5 Fast-Growing Chicago Companies Investing In Employee Well-Being

These companies leverage wellness initiatives to recruit and retain talented technologists.
Written by Olivia Arnold
February 14, 2023Updated: February 15, 2023

While caring for an employee’s wellness is undoubtedly kind, it also directly impacts the organization’s bottom line. 

According to Gallup, employees who are categorized as “thriving” take fewer sick days, perform better and demonstrate lower rates of burnout and turnover.

At five Chicago-based companies, leaders were eager to highlight their employee wellness initiatives, which they say are instrumental in recruiting and maintaining talented technologists. Through varied approaches, these companies are uniquely addressing Gallup’s five core elements of well-being: career, physical, social, financial and community. 

Millennium Trust, for example, provides employees with subscriptions to Calm, a meditation and sleep app, among its many other benefits. BigTime Software offers an expansive learning and development program. Caxy fosters social connections remotely through fun Slack channels and GIF challenges, SMS Assist promotes belonging through employee resource groups and volunteer opportunities, and Cleo conducts workplace surveys and takes action from the feedback to ensure its team has a voice and is heard. 

With flexible work environments and exciting professional opportunities, these five fast-growing companies are searching for experienced tech experts to join their teams. 


Fintech company Millennium Trust offers solutions that empower employers, advisors and institutions to assist with planning, saving and investing.


What sets Millennium Trust apart as an employer of choice? 

As cliché as it might sound, Millennium Trust is truly a unique place to work. We’re one of the few companies that offers retirement and financial services alongside consumer-directed health savings benefits. Our broad reach crosses multiple sectors, so you can learn about a whole different industry within one company. 

We want to continue being a leader in finding innovative, holistic approaches to short- and long-term financial security and wellness. There aren’t many platforms and services to support what we’re trying to do, so we’re building our own to fit our needs. Plus, it’s great to be involved from start to finish so we know exactly what the client experience will be like. 

At the end of the day, we’re solving complex business challenges across various industries and providing benefits and resources to other employers. Also, we’re proudly able to offer many of these top-class benefits to our own employees.

We find innovative, holistic approaches to financial security and wellness. We’re proudly able to offer many of these top-class benefits to our own employees.”

What other efforts help you attract top talent? 

Millennium Trust is a midsize company of about 1,200 employees. We’re small enough that everyone contributes, regardless of their role or title. However, we’re large enough that we have the resources and opportunities for career development and progression. 

Since acquiring PayFlex in 2022, our business spans both retirement and health savings, and we’ve refocused on becoming a single place for financial well-being. We’re building many of our products in-house, so our employees have direct ownership of our services. This is especially key, since some of these will be offered in our own benefits packages. 

We value and invest in the employee experience, from their first interview to their last day. We’re dedicated to creating an inclusive, connected and fun work experience and environment that celebrates our employees, embraces diversity and provides development and networking opportunities. 

We also have employee-led resource groups based around networking, professional development, inclusion and volunteering; they offer a little bit of something for everyone!


How has Millennium Trust adapted to the shifting wants and needs of employees over the last couple years?

Our major efforts have been supporting employees’ overall well-being. We've partnered with Calm, a mental wellness app focused on relaxation, happiness and sleep. We also advocate for continuing education and professional development. 

Aside from our internal learning courses, Millennium Trust proudly offers a student debt contribution program. Not enough time to give back to your favorite organizations? No problem, as we have paid volunteer time off. If you are a pet parent — as so many became during the pandemic — we offer pet insurance discounts. 

Millennium Trust’s flexible work environment is one of our biggest attraction points. Seventy percent of our employees are now fully remote, and we believe in having flexibility in where and when you work. All of our employee engagement activities are virtual, as well.

While we are primarily remote, some people do work from our offices. We’ve remodeled our Oak Brook office to be more team-focused, including equipping every meeting space with virtual meeting connectivity so our remote friends don’t miss anything. The goal is to make collaboration — whether at the office or at home — as easy and efficient as possible.



BigTime Software team
BigTime Software
Melissa Ryan
Vice President of People

BigTime Software delivers time tracking, billing and project management software for accountants, architects, engineers, law firms, IT services and more. 


What sets BigTime Software apart as an employer of choice? 

One thing that sets BigTime Software apart as an employer of choice is the investment in its people — from offering a fully built out learning and development program to professional growth opportunities. We invest heavily in the employee experience and cultivate an environment that is focused on learning and development.

We invest heavily in the employee experience and cultivate an environment that is focused on learning and development.”


What other efforts help you attract top talent? 

Given that we are a hybrid environment, we found that inviting final candidates into our office to meet with peers and managers has been really helpful in allowing them to experience our culture firsthand. 

Our office has really great energy, and you can get a sense for our collaboration when walking around the space; that is something that candidates have provided really positive feedback on.


How has BigTime Software adapted to the shifting wants and needs of employees over the last couple years?

BigTime Software completely shifted its focus to take into account what our employees want from a job, including where and how they work. Some changes that we implemented recently were moving to a hybrid work environment and adopting a flexible PTO policy. We give our employees the flexibility to take the time off that they need. 

Increasing our time off to include 15 holidays was something that was also very important to us. We also give all employees a floating holiday of their choosing and two mental health refresh days so they can unwind after particularly busy times. Lastly, all employees receive a Grubhub+ membership for free delivery and Friday lunch credits. 



The Caxy team.

Caxy is a custom-software development and technology-enablement consulting agency. 


What sets Caxy apart as an employer of choice? 

Too often, being a developer means you are subject to the whims of management and customers who want what can’t be done. We have something called “the Caxy Promise,” where we ensure the work you do is incredibly interesting, the people you work with are inspiring you to be better and what you’re being asked to do is reasonable. 

This shows up in us occasionally ending ties with a client because they are unreasonable or don’t treat our team well.

The metric that we're proudest of is our average tenure, which stands out in an industry where people jump around. We strive to make sure everyone on the team is a great value fit. If there’s ever a big disconnect, we work on helping the person get there. If they can’t, we find them a place somewhere else. 

We want you to wake up every day and think that this is the best team you’ve ever been on. We may not be 100 percent there, but we work on it every day.

We ensure the work you do is  interesting, the people you work with inspire you to be better and what you’re being asked to do is reasonable.”


What other efforts help you attract top talent? 

We started an internal talk show/podcast called “Chatty Caxy,” which candidates seem to really like. It’s new, so there are only a few episodes, but the idea is that listeners get to know people on the team by hearing us talk about various topics from tech in the news to coding problems, life as a developer and the state of our current stack.

We send snippets of those shows to candidates to give them a flavor of our company. It’s pretty common for candidates to mention that they watched the videos and that the episodes helped them make sense of the company, who we are and what we do.


How has Caxy adapted to the shifting wants and needs of employees over the last couple years?

Like many companies, we went fully remote in 2020. We found that we were able to be really productive from home, and our people who had been around for years were working well on their remote teams. 

However, we saw that we needed to do better with onboarding new hires. It’s a lot easier to meet people, figure out a culture and gel with a team when you are in person. We had to take a hard look at how we brought people on, so that they felt like they were a part of something. 

Today, we still have remote work options, but we also have our office in Chicago. A handful of local employees go into the office from Tuesday to Thursday, but it’s completely optional to do so. 

We are still finding ways for employees to be themselves and connect with each other. We don’t have it completely figured out, but we’ve gotten a lot better. We live a lot in Slack, and we’ve done a lot with GIF challenges and non-work-related channels about cats, video games and more. 

In the past 24 months, we’ve hired from all around the country in more than eight states, though two-thirds of our team is still local to Chicago. To make that work, we’re flexible on start times, open to when you need to deal with internet issues and make sure everyone knows what’s going on in Slack.



Shannon Kenny
Senior Vice President of Exterior Operations

SMS Assist provides a technology platform for the facilities maintenance industry. 


What sets SMS Assist apart as an employer of choice? 

I started with SMS Assist in August 2011. From our early days as a startup company to being an industry-leading provider of technology-driven facilities maintenance, we have always embodied an “all hands on deck” mentality. Everybody has a voice at the table. 

Our recent merger with Lessen will combine complementary strengths and incredible growth between the two companies, while providing endless opportunities for every employee. The mix of relentlessly pursuing innovation while leveraging companywide collaboration sets us apart from the competition.


What other efforts help you attract top talent? 

Throughout the interview process, a candidate has the opportunity to speak with multiple members of the team and greater organization. These conversations not only help us choose the top talent, but also allows the potential new hire to get a feel for our company culture right off the bat. 

One of our greatest strengths is the social aspect of our company. By allowing each candidate to speak with multiple leaders throughout the interview process, they get to experience that firsthand.

One of our greatest strengths is the social aspect of our company.”


How has SMS Assist adapted to the shifting wants and needs of employees over the last couple years?

Before and throughout the pandemic, we have continued to make great strides in investing in our employees. Signing a new office lease in Chicago’s Prudential Plaza allowed us to provide our employees with a place to work collaboratively and effectively, while also giving them access to the building’s physical and mental wellness amenities so they can be their best selves.

Throughout the pandemic, we emphasized the need for constant communication and connection between employees. We introduced seven ERGs that allowed employees to form relationships across departments based on common interests.

As we welcome employees back into the office, we also offer opportunities for them to make an impact in their communities. Our volunteer and service initiative allows employees to sign up for company-sponsored community events throughout the year. This provides employees with a chance to form relationships with one another while making a difference for those in need.

These efforts to invest in our employees ensure that everyone has the resources, connections  and information needed to be successful.



Stephanie Freeman
Human Resources Manager

Cleo helps business-to-business companies with ecosystem integration software. 


What sets Cleo apart as an employer of choice? 

Cleo is very strong on employee engagement and driving a people-first culture. The professional and personal well-being of the employees are paramount here. 

Having a global presence, Cleo has shown great strength in hiring candidates across geographies. Deep, strategic interviews and hiring focuses by our managers have helped build dynamic teams over the last two years. 


What other efforts help you attract top talent? 

Our efforts to optimize social media platforms have paid off, as we have seen a significant boost in job seeker traffic to the Cleo website and careers page. Both passive and active candidates are being attracted to the brand. 

Our collaboration with Built In has also been successful in broadening our pool of potential hires by raising awareness about Cleo's unique culture and identity.

Through conducting workplace surveys and taking actionable items from the feedback, Cleo is able to meet the needs and wants of employees.”


How has Cleo adapted to the shifting wants and needs of employees over the last couple years?

Cleo adapted to the hybrid work model, which allowed employees more control and flexibility over their work environments and schedules. Through conducting workplace surveys and taking actionable items from the feedback, Cleo is able to shift its focus to meeting the needs and wants of employees.


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