Keeping the Office Optional: 6 Chicago Companies Hiring Remote Workers

Remote workforces might be here to stay, but how do you keep your team connected when you’re miles apart?
Written by Rachael Millanta
January 19, 2022Updated: January 19, 2022

Sleep in late. There’s no traffic on the way to the office, since your office is at home. Work uninterrupted, since you can schedule most meetings around your breaks. Need a pen? It’s right where you left it — and nobody is even trying to steal the stapler off your desk. Schedule lunch whenever you want, as well. Oh, and the best bit? There’s no commute home! You can relax as soon as 5 p.m. hits.

Two years ago, this scenario was a fantasy for most Americans, but now that fantasy has become real. Tech professionals all over the world have experienced full-time remote work and it’s understandable why there is overwhelming support for keeping these options long term. In fact, 87 percent of American respondents to Business Insider’s 2021 Return-To-Work survey stated that they much prefer working from home than in the office, and 58 percent said that they were considering looking for a new job to better suit those needs.

It isn’t just employees benefiting from a more flexible arrangement, either — Omdia’s 2021 Future of Work survey reported that 68 percent of companies believe that productivity has significantly improved since the transition to remote work and as a result, 58 percent of employees will maintain an at-home or hybrid work style post-pandemic. It’s clear where the future of professional work is heading — but what are some of the businesses hiring for remote positions?

As many tech companies are ready to move forward with flexible options on a permanent basis, Built In Chicago caught up with six industry leaders to discuss how they stay connected and engaged in a remote workforce — and their hiring plans going forward.

 

Andy Koziol
Director of Cloud Engineering • Kin + Carta

 

Tell us a bit about your current remote workforce. What plans do you have to expand it?

At Kin + Carta, the majority of our workforce is remote. We’ve committed to being a hybrid workforce in the long term and the main deciding factor was that it honors the choice of our employees — or “Kin,” as we say. We empower our Kin to choose how and where they best work for most of our roles, allowing them the choice to be an office worker, a hybrid worker or a fully remote worker. This has enabled Kin + Carta to grow as a firm beyond the cities in which we have offices and has provided the opportunity for our Kin to move to new locations themselves. 

We’ll continue to empower our Kin to update their preferences as the environment around us continues to change and we are committed to ensuring that hybrid work at Kin + Carta remains inclusive and equitable. We’ll be expanding with this, as our growth trajectory is strong. Currently, we’re focused on hiring cross-functional roles, with the strongest demand being for software engineers with java, full stack, DevOps and architect experience.

We’ve committed to being a hybrid workforce in the long term — it honors the choice of our employees.”

 

Describe your remote work culture. How do you help remote employees feel connected, engaged and supported?

We prefer video-conferencing over audio calls and personal connection remains important to us. I often find that our agile teams begin meetings together by spending a few minutes talking about personal things, just like they would in person. This allows our Kin to get to know each other, which expands our culture and makes work a more rewarding experience. 

We use Slack to communicate and have specific channels to ensure all Kin know who to reach out to if they have any questions. Our executives even host quarterly coffee chats to encourage dialogue with our global Kin, as well as weekly one-on-one conversations. This dialogue between our team is one small way that we ensure that all voices are being heard. We’ve also translated many of our favorite traditions to be virtual — weekly team meetings, anniversary celebrations and even our recent “dreidel-off” for Chanukah have all remained a part of our employee experience. Our Kin, our cultural committees and even our executives are involved in the coordination of events like this, as it’s a priority that Kin + Carta remains an engaging and supportive place for all.

 

 

Vikki Caruso
Executive Vice President of People • Clearcover

 

Tell us a bit about your current remote workforce. What plans do you have to expand it? 

Prior to the onset of the pandemic, approximately 20 percent of our 130 employee workforce was remote. Two years later, our workforce has now grown to over 420 employees working across 27 states — 60 percent of which are remote!

When the pandemic hit, we already had the infrastructure and tools in place to support a remote work model, so like many companies, we’ve been working 100 percent remotely since then for the safety of our employees. Shortly after this transition, we asked our teams what was working for them and what wasn’t. Employee surveys told us that people were struggling with their mental health and burning out due to the stress and anxiety of the pandemic. After implementing a few changes including mental health support, employees began to embrace and appreciate remote work. In fact, a later survey proved that 97 percent of our employees would choose to return to work in a hybrid or remote role beyond the pandemic.

Today, we’re thrilled to be a remote-first company recruiting nationwide for all roles. Currently we have 70 open roles across the insurance, products and technology, claims and CX teams ranging from individual contributors to senior leaders. It’s an exciting time to join Clearcover!

We’re a people-first culture working in a remote-first work model.”

 

Describe your remote work culture. How do you help remote employees feel connected, engaged and supported?

At Clearcover, we’re a people-first culture working in a remote-first work model. We believe this is an important distinction because our people are our priority, regardless of whether they’re working in an office or from home.

At the root of our efforts to help our people feel connected, engaged and supported is our commitment to communication. We rely on a variety of communication channels and strategies to ensure we achieve this.

 

Strategies

  • Monthly all-hands meetings to bring our organization together for updates, wins and fun.
  • Weekly Team and 1:1 meetings to stay connected.
  • Slack channels to help us communicate efficiently and to socially connect with co-workers on special interests.
  • Employee engagement surveys to get feedback about overall happiness and satisfaction. We ask, listen and take action when necessary.

 

Additionally, we offer support with benefits that enhance the remote working experience including monthly snack deliveries, mental health workshops, a home office stipend, virtual yoga and meeting-free Fridays.

 

 

Tushar Pandit
Chief People Officer • Affinitiv

 

Tell us a bit about your current remote workforce. What plans do you have to expand it? 

In November 2020, Affinitiv announced our “Work from Here” program on a permanent basis for all team members. We continued the program as it allows for hybrid flexibility — people and teams have the flexibility of working remotely or from a campus to have meetings.

Our program allows for hybrid flexibility — people and teams have the flexibility of working remotely or from a campus to have meetings.”

 

Describe your remote work culture. How do you help remote employees feel connected, engaged and supported?

We host a lot of social events on Zoom, including trivia happy hours, bingo nights, yoga sessions and more. Teams are also encouraged to have social lunches where they bring a special guest like their pet or a family member. Additionally, Affinitiv created internal business resource groups that lead many of our activities throughout the year with participation across the board. We also host spirit weeks with different themes, such as supporting your favorite professional sports team, which brings out a friendly rivalry amongst associates. Because we were not able to have an in-person celebration for the end of 2021, every associate received a holiday gift basket that can be enjoyed at home with family and friends.

 

 

Nikita Lauren Word
HR Manager • Keeper Security, Inc.

 

Tell us a bit about your current remote workforce. What plans do you have to expand it?

We’ve been really fortunate to add a lot of wonderful talent to our team over the past two years, primarily due to opening up our remote hiring locations. We love the opportunity for continued diversity that remote work brings to the table and now have U.S. employees in 12 different states. Keeper is currently at a really interesting inflection point where we are expanding our team exponentially. Our hiring goal for 2022 is to double in size, primarily through hiring remote workforce team members. While we’re hiring in all departments across the board, the bulk of our new hires will be located in inside sales, quality assurance and development.

We love the opportunity for continued diversity that remote work brings to the table.”

 

Describe your remote work culture. How do you help remote employees feel connected, engaged and supported? 

Keeper has a diverse, fun, eclectic and fast-paced culture. We thrive on teamwork and collaboration, which has continued to evolve and grow during our transition to a remote-based workforce. It’s so imperative in these times that when onboarding a remote worker, you really go the extra mile to make them feel a part of the culture, but more importantly, a part of the overall team. To achieve this, we use a multi-pronged approach including personalized onboarding, small group training sessions, special team swag home deliveries and ongoing virtual team activities like trivia and happy hours. Keeper has a very flat management model and a true open door policy which allows team members to get to know their C-suite on a more meaningful mentorship-style level.

 

 

Group of people stand together on grass
ReviewTrackers

 

Maksym Ostapenko
Director of Product • ReviewTrackers

 

Tell us a bit about your current remote workforce. What plans do you have to expand it? 

Teams at ReviewTrackers are distributed throughout the country from Alaska to Florida. Flexible working hours allow our employees to balance their personal and work lives, as well as counteract inevitable time zone differences. We don’t let the physical distance and remote environment prevent us from feeling very connected and personally invested in each other! In 2022, we are growing our teams by hiring for a wide variety of roles across product and engineering, sales, marketing and customer success. We plan to continue hiring the most talented people we can find in the country.

We’re always trying to find new and better ways for our employees to connect with each other.”

 

Describe your remote work culture. How do you help remote employees feel connected, engaged and supported? 

We’re always trying to find new and better ways for our employees to connect with each other. We’ve had virtual sessions where we watched a cello-based meditation concert, made Argentinian empanadas and held meditation with a Japanese Buddhist monk. We also encourage both physical and mental wellness by providing a fitness membership program and counseling sessions through our healthcare provider. Steps have also been taken to further improve everyone’s work-from-home situation with a monthly stipend that goes towards office upgrades. Many of these initiatives wouldn’t have happened without proper feedback and we continue to practice what we preach by analyzing employee surveys to gauge the current state of our company culture.

 

 

Erin Yarnall
Chief People Officer • Sittercity

 

Tell us a bit about your current remote workforce. What plans do you have to expand it? 

While many of our employees are in the Chicagoland and Boston areas, we have recently added employees in several other states. This past year, we have expanded our number of squads — including an enterprise team that is focused on our Bright Horizons relationship and will be an exciting part of our growth in 2022. This year, we are looking to grow the company by 50 percent across all teams, with the majority of these roles in tech, operations and product.

We support and cheer on our employees so they can come to work as the best versions of themselves.”

 

Describe your remote work culture. How do you help remote employees feel connected, engaged and supported? 

At Sittercity, we highlight the importance of open communication and transparency within our teams. We support and cheer on our employees so they can come to work as the best versions of themselves. Every week we participate in a virtual company-wide meeting where we provide lunch and an opportunity for employees to share their current projects and ask questions in a judgment-free zone. Through Slack, our employees enjoy our informal chat groups and #donut-bot that fosters connections, a sense of belonging and an opportunity to meet teammates outside of our functional areas.

We also have dedicated internal groups that run virtual and in-person social events. Most recently, our culture crew ran our holiday events, which included a gift exchange, donation drive for a local charity called UCAN and a virtual holiday party that included trivia games and a cookie-decorating class. As we look towards a mostly remote culture in the long term, the people team at Sittercity will be developing more ways to form connections and build lasting relationships.

 

 

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