CEOs to know: 5 local leaders on success, challenges and the future of Chicago tech

James Risley

Successful tech companies usually have many great leaders. A technical founder may provide the programming prowess to power the product team, while a VP of sales ensures sound sales strategy. But companies need someone to lead the leaders, making sure the company moves as one and acting as a public face of the company.

We talked with five CEOs this week about how they define success, what advice they’d give their past selves and what they love about the Chicago tech scene. Read on below for the highlights, and click the links to read the full Q&A sessions.


Ashish Rangnekar offers his past self advice:

It takes time to build something impactful and worthwhile. ... I would advise my past self to start off with a 10-year plan, not a two-year plan. I would tell him to not try to save money on “talent” and hire the smartest people right away. And of course, ensure you have a sustainable product/market fit before you even utter the word scale!

Read more here.


Bill Ness on the resilience of the Chicago tech scene:

Ten years ago, our company was a boot-strapped real estate startup operating out of my living room. Even though 2007 proved to be one of the single worst years to start a real estate company since the great depression, we still haven’t taken a dime from any investors. Yet we’ve grown into a profitable organization of over 50 employees and 400-plus partner agents. I think there are a lot of companies like ours in Chicago, and it’s great that not everyone in this tech community has the mindset that you need millions in venture capital money to be considered a success.

Read more here.


Kimberly Miller has a three-pronged approach to team building:

I focus on education, environment and earned opportunity. Education comes first. Everyone has an area they can improve upon, and everyone is a subject matter expert in something. ... I also don’t believe leaders can directly motivate people, but I do believe they can build a motivating environment. ... Lastly, earned opportunity. I believe there are no limits for my employees. They can and will accomplish more than they could ever imagine.


Kevin Akeroyd on the importance of measuring success:

Success should be defined. It should be clearly defined, then it should have measurements, metrics and milestones on regular, consistent basis to track against that success. And that should be visible to the audiences. As much transparency as humanly possible for the employees should be the rule of thumb.

Read more here.


Victor Ciardelli on how the housing crisis showed him the power of his company:

The mortgage industry and housing market has had its share of ups and downs since I started the company in 2000. We survived the biggest housing downturn in decades – and I learned Guaranteed Rate can persevere under tough circumstances. You don’t really know a company’s resilience without tough challenges along the way.

Read more here. 


Images via featured companies

What other CEOs do you want to know? Let us know with a tip or a tweet @BuiltInChicago

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