Best Startups to Work For in Chicago, IL 2023

Radio Flyer

Design + eCommerce
About us
Radio Flyer is known for our iconic little red wagon, and we are always dreaming up FUNomenal new ways to bring the world out to play by introducing new products every year. Radio Flyer is a recognized leader in the toy industry, with our corporate headquarters located in Chicago. From wagons and tricycles to battery powered go-karts and the best ...
TOP PERKS + BENEFITS
Meditation space
Volunteer in local community
Paid volunteer time
Flexible Spending Account (FSA)
Some meals provided
Vision insurance

Pangea Money Transfer

Fintech + Mobile
About us
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 ...
TOP PERKS + BENEFITS
401(K) matching
Mother's room
Employee resource groups
Highly diverse management team
Mean gender pay gap below 10%
Flexible work schedule
What people are saying
"Pangea offers the opportunity to be involved in the full design and development process. I am able to fully understand the product and architecture, while putting the best solution forward. I have added many skills that have advanced me in my career."
Keerthi Maryala, Engineering Manager
Grand Studio logo

Grand Studio

Consulting + Financial Services
About us
Grand Studio is a strategic design firm—home to talented thinkers and makers who collaborate around digital and operational design. Together, we take on complex challenges to build clearer paths and tools for success.
We solve problems to meet users and businesses where they’re at. For some partners, our approach results in digital products ...
TOP PERKS + BENEFITS
In-person all-hands meetings
Pet insurance
Mean gender pay gap below 10%
Pet friendly
Hybrid work model
Mandated unconscious bias training
Network Perception Logo

Network Perception

Cybersecurity + Security
About us
Network Perception protects mission-critical assets by empowering cybersecurity and compliance teams to achieve high levels of cyber resiliency through verification, visibility, and velocity. Built by a government-funded research team of cybersecurity and industry experts in network security and critical infrastructure protection, the NP-View ...
TOP PERKS + BENEFITS
Company-sponsored outings
Hiring practices that promote diversity
Generous PTO
Some meals provided
Tuition reimbursement
OKR operational model

Supernova Technology

Cloud + Fintech
About us
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.
TOP PERKS + BENEFITS
Company equity
Job training & conferences
Paid holidays
Family medical leave
Lunch and learns
Fitness stipend
What people are saying
"I really enjoy working at Supernova and love our team! We are a small team, but we are so effective and productive in many ways. It feels super good to ‘grow up’ with the company together – and to see how different it is day by day. "
Daisy Yang, Manager, Data Analyst

Kalderos

Analytics + Big Data
About us
Kalderos is a data infrastructure and analytics company that’s solving challenges around drug discounts in the U.S. healthcare system. Through platform technology and big data, our team is delivering smart solutions that enable healthcare stakeholders to collaborate with greater transparency and trust. We’re passionate about our mission to take on ...
TOP PERKS + BENEFITS
Unlimited vacation policy
Generous parental leave
Vision insurance
Promote from within
Hybrid work model
Family medical leave
What people are saying
"A typical day here is full of interesting challenges, fun filled conversations, and growth opportunities. Everyone is friendly and eager to come together to help you succeed, and this motivates me to push my limits and deliver beyond expectations."
Sameer, Principal Data Engineer

Pareto Intelligence

Big Data + Healthtech
About us
Pareto Intelligence is a leading healthcare solutions company modernizing the way health plans and providers succeed in value-based care. We deliver analytics, technology and advisory solutions, supported by predictive models and advanced data science, that demystify complex healthcare data and deliver actionable predictions that improve outcomes.
TOP PERKS + BENEFITS
Dental insurance
Health insurance
Generous PTO
Paid holidays
Life insurance
Vision insurance

Allwyn North America

Consumer Web + eCommerce
About us
Allwyn North America is a full-service lottery operator, supplier, and business partner to North American lotteries. We make play better for all with innovative lottery technology and services, engaging content, and tried-and-tested playbooks that responsibly grow lotteries’ player base, revenue, and returns to good causes over time. As operating ...
TOP PERKS + BENEFITS
Fertility benefits
Life insurance
Continuing education stipend
Mother's room
Continuing education available during work hours
Performance bonus
What people are saying
"Working for Allwyn has been enjoyable in many ways! It's exciting & rewarding to be apart of building something special from the ground up. My co-workers are all helpful and very knowledgeable from many different backgrounds."
Michael , Senior Director of Retail Sales
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GeoWealth

Fintech + Software
About us
GeoWealth provides wealth management technology; combining a comprehensive and fully-integrated platform with best-in-class portfolio solutions. Our customizable open-architecture platform and our proven spectrum of investment strategies address all the essential needs of RIAs by helping them grow faster and serve their clients more efficiently.
TOP PERKS + BENEFITS
OKR operational model
Paid holidays
Promote from within
Job training & conferences
Recreational clubs
Bereavement leave benefits

Prosodica

Analytics + Artificial Intelligence
About us
Prosodica transforms the way organizations understand and improve human connection. Our AI-powered conversation analytics platform captures every nuance of human dialogue—tone, pacing, empathy, and engagement—and translates it into measurable data that leaders can act on. By quantifying what was once intangible, Prosodica helps enterprises build ...
TOP PERKS + BENEFITS
Volunteer in local community
Recreational clubs
Promote from within
Job training & conferences
Team workouts
Disability insurance
What people are saying
"Prosodica stands out for balancing cutting-edge technology with genuine human connection. We build meaningful solutions together, and the company’s focus on growth, support, and open communication has helped me become more confident and capable in my role."
Megan, Manager, Customer Success

Avaneer Health

Big Data + Healthtech
About us
Avaneer Health's mission is to unlock the potential of healthcare to do more for people. Built on secure technology to ensure privacy and reduce the costs of data exchange, we serve providers of services across the healthcare industry. Avaneer Health is a member-based, secure and open network supporting utilities developed for and by the ...
TOP PERKS + BENEFITS
Team based strategic planning
Free snacks and drinks
Open door policy
401(K) matching
Paid industry certifications
Some meals provided

ReviewTrackers

Business Intelligence + Enterprise Web
About us
ReviewTrackers is the award-winning customer feedback software that helps businesses measure and transform the customer experience. The platform collects review data from 100+ review sites to surface customer insights that enable brands to listen, comprehend and make data-driven decisions about what their customers truly need or want.
TOP PERKS + BENEFITS
Mandated unconscious bias training
Paid sick days
Mean gender pay gap below 10%
Company-sponsored outings
Remote work program
Customized development tracks
About us
High Definition Vehicle Insurance (HDVI): Technology meets Insurance. HDVI brings telematics, software and data together with commercial trucking insurance, taking transportation insurance and fleet risk management to the next level. Our platform arms fleets with an end-to-end solution that empowers them to save money, mitigate risk, and increase ...
TOP PERKS + BENEFITS
Life insurance
Pet friendly
Promote from within
Team based strategic planning
Open door policy
Vision insurance

OneSix

Analytics + Artificial Intelligence
About us
OneSix is a leading data and artificial intelligence consultancy that helps businesses build the strategy, technology, and teams they need to innovate and grow. We excel at solving complex problems through integrated teams of strategists, data engineers, data scientists, and AI and machine learning experts.
TOP PERKS + BENEFITS
Unlimited vacation policy
Vision insurance
Flexible work schedule
Paid sick days
Documented equal pay policy
Flexible Spending Account (FSA)

Cervantes Group

Information Technology
About us
At The Cervantes Group, we are laser focused on achieving our customers business strategic goals and global innovations on a collaborative basis. Our team specializes in delivering rapid Agile™ App Dev, Project Management, Business Analysis and Management Consulting leveraging an excellent multi-lingual, multi-cultural and multi-talented team ...
TOP PERKS + BENEFITS
Friends outside of work
401(K)
Free snacks and drinks
401(K) matching
Lunch and learns
Hiring practices that promote diversity

MVMNT

Fintech + Logistics
About us
Transform a Trillion Dollar Industry

When you work at MVMNT, you’re tackling real life problems—and shaking up a trillion dollar industry in the process. MVMNT is a Chicago-based freight tech startup founded in 2020. Our mission is to enable small & medium-sized brokerages with enterprise-level technology and embedded financial ...
TOP PERKS + BENEFITS
Paid holidays
Vision insurance
Mental health benefits
Volunteer in local community
Open door policy
Generous PTO

CityBase

Information Technology + Other
About us
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.
TOP PERKS + BENEFITS
Flexible Spending Account (FSA)
Mentorship program
Paid sick days
Hybrid work model
Pet friendly
Partners with nonprofits

Focused

Artificial Intelligence + Cloud
About us
Focused is a software services company that builds agentic AI and custom software. Our expert engineers and designers build custom agents that integrate seamlessly with the systems you already run. What sets Focused apart is our hands-on, collaborative approach. We don’t just build and deliver software, we partner with your teams to ensure that we ...
TOP PERKS + BENEFITS
OKR operational model
Team based strategic planning
Return-to-work program post parental leave
Lunch and learns
Adoption Assistance
Company sponsored family events

Black Spectacles

eCommerce + Edtech
About us
Black Spectacles helps educate and inspire architects around the world to thrive in their career. We are an online learning platform, offering ARE® prep, software curriculum and career insight from the best and brightest in the biz. We are the industry leader as the first NCARB-approved test prep provider for all six divisions of the ARE 5.0.
TOP PERKS + BENEFITS
Continuing education available during work hours
Commuter benefits
401(K) matching
Flexible Spending Account (FSA)
Life insurance
Daily sync

Obie

Insurance + PropTech
About us
Obie is the leading investment property insurance platform, providing landlords, real estate investors, and partners with instant quotes, tailored coverage, and an entirely digital experience. Backed by proprietary technology, Obie simplifies insurance so deals can close faster and investors can move forward with confidence. Whether they’re ...
TOP PERKS + BENEFITS
Unlimited vacation policy
Pet insurance
Virtual coaching services
Hybrid work model
Company-sponsored outings
Company-sponsored happy hours

CPI OpenFox

Legal Tech + Software
About us
Computer Projects of Illinois, Inc. (CPI), is a privately held corporation that delivers market-leading software solutions to the law enforcement industry. CPI develops & maintains many different best-in-class, mission-critical criminal justice solutions to law enforcement & public safety agencies around the world with their OpenFox® ...
TOP PERKS + BENEFITS
Paid sick days
In-person all-hands meetings
Employee-led culture committees
Team workouts
Dental insurance
Remote work program
What people are saying
"What I like working about working at CPI is the people. I laugh at least once every day (even on the "bad" days)."
Milette, Sr. Software Engineer

cohesion

PropTech + Real Estate
About us
Cohesion is a smart building technology company offering a suite of software products, AI solutions, and advisory services that integrates people, systems, and spaces for real estate, providing seamless solutions for modernized security access control, smart maintenance, enhanced people experiences, and energy management.
TOP PERKS + BENEFITS
Volunteer in local community
Fitness stipend
Paid industry certifications
Company equity
Family medical leave
Paid volunteer time

Purchasing Platform

eCommerce + PropTech
About us
Purchasing Platform is a unique B2B marketplace tailored for all sectors of property management. We leverage cutting-edge technology to empower property portfolios, enabling them to manage purchasing activities efficiently across all properties while driving real cost savings from trusted suppliers. Our platform services portfolios across the ...
TOP PERKS + BENEFITS
Open door policy
Paid holidays
Company-wide vacation
Performance bonus
Company equity
OKR operational model
What people are saying
"Purchasing Platform has allowed me to grow along with the business. Our leadership team is transparent, supportive, and willing to explore ideas from anyone within the organization. I'm constantly looking forward to what comes next. "
Elliot , Strategic Projects Coordinations Manager
Analytics8 logo

Analytics8

Analytics + Big Data
About us
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 ...
TOP PERKS + BENEFITS
Volunteer in local community
Vision insurance
Diversity manifesto
Paid industry certifications
Quarterly engagement surveys
Dental insurance
What people are saying
"My skills and opinions are valued at Analytics8. I love that I am continually learning and growing my skill set."
Jen, Marketing

CardX

Fintech + Payments
About us
CardX provides solutions for businesses to accept credit cards at 0% cost, making payments more fair for everyone. We offer technology-enabled compliance with the card brand rules, allowing businesses to keep their payments acceptance simple while providing their customers the option to pay by card.
TOP PERKS + BENEFITS
Online course subscriptions available
Generous parental leave
Some meals provided
Paid sick days
OKR operational model
Pair programming

UPshow

Digital Media + Marketing Tech
About us
UPshow, the leading in-venue entertainment and marketing platform, is the first and only provider of white-labeled, digital interactive networks for retail and hospitality brands to engage customers and employees directly from their mobile devices.

UPshow’s technology makes it simple for large brands to build and launch engaging and ...
TOP PERKS + BENEFITS
Open office floor plan
Hiring practices that promote diversity
Team based strategic planning
Promote from within
Diversity manifesto
Summer hours

oak9

Cloud + Cybersecurity
About us
At oak9, we are passionate about removing the friction between development and security so that businesses can achieve development velocity and agility without compromising on security. We are a SaaS company with a cloud native security automation platform that analyzes infrastructure-as-code and seamlessly integrates into existing development ...
TOP PERKS + BENEFITS
Return-to-work program post parental leave
Health insurance
Casual Dress
Paid holidays
Eat lunch together
Continuing education available during work hours

Topstep

Fintech
About us
Trading is more than an activity, more than a passion, more than a calling. It’s a lifestyle, a set of rules, and a mentality towards every aspect of your day. We’ve seen what happens to people who don’t buy into the rules or the mentality—they fail, time and time again. At Topstep, we are passionately committed to helping our customers find true ...
TOP PERKS + BENEFITS
Onsite office parking
Commuter benefits
Friends outside of work
Paid industry certifications
Volunteer in local community
Wellness programs

Tandym

Fintech
About us
Tandym helps merchants drive deeper loyalty with their customers. With Tandym’s modern, API-driven platform, merchants can configure and deploy their own branded credit and loyalty program with just a few clicks. This branded payment product helps merchants convert credit card transaction processing costs into future customer revenues through ...
TOP PERKS + BENEFITS
Dental insurance
Flexible work schedule
Vision insurance
Group brainstorming sessions
Generous parental leave
Life insurance

Adage Technologies

Artificial Intelligence + Consulting
About us
Who We Are
Founded in 2001, Adage Technologies is a digital engineering firm building modern, AI‑enabled solutions that help organizations engage their audiences and operate more efficiently. With offices in Chicago and Medellín, our 120‑person team blends strategy, design, engineering, and data to create impactful digital experiences for ...
TOP PERKS + BENEFITS
401(K) matching
Remote work program
OKR operational model
Employee resource groups
Life insurance
Performance bonus
What people are saying
"At Adage I'm surrounded by people who are not only smart, but dedicated and passionate about what they do. Everyone here is actively trying to do their best work and help one another to do the same."
Victoria Sullivan, Director of People and Culture

Aclaimant

Analytics + Financial Services
About us
We are an innovative insurance tech startup redefining the way companies and employees work together to manage risk. When incidents happen in the workplace, the process is often confusing, scary, and frustrating – for both employers and employees. We build software that changes all that. Join our team to help revolutionize commercial insurance!
TOP PERKS + BENEFITS
Mandated unconscious bias training
Family medical leave
Lunch and learns
Continuing education available during work hours
Wellness programs
Promote from within

Neighborhoods.com

Real Estate + Software
About us
Neighborhoods.com is the first online real estate resource to put the neighborhood at the center of the home search. The platform invites visitors to imagine their life in a new area by providing a local’s perspective, including detailed descriptions and resident reviews of schools, amenities, and the surrounding community.
TOP PERKS + BENEFITS
Disability insurance
401(K)
Mandated unconscious bias training
Life insurance
Onsite gym
Company-sponsored outings

Redstone

Artificial Intelligence + Fintech
About us
Redstone is one of the fastest growing fintech startups in the country focused on streamlining creation of esoteric alternative asset classes. The fintech disruptor dismantled the MBS ecosystem, streamlining it with a digital platform that employs AI and machine learning tools to eliminates unnecessary steps and redundant approval processes.
TOP PERKS + BENEFITS
Vision insurance
Promote from within
Free snacks and drinks
Lunch and learns
Open office floor plan
Paid sick days

ClearCut Analytics

Big Data + eCommerce
About us
ClearCut is a leading provider of retail analytics for CPG brands. With over $50B in eCommerce and Amazon sales data analyzed, our intelligence delivers actionable insights into today's complex retail marketplace to power successful product innovation and optimize digital shelf performance. Beyond analytics, we offer expert-led services for ...
TOP PERKS + BENEFITS
Pet friendly
Continuing education available during work hours
Tuition reimbursement
Open office floor plan
Company sponsored family events
Friends outside of work

MARKT-PILOT

Analytics + Artificial Intelligence
About us
Feel the pulse of the market for the first time with MARKT-PILOT!

Our mission is to provide complete market intelligence for your entire spare parts offering.

With the help of our innovative software, PRICE-RADAR, we revolutionize spare parts pricing and create sustainable growth for OEMs' parts revenue. ...
TOP PERKS + BENEFITS
OKR operational model
Home-office stipend for remote employees
Casual Dress
401(K) matching
401(K)
Team based strategic planning

Accelerated Digital Media

Agency + Digital Media
About us
Accelerated Digital Media is a bootstrapped company that has recruited some of the top talent in digital marketing. We're on a mission to create one of the country's top digital marketing firms.

ADM is a team of performance marketers specializing in paid media management for high-growth Digital Health and e-commerce ...
TOP PERKS + BENEFITS
Remote work program
Some meals provided
Quarterly engagement surveys
Continuing education available during work hours
Generous PTO
401(K) matching

Cured

Digital Media + Healthtech
About us
Cured’s platform solutions enable leading healthcare organizations to better manage patient and key partner relationships in their networks, perform outreach directly to patients via the channels of their preference, and improve patient access experience and efficacy.
TOP PERKS + BENEFITS
Friends outside of work
Continuing education available during work hours
401(K) matching
Documented equal pay policy
Company equity
Group brainstorming sessions

Live Bash

News + Entertainment + NFT
About us
Live Bash is an entertainment technology startup that is building high-tech performer centric stages for Livestream performances. Performers of all types (musicians, comedians, interviewers, dancers, etc) can easily reserve a fully staffed turnkey venue where digital collectibles of their Livestream performance can be purchased by fans.
...
TOP PERKS + BENEFITS
Health insurance
Team workouts
Friends outside of work
Daily sync
Company equity
Hiring practices that promote diversity

2nd Watch

Analytics + Big Data
About us
Aptitive is a Chicago-based IT consulting firm with solutions focusing on the management, design, and development of data-centric projects. Our high-aptitude consultants bring innovative technology solutions to your business problems.
TOP PERKS + BENEFITS
Company sponsored family events
Unlimited vacation policy
Dental insurance
Cross functional training encouraged
Group brainstorming sessions
Commuter benefits

ShoppingGives

eCommerce + Fintech
About us
ShoppingGives is connecting cause with commerce. From DTC brands to Enterprise retailers, thousands of businesses are using ShoppingGives to launch, scale, and optimize their charitable giving strategies. Our Social Impact Stack is at the center of where purpose meets profit, and exists to empower brands to motivate giving, build loyalty, and ...
TOP PERKS + BENEFITS
Free snacks and drinks
Flexible work schedule
Open door policy
Volunteer in local community
OKR operational model
Paid holidays

Milyli

Enterprise Web + Information Technology
About us
Milyli builds secure, intuitive software that makes managing sensitive information tasks easier. Milyli has worked with Relativity and other eDiscovery technologies since 2008, building custom solutions and developing innovative applications like our flagship redaction tool, Blackout. The world’s top law firms, services providers, and government ...
TOP PERKS + BENEFITS
Paid sick days
Friends outside of work
Free snacks and drinks
Remote work program
Company sponsored family events
Onsite office parking

Equilibria

Cannabis + eCommerce
About us
Equilibria is a high-growth, omni-channel premium CBD platform for women. We are dedicated to restoring balance to our community — physically and mentally — through our high quality CBD products and personalized dosage & delivery support.
TOP PERKS + BENEFITS
Remote work program
Generous PTO
Hiring practices that promote diversity
Eat lunch together
Vision insurance
Some meals provided

Bento for Business

Fintech + Software
About us
At Bento, our mission is to give businesses the freedom to drive their vision, empower their employees and deliver business growth. We do that with our awesome financial operating platform that makes it easy for SMBs to manage daily expenses, virtual payments and cashless workflows. We are serving thousands of (very) happy customers and growing!
TOP PERKS + BENEFITS
Dental insurance
Online course subscriptions available
Highly diverse management team
Team based strategic planning
Casual Dress
Volunteer in local community

Heggerty

eCommerce + Edtech
About us
Heggerty is a literacy education company providing the #1 phonemic awareness curriculum for preschool and elementary classrooms. Founded nearly 20 years ago by Dr. Michael Heggerty, a reading instruction pioneer, we provide digital and print curriculum, classroom resources, and professional development to help educators empower the next generation ...
TOP PERKS + BENEFITS
OKR operational model
Cross functional training encouraged
Generous PTO
Paid industry certifications
Open office floor plan
Promote from within

WayFinder Logistics

Logistics + Transportation
About us
WayFinder Logistics is a third-party logistics provider located in the heart of Chicago. WayFinder combines experienced professionals, a culture predicated on integrity, accountability, and an undying thirst to provide solutions for customers and carriers alike. At WayFinder, we will outwork and outperform the competition to deliver a best-in- ...
TOP PERKS + BENEFITS
Vision insurance
Team workouts
Hiring practices that promote diversity
Charitable contribution matching
Documented equal pay policy
Fitness stipend
About us
Yakkety Yak helps business find the right words to connect with their target audience. Our content marketing services encompass everything from website copy, custom blogs and newsletters, content audits, press releases, case studies, social media marketing and custom publishing. We want to figure out how to say what you want to say – so let’s YAK.
TOP PERKS + BENEFITS
Generous parental leave
Remote work program
Performance bonus
Eat lunch together
Group brainstorming sessions
Volunteer in local community

Anthill

HR Tech
About us
Connect your frontline workforce to company resources with Anthill - the only two-way text-based communication tool designed for frontline workers to provide simple-to-use, secure employee communication in over 110 languages. Developed by workforce experts, Dr. Muriel Clauson and Dr. Young-Jae Kim, the award-winning 24-7 channel provides all ...
TOP PERKS + BENEFITS
Group brainstorming sessions
Job training & conferences
Paid sick days
Mean gender pay gap below 10%
Company equity
Health insurance

Nextpoint

Big Data + Cloud
About us
Nextpoint is the industry leader in delivering cloud-based services for eLaw. Our market leading software and services help legal related organizations conquer their eDiscovery, Litigation and Admin needs. We do this by providing a powerful SaaS platform with world-class support and engagement teams that help hundreds of law firms across the ...
TOP PERKS + BENEFITS
Customized development tracks
Bereavement leave benefits
Vision insurance
Dental insurance
Mother's room
Disability insurance
What people are saying
"It mattered to me to join a company whose culture I could speak about with honesty and pride. Nextpoint continues to strengthen its commitment to inclusion, creating a workplace that feels like a connected, supportive community for everyone."
Grace, Recruiter

Perfect Search Media

AdTech + Design
About us
Perfect Search Media is a Chicago-based digital marketing agency.

We’re experts in Paid Search and Social Media Advertising, SEO, Remarketing, Display, UX, Design, and Content. We’re a results-driven, remote company with teammates from coast to coast.
TOP PERKS + BENEFITS
Daily sync
Documented equal pay policy
Pet insurance
Group brainstorming sessions
Unlimited vacation policy
Paid sick days

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