Top Companies With Generous PTO (10,000+)

We believe in the life-changing impact youth sports have on and off the field because they encourage leadership, teamwork, responsibility, and confidence—important life lessons that have the power to propel our youth toward meaningful futures. We recognize that without coaches, parents, and volunteers, organized youth sports could not exist. By building the first and best place to experience the youth...

Pie is transforming small business insurance. Our team of seasoned technology and insurance experts are on a mission to empower small businesses to thrive by making insurance affordable and as easy as pie.

IG North America is home to tastytrade, tastylive, tastyfx, and tastycrypto—a family of brands built to democratize trading and empower individual investors. Founded in Chicago by the creators of thinkorswim, acquired by London-based IG Group in 2021, we combine startup innovation with the backing of a global fintech leader with 50+ years of experience. From our headquarters in Chicago's Fulton...

Parsec Automation, LLC (Parsec) is a trailblazing creator and provider of manufacturing operations management software. Consistently recognized by organizations like Gartner and IDC and a winner of numerous awards, including the Data Breakthrough Awards, American Business, and Best in Biz, Parsec exemplifies leadership in the dynamic, fast-paced manufacturing sector. With global manufacturers leveraging its innovative TrakSYS™ platform to tackle even the most complex manufacturing challenges, Parsec’s...

OneImaging is the nation's leading comprehensive radiology network, reducing the cost of medical imaging by as much as 80%

Headquartered in Boston, Massachusetts, CarGurus is the #1 visited digital auto platform in the U.S. for shopping, buying, and selling new and used vehicles and an award-winning place to work. We give drivers and dealers the confidence to buy or sell cars exactly how they want: online, in-person, or a combination of both. Our culture fosters kindness, collaboration, and innovation,...

Caliola Engineering, LLC’s staff of systems, security, and software engineers team with PhD researchers to identify and solve mission-critical problems for customers across the US Government. We have subject matter expertise in wireless communications, cryptography, protected MILSATCOM, software defined radio, and unmanned airborne systems. Our team has experience developing and transitioning innovative technologies to Programs of Record. We are a 100%...

Trusted by thousands of service businesses, FieldPulse is an all-in-one platform that gets your entire field service team on the same page, across the office and the field, so that time is focused on growing the business and serving customers. Built with customization at the center, FieldPulse is the only service management software that adapts to the unique ways each service...

SambaSafety is a recognized innovator and leading provider of cloud-based risk management solutions for over 15,000 organizations with automotive mobility exposure, including many on Fortune’s Global 500 list. Employers and insurers benefit from SambaSafety’s continuous monitoring, intuitive insights, risk reduction tools, and configurable pricing solutions. Through the collection, correlation, and analysis of federal, state, local, and telematics data sources, SambaSafety's...

Motive builds technology to improve the safety, productivity, and profitability of businesses that power the physical economy. The Motive Automated Operations Platform combines IoT hardware with AI-powered applications to automate vehicle and equipment tracking, driver safety, compliance, maintenance, spend management, and more. Motive serves more than 120,000 businesses, across a wide range of industries including trucking and logistics, construction, oil...

Prolaio is a clinical intelligence company dedicated to unlocking continuous, predictive and shareable heart data to liberate patients from hospital-based reactive care and accelerate every new therapy. The company was created by cardiologists, cardiovascular practitioners, and data scientists specifically to address the world’s number one cause of death — cardiovascular disease. By combining scientific rigor with cutting‑edge technology, Prolaio aims...

Flourish provides innovative access to financial products that help advisors secure their clients’ financial futures. We work with over 1,100 wealth management firms that collectively represent more than $2.6 trillion in assets under management across two products: Flourish Cash and Flourish Lending. Headquartered in New York City, we are an independent subsidiary of MassMutual Life Insurance Company (MassMutual). Please visit flourish.com for...

As part of the Central bank of the United States, the Boston Fed works to promote sound growth and financial stability in New England and the nation. We contribute to communities, the region, and the nation by conducting economic research, participating in monetary policy-making, supervising certain financial institutions, providing financial services and payments, playing a leadership role in the payments...

We started a movement in which everyone can win – shoppers, retailers, society and every person on our team. To play fair, trust people and reward them for doing the right thing. We see and feel the impact of our work as more and more people gain financial freedom and retailers grow across the globe. Founded seven years ago in Sydney,...

At Rula, our mission is to create a world where every person can access high-quality mental health care. We’re building the future of behavioral health by making it easier to connect with licensed professionals at a time and cost that works for them. Our approach is evidence-based, outcome-driven and compassionate, with a focus on the whole person. By empowering our...

About Coursera: Coursera was launched in 2012 by Andrew Ng and Daphne Koller with a mission to provide universal access to world-class learning. Coursera partners with leading university and industry partners to offer a broad catalog of content and credentials, including courses, Specializations, Professional Certificates, and degrees. Coursera’s platform innovations — including AI-powered personalized guide and features, like Role Play and...

Justworks is a cloud-based software platform that takes the busyness out of growing a business and alleviates the unknown. We've combined a simple platform and exceptional 24/7 customer service to help entrepreneurs and businesses grow with confidence by giving them access to corporate-level benefits, automated payroll, HR tools, and compliance support— all in one place.

Posh is the first social media platform dedicated to real-life social experiences. We have democratized event creation, making it easy for anyone to host events and empowering organizers to curate unique experiences. In doing so, Posh enables consumers to discover social events in their community, connect with peers around shared interests, and start and scale their own social communities.

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.

Apollo is a $1.6B AI-powered sales platform that helps revenue teams find and engage leads, automate outreach, manage deals, and enrich data — all in one place. Known for its industry-leading B2B database of more than 210 million contacts and 35 million companies, Apollo’s end-to-end platform helps businesses of all sizes unlock their full market potential with unparalleled precision and...