Why 5 Chicagoans picked the tech scene over corporate life

March 29, 2017

“If we don’t like something we’re doing, we change it. No questions asked.”

That’s not something you’d often hear at a corporate office, which is a big reason why employees are flocking to the tech scene. But the lack of red tape isn’t the only big advantage growth-stage tech companies have over your typical nine-to-five. We spoke with five Chicagoans who made the leap to learn more about why they went for it — and how their experiences lined up with expectations.


Target Data helps companies unlock the insights hiding within their customer data and boost their bottom lines. Director of business development Anthony Pauley, who joined the company by way of Dow Jones, was drawn in by the opportunity to help mid-size companies compete with major corporations.

What drew you to make the move from Dow Jones to a growth-stage tech company?

What excited me most was being a part of something unique to the marketplace with regard to marketing services. The ability to provide midsize companies with the same services as larger companies, but with a more intimate relationship, was a huge selling point. These companies have a lot of very bright individuals who just don't have the same capabilities as larger organizations due to their size, and we can help fix that.

What are the biggest differences between Target Data and the other places you’ve worked?

The excitement of the unknown and the possibility of building something great. Every day there's a new challenge or something that we haven't faced before, and we get the opportunity to figure out a way to overcome it. Plus, the lack of red tape means we can think more outside the box instead of having a "this is how we’ve always done it"-mentality.

Has anything about the move really differed from your expectations?

There are growing pains as we continue to develop and scale our business, which certainly can be challenging at times. But on the flip side, that means we can figure out new ways of overcoming those pains. The best part, though, is that everyone works together to accomplish our organizational goals. There is a team atmosphere and fun environment that helps us drive more collaboration as a company.


Sertifi makes sales processes paperless through services like electronic signature capture and payment solutions. Having used Sertifi at his former role in advertising sales for a newspaper publisher, account executive Brent Bergandine was excited by the company's product and growth potential.

What drew you to make the move from a major publisher to a growth-stage tech company?

My previous company actually used Sertifi so clients could electronically sign their sales contracts. I loved the idea that Sertifi was a growing technology company located in Chicago. I already knew how well Sertifi’s solutions worked, and I saw that they had many high-profile customers. I was confident about the great opportunity to build my sales career by representing an excellent company.

What are the biggest differences between Sertifi and the other places you’ve worked?

The collaboration among everyone has definitely been amazing. With a large company, you will rarely see the various departments and management teams come together to solve a problem or bring on a new customer. A smaller organization can also be much more flexible if changes need to be made to a product.

Has anything about the move really differed from your expectations?

The only surprise has been how quickly Sertifi has grown since I joined the company! We’ve brought on several new employees in various departments, and we seem to add clients almost daily.


An online marketplace for new and used music gear, Reverb helps musicians hone in on their perfect sound. That mission resonated with director of marketing Dan Abel, whose previous job was to grow YouTube’s presence in the music industry.

What drew you to make the move from YouTube to a growth-stage tech company?

The cause. The energy. The sweat. The ability to make an impact. From my first conversation with the team at Reverb, I saw the opportunity to sit beside more than 100 musicians who realize Reverb’s movement to positively inspire and change the music industry. We are bringing music to more places, we are making it easier to learn to play music and we are eager to discover more ways for musicians to connect and find their dream gear. And I get to lead and grow a team that is integral to achieving those goals.

What is the biggest difference between Reverb and the other places you’ve worked?

While there are certainly opportunities at large companies to take ownership of projects and initiatives, smaller and younger companies can provide more open-ended and entrepreneurial opportunities to lead at all levels. The responsibilities are bigger, but so is the direct impact you’re able to make on the company’s culture, strategy and bottom line. At Reverb, in particular, hierarchies are essentially non-existent — whether you’re an intern or a director, you’re expected and encouraged to voice and act on your ideas and opinions.

Has anything about the move really differed from your expectations?

While I expected the environment to be fast-paced, I never anticipated the speed and aptitude of the team to embody an Aaron Sorkin script. Every day is a sprint, but it's exhilarating. Further, at a smaller company, there’s a huge opportunity to proactively improve everything from newly introduced ideas to longer-standing processes and policies. If we don’t like something we’re doing, we change it. No questions asked. That’s pretty motivating.


Veritas Health publishes comprehensive, doctor-authored medical content for patients with chronic pain and musculoskeletal conditions. For visual designer Karyi Hennessey, whose resume includes jobs an ad agency, the Chicago Tribune and Reader’s Digest, ownership opportunities were a major attraction to joining the company's team.

What drew you to make the move from Reader’s Digest to a growth-stage tech company?

I was excited to be a part of tight-knit team where my design choices would make a big impact. My design decisions could be launched almost immediately and be exposed to user testing and feedback quickly.

What is the biggest difference between Veritas Health and the other places you’ve worked?

Ownership. In a small organization, the work is never ending. It is up to each employee to determine which changes can make the biggest impact and decide how best to implement those.

Has anything about the move really differed from your expectations?

My passion for the work has really surprised me. In a large organization, there are a lot of hands in the pot on every project. Within a small organization, you become the decision maker about your work and feel a real attachment to the influence you can have on the final product — as well as those around you.


Supernova Companies builds software for financial advisors. Its primary product is a customizable lending platform that lets advisors make low-interest loans to clients, using their portfolios as collateral. Chief Technology Officer Jenny Sun, who is a Morningstar veteran and former financial industry consultant, joined Supernova for the opportunity to have a big impact on a young organization.

What drew you to make the move to a growth-stage tech company?

I am inspired and truly believe that we are going to change consumer debt and bring lower rate financing to millions of people.

What is the biggest difference between Supernova Companies and the other places you’ve worked?

I feel like I am making a difference every day. Whether within the organization or outside of it with clients and financial advisors, the impact feels tangible. I have really enjoyed building something cool from the ground up.

Has anything about the move really differed from your expectations?

It is amazing how many hurdles we need to overcome on a daily basis and how fast we need to adjust the direction. The workload can be a little crazy at times, but no matter how hard it gets, it never ceases to amaze me how fun this whole thing is.


Images via participating companies. Answers have been edited for clarity and length.

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