Stride Is Starting a New Chapter in Chicago. Here’s What the Future Holds.

With new leadership, a refined business model and a move to Chicago on the horizon, Stride is set for reinvention.

Written by Olivia McClure
Published on Jul. 20, 2021
Stride Is Starting a New Chapter in Chicago. Here’s What the Future Holds.
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Stride Consulting CEO Ken Judy doesn’t consider himself a thought leader. 

Judy laughed when recalling that there was once a time when he aspired to be one, but that idea no longer aligns with his current approach to leadership. For him, being in a position of power doesn’t make him the sole instigator of change at his company. That’s because he prefers to let his teammates drive transformation alongside him.

“The way you create impact is by helping other people create impact,” Judy said. 

Indeed, magnifying the impact of others has been a defining feature of Stride since its founding in 2014. For the past several years, the software consultancy has been a staple of the NYC tech scene, helping brands like Casper, Spotify and Codecademy develop software products and ultimately thrive within their industries. 

As Stride acclimated to a new reality during the pandemic last year, the company simultaneously entered a new phase in its growth journey. Over the past 18 months, the team has taken a closer look at its business model, values and more in an effort to redefine the way they deliver value to clients and empower their own employees. 


Stride Chicago tech company


A New Way to Serve

According to Judy, Stride’s services were largely founded on “elite staff augmentation” prior to the current phase of reinvention, which meant the company’s consulting developers were embedding on client sites in an effort to deliver software alongside their teams. Now, the company is focused on being more intentional about the objective they’re trying to accomplish within their relationships with brands and relying more on autonomous teams to get the job done. 

“It's about really understanding what clients want in their business and working closely with them to make sure that they can own and maintain that software after it’s been built,” Judy said. “We're trying to focus on being incredibly effective and good at what we do while having a really tight, collaborative relationship with clients.” 

For Principal Product Manager Consultant Rob O’Brien, this newfound approach to client relations creates a win-win situation.

“From a Stride employee perspective, it makes the job more exciting and meaningful,” O’Brien said. “From a client perspective, it also justifies the cost.”

By agreeing upon a specific outcome upfront, such as attracting 100,000 new users to a product, it makes it easier for clients to recognize the value Stride brings to the table, O’Brien said. 

While Stride’s new business strategy may be a focal point within the company’s growth plans, it’s far from the only transformation taking place at the organization.  


Stride Chicago tech company


A Move to the Midwest

For many companies, the pandemic eliminated the need for local hiring practices. With entire teams working remotely worldwide, organizations began looking for talent outside of their respective regions. 

At Stride, the remote-work era convinced the team that NYC wasn’t the only place that held opportunities for the company. That’s partly why the company chose Chicago as its new home. 

As Stride scaled, finding the right people to facilitate rapid growth was a priority, and the Windy City’s high concentrations of diverse talent stood out. “It seemed like a good place for us to find a community,” Judy said. 

According to Consulting Software Developer Madelyn Freed, Chicago is home to the kind of professionals that align with Stride’s overarching mission and values. 

“I think it’s an amazing city for the kind of Striders we want to attract: people who care a lot about doing quality work but also care very much about quality of life,” Freed said. “I've known a lot of Chicagoans who are really dedicated to that.”

While Chicago boasts the type of talent the company is looking for, the city also holds greater possibilities from an operations perspective. In O’Brien’s mind, Stride’s Midwestern move presents the perfect opportunity to break outside of their “New York bubble.” 

“It’s going to be great to have new ways of thinking and working and just different perspectives on things, especially if we can bring that to clients as well,” O’Brien said. 

Stride Chicago tech company


A Mission Reimagined

With a move to Chicago on the horizon, Stride is reaching a pivotal moment within its journey.  In order to achieve its ambitious goals, the company decided to rethink its founding mission. 

Judy said this new overarching vision, which is to “unlock human potential by engineering better systems,” is meant to acknowledge the reality of the world and embolden the company’s effort to “build a brighter future for the planet and upcoming generations.” According to Judy, this potentially 15-year goal is a roadmap of the company’s plans to influence the globe. 

“The way we've tried to envision that happening is by building a place where we support and develop Striders into leaders and great, happy people focused on being really good at what we do with our clients, so that we can compete for work on that emerging portion of the capitalist economy centered around doing good in the world, governing businesses well and focusing on net benefit to ecology and contribution to society,” Judy said. 


Staying Connected While Apart

Like many companies, Stride has had to find ways to make remote work more manageable for its employees. That’s why the company encourages Striders to take part in things like remote pairing, virtual coffee chats and after-work gaming sessions to help them stay connected. 


According to Freed, Stride’s dedication to social equity goes beyond their mission statement. In fact, the organization’s commitment to its people can be felt across its company culture. 

“When I was talking to teammates about our values, a lot of people would say, ‘I know I get special treatment, but does everyone else feel the same way?’” Freed said. “Every person feels that they are being cared for in exactly the way that they asked.”  

Stride also offers various social groups for employees to share their passions, whether that’s fighting against racism or refactoring code, all of which hearkens back to the passion that defines Stride’s people.

“If there’s one thing you can count on Striders to do, it’s to care about everything,” Judy said. 


Stride Chicago tech company

Building a Brighter Future 

As Stride embraces change in various forms, the team is looking to encourage communication and relationship-building at the company, with Freed at the helm of this ambitious objective. 

“My biggest goal is to help other people breathe easier in their lives,” Freed said. 

In her mind, technical and soft skills should go hand in hand, which is why she wants to give employees equal access to opportunities that allow them to strengthen their workplace acumen. 

“If there's one thing you can count on Striders to do, it’s to care about everything.”


For O’Brien, “constant evolution” defines the ethos of Stride, which is what makes him eager to tackle the future. 

“What excites me is actually getting new Striders in here to challenge what we’ve been thinking and what we’ve been doing,” O’Brien said. “As excited and proud of the company as we are, when you get someone fresh in, they start to point things out and make it better.” 

Seeing this commitment to helping others thrive is what motivates Judy to lead the company into its next chapter. 

“Working with people like Rob and Madelyn, and seeing what they're capable of and helping them do more and be more: That is entirely why I'm in this,” Judy said. 


Images via listed companies. Responses have been edited for length and clarity.

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