Scalable culture: How 5 Chicago startups support employees as they grow

Andreas Rekdal

Periods of rapid growth are an exciting part of startup life, but the process of scaling also comes with a set of serious challenges. Onboarding new employees inevitably strains a startup’s already limited resources, and existing employees often need additional support as they take on new roles they’ve never tried out before.

Overcoming those challenges is a lot easier for companies with cohesive cultures, where employees feel like they’re all in it together. We spoke with five fast-growing Chicago startups to learn more about how they work to promote that sense of togetherness.


NowSecure provides mobile security solutions for enterprise clients, ranging from app security testing to threat intelligence, endpoint risk and incident response solutions. In a specialized field like mobile security, talented experts are bound to be scattered all over the country, providing the company with some unique cultural challenges.

What they do to maintain their culture

NowSecure regularly brings remote employees to its Oak Park headquarters so that they can collaborate with their teams and across departments face to face. The team also embraces these summits as an opportunity to have fun together, whether that means attending industry events or going on scavenger photo hunts throughout downtown Chicago.

Why they do it

“Your culture is the unique things you do, not the same things everyone else does,” said VP of Marketing Jeff Nolan. “A growing company simply has to grow culture as new employees join, and those new things reflect who you hire as much as what you hope to be. We're a remote team so creating opportunities to bring people in for face-to-face is critical, and because social bonds don't develop quickly over distances it is critical to sponsor activities to foster social bonds that high-functioning teams depend on.”


Narrative Science uses advanced natural language generation to turn data into narratives, making it easier for companies to grasp and communicate relevant insights. Its Quill platform has a number of uses ranging from customer communications to regulatory reporting and internal compliance reporting, to name a few.

What they do to maintain culture

Narrative Science incorporates questions pertaining to its core values into the interview process to ensure that new hires are a good fit. Moreover, the company is continuously developing new initiatives to support employees personally and professionally, including a Women’s Leadership Group, lunch-and-learns, soft skills courses and meetups with other tech companies. Narrative Science also recently conducted its first employee engagement survey to garner feedback about how it can improve work experiences and to identify gaps where further support is needed.

Why they do it

“We kicked off initiatives such as our Women’s Leadership Group because there was a desire to create a trusting, supportive network of women across the company where ideas and thoughts could be exchanged,” said Director of Human Resources Katie Grinberg. “The group has been wonderful and we continue to look for ways to support each and every one of our employees in 2017 and beyond.”


ParkWhiz connects drivers in 150 cities with discounted on-demand parking spaces. The company made its debut on our top 100 list of Chicago’s biggest tech employers this year, and has been hard at work to ensure that the rapid scaling leaves its culture intact.

What they do to maintain their culture

This summer, ParkWhiz launched an employee advisory council with representatives from every department of the company to address employee-related concerns. The council’s main tasks are to promote harmony and tolerance among employees and departments, and to ensure that all employees are treated as equals and offered opportunities for advancement. The council also helps the staff engage with the broader community through projects like its Adopt A Family initiative, which was set up in partnership with Chicago Children’s Home & Aid.

Why they do it

“ParkWhiz takes culture and employee engagement seriously and the EAC is one of the many things we have in place to make sure employee happiness is a top priority as we continue to grow,” said Customer Advocate Lead Rick Foresee. “I’ve been in the EAC for three months and I’m already down 20 pounds!"


DialogTech helps companies track and analyze which of their calls are generated by their marketing initiatives, how those conversations go and how many of them turn into conversions. In doing so, they help customers optimize their marketing ad spends to acquire more customers at a lower cost.

What they do to maintain their culture

DialogTech believes that the key to building a healthy culture is hiring people who align with its core values and giving them the autonomy to do their best work. That trust is also embodied in policies like unlimited vacation, flexible working hours and evaluating employees based on their results rather than the time spent at their desks. The company also seeks to foster deliberate "over-communication" through company-wide email updates, Slack, an anonymous suggestion box and an open door policy.

Why they do it

“We are committed to bringing on smart, hardworking, ambitious, and nice individuals — SWANs,” said CMO Susan Bryant. “By hiring the best individuals, providing a fun culture that enables growth, communicating our goals and values, rewarding achievement and celebrating success, we ensure that our employees are invested in the long-term vision of DialogTech as we continue to scale.”


With its intelligent used-car marketplace, DRIVIN provides dealers with the tools they need to keep their lots stocked with cars their customers want. Having raised more than $24 million in a short two years, the company also knows a thing or two about scaling.

What they do to maintain their culture

To ensure that employees feel empowered to take ownership, DRIVIN embraces transparency as one of its core values. The staff receives updates on the state of the business at monthly company meetings where questions and discussions are welcome. DRIVIN also has a “no door policy” in its agile workspace, so an employee can stop by at a senior team member’s desk at any time to ask questions or voice concerns.

Why they do it

"We look for driven, self-motivated and engaged employees,” said CEO Kayne Grau. “Providing that sort of open, transparent atmosphere allows our employees to be independent thinkers who aren’t afraid to speak up and voice their ideas. Those are the people we pride ourselves on hiring.”


Images via listed companies.

What's your company's story? Drop us a line or tweet us @BuiltInChicago.

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