Skip Glass 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.
Beyond some of the obvious concepts – hire well, find product-market fit, grow profitably – what are some critical factors needed in order to scale a company?
I think it is very important from the outset to build up a set of advisors who know your market and product. They help you to define your initial and future products to address real customer problems. Oftentimes those advisors can become customers because they’re helping you to craft the value proposition with their unique lens on your space, and the product starts looking like something they want to deploy within their own company. So they’re helping you understand the market, but you’re also building an advantage for your sales team in the early days.
Also, I like to remind founders that you can't be all things to all people. A good practice is starting with a focused product, but within a broad-based platform, establishing a product you can expand over time. Often, young companies in the deep tech space have a great understanding of their market and they create a product that is very thorough in its capabilities, features, and functions. But it is so broad or complex that it becomes difficult to implement. A land and expand strategy helps you maintain a low barrier to entry.
It can be very lonely running a startup and a CEO needs someone they can turn to for help through the challenging times. The best investors are the ones who will roll up their sleeves and help when the times are tough and the future is cloudy.
What notable trends are you seeing in the spaces you’ve worked, such as enterprise software, security, or data storage?
Across the board in software, artificial intelligence or machine learning have become essential for any company that's new to market to incorporate into their products. AI and ML provide a level of analysis, automation, and computing power not seen before. Software markets are heavily saturated and you must bring something that is different or new. This is also true for hardware and services companies. Atonarp, Calumino, and Recogni and great examples of companies introducing AI to new sectors (molecular imaging, thermal sensing, and automotive, respectively).
Companies also need to be thinking much more globally in their makeup from day one – looking to India, Eastern Europe, South America, Canada, etc. Very few companies have 100% U.S.-based teams anymore. With that shift, you need focused effort in working well as a distributed team, creating a culture that everyone wants to be part of so people are still operating as a cohesive team.
How do you believe an investor can best support a founder working to grow an early-stage company?
A good investor is with you through the good and the bad. It's always easy to make a call to your investors when you have a phenomenal quarter – but I want to be the person my portfolio companies know they can call when things don't go well. You just had a bad quarter, lost a major customer, or had a key executive give notice: those are the calls I want to get.
It can be very lonely running a startup and a CEO needs someone they can turn to for help through the challenging times. Founders need to know they have someone to reach out to, even if it's just to vent. And hopefully in the discussion I am able to provide some guidance that can help them solve the problem. The best investors are the ones who will roll up their sleeves and help when the times are tough and the future is cloudy.
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.
What do you enjoy most about your role as a Venture Partner at Celesta?
It's quite rewarding at this stage of my career to mentor founding teams who are out to make a significant impact in their sectors. At Celesta, I am really enjoying working closely with companies like Baffle and Deep North. I get a great sense of satisfaction in being actively involved – helping to set long term strategy, hiring key senior executives, putting in place effective and efficient processes, evaluating marketing and sales effectiveness, and assisting with architecting modern cloud infrastructure operations.
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.
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.