4 Leaders At Chicago Companies Committed To Building Resilient Teams

After a challenging few years, these leaders know that developing employee resilience is the only path forward.
Written by Olivia Arnold
March 17, 2023Updated: March 17, 2023

Fast-paced work environments have always demanded adaptability, but over the last couple of years, employee resilience has become more important than ever.

While Americans’ stress levels have been steadily rising over the last decade, increased concerns over illness, financial insecurity and racial trauma during the Covid-19 pandemic contributed to a recent spike. According to a 2022 report by the American Institute of Stress, 83 percent of U.S. workers suffer from work-related stress, with one in four saying that their jobs are the number one source of stress in their life.

When it comes to combating work-related stress, employees are more likely to persevere and succeed if they have developed a strong sense of resilience. The American Psychiatric Association defines resilience as a person’s ability to bounce back from major challenges and thrive during stressful periods. The foundation’s Center for Workplace Mental Health found that resilience is associated with greater job satisfaction, organizational commitment and employee productivity. 

At these four Chicago-based companies, leaders know that resilience, like any other skill, needs to be modeled, developed and fine-tuned over time. In the face of adversity, these featured leaders never shy away from obstacles and instead promote mistakes and setbacks as critical parts of learning and growth. To further encourage their employees, they adopt practices that nurture personal well-being and foster teamwide connectedness. 

From Keeper Security, iManage, BenchPrep and Convr, the featured respondents shared helpful philosophies and strategies for those hoping to inspire team strength and flexibility during trying times.

 

Brad Cain
Director of Business-to-Business Marketing • Keeper Security, Inc.

Keeper Security offers a cybersecurity platform for preventing password-related data breaches. 

 

How do you, as a leader, model resilience for your team?

Developing a culture of transparency, clear expectations and honest self-reflection is absolutely critical to building resilience. We all make mistakes, myself included, and it’s best not to run from them. Leaders need to demonstrate the ability to bounce back from adversity, overcome challenges and adapt to change. 

In practice, that means clearly articulating challenges to the team while also focusing on potential solutions. Even in difficult situations, leaders need to model a positive attitude and focus on the possibilities for growth and improvement. 

When a leader identifies the opportunities presented by challenges or changes, they refocus the conversation toward a positive goal. Something can always be gained; it’s often just a matter of perspective.

 

Even in difficult situations, leaders need to model a positive attitude and focus on the possibilities for growth and improvement.

 

What do you do to keep your team engaged, happy and motivated?

Like it or not, distributed workforces are here to stay. Engaging with and developing a close rapport with remote team members is not easy. There is no simple solution for building a bond with someone over instant messages or video chat. However, the same principles that apply to in-person communication also work with remote teams; it just takes a lot more effort. 

Managers need to actively listen, not just talk. Asking the right questions goes a long way, and it’s important to learn about people beyond their work or the task at hand. If I learn about my colleagues, I instill openness in them. 

We are all busy, but it’s important to carve out time to discuss things outside of work. It reminds people that we are all human and have lives outside of the office or Slack. I want everyone on my team to know at least a little bit about all of their colleagues. To get there, I have to lead by example.

 

What are some activities your team does to create the camaraderie that supports resilience?

I don’t think there are one or two tactics that work on everyone. People are too different, and remote work makes traditional activities awkward and counterproductive. I can tell you that I will never attempt a virtual magician show again. 

I do think that slowing down the pace every once in a while is incredibly helpful. That may mean taking 10 or 20 minutes to chat before starting a meeting or, even better, canceling unnecessary meetings altogether. 

On top of that, I’d say that details matter. It’s something that I am working on improving. When I remember a colleague’s pet, favorite basketball team or other small personal details, it really helps in getting to know them.

 

 

The iManage team on a Zoom call.
iManage 

 

Dan Rimland
Senior Director of Sales • iManage

The cloud-enabled platform operated by iManage helps organizations activate knowledge within their business content and communications.

 

How do you, as a leader, model resilience for your team?

We’ve worked hard to establish a performance-driven culture. This means taking ownership of outcomes, hustling constantly and never resting on our laurels. We really, really want to win, and that means doing what’s right for our customers, partners and teammates. It means doing whatever it takes to make things right, as cliché as that may sound, and never making excuses. 

What that looks like in action is fairly simple; it’s about showing up every day and putting in the effort. I’ve always loved the adage that a lot of people will be smarter, more gifted, more attractive and have better resources than you, but effort is something that you have full control over. 

Our goal is to never get outworked or outhustled. That means being super responsive, highly empathetic and taking action quickly and decisively. 

 

What do you do to keep your team engaged, happy and motivated?

I hope and believe that my team knows that I would run through walls for them. They have my complete support, and my day is prioritized around their needs. I try to make myself incredibly accessible. If you can’t find me within a couple of hours, I’m possibly lying in a ditch. 

My one-on-one weekly calls are sacred to me. It’s the best way to stay engaged and hear about the team’s successes and challenges. During our weekly team calls, a different team member presents to the group each week. We share news, best practices, wins and challenges. We also have a team Slack channel for quickly sharing ideas. 

During the Covid-19 pandemic, we tried to have as much fun as possible over Zoom by dressing up for various holidays and themes. Nothing beats getting together in person, but those opportunities have been fairly rare over the last three years, so we’ve made the most out of Zoom. We take our jobs really seriously, but laughter and fun are a big part of our daily existence. 

As a team, we talk about our families, friends, dogs, homes, vacations and the world at large. I am maniacal about ensuring that we don’t ever prioritize work over the other most important things in our lives.

 

Mistakes happen and are totally OK. The most important thing is that we learn something from them.”

 

What are some activities your team does to create the camaraderie that supports resilience?

In addition to what I’ve already talked about, we do a lot of shadowing and teaming to ensure a smooth transfer of knowledge and that we’re always learning from each other. Gong has been a tremendously helpful tool in recording all our calls, creating automatic transcriptions, building a library of calls and gaining valuable insights into what customers share with us. The team has access to the entire library and regularly listens to each other’s calls. Highspot has been another valuable tool that enables us to quickly and easily share useful content with our customers. The team regularly shares Highspot pages, which allows us to leverage others’ work and approaches. 

When we lose, we dust ourselves off, figure out what we could’ve done differently and move on. Mistakes happen and are totally OK. The most important thing is that we learn something from them. We constantly discuss how we can refine our approach and do better next time. 

We are legitimately excited and passionate about the company we work for, the products we sell and the customers we serve. I hope this shows in every interaction we have.

 

 

The BenchPrep team
BenchPrep

 

Matt Albery
Senior Director, Product Management • BenchPrep

BenchPrep creates and delivers online learning programs for certifications, credentials, test prep, continuing education and training. 

 

How do you, as a leader, model resilience for your team?

Amid a global pandemic and economic downturn, BenchPrep leadership responded to adversity with timely reflection and thoughtfulness about the immediate and future implications for employees, partners, and the communities and individuals whose academic and professional progress we collectively strive to facilitate.

Most critically, our commitment to the mission never wavered. By proactively and transparently communicating strategic shifts and their related reasoning, we fostered internal trust and calm, even when those shifts were disruptive and urgent.

As a software product lifecycle leader, I know it is imperative to adopt the company-level philosophy and lead with authenticity and compassion. I continuously solicit and gain understanding of market problems and opportunities, engage technology and user experience experts to inform solutions, and avail colleagues the requisite resources, autonomy and support to succeed. 

 

By proactively and transparently communicating strategic shifts and their related reasoning, we fostered internal trust and calm.”

 

What do you do to keep your team engaged, happy and motivated?

It starts at the top. BenchPrep’s employee engagement and satisfaction can be attributed to our founders’ purposeful focus on organizational culture as well as our number one core value of putting our people first. 

As BenchPreppers, we’re privileged to drive global impact by innovating to solve problems for individuals and organizations, work with one another, and access company-sponsored volunteer and professional development activities.

As a leader in the organization, I encourage my team members to embrace these valuable opportunities. I enjoy the luxury of focusing much of my time and effort on supporting colleagues’ individualized career progression plans, celebrating their successes and procuring and providing new experiences and professional advancement opportunities. 

 

What are some activities your team does to create the camaraderie that supports resilience?

BenchPrep nurtures a culture of inclusivity, transparency and collaboration, absent of hierarchical barriers. We regularly celebrate one another’s efforts and accomplishments, individually and in companywide or team forums. On a daily basis, team members send Slack shoutouts to each other to recognize great work and broadcast their appreciation. We also frequently share customer success stories internally and occasionally welcome customers to share how our people contribute to the mission. 

Though we are a remote-first company, BenchPrep prioritizes opportunities for togetherness and fun. Twice a year, we rally the whole team for “Together Weeks,” which is a combination of fun, work and collaboration. Teams also have a designated budget for team outings and “catch-up coffees” to encourage connections while remote.

 

 

The Convr team.
Convr

 

John Stammen
CEO • Convr

Convr is an AI company for the property and casualty insurance industry. 

 

How do you, as a leader, model resilience for your team?

As a leader, I focus on the positive and recognize the good that comes from making mistakes and learning from them. I focus on solutions and try not to dwell on the negative or what could go wrong. 

I promote open “Convr-sations” among Convr team members and leaders about how we can take an honest look at our work and identify ways to improve it. I also identify qualities in team members that bring out their best work and partner them with others on the team who might complement their ideas or amplify their efforts.

I find that getting ideas, concepts and new product introductions in writing helps leaders crystalize their thoughts, communicate and help teams move forward with more resiliency.  

I keep a forward-thinking mindset and provide that type of direction for our team. I hold weekly leadership team meetings to get our leaders on the same page. We discuss arising issues, wins and opportunities to foster growth and development among our departments.

 

As a leader, I focus on the positive and recognize the good that comes from making mistakes and learning from them.”

 

What do you do to keep your team engaged, happy and motivated?

All Convr team members use the Bonusly recognition and rewards platform to enrich our company culture by recognizing wins in real time. I also email team members directly to recognize their successes.

I hold weekly one-on-one meetings with our leaders to discuss upcoming projects, goals, objectives and areas where they might need my help or the CEO’s voice. Together, we discuss the best ways to improve engagement and interest on their teams and identify learning and growth opportunities for their individual team members.

 

What are some activities your team does to create the camaraderie that supports resilience?

We regularly host virtual trivia, games and other fun, engaging events that bring folks together who might not always work with one another. This year, Convr now supports and encourages monthly social club meetings. We recognize that, within diverse teams and a remote work environment, some folks need socialization to find greater ease and comfort when collaborating with their team members.

Our leaders support team members’ continued learning and growth through online workshops that tackle some of the most common areas where employees seek professional growth. By partnering with Hone, a live workshop platform, we’ve invested in improving and expanding our team members’ skill sets and professional growth.

We’re also starting to expand internal learning opportunities through the Notion platform, an online workspace built for collaboration and real-time transfers of knowledge. In 2022, we introduced the “Learn ‘N Go” series. These are hosted bimonthly by team members and industry leaders to foster a greater understanding of how our platform and team are revolutionizing the commercial property and casualty insurance industry.

 

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