Driven: How Did I Get Here Ep.14 – Software to CEOs: The Art of Scaling Up

Greg Head, strategic growth advisor, speaker and writer, talks with host Justin Gray about how he got his start in the software business, qualities he looks for when connecting with early stage founders and what every entrepreneur should know as they prepare for growth –– all on the the latest episode of Driven: How Did I Get Here?

What are you involved with right now?
After 30 years in the software business, I’m now advising CEOs of growing companies and consulting when they get stuck in their growth phases. These are typically CEOs of companies in the $1M – $10M range.

Let’s go back to the beginning. What did you want to be when you grew up?
I wasn’t sure, and I think in high school I didn’t want to grow up at all. I was an undeclared major at the University of Iowa for a couple years until I fell in love with business and economics. I wasn’t sure about software or being in sales and marketing or even what it meant to help grow companies. In some ways, 30 years ago it was only the misfits who got in the software business.

What happened after college?
After college I headed to Chicago to look for a “real” job. A friend of mine invited me to work at this retail store called Egghead Software, which was one of the fastest growing companies in America at the time. ACT! had just been created and most salespeople didn’t even use computers at that time; they had shoeboxes of business cards. But a few salespeople were starting to use software and discovered they could sell more because they used software like ACT!

At the time, ACT! and companies like Microsoft and Intuit used to send their employees to the Egghead stores to do demo days. And all of a sudden there was one Egghead store that was selling 10x more ACT! than anybody else. It was because I had taken it under my wing and taught everyone how to sell it, so I came up on their radar.

Everybody in my family was waiting for me to get a real job, and then I joined this scrappy software company at a time when everyone thought salespeople would never use software. But, 30 years later, salespeople definitely do use software. That’s where opportunities are – getting in early when it looks crazy and then it becomes obvious years later.

Is there something definitive you can point to that successful organizations had during the growth phase that failed startups didn’t have, other than money?
Money is a reflection of it, not the cause of it. There’s a myth you have to be the smartest person with the biggest degree and have the most money, but really who finds success is someone who really cares, thinks big and never lets go of the dream. It’s the people who can overcome the 100 things that would kill most other companies in their growth path. People underestimate the tenaciousness it takes to scale a company. There’s a science to it but it’s not rocket science.

Is there one piece of advice you typically share with CEOs?
It’s way harder than you think it’s going to be so don’t give up when you bump your head a few times. Also, I talk to them about the focus challenge. Many small companies are many things for many people as they get up and running and try to survive. But people don’t want many things – they want the best thing for them. So companies that go through a growth spur tend to go through a phase of narrowing so the world hears them and they can execute best. I compare it to Chipotle owning the burrito.

Tell us about Gregslist?
Gregslist started from me just being out and meeting people in the software community in the Valley. One day I looked at my notes and realized there must have been over 100 based here. People didn’t believe there were so many. So I published a list of 129 SaaS platform and app companies to my website two months ago. Now there’s 230 on the list because I update it weekly and keep finding out about more companies that are here. They make up 20,000 jobs in Arizona, half a billion in funding that’s been visible. There’s just a ton going on. So far 10,000 people have visited the page and now they can click on links for jobs, investors know where to find software companies and founders know where to connect with each other. I recently made a map so people can know who’s next to them so they can make connections and come together.

To connect with Greg Head, connect on, LinkedIn or Twitter.

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