only comprehensive digital media solution that seamlessly integrates programmatic, site-direct, advanced TV, search, and social media within a single interface. By unifying these functions, Basis simplifies complex and disconnected media operations, automates repetitive tasks, and minimizes manual processes, enabling marketing...

EDGE is a data and analytics platform that harnesses bank transaction data to measure consumer credit risk. Founded in 2021, EDGE is part of a larger family of FinTech brands that sits underneath our parent company, NinjaHoldings (www.ninjaholding.com). NinjaHoldings’ brands also include CreditNinja, an online consumer lending business, and NinjaCard, a neobanking platform focused on consumers in the emerging credit...

We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the flexibility of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who...

Flatfile, the pioneer of AI-assisted data exchange, provides companies and their software development teams with the easiest, fastest, and safest way to build the ideal data file import experience for their users. Hundreds of companies such as AstraZeneca, Square or Sage rely on Flatfile’s extensible, API-first platform to create enterprise-scale, intelligent, file-based data import solutions, increase developer productivity, reduce cost...

Taboola empowers businesses to grow through performance advertising technology that goes beyond search and social and delivers measurable outcomes at scale. Taboola works with thousands of businesses who advertise directly on Realize, Taboola’s powerful ad platform, reaching approximately 600M daily active users across some of the best publishers in the world. Publishers like NBC News, Yahoo, and OEMs such as Samsung,...

Founded in 2001, Vivid Seats is a leading online ticket marketplace committed to becoming the ultimate partner for connecting fans to the live events, artists, and teams they love. Based on the belief that “Life Happens Live”, the Chicago-based company provides exceptional value by providing one of the widest selections of events and tickets in North America and an industry...

Metropolis Technologies, Inc. is an artificial intelligence company whose computer vision platform enables checkout-free payment experiences for the real world. Its proprietary AI-driven technology reaches more than 50 million customers while reducing costs, increasing transparency and capturing additional revenue for real estate partners. Following its take-private acquisition of SP+, Metropolis is now the largest parking network in North America with...

Rundoo is the AI-native, all-in-one ERP for independent supply stores: point of sale, inventory, payments, and the general ledger in one system. We serve independent paint, hardware, and farm & feed retailers who've been stuck running their business on outdated point-of-sale systems and a patchwork of disconnected software, and we're built to help them modernize: better experiences for them, their...

Halo Investing is an award-winning technology platform that disrupts how protective investment solutions are used worldwide. Headquartered in Chicago, with employees worldwide, we’re on a mission to change the world by democratizing access to investment solutions that were previously unavailable to most investors. Our marketplace connects financial advisors and investors to protective investment products – including structured notes and annuities...

We help companies translate their data into meaningful and actionable information so they can stay ahead in a rapidly changing world.   We know data and analytics can be complicated and overwhelming. But data and analytics is all we do, and we are here to guide you through the complexities - so you can make sense of your data and use it...

Join. Grow. Lead the Future of Supply Chain. At Cleo, we don’t just integrate supply chains—we orchestrate them. As the pioneer and global leader of the Supply Chain Orchestration software category, Cleo is helping thousands of companies around the globe drive transformation, deliver excellence, and shape the future of their global operations. Whether you're joining us from outside or growing within, Cleo...