Venture capital firm Bessemer taps former SendGrid CEO to co-lead investments in growth startups

After taking his email marketing company public and steering it to an acquisition by cloud communications company Twilio in 2018, the former CEO of SendGrid is now joining the venture capital firm that was originally both.

Sameer Dholakia joins Bessemer Venture Partners as a partner co-leading its growth-stage practice, the firm announced Wednesday, investing at the Series B stage and later in start-ups. The move comes after Dholakia left SendGrid following its integration into Twilio in June 2020.

In an interview, Dholakia said he made the decision to turn to investing after around 75 calls about potential CEO roles in the tech ecosystem. Several seemed like strong possibilities, but the timing didn’t work out, or Dholakia couldn’t overcome some doubts. Approaching them as a potential investor and getting to know their teams, he says, was more fun.

“After 25 years of doing something, you feel like you know how to do it reasonably well,” he says. “I didn’t know anything about this particular business line, but what I know I can say with 1,000% authenticity to founding CEOs looking for growth investments is, ‘I’ve been through this way ; I have been in your place.

A product manager and executive at software company Trilogy in the 1990s and 2000s, Dholakia took his first CEO job at startup VMLogix in 2007. He sold that company to Citrix, where he headed his developing cloud business unit to Bessemer’s Midas List investor. Byron Deeter called in 2014 for a CEO position at SendGrid, a Colorado-based email marketing software boutique. In 2017, Dholakia released SendGrid; at the time, Bessemer owned over 8 million shares, or about a quarter of the company. (Disclosure: Bessemer partners with Forbes on producing the Cloud 100 list.)

At Twilio, CEO Jeff Lawson had made three offers to acquire SendGrid before it went public, as detailed in Forbes‘2019 deep dive into their eventual combination. Reconnected by Deeter, also a member of Twilio’s board of directors (and who later recused himself from their subsequent discussions of the deal), Lawson and Dholakia announced the deal, worth around $3 billion. dollars in Twilio stock at the time, in October. Twilio’s stock is up around 60% since that announcement, though it’s trading just a quarter off February 2021 highs. The combined company today has a market capitalization of around $20 billion.

Bessemer, who typically hires investors at a junior level and grows them from within rather than making partner-level hires, remained close to Dholakia after he left. He joined the boards of holding company Bessemer Auth0, an identity management provider, until it was acquired by Okta, as well as two others: publicly traded IT holding company PagerDuty and provider ServiceTitan service software.

As an investor, Dholakia plans to focus on software categories consistent with these past experiences: developer tools, business APIs, marketing and sales technology, and business applications for artificial intelligence. He is no novice when it comes to total investing. Personal investments made over the past year include developer-focused startups CodeCov and Mux, marketing tech startup Spellbound, sales tech startup UserGems, vertical software firm ShopMonkey, and software maker Reprise product demonstration.

In a patchy startup fundraising market, with companies with millions in capital to deploy, but also stringent valuation multiples given the pullback of tech stocks in public markets, Dholakia says his experience in sale will help him win contracts, alongside Bessemer’s thesis-driven approach.

During the 2008 recession, Dholakia’s first startup nearly ran out of money and closed down. “We’re not that bad, and I don’t want it to be,” he said. “But I think we are heading into rough waters. I would encourage founders and CEOs to become more efficient. Focus on how you’re doing if the market goes down 20% and all of a sudden selling is a lot harder.

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