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Top Chicago, IL Payments Companies With Best Work-Life Balance (96)

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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Teams commonly follow an office-first approach with flexibility when needed, creating a practical hybrid rhythm. In-person collaboration is balanced by remote options that help maintain day-to-day routines.

Wellbeing Programs: Flexible time off, monthly Adyen+ stipends for needs like childcare or home-office setups, and wellness days are highlighted. Parental leave, catered lunches, commute allowances, and access to mental-health support further support wellbeing.

Workload Manageability: Workloads are frequently described as manageable with reasonable hours for many teams. Baseline balance is attainable, with heavier periods concentrated around big launches or cross-time-zone coordination.

Moov
Fintech • Payments
9 Offices
63 Employees
47 Benefits Hiring Now
We make money movement work for everyone so that businesses, merchants, and users can do great things with their money.

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.

Moov

Moov's Top Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: A fully distributed, remote‑first setup with flexible schedules allows people autonomy over where and when they work. Home‑office support and a formal remote program are described as making this model sustainable.

Time Off Access: “Take what you need” PTO and flexible/unlimited time off are highlighted as core benefits. Company materials emphasize access to time away alongside policies intended to support real usage.

Recovery Time: A company‑wide closure between Christmas and New Year’s and team cooldowns after major pushes are cited to encourage rest and reinforce boundaries. These practices are framed as supporting recovery and preventing burnout.

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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Company materials describe a Work Reimagined model allowing employees to work remotely, in‑office, or hybrid based on where they do their best work. Public employer pages and listings reinforce that hybrid/remote pathways are available across locations and functions.

Time Off Access: Benefits highlight paid vacation, personal/sick time, paid holidays including a birthday day, paid parental leave, and volunteer time off. Messaging encourages use of PTO, signaling that time away is supported in practice.

Supportive Culture: Leadership is described as promoting balance and showing care for staff, with clear boundaries between professional and personal life emphasized in some teams. Team camaraderie and supportive direct managers are cited as positives for day‑to‑day balance.

Block
Blockchain • eCommerce • Fintech • Payments • Software • Financial Services • Cryptocurrency
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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Company materials describe a distributed-by-default setup where most roles can be remote, office, or hybrid by choice. Messaging frames this as working 'from wherever you thrive,' indicating meaningful location autonomy.

Time Off Access: Benefits information highlights flexible PTO alongside paid parental, medical, and caregiving leave. These programs are positioned to make it easier to step away when needed.

Mental Health Support: Careers content points to mental‑health resources such as Lyra/EAP. These supports are presented as positives for maintaining balance.

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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Company materials highlight a team‑driven hybrid model averaging about three in‑office days with purposeful in‑person time. Options like four weeks of “work from elsewhere” and quarterly meeting‑free days extend where and how work gets done.

Time Off Access: Benefits include five paid volunteer days per year and a global minimum of 16 weeks of paid new‑parent leave regardless of caregiver status. These paid time‑off provisions are positioned to support life events and balance.

Wellbeing Programs: Well‑being resources and mental‑health support are emphasized in company materials and the 2024 Impact Report. Quarterly company‑wide meeting‑free days are framed to create focus time.

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 Work-Life Balance & Wellbeing Strengths

Time Off Access: Unlimited or generous PTO, paid holidays, sick days, and bereavement leave are positioned to support time away and balance. Policies on Built In and company materials frame vacation as designed to achieve work-life balance.

Mental Health Support: Wellbeing initiatives include therapy sessions, mental health resources, yoga sessions, and access to an on-site gym. These offerings are presented to help employees manage stress alongside a fast-paced environment.

Remote or Hybrid Flexibility: A hybrid model with flexibility in choosing in-office days allows a blend of on-site and remote work. Scheduling flexibility is highlighted as part of day-to-day arrangements.

Coupa
Artificial Intelligence • Fintech • Information Technology • Logistics • Payments • Business Intelligence • Generative AI
13 Offices
2,500 Employees
52 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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Employer materials describe a remote-first setup and real remote options that let many roles manage schedules without commuting. Feedback suggests this flexibility is actively used across parts of the organization.

Time Off Access: Policies highlight generous PTO, Wellness Days, and paid volunteer time, with accounts indicating unlimited PTO can be taken in practice. Feedback suggests time away is generally honored on supportive teams.

Supportive Culture: ERGs, inclusion programs, and community initiatives provide peer networks that can ease daily demands. Feedback suggests collaborative teams and helpful colleagues are common in the right orgs.

Square
eCommerce • Fintech • Hardware • Payments • Software • Financial Services
18 Offices
12,000 Employees
58 Benefits Hiring Now
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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Block describes a distributed setup where most roles can choose remote, office, or hybrid, with some international work flexibility that helps people align work with life. The company’s move to permanent WFH supports location choice for many roles.

Time Off Access: Benefits materials highlight flexible time off, paid holidays and sick leave, and mental‑health support that make it easier to disconnect when team norms support it. These offerings create space to step away and recharge.

Sustainable Pace: Many engineering and data groups are characterized by reasonable hours and healthy team culture, indicating workloads can be steady on several tech teams. Flexible scheduling and a distributed model further support a manageable cadence.

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 Work-Life Balance & Wellbeing Strengths

Time Off Access: Public materials highlight unlimited PTO for exempt staff with a minimum-use expectation, paid holidays, and comprehensive parental leave. These policies can support taking time away when workload and coverage allow.

Remote or Hybrid Flexibility: Employer and third‑party profiles describe hybrid options for some corporate and tech teams alongside intentional in‑person collaboration. This can reduce commuting and offer some discretion over where work is performed in eligible roles.

Flexible Scheduling: Operations descriptions note consistent 40‑hour weeks in some locations with optional overtime and site‑level adjustments for personal needs. Such predictability can help plan outside commitments when sites are adequately covered.

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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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: A hybrid model with remote options (“FlyBrid”) and support for distributed work enables many roles to choose where they work. Practices and guidance for remote collaboration indicate norms that help flexibility stick.

Flexible Scheduling: Flexibility around start and end times allows people to align work with personal commitments and time‑zone coordination. This autonomy supports day‑to‑day balance across different locations.

Time Off Access: Generous PTO combined with companywide unplug days and paid volunteer time encourages real disconnection from work. These programs signal leadership support for taking time away.

Affirm
Big Data • Fintech • Mobile • Payments • Financial Services
7 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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Company describes a remote‑first setup with optional offices in several hubs, giving teams broad flexibility in where and how they work. Location freedom supports both fully remote work and occasional in‑person collaboration.

Time Off Access: Benefits materials highlight generous/flexible PTO, company “Away Days,” and parental leave with a structured return‑to‑work transition, signalling that time away is readily available. Cultural messaging that “time off isn’t a dirty word” reinforces regular use of these programs.

Manager Support: Employer spotlights and FAQs emphasize leaders modeling and encouraging time away, indicating managers actively support using PTO and recharge days. Feedback suggests this normalization helps employees disconnect without stigma.

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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Roles are offered in office, hybrid, or fully remote formats, with a flexible work schedule and a remote work program highlighted. This setup gives individuals latitude to align work location and hours with personal needs.

Time Off Access: Unlimited PTO and paid holidays are explicitly offered. Clear time-off options provide avenues to disconnect when coverage is arranged.

Wellbeing Programs: Benefits highlight mental health resources, wellness initiatives, fitness stipends, and company-sponsored well‑being activities. These programs signal an emphasis on supporting employee wellbeing beyond core benefits.

Federal Reserve Bank of Chicago
Agency • Fintech • Payments • Sharing Economy • Social Impact

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 Work-Life Balance & Wellbeing Strengths

Time Off Access: The Bank advertises generous paid time off, eight weeks of paid family care leave, backup care, and a no‑cost employee assistance program that support balance. Additional paid holidays, wellness days, bereavement leave, and paid volunteer time further expand time away options.

Remote or Hybrid Flexibility: A clearly defined hybrid cadence exists in the Research, Policy & Public Engagement group (Tuesday–Thursday in person; Monday/Friday from home), with schedule adjustments possible for classes. Flexible work schedules, occasional work from home, and a remote work program are also described.

Wellbeing Programs: Wellness initiatives include company‑sponsored outings, fitness stipends, an onsite gym/Thrive Wellness Center, and the Live Smart, Plan Smart program with 24/7 nurse access. A confidential assistance service and wellness reimbursements provide additional wellbeing support.

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 Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Hybrid work with two remote days per week enables flexibility while maintaining collaborative in‑office time. Role- and team-based remote options provide additional balance between focus work and onsite interaction.

Time Off Access: Generous paid time off, company holidays, sick time, and a paid volunteer day create multiple avenues to disconnect and recharge. A paid sabbatical for longer-tenured employees further supports stepping away for extended recovery.

Wellbeing Programs: Access to free mental‑health platforms, comprehensive healthcare coverage, and discounted gym memberships bolster overall wellbeing. These resources help employees manage stress and sustain healthy routines.

SpotOn
eCommerce • Fintech • Payments • Software
Helping businesses to compete and win with intuitive software, point-of-sale systems, and payment solutions.

We’re not just building restaurant tech—we’re giving independent restaurants the tools to compete and win. From our award-winning point-of-sale to AI-powered profit tools, everything we do helps operators boost profit, work smarter, and keep their best people. And every solution is backed by real humans who actually give a sh*t about helping restaurants succeed.

SpotOn
Waystone
Fintech • Payments • Financial Services
4 Offices
1,413 Employees
Hiring Now

Waystone is the leading provider of institutional governance, risk and compliance services to the asset management industry. Partnering institutional investors, investment funds and asset managers Waystone builds, supports and protects investment structures and strategies worldwide. With over 20 years’ experience and a comprehensive range of specialist services to its name, Waystone is now supporting asset managers with more than US$2Tn...

Waystone
Solomon Partners
Payments • Financial Services
3 Offices
363 Employees
19 Benefits

Founded in 1989, Solomon Partners is a leading financial advisory firm with a legacy as one of the first independent investment banks. We advise clients on mergers, acquisitions, divestitures, restructurings, recapitalizations, capital markets solutions and activism defense across a range of industries. We offer unmatched industry knowledge in the sectors we cover, providing comprehensive strategic solutions tailored to generate long-term...

Solomon Partners
ARMStrong Insurance Services
Fintech • Payments • Financial Services
Itasca
699 Employees
32 Benefits 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
MB Financial Bank
Fintech • Payments
Chicago
4,000 Employees
16 Benefits

MB Financial Bank is a customer-driven company and views every customer contact as an opportunity to add value and enhance our relationship. MB strives to be the best provider of financial services to small- and mid-sized businesses in all the markets we serve, as well as to individuals living or working near our banking centers.

MB Financial Bank
Fetch
Big Data • Food • Mobile • Payments
7 Offices
800 Employees
55 Benefits Hiring Now
Fetch Rewards gives shoppers an easy and fun way to save on their everyday purchases.

Fetch Rewards is a mobile app that connects and rewards everyday shoppers for buying the brands they love. Fetch gives users the easiest way to save on their purchases by simply scanning any grocery receipt, from any store. For our brand partners, Fetch helps them build long-term loyalty, and understand a true 360 degree view of purchase behavior.

Fetch

Fetch's Top Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Roles are commonly remote within a remote-first hybrid model with optional office hubs, giving people discretion over where they work. Time and location flexibility is emphasized alongside trust to manage what is needed to be successful.

Time Off Access: Policies include flexible paid time off, robust leave, paid holidays, and a year-end break, enabling planned downtime. Parental leave and a flexible return-to-work ramp further support taking real time away.

Wellbeing Programs: Offerings such as 1:1 wellness coaching, nutrition counseling, and Gympass memberships are positioned to support health and balance. A people-first culture and empathetic leadership are highlighted alongside these resources.

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