Skip Glass
Skip has a background that combines more than 15 years of experience as a senior executive team member running four separate startups followed by 15 years working in venture capital and investment banking. In addition to his work as an operator and venture investor, Skip has been an angel investor for over two decades. He has worked with dozens of successful software, networking and security companies.
His operational experience includes roles such as Chief Executive Officer and President of URoam (acquired by F5), Chief Operating Officer of Kiva (acquired by Netscape), VP of Field Operations at Illustra (acquired by Informix), VP of Marketing at Sybase (IPO) and trading area manager at IBM.
Skip later transitioned to venture capital where he worked with Foundation Capital, Canaan Partners, and Lightspeed Ventures. While at those firms, he worked as a Board member and Board advisor to numerous successful companies including Venafi (acquired by Thoma Bravo), ON24 (IPO), Informatica (IPO), Riverbed (IPO), SpringCM (acquired by Docusign), Cloudshield (acquired by SAIC), Tealeaf (acquired by IBM), Silver Spring Networks (IPO), MobileIron (IPO), MSDS online (acquired by ICG), Cantaloupe Systems (NASDAQ: CTLP), Guardian Analytics (acquired by NICE), Interact 911 (acquired by Constellation), Forgerock (filed for IPO), and Visier Software.
As an early stage investor, Skip has invested in several technology startups including Riverbed (IPO), Responsys (IPO), Sygate (acquired by Symantec), SleepyCat Software (acquired by Oracle), eHealth Insurance (IPO), ON24 (IPO), Elastic Beam (acquired by Ping Identity), and Venafi (acquired by Thoma Bravo).
Focus Areas
Boards
Over the years I have built a massive content library that includes a database of hundreds of documents covering engineering, sales, marketing, support, and finance functions. They serve as a foundation upon which companies can leverage the work of others to build a solid operational base of their own. Thirty years of experiences across dozens of companies and hundreds of use cases gets leveraged for insights and company scaling. There are numerous times when this content library has been able to help entrepreneurs address challenges by seeing how their peers have addressed similar issues in the past.
Q&A
Please share a bit about your training and professional background.
I have a fairly eclectic background, which helps me add value as a Venture Partner. I spent the first 10 years of my career at IBM, taking a $200 million annual revenue business unit and scaling it to $400 million in annual revenue. The next ten years were spent as part of the senior management team of four startups. Outcomes for all four companies were positive, ranging from exits of $50 million to $6 billion, within sectors like database, security, and application development.
The next stage of my career involved a move into venture capital. I was consulting with a number of VC firms when Foundation Capital approached me with an opportunity to become an Operating Partner, a new concept at the time. I spent over ten years in that role, with the majority of my time focused on helping portfolio companies to scale – bringing in strategic hires and executives, introductions to key customers, and supporting overall strategy development.
Is there a professional achievement you’re most proud of to date?
Big picture, I really value that I’ve been able to help create long-term lasting employment for tens of thousands of people and those jobs have helped them to provide for themselves and their families. I believe creation of employment opportunities is one of the key ways that venture investors should measure themselves.
This of course leads back to building scalable companies. For example, in recent years I’ve consulted with a struggling cyber security company, engaging with them to reshape their strategy and helping to put in place a new senior management team. I then had the pleasure of watching the company grow, and, after a number of years, it ended up being a $1 billion exit. That kind of shared team success is not only economically rewarding, but also fun to be involved with.
You have a lot of experience at venture capital firms. How is Celesta’s investment approach unique compared to others?
All of the partners at Celesta care deeply about the portfolio companies. I've seen the firm drop everything they're doing to help a portfolio company that is in a bind. From the very top down, at the end of the day, they are thoughtful and caring people who go out of their way to help solve problems. Whether it’s helping companies build a stronger pipeline, growing their team, or strategizing a refined value proposition. They want to provide meaningful added value for their portfolio companies. It’s the reason why I’m here.
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