These Chicago Tech Companies Have Advice for Founders Scaling Startups

May 22, 2020
The Chicago Skyline
PHOTO VIA PEDRO LASTRA FOR UNSPLASH

Getting a tech company off the ground, acquiring customers and courting venture capitalists isn’t easy. Unfortunately, things don’t get any simpler after companies find their footing. Scaling a startup can be as tough as launching one, as CEOs find themselves answering to investors and making decisions that impact hundreds of employees.

Although there’s no playbook for how to scale a company, founders aren’t left to fend for themselves. Chicago is full of tech companies that have survived the growing pains and have shared tips, in interviews and in blog posts, about how to overcome them.

 

Keeping the Startup Spirit Through Scale

Some tech companies spend years searching for product-market fit only to find there’s not a need for their services. CraftJack is not one of those companies.

The company, which connects home contractors with local and vetted leads, launched in 2011 and was acquired by HomeAdvisor one year later. HomeAdvisor is in turn owned by IAC, an internet powerhouse with more than 150 digital companies in its portfolio, including OkCupid, The Daily Beast and Vimeo. Instead of smothering CraftJack’s startup spirit, VP of Operations Noah Mishkin said the resources provided by HomeAdvisor have put the company in a “sweet spot.” 

“We can provide the resources, benefits and compensation that are appropriate and competitive — and often challenging to supply during the startup phase — without sacrificing any of the startup spirit,” Mishkin told Built In last year.

Mishkin said maintaining the startup spirit is about more than providing competitive perks. As the company has scaled, he said the team has made it a point to ensure that empathy remains at the forefront of its culture.

Human empathy and understanding can’t be defined by a single benefit.”


“The most important element that should always be paramount, regardless of how quickly a startup scales or how large it becomes, is human empathy and understanding,” said Mishkin. “Human empathy and understanding can’t be defined by a single benefit. Rather, it’s demonstrated through meeting the individual needs of employees.”

 

Maintaining Focus During Rapid Growth

Flexport has experienced plenty of growing pains in its relatively short history. The tech-enabled freight forwarding and customs brokerage has raised more than $1 billion in funding, made 1,800 hires and opened 15 offices around the world since opening in 2013. While many technologists dream of working at a high-growth startup, scaling so quickly means a team’s structure and goals often shift from quarter to quarter.

Flexport Midwest GM Scott Holloway said his secret for keeping his team on track during periods of rapid growth is simple: talk to them.

Tight feedback loops are critical during periods of scaling.”


“The best way to keep people focused during perpetual change is by establishing and communicating clear priorities and OKRs that teams can work toward,” Holloway told Built In earlier this year. “You then want to get out of the way, giving your teams enough flexibility to experiment and solve problems as they see fit in the service of those objectives.”

But it’s not enough to issue marching orders. To ensure strong communication during periods of rapid growth, Holloway said it’s essential to ensure that employees are able to provide feedback to leadership.

“Tight feedback loops are critical during periods of scaling,” Holloway said. “To drive these feedback loops, ensure that the people closest to your customers are empowered to solve problems and share learnings upward. Similarly, all levels of the organization need to be receiving clear, consistent communication from leadership.”

 

Taking a Measured Approach to Tech

DoorDash, like many companies, is invested in machine learning. However, the on-demand food delivery giant takes an intentional approach to implementing ML technologies. Alok Gupta, head of data science and machine learning, detailed the strategy in a company blog post. 

Upon joining DoorDash, Gupta’s first order of business was to draw up an “ML charter” spelling out the company’s vision and principles.
 

The Principles of Gupta’s ML Charter

  • Democracy: Everyone can build and run an ML model given sufficient tooling and guidance.
  • Talent: We want to attract and grow the best business-impact focused ML practitioners.
  • Speed: If a cost-effective third party ML solution already exists then we should use it.
  • Sufficiency: If a function (typically engineering) can implement a good-enough ML solution unaided then they should do so.
  • Incrementality: If a function (typically data science) can add enough incremental value to an ML solution then they should do so.
  • Accountability: Each ML solution has a single technical lead acting as the technical decision-maker.


“The idea behind the vision is that we only want to build ML where it is actually needed — not where it might be interesting,” Gupta wrote. “This ensures the return on an ML practitioner’s time is super high for the business. The principles ensure that we can hire the best people and that we are as efficient with our talent as possible.”

In addition to the charter, Gupta also created a council made up of senior team members from across the company with deep machine learning experience. Their responsibility includes reviewing and approving job descriptions for ML engineers and data scientists, deciding whether to build or buy technologies and approving requests for new implementations of machine learning from across the business. 

By laying this foundation, Gupta is able to both to guide the team’s work, ensure DoorDash is making the best use of machine learning and attract a diverse range of talent.

“We want people of all different backgrounds and titles with ML expertise to come in and feel able to do their best work,” Gupta wrote. “So we chose to do things differently, more inclusively.”

 

Helping Employees See the Big Picture

As companies grow, it can be difficult for employees to know how their work impacts the business. That’s especially true of large companies with teams spread across the globe, like Ensono, whose services help businesses move their operations from mainframes to the cloud. Ensono has more than 2,000 employees spread across offices in the United States, Poland, the United Kingdom and India.

In a company blog post, CEO Jeff VonDeylen wrote that Ensono helps employees keep the big picture in focus by sharing news of client wins throughout the company.

“Everyone on the team, regardless of their role, has the right to reflect on and take some pride in these achievements where we, along with our clients, have been part of a team that made it happen,” VonDeylen wrote. “Who wouldn’t get excited about some of the great things our clients do with our help?”

Everyone on the team, regardless of their role, has the right to reflect on and take some pride in these achievements.”


Client wins are important, but not everyone at Ensono works in a client-facing role. VonDeylen wrote that internal wins are celebrated equally, like when the company replaced the power supply at one of its data centers. The team that replaced the power supply helped lower Ensono’s carbon footprint, and VonDeylen wrote that their accomplishment was broadcast to the entire company.

“By communicating these things regularly to the whole team, and celebrating them together in out of work activities, we maintain a high level of positive excitement that has played such an important part in our transformation, and which continues to do so today,” VonDeylen wrote.

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