Sierra Ventures: How This Venture Firm Helps Entrepreneurs Grow Companies At The Early-Stage

By Amit Chowdhry • May 11, 2023

Sierra Ventures is an early-stage venture capital firm investing in the future of enterprise, healthcare, and infrastructure – which currently has about $2 billion in assets under management. To learn more about the firm, Pulse 2.0 interviewed Sierra Ventures’ managing partner Tim Guleri.

Tim Guleri’s Background

Tim Guleri is a former serial entrepreneur who built two successful software infrastructure companies: Scopus Technology (IPO in 1995) and Octane Software (M&A – Epiphany $3.2 billion). And Guleri joined Sierra Ventures as Managing Director in 2001, focusing on Big Data and Artificial Intelligence. After joining Sierra, he invested and helped Sourcefire and MakeMyTrip go public and has been responsible for several M&As. Guleri holds a BA in Electrical Engineering from PEC University of Technology (India) and an MS in IEOR/Robotics from Virginia Tech. His passion (outside of his family and companies) is soccer.

“I’m an entrepreneur turned venture capitalist. My journey to entrepreneurship was really anchored in two early-stage companies. The first one was a company called Scopus, where I was one of the first employees. Scopus was in the business of customer support software. I joined them about six months after the company got started. I joined in a technical role, but then pivoted into sales and ultimately into product management. We were lucky to catch the Customer Relationship Management (CRM) wave,” said Guleri. “The business grew to about $120 million in revenue and went public in 1995. Right after going public, we sold to a large public company called Siebel Systems for $750 million.”

So at that point, having seen how to build a company and scale a company in close proximity, Guleri caught the entrepreneurial bug.

“That gave me the confidence to branch off on my own. I started my first company, Octane Software, in my basement. We did consulting for the first year, but we built an incredible product and then started to raise venture capital and scaled that business,” added Guleri. “It was also customer service software but focused on banking and telecom. Later, just after we started the process to go public, we got approached by a public company called Epiphany to sell the company. I sold Octane to Epiphany for $3.2 billion, which was a great outcome for employees, customers, and investors.”

Evolution Of Sierra Ventures’ Thesis

How has Sierra Ventures’ thesis evolved over time? “I think our thesis has been shaped over the last 40 years that Sierra has been in existence. Peter Wendell founded the firm and was one of the pioneers of venture capital. As a result, Sierra’s name has been associated with the founding and evolution of venture capital here in the Valley,” Guleri replied. “The first phase of Sierra was around becoming the capital of choice for industry disruptors. We were the first money into Intuit, which is one of the foundational companies in personal finance. We also were the first investor in companies like Stratacomm, which became a core of Cisco, the disruptor in enterprise networking technology, and Teradata, which was one of the first big global data companies. That was the first incarnation of Sierra, which lasted about 30 years.”

Plus there was a second chapter of innovation starting on the back of the internet – which is when Sierra shifted its focus to solely invest in early-stage ventures.

“We’re now specializing as a firm on the second cycle of innovation behind the open internet, deep tech, cloud computing, and AI as our four major themes,” Guleri pointed out.

Significant Milestones

What have been some of Sierra Ventures’ most significant milestones? “Our first fund was established in 1982, and the first couple of funds consisted of capital from friends and family. The first significant milestone was Fund 3 when Sierra started taking institutional venture capital. The next significant milestone was when the firm expanded beyond the founding team, which was during our Sierra Fund 7 in the mid-1990s,” Guleri noted. “That strategic move was a huge success for us. This carried forward until around 2012 when the baton was passed to our current leadership team. We focused even earlier after 2012  (seed and series A investments) in early-stage B2B which will now power the next 30 years of Sierra in support of these entrepreneurs.”

Customer Success Story

When I asked Guleri about a specific investment success story, he cited a portfolio company based in Philadelphia called Phenom. “Phenom encapsulates all that Sierra stands for and envisions as we look toward the future. We love big markets and support founders that innovate in those markets. With respect to Phenom, I think the future is still to be written, but it has had a very strong start. Phenom is a recruiting platform for the largest enterprises in the world. It was founded by two brothers and its mission was and remains to generate a billion jobs for people,” Guleri explained. “In 2015, on the back of this noble mission, they chose us as their first institutional partner. Since then, the company has mushroomed into a market leader with more than 600 global customers. We believe Phenom will become an independent company over the next few years. We believe this was a successful investment because we invested in a large market that is expanding quickly and bet on the right team. We also invest in teams that are mission-driven and who want to build a foundational company independent of location. Phenom was that founding team. We also invest in foundationally different technologies that can wait and pass the efficiencies on to the customer. In this case, the disruption was all around AI and how that would enter the application stack.”

Industry Focus

What are some of the industries that Sierra Ventures is focused on? “We are an early-stage venture firm investing in seed and series A startups, focusing on the future of the enterprise, healthcare, artificial intelligence, commerce, and infrastructure,” Guleri replied.

Differentiation From Other Firms

What differentiates Sierra Ventures from other firms? “At Sierra, we pride ourselves on being more than just capital to founders. We are often the first call at those moments in an early-stage founder’s life when they need help,” Guleri concluded. “I will always be an entrepreneur at heart and our team’s first instinct will always be to roll up our sleeves and help. I think this type of culture is challenging to execute at larger firms, but with a tight-knit team like Sierra, where everyone was a previous operator, we thrive on the opportunity.”