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Knowledge Institute Podcasts

  • Scaling Software Companies with Greg Head

    January 28, 2021
  • Starting a business has never been easier, but growing and scaling a startup is harder than ever. Greg Head, founder of Scaling Point and Greg’s List and 30 year veteran of the software industry, shares how he helps software companies navigate changing consumer expectations, funding opportunities, experimentation and product/service innovation as they scale… or fail.

    Hosted by Jeff Kavanaugh, VP and Head of the Infosys Knowledge Institute.

    “There's a chemistry project in every startup between the founder, their market, the current situation, their luck, the situation, their resources. That's a wonderful puzzle that is different every time.” -

    - Greg Head


Show Notes

  • 00:33

    Can you share a particularly stark example of [the] digital ceiling?

  • 01:48

    Jeff introduces Greg.

  • 04:03

    Greg explains the software industry beyond Sillicon Valley.

  • 05:51

    Can you characterize any differences in philosophies from these founders who aren't in Silicon Valley, or there's some common threads?

  • 07:39

    It's almost like it's the adulthood of the software industry, all these mature niches start to, profitable niches, that might not make someone rich immediately or grow quickly. And yet, they're good, viable businesses.

  • 08:58

    It's interesting over time, if we see that these software leaders are no longer the Jack Dorsey type of folks, and you more have this breaking the stereotype.

  • 10:08

    Are you involved in the so-called crossing the chasm phase or is it even before that, where they're trying to get to the point where they're at the chasm?

  • 12:29

    And as you're looking at companies, what are the critical success factors to get from that 20 employee, million or two of revenue, to go to that next level? What is it that allows you to get to that next level where a lot of companies fail?

  • 14:51

    You said they have to climb up the stairs and get people lined up. Does that follow the product market fit?

  • 16:23

    What about the people side of things?

  • 18:16

    Can you talk about what SaaS means?

  • 20:45

    What could a corporate larger company do to embrace the SaaS startup concepts and maybe grow themselves?

  • 22:51

    Greg describes how growing companies can turn aggressiveness and impatience into positive output.

  • 24:54

    What are some other nuggets or insights that you can share, especially that made the difference?

  • 26:48

    What is one thing that large companies aren't aware of that is essential for them to be able to do this going forward, to take advantage of SaaS and to create these new offerings and capabilities that they might be overlooking?

  • 28:21

    What's the one thing that either someone in the trenches today that's trying to get a software company going, or even that business school or engineering student who is trying to tinker on the side and really wants to launch, what is one thing that you'd leave with them to give them something to think about?

  • 29:21

    You talk about the scaling point system. What exactly is that?

  • 30:44

    Greg shares his contact information.

About Greg Head

Greg Head

Greg Head is a 30-year software industry veteran who was part of the startup-to-scale journeys of three different software companies in the CRM industry, including one IPO. He is now an active mentor, advisor, consultant, and speaker helping founders of early-stage software startups all over the world.

His consulting company is Scaling Point where he works with startup tech founders on positioning strategy, product-market fit, messaging, and scalable marketing execution. He is also the founder of Gregslist. is the curated and up-to-date list of local software companies used by thousands of founders, tech leaders, investors, and job seekers each month. Gregslist is now available for tech communities in Phoenix, Salt Lake City, Dallas, Austin, Chicago, and more cities.

Greg and his wife live in the Dallas area. They spent 23 years in Phoenix before returning to her Texas hometown in 2019.

Crossing the Chasm Crossing the Chasm by Geoffrey Moore