Shortly after he took a job as a software engineer at Microsoft's (Nasdaq:MSFT) Expedia (Nasdaq:EXPE) division in the late 1990s, management gave Ajai Sehgal an ultimatum.
Either he could join Expedia permanently when it spun off into its own company in 1999 or he'd have to find a new position at Microsoft within two weeks before being cut loose.
“I didn't know it was going to be a golden opportunity,” he said. “All of us but one person went with Expedia. It was probably the best thing we ever did because Expedia became one of those rocket-ship IPOs.”
And it appears fortuitous Sehgal has ended up at Hootsuite, a company seemingly poised to explode if and when an initial public offering comes.
The social media management firm's new chief technology officer has been on the job four months. He's responsible for transitioning the startup's computer systems to handle massive growth.
He's done it before. First at Expedia in the late 1990s and again at Groupon (Nasdaq:GRPN) in the early 2010s.
“If I had tried to plan getting to Hootsuite, I couldn't have [done] it,” said Sehgal, whose resumé includes time as a military officer and a search-and-rescue worker.
Hootsuite CEO and founder Ryan Holmes recruited Sehgal in April to take over for outbound CTO Simon Stanlake, who remains with the company as vice-president of technology.
“You have problems sometimes with not knowing what you don't know and thinking about what the next quantum leap is in growth,” Holmes said.
“And Ajai's experienced that. … [He's] really thinking about our IT operations in terms of how we're going to be able to scale in terms of tens of millions of customers to hundreds of millions over the next few years.”
Information technology scalability – building user-friendly internal computer systems that can sustain significant expansion – has been Sehgal's specialty for nearly two decades.
“Hootsuite's looking for someone who's been there, done that in the globally scaling business,” said Sehgal, an amateur astronomer who flies a Piper Saratoga in his free time.
“It's not easy. There's lots of mistakes to be made. I made all those mistakes [at Expedia and Groupon]. That helps the company.”
But it's a task seemingly far removed for someone positioned to be a career military man who joined the Canadian Forces in the early 1980s.
“I really joined the military because I wanted to be an astronaut. Little did I know back then, Canadians couldn't be astronauts quite yet,” said Sehgal, who owns observatories in Seattle and Osoyoos.
While resigning himself to being (somewhat) earthbound, the Quebec native flew training aircraft, earned a master's degree in engineering from Carleton University and rose to the rank of captain during his 17 years in the Air Force.
He also spent an extended period in military intelligence “doing fun stuff that I can't talk about.”
Meanwhile, his free time outside the military was still occupied with the stars as he and a friend developed a computer program that processed Hubble Space Telescope imagery.
A client, Microsoft's former CTO Nathan Myhrvold, later tipped him off to a job opening in the company's digital imaging division in the mid-1990s.
“When you're in the military in Canada, you don't get paid a lot of money. You do it for the love of country and for the experience,” Sehgal said, adding he eventually took the job and moved his wife and young daughters to Microsoft's headquarters in Washington state.
He was later assigned to the company's Expedia division, where he worked on the travel website's flight search and pricing product.
After Microsoft's ultimatum, Sehgal remained with Expedia for 15 years and became its vice-president of technology.
Hootsuite's rapid growth is nothing new to Sehgal.
Its workforce has more than doubled in the past two years, and about a month ago the company opened another building – HQ2, as it's called – a few blocks from HQ1 in Mount Pleasant.
Again, all that falls into the “been there, done that” category that drew Hootsuite and Sehgal together.
“Most startups follow a very common path. They go for features very, very quickly without very much thought to [computer] architecture and how they're going to scale in the future,” Sehgal said, acknowledging that's what happened at Expedia and Groupon.
But he worked with his Seattle teams to switch from a mish-mash of different systems to well-organized computer architecture that could accommodate growth as millions of users signed up for the services.
That's the same game plan he has for Hootsuite.
“He's been able to help us really think about scale, security – which is important to our enterprise clients,” Holmes said.
“We are looking for the best and brightest people in all facets, and so he matches completely with our culture.”
But Sehgal figured he'd be retired by now and even gave it a shot after leaving Expedia.
“I discovered that's just a bad idea for me,” he said. “I do too much, and I need to work, otherwise I'll drive my wife nuts.”
Time spent as a search-and-rescue worker in Washington state and a volunteer firefighter in Osoyoos fulfilled his desire to keep busy and engage in community service – a trait going back to his time in the Air Force.
“He's fully dedicated to helping the community and being part of that. Any time he's in Osoyoos, he checks right in to tell me that he's here and, if we need him, to give him a call,” Anarchist Mountain fire Chief Rob Burk said.
“He's outfitted his own truck for doing firefighting and search and rescue with King County. I mean, the guy's a good guy.”
But fighting fires and rescuing lost hikers did not scratch Sehgal's technology-driven itch. In 2012, he put retirement on hold and helped open Groupon's Seattle office, building its travel development team from the ground up.
“He is a true renaissance man, as far as I'm concerned,” said Milkana Brace, senior director of product and engineering in Groupon's global travel division, whom Sehgal recruited after they worked together at Expedia.
She said her former boss is well known for his culinary skills in addition to his love for astronomy and firefighting.
But more significant than his tandoori chicken recipe, Brace said, is his ability to dive deeply into technical details and assess what was a “true” problem versus a “made-up” problem that could be eliminated by simplifying things.
“He's used the role of a leader to hire great people, give them clear direction and remove obstacles from their way – and mostly get out of their way.”
Sehgal said his toughest decision was moving to Hootsuite after building his team at Groupon.
Brace said it was evident her ex-boss was incredibly happy at Groupon and really wrestled with what his next move was going to be.
“It was definitely not a no-brainer for him to leave all that behind and to go join an earlier-stage company,” she said. “He really struggled with the decision for a number of months.”
But Sehgal had followed Holmes' blog posts for years, and the temptation to join a social media firm was too much.
“It was an opportunity to get into a business that is absolutely essential to virtually every business on this planet because of the way technology is moving,” he said.
“It's a very exciting business where a Canadian startup is at the forefront. When you weigh those two opportunities, it was very hard to say no to Ryan.”