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During meetings at SendGrid, Sameer Dholakia encourages employees to be honest with him: “I can tell you, if you were sitting in that room today, there’s no holds barred. Nobody’s tap-dancing around things.” Photo by Matt Nager

Can Sameer Dholakia Turn SendGrid Into Denver’s Next Iconic Tech Company?

The universe has a way of kicking the SendGrid CEO when he's up. Maybe this time he'll finally catch a break.

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Sameer Dholakia is one of the nicest, most personable leaders in tech—an industry well known to be populated by terrible people.

In college, esteemed Kappa Sig bro and future Snapchat co-founder Evan Spiegel referred to female members of the Greek community as “Sororisluts” and offered to “roll a blunt” for the brother who “sees the most [private body parts] tonight.” (Call us prude, but the word Spiegel used made us blush.) At Pixar, Steve Jobs laid off people without notice. When an executive complained that those being let go should get two weeks’ warning, Jobs replied: “OK, but the notice is retroactive from two weeks ago.” Even Elon Musk, one of tech’s more endearing characters, allegedly told his wife, “I’m the alpha in this relationship”—while they danced at their wedding.

You won’t hear any such horror stories about Dholakia, CEO of SendGrid, a billion-dollar startup that was founded in Boulder and now is headquartered in Denver. Or, at least, we didn’t—and we asked a lot of people. Ajay Agarwal was Dholakia’s first boss: “He’s just a special human being.” Rob Vigil worked under Dholakia at a startup called VMLogix: “He leads the dance without looking like he’s leading.” Leandra Fishman was at VMLogix too, then started her own consultancy, then left it to reunite with Dholakia at SendGrid: “He was on the shortlist of executives I’d work for again, no matter if it were selling ice to Eskimos.” The jobs website Comparably ranks him as the best CEO of a small or midsize company in the country, based on employee voting.

Here at SendGrid’s downtown Denver HQ on a Monday morning, Dholakia is at his saintly best while welcoming the newest crop of incoming “Gridders.” Well, he’s not actually here in the literal sense of the word. He lives with his wife and two young children in Menlo Park, California. But it’s important to him to personally introduce himself to each hire—a gesture that’s becoming arduous now that SendGrid’s employee tally is more than 400—so his face is on a monitor, beaming from behind a standing desk in Redwood City, California. “Hey guys, we can’t see you,” Dholakia says. Despite the technical difficulties, his intonation is relentlessly upbeat, like a game show host’s. “I hear some giggling going on. What are you guys talking about?”

There are nine hires at today’s orientation, defectors from Oracle, PayPal, and HomeAdvisor, to name just three of the tech outfits losing talent to SendGrid. Founded in 2009, the company sends emails—Uber receipts, Airbnb confirmations, Spotify playlists—for its clients. Businesses pay SendGrid to be their postman because its developers are trained in the “dark arts of email,” as Dholakia says. Consider your spam folder, stuffed with promotions from Elitch Gardens and cruisecompete.com. Now consider the fact that 20 percent of the world’s wanted emails, the ones we sign up for, don’t even reach our inboxes; Google, Yahoo, and other providers swat them away before they can make it through. SendGrid, then, is the Han Solo of the virtual universe, a smuggler paid to courier emails past the most stringent online defenses.

Dholakia tells his audience about how he fell “in love with ‘the Grid.’ ” When he was interviewing to become CEO of SendGrid, his “business nerd” side adored the company’s sales model (most software-as-a-service companies spend 50 percent of their revenue on sales and marketing; SendGrid only spends 25 percent). His “emotional sap” side clung to the company’s culture—in particular, the emphasis placed on humility in an industry filled with giant egos. Dholakia is tall and trim, and his thin fingers slice through the air as he talks, often landing over his heart. With the light from the window behind him obscuring his features—all except the wide, white smile and prominent ears—there’s something Obama-like about his presence. The newbies are nodding along. With their help, Dholakia concludes, “We can build an iconic company that’s built for the ages.” His audience is clearly smitten.

Maybe these folks can turn SendGrid into Denver’s Microsoft. But here’s the thing about tech: Evan Spiegel runs a company worth more than $15 billion (and married a former Victoria’s Secret model). Steve Jobs invented the Mac and the iPhone and the iPad. Elon Musk is taking us to Mars in a Tesla. Being a class A jerk is considered by many a necessary character trait to drive a startup through its turbulent early years, to scale to hundreds and then thousands of employees, and to keep the company hungry once even the janitor’s stock options are worth millions. “Silicon Valley CEOs are egotistical and micromanaging,” Vigil says, “and you have to be, to some extent.”

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Dholakia, though, is different.

“Can a nice guy be successful in this rough-and-tumble world of technology and high-growth business?” Agarwal muses. As a SendGrid investor, a member of its board of directors, and a friend, Agarwal believes Dholakia has already answered that question.

Dholakia smiles a lot, but never more patiently than when someone asks if email is dead. It’s a fair question, considering that with Twitter, Facebook, Google Hangouts Chat, and Slack now around, email can seem as outdated as your parents’ AOL dial-up connection. But like a virus, it continues to grow: Almost half the Earth’s residents have an email account, and daily traffic is expected to increase by more than four percent annually until 2021, when it would reach 319 billion.

So, no, Dholakia doesn’t believe SendGrid’s wellspring of revenue will share the fate of the BlackBerry anytime soon. With that said, he’s still pretty sure something awful is going to happen. And he’s got good reasons for feeling that way.

Photo by Matt Nager

Dholakia is the second and youngest child of Indian immigrants. His father, Pratap, was raised in Bombay (now called Mumbai) with 10 siblings in a two-room apartment. He moved to America around 1968 to study chemical engineering. His young wife, Pravina, joined him soon after. While Pratap studied and earned $1.80 an hour working at the Prince Macaroni Manufacturing plant in Lowell, Massachusetts, Pravina learned English from watching All My Children and raised two squabbling boys.

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“We fought a lot,” Sameer says. “I remember vividly one day, she told us to knock it off. We didn’t, she came in, and you could just see: Uh oh, this is not going to be good.” Pravina first tore into his brother, Sanjay, while Sameer giggled behind her back. Then she spun on Sameer, grabbed both her children’s arms, and gestured to the delicate knots of veins visible through the thin skin on the undersides of their wrists. Do you see these little green lines? she asked. No one else is half Mom and half Dad but you two. You’re two parts of a whole. You’ve got to stay together. Pravina, a religious woman, often made her points with allegories.

Pratap found success, creating a patent for a cheaper and faster way to manufacture the foam padding under carpet, and in 1983 the family moved from Boston to Los Angeles for his work. Sameer settled into a typical childhood, playing baseball, football, and basketball. His chief concern? Being a diehard Boston Celtics fan cast into a sea of Magic Johnson jerseys.

That changed about six years later. Despite Pratap’s professional rise, the Dholakias remained entrepreneurial, first buying a hotel in Massachusetts and then another in Fullerton once they’d moved to California. Pravina didn’t stay home and watch soaps; she used her accounting degree and worked as a bank teller before managing the business side of the motel. When the Dholakias were thinking of selling their California hotel and its managers left to explore other job opportunities, she replaced them temporarily.

One day in July 1989, the hotel’s maintenance man entered the suite off the lobby to find Pravina’s slain body. She’d been strangled to death; the local police charged a teenager in the murder. “As a 15-year-old, how do you rationalize something that awful happening to somebody that good?” Dholakia asks today.

For about a month, Sameer collapsed on himself, furious with the world. Then Sanjay, Sameer’s other half, confronted him. “You can stay down and let it be the thing that you reflect back on in life that knocked you off your track,” Sanjay said. “Or you can pick yourself up and use it as fuel and energy to achieve and live a life that she would be proud of.”

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Sameer chose the latter and worked tirelessly to get into Stanford University, where he earned a bachelor’s in economics and, concurrently, a master’s in organizational studies. As an adult, Dholakia’s first job was at a Texas software company called Trilogy. The culture at tech companies is often reminiscent of the beauty pageant world: You can get along with co-workers, or you can be successful. Both rarely happen. “Sameer was not only one of the stars of the company,” Agarwal says, “but he was universally liked.” Dholakia rose from product management to marketing to business development, popped into Harvard Business School for an MBA, which he completed in 2004, and then headed back to Trilogy for three years in sales.

By 2007, Dholakia believed he understood almost every aspect of running a software company short of writing code. He wanted to put all of his skills to use and become a CEO. Fortunately, Agarwal, by then at Bain Capital Ventures, needed a boss for one of his seed companies, VMLogix. Unfortunately, the opportunity came with a complication. VMLogix was one of those tech startups whose function was so specialized it would take two pages of technobabble to explain. (It had something to do with the cloud.) Regardless, the company was in trouble. VMware, a huge company worth almost $54 billion today, had entered its highly technical market. VMLogix didn’t possess the resources to compete.

Success in tech isn’t always becoming the next Apple, though. Sometimes (most times) it’s getting acquired—a favorable exit to get founders and investors paid. Dholakia began flirting with Citrix, a multibillion-dollar cloud computing company, and integrated VMLogix with XenSource, a software company Citrix had recently acquired. Dholakia’s plan worked. According to Dholakia, in summer 2008, a year after becoming CEO, he was negotiating a sale to Citrix. VMLogix’s prospects suddenly looked promising.

Even more suddenly, however, the economy did not. The Great Recession forced Citrix to lay off part of its workforce; it couldn’t, Dholakia says, be seen buying a startup at the same time. VMLogix burned through its cash and, because the GDP was busy tumbling, couldn’t raise more from investors. Dholakia had made his play, and it had worked—until yet again something unforeseeable had appeared out of nowhere to squash him. “So there’s this theme in my life: I’m always waiting for the universe to hose me,” Dholakia says. VMLogix limped along before the Citrix deal finally went through in 2010. “Those,” he says today, “were the two darkest years of my professional career.”

Although SendGrid claims three founders, the Mark Zuckerberg of the trio is Isaac Saldana, a California developer with a few failed startups on his resumé. Saldana had noticed each of his shuttered businesses had struggled with getting its emails into customers’ inboxes. Surely others had the same problem.

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He was right. Saldana and his partners took their startup to the Techstars accelerator in Boulder in 2009 and, sure enough, small startups that didn’t want to waste time developing their own email-delivery applications were willing to pay SendGrid to do it for them. Some of those companies that were fledgling at the time, such as Uber, are now worth billions. SendGrid has grown with them.

Saldana may have been the startup’s resident visionary, but he was an inexperienced chief executive. His founding name for SendGrid, for example, was SMTPAPI (simple mail transfer protocol application programming interface), which, because of its obliqueness, calls to mind another acronym: WTF. In 2011 the board and Saldana agreed to bring in Jim Franklin, a veteran Colorado tech exec and Techstars mentor, as SendGrid’s second CEO.

By all accounts, Franklin’s tenure was a success. He grew the company from 25 employees to 250. Revenue skyrocketed from a million per year to $43 million annually. Franklin is also responsible for SendGrid’s cultural manifesto, the four H’s: happy, hungry, honest, humble. “Jim did a fantastic job there,” says David Cohen, a Techstars co-founder and a SendGrid board member at the time. “He amplified and codified the culture.” But, Franklin says, the board wanted revenue to double every year until it hit $100 million. Cohen denies this but concedes the board wanted SendGrid to grow faster. “We had gotten as far as we could go with his skills and experience,” Cohen says. “At the time, you feel like you get to a plateau and you need to do something.” In this case, that meant hiring a new CEO.

Franklin helped in the search for his replacement, bringing in 33 people over 15 months to interview. Most, Franklin says, took a look at the board’s expectations and ran away screaming. Dholakia turned the job down twice, too, before accepting. “[He] had been the CEO of a company of like 35 people,” Franklin says. “He hadn’t scaled a business from 100 to 1,000 or gone public. So it was a risky choice, frankly.” Many in the company’s rank and file were worried, too. “I definitely had concerns,” says Carly Brantz, SendGrid’s vice president of revenue marketing. “Not to slam Silicon Valley, but to hire from outside the state, especially the Boulder Bubble, I thought an iron fist from Silicon Valley might come in and rule.” Dholakia didn’t arrive brandishing a gauntlet, but he was demanding in his own we’re-all-friends-here way.

Soon after he became CEO in September 2014, Dholakia says he helped push through one of SendGrid’s most important projects, which was already more than a year late. Dholakia adores the four H’s, but he thought the company was perhaps too happy—and not hungry enough. “Our reflex here is we hit a wall and then we immediately go, hmm,” Dholakia, shrugging his shoulders, says of that time. “How about we try and run through the wall?” The team worked nights and weekends for months to complete what came to be called Marketing Campaigns, which now generates almost a fifth of SendGrid’s revenue. “I do think the focus weighted to happy,” Brantz says. “It was the Colorado mentality of not wanting to hurt other people’s feelings. He had to bring that friendly competitiveness to SendGrid. We were being too careful with each other.”

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Pravina Dholakia’sfavorite allegory came from India, and she recited it often: We are born, she would tell her children, with our fists clenched. We die at peace with our hands open. That’s because we enter the world bearing a gift. We die when we are done giving it away. The reason we exist is to discover what that gift is and present it to as many people as possible.

Pravina’s youngest son says he doesn’t know what his gift is yet. “I hope,” Dholakia says, “it’s helping others do their best work.”

Most would say SendGrid is thriving under its current CEO. It hauled in $43 million the year Dholakia arrived. In 2017, revenue topped $110 million. SendGrid moved its headquarters from Boulder to Denver in 2016. Most notably, SendGrid went public this past November, and as of April, the company was worth more than a billion dollars. “That’s a huge number around here,” Franklin says of the valuation. But it’s not big enough for Dholakia.

“Sameer sets such a high bar,” says Fishman, now SendGrid’s senior vice president of sales and customer success, “and has such a desire to win you can feel it.” That’s partly why he tries to get to know people personally—so they feel comfortable pushing back against him. When Dholakia attends a random meeting, as he is wont to do, Jillian from revenue marketing feels comfortable telling the CEO of her billion-dollar company that her team has been doing this for five years and they know what they’re doing, so let them do it their way. Then there’s his famous line of inquiry, known around the SendGrid hallways as “the double-click.” “He asks questions and probes and probes and probes until we uncover those questions we didn’t even know to ask,” Fishman says.

Dholakia admits that this constant need to always drive forward might be his way of staying in front of the next unexpected disaster life tosses his way. “We have done extraordinary things in the three-plus years I have been at SendGrid, and I am so proud of it all,” Dholakia says. “And I’m like, ‘Yeah, that was yesterday. Let’s talk about what we need to do in the next year, two years, three years.’”

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SendGrid still has plenty of room to grow in transactional and marketing emails. Now, however, it’s pursuing a multichannel communications platform—which means delivering email, social media messages, and push notifications. The company’s developers have only begun chasing that dream, and the product’s arrival is years away. Still, if SendGrid wants to turn into a renowned tech company, offering one-stop virtual-delivery services would be a good next move. “That’s how we become the billion-dollar revenue company,” Dholakia says, “not the billion-dollar valuation company.”

And that’s how Dholakia will give his gift. “I talk a lot about how I’d love for SendGrid to spawn dozens of new startups and new ventures that will be instrumental parts of building a new tech ecosystem here in Denver and Colorado that people trace back,” Dholakia says. Just as long as the universe doesn’t hose him again this time.


Editor’s Note 10/17/18: SendGrid announced it accepted a $2 billion buyout from San Francisco-based Twilio Inc. on Monday, October 15.

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