VC Firm Bessemer Taps Former SendGrid CEO To Co-Lead Growth Startup Investments – Forbes

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

Sameer Dholakia is joining Bessemer Venture Partners as a partner co-leading its growth stage practice, the firm announced on Wednesday, investing at the Series B stage and later in startup companies. The move comes after Dholakia stepped down from SendGrid following its integration into Twilio in June 2020.

In an interview, Dholakia said he made the decision to turn to investing after 75 or so 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 get over certain doubts. Approaching them as a potential investor and getting to know their teams, he says, was more fun.

“After 25 years of doing one thing, you feel like you know how to do that reasonably well,” he says. “I didn’t know anything about this particular craft of venture, but what I know I can say with 1,000% authenticity to founder CEOs looking for growth investments, is: ‘I’ve walked this path; I’ve been in your shoes.”

A product manager and executive at software business Trilogy in the 1990s and 2000s, Dholakia took his first CEO job at startup VMLogix in 2007. He sold that business to Citrix, where he was a leader of its developing cloud business unit until Bessemer’s Midas List investor Byron Deeter came calling about a CEO gig at SendGrid, a Colorado-based email marketing software shop, in 2014. In 2017, Dholakia took SendGrid public; at the time, Bessemer owned more than 8 million shares, or about one quarter of the business. (Disclosure: Bessemer partners with Forbes on the production of the Cloud 100 list.)

At Twilio, CEO Jeff Lawson had made three bids to acquire SendGrid before it went public, as detailed in Forbes2019 deep dive into their eventual combination. Reconnected by Deeter, a board member at Twilio, too (and who then recused himself from their later deal talks), Lawson and Dholakia announced the deal, worth about $3 billion in Twilio stock at the time, that October. Twilio’s stock is up about 60% since that announcement, although it trades at just one quarter of February 2021’s highs. The combined company has a market capitalization of about $20 billion today.

Bessemer, which typically hires investors at a junior level and grows them from within versus making partner-level hires, stayed close to Dholakia after his departure. He joined the boards of Bessemer portfolio company Auth0, an identity management provider, until its acquisition by Okta, as well as two others: publicly traded IT portfolio company PagerDuty and service-industry software provider ServiceTitan.

As an investor, Dholakia plans to focus on software categories consistent with those past experiences: developer tools, API businesses, marketing and sales technology and business applications for artificial intelligence. He’s not a total investment novice. Personal investments made over the past year include developer-focused startups CodeCov and Mux, marketing tech startup Spellbound, sales tech startup UserGems, vertical software business ShopMonkey and product demo software maker Reprise.

In an uneven startup fundraising market featuring firms with many millions of capital to deploy, but also valuation multiples constricting given the pullback of tech stocks on the public markets, Dholakia says his sales background will help win deals, alongside Bessemer’s thesis-driven approach.

During the recession of 2008, Dholakia’s first startup almost ran out of money and closed its doors. “We’re not as bad as that, and I don’t want it to be that,” he says. “But I do think we’re headed for some rough waters ahead. I would encourage founders and CEOs to get more efficient. Focus on how you’re getting through if the market goes down 20% and all of a sudden, sales are a lot harder.”

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