Close connections and remote work: Investor in Seattle helped Ohio dad land at portfolio company

Ben Gilbert, left, and his dad Alan Gilbert during a backpacking trip on the Olympic Peninsula in Washington state. (Photo courtesy of Ben Gilbert)

As a co-founder and managing director at Seattle venture capital firm Pioneer Square Labs, Ben Gilbert spends a lot of time helping companies get off the ground and find the key personnel needed to achieve success.

When PSL spinout Boundless, an online immigration services startup, was looking for a VP of engineering last fall, he thought he might know a handful of qualified candidates. In the mix was an Ohio-based tech veteran who Ben credits with turning him into a tech nerd — his dad, Alan Gilbert.

Ten years after moving to Seattle to take a job at Microsoft, and 10 months after his dad landed the Boundless role, Ben chuckles at how tech is a lasting connection across the miles for he and his father. And the hire is another lesson in how the COVID-19 pandemic has reshaped how companies view remote work.

“We never really thought our paths would cross,” he said of life after moving away from his family. They’d only shared one previous job connection, when Ben was a product test engineer in high school at a company called Codonics, where his dad spent 16 years and rose to VP of engineering.

PREVIOUSLY: Immigration startup Boundless raises $25M, eyes opportunity with ‘pro-immigrant administration’

Ben wasn’t directly involved in the launch of Boundless out of PSL in 2017, but has since gotten to know co-founder and CEO Xiao Wang and support the company in any way he can. When Wang brought up the need to hire a VP of engineering, Ben figured suggesting Alan would be a long shot.

“I sent one email and then stayed entirely out of it from there,” Ben said. “At some point I was like, ‘I kind of want neither of you to talk to me, everyone go make your own independent decisions and then give me a thumbs up if it works out.'”

It worked out.

Alan said that although he was looking at a few other opportunities, Boundless was always the frontrunner. He’d first heard about the company through PSL when it was started and said “it always seemed like a great concept and a fantastic mission.” He jumped at the opening.

“The Boundless mission and culture really aligned with where I personally wanted to learn and grow,” Alan said.

Wang said Ben has been pretty knowledgeable about Boundless and the startup’s needs as it grew, and that they had a list of “superpowers” they were looking for in their first VP of Engineering. The fast-growing startup, which has raised $45.3 million to date and employs around 150 people across several offices, sought the experience of someone who’s been through the ride before, from early-stage through billion-dollar exit.

Boundless CEO Xiao Wang. (Boundless Photo)

After interviewing more than 40 candidates, Alan was the guy.

“I think this was truly one of those serendipitous moments when the stars aligned,” Wang said. “I think Ben was a little sheepish about suggesting his father as a candidate, but I have always viewed saying yes as the genesis of everything good that happens in life.”

While some might worry about how things could go wrong between Ben, PSL and Boundless, Wang focuses more on how webs of employee connections lead to a higher chance of things going right. And he stresses that Boundless is not sacrificing commitments to diversity, with a team that is more than 50% female and people of color, at every seniority level.

The fact that a Seattle startup hired an engineering lead who is based in Columbus, Ohio, speaks to the changing dynamic around remote work in the wake of the pandemic. Wang, previously a strong believer that in-person collaboration was essential for team building and productivity, has changed his perspective, and like all companies they’ve been forced to adapt.

“I would have normally focused our search for this role in Seattle,” Wang said. But opening up many roles to remote candidates has allowed Boundless to access a much larger and more diverse talent pool. “The ability to hire great talent all over the country has resulted in a high-performing engineering team that is more diverse than our team pre-COVID.”

Boundless has also brought on Chief of Staff Ann Souza, who is based in New York City; VP of People Heba Williams, based in San Francisco; and the company is currently looking for a VP of Product who can also be based anywhere, Wang said.

Alan had never held a previous remote role in the nearly 40 years since his first job as a robotics engineer at IBM. As travel has opened up, he took his first trip recently to meet his co-workers in person. It made him realize what he misses when only meeting in scheduled Zoom calls.

“For instance, when someone wants to subtly make a point to a specific person in a meeting, they look that person in the eye. And that person then listens more carefully and responds non-verbally,” Alan said. “That kind of communication has to be a lot more deliberate when you have a screen full of faces and no eye contact.

“I also miss the serendipity of a shared lunch or cup of coffee with no agenda,” he added. “I think overall it is worth it to be able to hire from anywhere, but you need to get some face time once in a while, too. Startups are hard and you need to build relationships to get through the rough spots.”

A relationship with his son, rooted in part over tech and business, was a good place to start.

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Startups Alan gilbert Ben gilbert Boundless Pioneer square labs Remote work Xiao wang