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Top Chicago, IL Payments Companies With Best Company Culture (99)

Block
Blockchain • eCommerce • Fintech • Payments • Software • Financial Services • Cryptocurrency
23 Offices
12,000 Employees
68 Benefits See Our Teams
Block builds technology for economic empowerment.

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...

Block

Block's Top Culture & Values Strengths

Collaborative & Supportive Culture: Coworkers are frequently characterized as helpful and inclusive, which supports day-to-day belonging within immediate teams. Flexibility in where and when work happens also reinforces a sense of support in how teams operate.

Fair & Equitable Treatment: Benefits and compensation are repeatedly framed as fair or competitive, signaling investment in employees’ lives and contributions. Inclusion mechanisms such as ERGs and bias checks in people processes further reinforce fairness as an operating principle.

Cultural Alignment: A consistent emphasis on “economic empowerment” provides a shared mission that can help employees connect their work to a broader purpose. Social-impact initiatives and community programs strengthen the sense that the company’s values extend beyond rhetoric.

Square
eCommerce • Fintech • Hardware • Payments • Software • Financial Services
18 Offices
12,000 Employees
58 Benefits
Invent today. Shape tomorrow.

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage...

Square

Square's Top Culture & Values Strengths

Collaborative & Supportive Culture: Collaborative, supportive teammates and managers are a recurring strength in day-to-day work, contributing to psychological safety and a sense of being valued. Cross-functional partnership is described as a default operating mode in many areas.

Healthy Workload & Retention: Work–life balance and flexibility (including remote-friendly norms on many teams) are often framed as signals of respect for employees’ time. This flexibility can make the culture feel more humane when teams are stable.

Fair & Equitable Treatment: Inclusion efforts are described as structured and intentional, including employee communities and mechanisms aimed at reducing bias in promotion and compensation decisions. Competitive pay and benefits are also positioned as a tangible indicator of being valued.

Adyen
Fintech • Payments • Financial Services
Meet the financial technology platform helping the world’s leading businesses achieve their ambitions faster.

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.

Adyen

Adyen's Top Culture & Values Strengths

Accountability & Ownership: Teams are framed around speed with ownership, with autonomy and end-to-end responsibility described as a core operating norm. This can translate into feeling trusted to own outcomes and ship quickly while iterating.

Open Communication: Direct, candid communication norms are emphasized, including “talk straight without being rude” and a preference for real-time conversations to unblock work. This creates a shared expectation of clarity and fast resolution when it is practiced well.

Collaborative & Supportive Culture: A “one global team” and low-ego teamwork orientation is highlighted, prioritizing shared wins over individual credit across functions and time zones. The environment is often depicted as high-caliber and collaborative, supporting a sense of belonging through strong peer partnerships.

Applied Systems
Cloud • Insurance • Payments • Software • Business Intelligence • App development • Big Data Analytics
Creating the best products with the best people in insurance technology!

Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other, too....

Applied Systems

Applied Systems's Top Culture & Values Strengths

Recognition, Pride & Shared Success: External workplace certifications and “best workplaces” recognitions are positioned as trust and employee-experience markers that reinforce pride and a sense of being valued. Internal recognition programs (e.g., “Applied All Star”) further signal celebration of contributions tied to stated values.

Collaborative & Supportive Culture: Day-to-day interactions are frequently framed as friendly and team-oriented, with colleagues described as supportive and approachable. The “teammate” identity and community-building initiatives contribute to a shared-support narrative across groups.

People-First Culture: Company messaging repeatedly emphasizes being “people people,” belonging, and flexibility in where/how work happens, supported by benefits starting day one and wellbeing/volunteer programs. These signals align with an environment intended to prioritize employees’ lived experience alongside performance expectations.

Mastercard
Blockchain • Fintech • Payments • Consulting • Cryptocurrency • Cybersecurity • Quantum Computing
We are a global technology company in the payments industry.

Mastercard powers economies and empowers people in 200+ countries and territories worldwide. Together with our customers, we’re building a resilient economy where everyone can prosper. We support a wide range of digital payments choices, making transactions secure, simple, smart and accessible. Our technology and innovation, partnerships and networks combine to deliver a unique set of products and services that help...

Mastercard

Mastercard's Top Culture & Values Strengths

Collaborative & Supportive Culture: Collaborative norms are emphasized through language around “one team,” candor, and care, which signals strong peer support in day-to-day work. Teamwork across functions and regions is framed as a core way results get delivered.

Fair & Equitable Treatment: Inclusion and belonging are positioned as central operating priorities, supported by visible employee communities and equity-oriented commitments. Pay-equity disclosures and structured inclusion programs reinforce expectations of fairness and respect.

Learning & Knowledge Sharing: Continuous learning is highlighted through internal development platforms, guilds, mentorship, and global mobility that encourage skill-building and movement across the organization. This focus signals investment in employee growth rather than purely near-term output.

Federal Reserve Bank of Chicago
Agency • Fintech • Payments • Sharing Economy • Social Impact
Chicago, Illinois, USA
1,515 Employees
40 Benefits Hiring Now

The Federal Reserve Bank of Chicago is one of 12 regional Reserve Banks across the United States that, together with the Board of Governors in Washington, D.C., serves as the nation's central bank. The role of the Federal Reserve System, since its establishment by an act of Congress in 1913 , is to foster a strong economy and a stable...

Federal Reserve Bank of Chicago

Federal Reserve Bank of Chicago's Top Culture & Values Strengths

Collaborative & Supportive Culture: Colleagues and managers are often described as supportive, collegial, and collaborative, contributing to a day-to-day environment where people can feel respected and helped. The mission-oriented setting also appears to reinforce teamwork across different functions.

Fair & Equitable Treatment: Inclusion infrastructure such as employee resource groups, mentoring, enhanced family leave, and recognition on external equality-focused indexes signals deliberate efforts to support belonging and equitable treatment. These structures typically strengthen the sense that employees are respected across backgrounds.

Respectful & Positive Atmosphere: Work–life balance and generous benefits are repeatedly framed as a meaningful form of institutional support, reinforcing a generally respectful environment. Many descriptions point to a professional, stable, and civility-oriented workplace in numerous teams.

Flywire
Fintech • Payments • Software
14 Offices
1,200 Employees
47 Benefits Hiring Now
Delivering the most important and complex payments.

Flywire is a global payments enablement and software company. We combine our proprietary global payments network, next-gen payments platform and vertical-specific software to deliver the most important and complex payments for our clients and their customers.

Flywire

Flywire's Top Culture & Values Strengths

Recognition, Pride & Shared Success: Recognition is treated as a visible operating rhythm through awards and values-linked celebration, reinforcing that contributions are noticed. A shared “FlyMates” identity and purpose-driven work are repeatedly framed as sources of pride and meaning.

Collaborative & Supportive Culture: Day-to-day culture is portrayed as collaborative, friendly, and globally connected, with colleagues described as caring and supportive across teams and geographies. Belonging efforts such as ERGs and psychological-safety language reinforce an environment oriented toward inclusion and mutual support.

Authentic & Consistent Values: A clearly articulated set of core values is positioned as a consistent guide for hiring, performance, and everyday behaviors. The emphasis on authenticity, learning, and global collaboration suggests an intentional culture design rather than ad hoc norms.

Coupa
Artificial Intelligence • Fintech • Information Technology • Logistics • Payments • Business Intelligence • Generative AI
12 Offices
2,500 Employees
39 Benefits Hiring Now
Help Shape What's Next

Coupa is a global technology company that helps businesses run smarter by connecting all the ways they spend money — from procurement and expenses to payments and supply chain decisions — in one intelligent platform. In simple terms, Coupa gives organizations the visibility and control they need to make better financial choices, reduce waste, and drive real impact. It’s where...

Coupa

Coupa's Top Culture & Values Strengths

Collaborative & Supportive Culture: Colleagues are often characterized as friendly and supportive, with strong peer help shaping the day-to-day experience. Team-level camaraderie is reinforced through community language such as “The Village,” which signals an expectation of working together.

Learning & Knowledge Sharing: Learning opportunities show up repeatedly as a meaningful part of the employee experience, with room to pick up new skills and take on challenging work. Flexibility in how and where work is done can further enable ongoing development for many roles.

Authentic & Consistent Values: Core values explicitly emphasize belonging, shared success, and building together, supported by recurring programs like ERGs, bias training, and pay-equity checks. Purpose-oriented initiatives such as volunteer time off and impact programming provide visible “values in action” mechanisms.

Affirm
Big Data • Fintech • Mobile • Payments • Financial Services
9 Offices
2,200 Employees
70 Benefits Hiring Now
We create honest financial products that improve lives. Ready to make a difference?

At Affirm, we help people say yes to the things that matter with flexible, transparent ways to pay over time. No hidden fees, no compound interest, and no fine print—just a smarter way to spend.

Affirm

Affirm's Top Culture & Values Strengths

Transparency & Integrity: Ethical management and “no fine print” norms are emphasized as cultural anchors, framing decisions around clarity and responsibility. The mission to build honest financial products provides a principles-based lens that many people can rally around.

Collaborative & Supportive Culture: Day-to-day teamwork is often framed around smart, supportive colleagues and cross-functional collaboration. The remote-first operating model is paired with practices intended to sustain connection and cohesion across distributed teams.

People-First Culture: Benefits and flexibility are positioned as tangible signals that employee experience matters, including well-being and time-off norms. Investments in inclusion infrastructure (e.g., ERGs and inclusion surveys) reinforce an intent to support belonging and community.

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Metropolis Technologies
Artificial Intelligence • Computer Vision • Machine Learning • Payments • Real Estate • PropTech
7 Offices
23,100 Employees
37 Benefits Hiring Now
Metropolis is an artificial intelligence company for the real world.

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...

Metropolis Technologies

Metropolis Technologies's Top Culture & Values Strengths

Collaborative & Supportive Culture: Colleagues are often characterized as intelligent, driven, and team-oriented, with pockets described as “family-like” and supportive. Day-to-day collaboration can feel energizing, especially where local teams and managers are seen as helpful and approachable.

Recognition, Pride & Shared Success: Mission and product impact are framed as meaningful, which can create pride in building real-world AI and operating at visible scale. Benefits and occasional recognition mechanisms are positioned as signals of investment that can reinforce a sense of being valued in certain roles.

Accountability & Ownership: Stated values emphasize ownership, leadership, and a high bar for outcomes, which can feel empowering for self-directed builders. In some technical narratives, end-to-end responsibility and visible real-world impact reinforce this ownership mindset.

Pangea Money Transfer
Fintech • Mobile • Payments • Social Impact
2 Offices
70 Employees
62 Benefits
Moving Money With Purpose

Pangea is a digital money transfer platform that makes sending money abroad simple, reliable, and cost-effective. Founded in 2012 and based in Chicago, we’ve helped millions of people send money securely and efficiently, empowering financial freedom across borders. We serve a global customer base with a mobile-first platform that offers low fees, competitive exchange rates, and fast*, secure delivery. Our work...

Pangea Money Transfer

Pangea Money Transfer's Top Culture & Values Strengths

Recognition, Pride & Shared Success: Peer recognition is operationalized through “Pangea Props,” where accomplishments are celebrated publicly and can be redeemed for rewards. Cultural language also emphasizes tying work to impact for immigrant and cross‑border families, reinforcing pride and purpose.

Authentic & Consistent Values: Values are explicitly codified (e.g., Empowerment, Accountability, Kindness, No Drama, Closing the Loop) and presented as day‑to‑day behavioral norms. The same values are echoed across company culture materials, signaling a consistent internal narrative about how people should work together.

Accountability & Ownership: Autonomy and meaningful work are emphasized through real ownership over projects and opportunities to learn and grow. The culture frames performance around outcomes and follow‑through, reinforcing responsibility and individual agency.

Supernova Technology
Cloud • Fintech • Payments • Software
2 Offices
118 Employees
64 Benefits Hiring Now
Our digital wealth management lending software democratizes access to flexible liquidity solutions.

Supernova is the technology leader in securities-based lending ("SBL") solutions that connect and empower the entire financial ecosystem. We offer the world’s first and only cloud-based, fully-customizable, end-to-end software solution to automate securities-based lending from origination through the life of the loan.

Supernova Technology

Supernova Technology's Top Culture & Values Strengths

Mission-Driven Culture: The company messaging emphasizes a purpose-driven mission and frames work around “enabling investors to achieve financial wellness,” which can create a shared sense of meaning. Careers-page testimonials also highlight building something “from the ground up,” suggesting pride in impact.

Collaborative & Supportive Culture: Employee-facing materials describe camaraderie, small-team impact, and a “fun and collaborative atmosphere,” implying strong peer support. Additional content highlights rituals and team-building (e.g., outings, monthly meetings) that can reinforce connection.

Innovation & Creativity: Public materials describe experimentation (including hackathons and AI/LLM initiatives) and state that new ideas and creativity are “actively encouraged.” This signals an environment that may reward initiative and problem-solving.

Upside
Artificial Intelligence • Fintech • Machine Learning • Mobile • Payments • Retail • Software
4 Offices
275 Employees
71 Benefits Hiring Now
We exist to advance the economic power of people living and working in the real world.

Upside is a technology company that increases the financial power of people and businesses in the real world. Our technology has helped millions of people get more purchasing power on the things they need, and tens of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes...

Upside

Upside's Top Culture & Values Strengths

Transparency & Integrity: Leadership is portrayed as promoting “radical transparency,” including regular AMAs and a norm of sharing successes and failures. Public-facing disclosures such as workforce demographics also reinforce an emphasis on openness.

Collaborative & Supportive Culture: Day-to-day work is often characterized as collaborative, with smart teammates and cross-functional partnership highlighted as a cultural strength. Inclusion programs like ERGs are described as creating spaces where people feel safe and supported to contribute.

Accountability & Ownership: Values such as “Be an owner” and “Make it measurable” signal strong expectations for individual ownership and data-backed decision-making. Autonomy and the ability to drive visible impact are repeatedly framed as energizing aspects of the environment.

Braintree
Payments • Financial Services
3 Offices
409 Employees

Braintree enables merchants in more than 45 countries worldwide to accept and process payments in more than 130 currencies. We are a leader in mobile payments because we believe payments technology can drive innovation and revenue. We provide the commerce tools merchants need to minimize security concerns, expand globally, and enable new commerce experiences. And, as a PayPal service, Braintree...

Braintree
youtip, Inc.
Fintech • Payments • Software
Fully Remote, USA
4 Employees
youtip creates digital solutions for the evolving cashless tipping economy.

The company was founded in 2020 to serve as an enterprise system for digital gratuity. With the global pandemic increasing demand for contact-free business interactions, youtip provides a cashless, contactless, and app-free digital tipping service with full reporting for all business types. Tippers scan QR codes or tap through links in text and email messages to arrive at youtip's simple,...

youtip, Inc.
Cumulus Funding
Fintech • Payments
Chicago, Illinois, USA
16 Employees

At Cumulus Funding, we believe American workers deserve access to capital and a financial partner aligned with their interests. We promote financial wellbeing by offering a simple, innovative lending tool called an Income Share Agreement. Through ISAs, our customers receive cash today in exchange for a small percentage of their future incomes.

Cumulus Funding
Loop (loop.com)
Artificial Intelligence • Fintech • Payments • Software • Financial Services
2 Offices
92 Employees
Hiring Now

AI-powered cost savings for modern logistics

Loop (loop.com)
First American Bank
Fintech • Payments • Financial Services
Elk Grove Village, Illinois, USA
1,067 Employees

We do more for your money. Please never disclose any personal or confidential information on this site. Member FDIC | Equal Housing Lender

First American Bank
ARMStrong Insurance Services
Fintech • Payments • Financial Services
Itasca, Illinois, USA
699 Employees
Hiring Now

ARMStrong Insurance Services is the parent company of the leading and most trusted brands in the debt recovery and financial solutions industry. With a track record of excellence and reliability, we have proudly served businesses across various industries for decades, ensuring efficient B2B collections and tailored debt recovery solutions. As the parent company, ARMStrong is proud to own and operate...

ARMStrong Insurance Services
CityBase
Information Technology • Other • Payments • Software
Chicago, Illinois, USA
85 Employees
55 Benefits
CityBase makes government and utilities easier for everyone.

Our technology helps people find, apply, and pay for public services — and helps staff manage those interactions. The CityBase platform equally serves people who want to complete a task from their phones, those who are underbanked and must pay a bill in cash, and the public servants who keep government and utilities running smoothly.

CityBase

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