An irresistible opportunity: How Jason Holmes came to launch Showpad’s Chicago office

by Michael Hines
August 24, 2018
Jason Holmes Showpad interview
PHOTO VIA SHOWPAD

To say that Showpad President and COO Jason Holmes is rooted in Chicago would be an understatement.

For more than a decade, Holmes commuted every week to the Bay Area for work, returning home to Chicago on the weekends. Needless to say, the longtime tech exec jumped at the chance to launch Showpad’s Chicago office.

“I saw an irresistible opportunity to diversify our local economy, add jobs, attract investment capital and mentor others in the space,” said Holmes.

Showpad, whose platform is designed to make it easier for sales and marketing teams to share and collaborate on content, opened its Chicago office less than a year ago and has already made some serious noise. The company raised $25 million in January and acquired sales training startup LearnCore for $50 million earlier this summer.

We recently caught up with Holmes to learn more about what it’s been like to build a tech company in his own backyard, and what he looks for when hiring.

Jason Holmes
President and COO

What was it about Showpad that initially attracted you to the company?

It was the perfect storm of an incredible market opportunity, unmatched product and an incredible team. Showpad was, and still is, seeing success in the United States and Europe, which is no easy feat for a SaaS business. Most importantly, joining Showpad offered me the opportunity to make a positive impact within the Chicago tech ecosystem.

With a teenager at home who is an aspiring software engineer, one of my requirements for my next role was to contribute to the Chicago tech community. With Showpad, I saw an irresistible opportunity to diversify our local economy, add jobs, attract investment capital and mentor others in the space.

You were the first member of Showpad’s Chicago office. Can you describe what it’s been like to build this team from scratch?

The growth thus far has been incredible. We initially set out to hire 20 people and have far surpassed that. With the acquisition of LearnCore, our Chicago team is at a whopping 100 people. And the caliber of talent we’ve been able to attract is unmatched. It’s clear that the tech ecosystem in Chicago is flourishing.

 

What challenges is your team currently tackling?

Our biggest goal is to continue scaling the company and hiring the talent necessary to support this growth. Outside of that, we’re dedicated to continuing to set the pace of innovation for the sales enablement industry. We’ve delivered some incredible new solutions recently, from Shared Spaces, which are microsites that bring the sales process out of email, to support for 3D models and augmented reality.

We’ve created a space where employees are free to be themselves and use their talents.”

 

How does the culture of the local office both reflect and differ from Showpad’s broader culture?

It very closely reflects the culture in all our offices and centers on two key principles: be authentic and aim for maximum impact. We’ve created a space where employees are free to be themselves and use their talents to drive the company forward. One of the best parts about the Chicago office is that, as we’ve grown, we’ve kept the scale-up mentality. Everyone at the company understands their role in contributing to the greater vision.

 

Speaking of growth, what roles are you hiring for and what do you look for in candidates?

We’re looking for talent on a variety of teams, from sales and marketing to engineering, finance and operations. We’re looking for good-natured, authentic ass-kickers. We like to hire people with a strong work ethic who take ownership and get the job done, but who also take the time to give back so the entire organization can grow. We operate in a fast-paced, performance-driven environment, so our ideal candidates aren’t afraid to stretch themselves and stay focused on impact and growth.

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