How Sri Pangulur went from building his own syndicate to co-leading Mayfield’s Series B investing practice

Sri Pangulur, partner at Mayfield

Sri Pangulur embraced the after-work hustle to invest in early-stage startups. By day, he was a CloudFlare sales executive. But after work, he spent up to 15 hours a week attending hackathons, meetups, and venture events to source the next hot startup.

There were many times when Pangulur just jumped straight into chasing a deal after a long day of work. He recalled when his CloudFlare team closed a high-stakes deal late on a Friday at the end of a quarter. But instead of celebrating with this team, he met with a hot seed stage company.

“I was trying to get into a pretty high profile seed round as well that had very little allocation left in the deal,” he said, adding that he had to really beg to get a spot. After chatting with the CEO until midnight, Pangulur got into the deal.

He started his side hustle investing efforts by writing small checks but soon found himself flooded with deal flow. He decided to formally create a syndicate called Overtime VC, investing up to $250,000 in seed and Series A rounds. Through Overtime, Pangulur invested nearly $20 million in 65 companies, with a focus on enterprise infrastructure and apps. Among those startups in his portfolio were Abnormal Security, currently valued at $5.1 billion, and Airbyte, now valued at $1.5 billion.

Pangulur met Mayfield Fund managing partner Navin Chaddha through investing. In 2016, the pair met at a tech networking event and kept in touch, discussing industry trends and collaborating on deals.

“This guy will go places,” Chaddha recalled of his first impressions of Pangulur. Seven years later, Pangulur joined Mayfield as a partner.

The path to VC

Born in Michigan and raised in Ohio, Pangulur grew up in a family of doctors. He initially was pre-med at Case Western University, intending to follow in his family’s footsteps. But as the dot-com bubble brewed in the late 1990s and early 2000s, Pangulur decided to pursue finance.

After college, he worked on the M&A team at KeyBanc Capital Markets and then joined Lehman Brothers, focusing on software investments. He also got a taste for venture capital at TeleSoft Partners, an early-stage firm, before jumping to the operating side.

Over the next decade, Pangulur worked in a range of sales roles, ultimately landing at CloudFlare to lead one of the company’s first sales teams in North America. At CloudFlare, he gained experience selling to CTOs and CISOs across various companies, from startups to the Fortune 500.

He also continued investing through his syndicate, Overtime VC, and brought these firsthand experiences to the founders he advised.

Pangulur helped founders with recruiting, answering questions like, “Who’s that first VP of sales you should hire? What does that profile look like, and how does that evolve over time as you scale?”

The Overtime business kept scaling, and then he said he pondered whether he wanted to work at one company most of the time or work with many entrepreneurs full-time rather than on the side.

“That’s when I had the realization that maybe I should do venture, ” he said.

‘Cooking’ at the Series B

Pangulur began raising his own venture fund based on the success of his syndicate fund, Overtime VC. But a few months into fundraising, he received an unexpected offer from Tribe Capital, a VC firm that uses data science to invest in crypto and software startups.

With Tribe’s $1.6 billion assets under management, Pangulur was drawn to the idea of writing bigger checks and advising founders as a board member. “I decided to take that jump,” he said.

At Tribe, Pangulur built out the firm’s software investing practice. With a focus on enterprise infrastructure and software-as-a-service, Pangulur led six deals, including the sales intelligence startup Apollo, which is now valued at $1.6 billion.

Last September, Pangulur joined Mayfield. “I wasn’t actively looking to make a move,” he said, but after working with Chaddha over the years through Overtime and Tribe, Pangulur was intrigued at a new opportunity to join the firm.

He and Chaddha met for an in-person catch-up in the fall of 2022. “I went into the meeting thinking it would be a normal catch-up,” Pangulur said. “But that’s when he told me about the opportunity he sees in the market for the Spring Fund.”

Mayfield is one of Silicon Valley’s oldest venture firms, with $3 billion in assets under management. While the firm has traditionally invested at the seed and Series A stages—it announced its seventeenth fund of $580 million focused on seed and Series A in 2023 — there was still a gap in the market for investment.

“Our Select/Spring Fund is aimed at founders who are beyond the ideation stage, with a team, early product-market fit, and initial market adoption,” said Chaddha. “Their financing stage is typically at the A prime or Series B.”

The firm first raised a $125 million Spring fund in 2016 to invest in its breakout portfolio companies for follow-on investments. Last year, Mayfield raised a Select III/Spring Fund of $375 million, aiming to focus the vast majority of its investments on new outside opportunities.

Pangulur was brought in to co-lead the firm’s Select/Spring fund with Chaddha.

“He came from a sales background,” Chaddha said. “He’s investing at a stage where there’s already product and customers— his go-to-market expertise is his superpower.”

This is the stage “where you need to get in the weeds, work with the founders, help them do some of that cooking,” Pangulur said.

Earlier this month, Pangulur announced two new investments he led: a $25 million Series B for billing infrastructure startup Orb and a $28 million Series B for TeamBridge, a workforce operating software startup.

Despite the overall tepid funding market, Pangulur is optimistic. “The Spring Fund is a relatively new initiative,” Pangulur said. “I want us to be one of the first calls that a lot of founders call when they’re hitting that inflection between being at inception early stage to finding those early elements of product market fit and go-to-market repeatability.”