To understand why Steve Woods is leaving Google, you first need to know about the orange backpack.

The backpack belonged to Patrick Pichette, the Canadian who became Google’s Chief Financial Officer in 2008, the same year Woods joined the internet giant to lead its Waterloo Region engineering office.

Despite a corporate pedigree that included a stint at Bell Canada, Pichette was no suit-clad bean counter. A fitness buff, he wore athletic clothes even “to the most important meetings,” Woods recalled, in line with Google’s come-as-you-are culture.

As for the orange backpack, Pichette’s version of a briefcase, it quickly became a powerful symbol of possibility inside Google – a figurative container full of fuel to power the company’s world-changing ambitions.

“At Google, what it meant was, ‘We have a lot of money,’” Woods said, “but that wasn’t the point. The point was, ‘You can’t do everything, but the things we choose to invest in, we’re going all-in on.’ It was quite inspirational.”

Pichette, who left Google in 2015 for a short-lived early retirement, now helps Canadian startups do big things as a General Partner with Montreal-based Inovia Capital.

Woods, whose last day at Google was today, will follow him there next week, as Inovia’s newest Partner and Chief Technology Officer, based in Waterloo Region.

In a recent interview with Tech News, Woods reflected on his 13-year tenure building Google’s Canadian engineering operation, a period of explosive growth not only for the Waterloo Region office he led, but for the tech community surrounding it.

A fiercely proud Canadian from Saskatchewan with a PhD in computer science from the University of Waterloo, Woods has arguably made as big an impact outside Google’s walls as he has inside, mentoring startup founders, sharing Google resources and giving time to various organizations, including Communitech.

The tiny Waterloo outpost of about 20 Googlers he came to lead in 2008 has since ballooned to nearly 1,400 and counting, headquartered in downtown Kitchener’s historic Breithaupt Block, where an 11-storey expansion is under way.

At times described as Google’s most important development site outside the U.S., the Waterloo Region office has given rise to products used by hundreds of millions of people, including mobile Gmail and Chrome apps. More recently, it became home to the Google Cloud Healthcare and Life Sciences platform headed by Ilia Tulchinsky, one of the company’s first Waterloo Region employees.

For all the technical achievements Woods oversaw, “the most rewarding thing will always be about putting the people together,” he said. “For me, it wasn’t about having the world’s best idea. I have lots of ideas; some have gone well, some have not gone well. My passion is getting these people together, finding out what they want, finding out what they think they can do, and finding out what they think matters, and helping them get to a point where they can start doing.”

Woods, 56, is a team-builder from way back. 

“Don’t get me wrong; I didn’t do it professionally,” he said, laughing. “I did it in sports, I did it in school, I did it with my friend group. The people I grew up with are still my best friends, the ones from when I was 3. How many people can say that?”

After graduating from UW, working abroad and landing an enviable post at the Carnegie Mellon Software Engineering Institute in Pittsburgh, Woods and a young colleague left in 1998 to launch a voice portal internet startup called They moved to Silicon Valley and failed to impress the venture capitalists along Sand Hill Road. Eventually, they found a willing investor back in Toronto, and in September of 2000, sold Quack to America Online (AOL) for US$200 million.

The story of Quack landing a Canadian investor ran counter to the conventional narrative that cast Silicon Valley VCs as the swashbuckling risk-takers, while conservative Canucks sat on their wallets. The irony is not lost on Woods, whose new role at Inovia will put him on the receiving end of pitches from young entrepreneurs, but he said he was never bitter that U.S. investors spurned him.

It’s all well and good to seek investment, he said, but “you need to understand what they are looking for, and why. And I didn’t.”

Good ideas are just the start, said Woods, who recounted a failed pitch he once delivered to Jean-Louis Gassée, a former Apple executive of pivotal influence during the computing pioneer’s early years. 

Woods was making the case that peer-to-peer technology to enable direct online communication would be increasingly important when Gassée asked him, “Could you get up on the whiteboard here, and just draw the internet?”

“I said, ‘What do you mean, draw the internet?’” Woods recalled. “And he goes, ‘Be creative.’”

Woods drew for 45 minutes “and when he finally stopped me, I was literally drawing how a DMS-100 switch works,” he said. “And he says, ‘OK, you get the internet. Now tell me why your idea is right.’”

Woods adjusted his artwork to illustrate how he thought the internet would look in five years, to which Gassée replied, ‘I believe you. Now tell me why this is going to matter to making a bunch of money.’

“These are good questions,” Woods said. “I want to be like that, because you know what? Who knows what he learned by asking that question?”

The question of Google’s ongoing evolution in Waterloo Region will be answered by three veteran Canadian tech leaders who will replace Woods: Derek Phillips, Engineering Director; Jennifer Smith, Director of Product Management for Google Cloud; and David Yach, also of Google Cloud. Phillips previously led Google’s Motorola Mobility division and worked at local edtech firm D2L; Smith held senior engineering VP roles at Cineplex Digital Media and Christie Digital Systems; and Yach was Chief Technology Officer for Software at Research In Motion (BlackBerry).

The capabilities of these leaders, among many more at Google, are a comfort to Woods as he prepares to join Inovia next week.

Not that the move was sudden, though.

“It’s not like they just phoned me yesterday,” Woods said. “We’ve been having this conversation now for two and a half years, where they’d say, ‘Hey, it would be fun to do some other things, right?’”

Many of those conversations were with his old colleague Pichette, and with Inovia co-founder Chris Arsenault, who mortgaged his own house to launch the firm in 2007.

“In the conversations with Patrick, he’s like, ‘Hey, I’ve still got the orange backpack. Let’s do something great,’” Woods said.

On the day Google announced his departure earlier this month, Woods and Pichette spoke on the phone again.

“As Patrick said to me this morning, ‘How does it feel today with no more safety net? It’s just us,’” Woods said. “I think that’s the uncomfortably exciting thing. It’s just like (being) a startup founder; it’s just us again. So, I’m looking forward to that, in a terrifying way.”