Close ties and remote work: Seattle investor helped Ohio dad land in holding company

Ben Gilbert, left, and his father Alan Gilbert on a hiking trip to the Olympic Peninsula in Washington state. (Photo courtesy of Ben Gilbert)

As the co-founder and CEO of Seattle-based venture capital firm Pioneer Square Labs, Ben Gilbert spends a lot of time helping businesses get started and finding the key people needed to succeed.

When PSL spinout Boundless, an online immigration services start-up, searched for a vice president of engineering last fall, he thought he might know a handful of qualified candidates. In the mix, there was an Ohio-based tech veteran who Ben credits with turning him into a tech nerd – his father, Alan Gilbert.

Ten years after moving to Seattle to work at Microsoft, and 10 months after his father landed the role of Boundless, Ben laughs at how technology is a lasting connection across the miles for him and his father. And hiring is another lesson in how the COVID-19 pandemic has reshaped the way companies view remote working.

“We never really thought our paths would cross,” he said of life after moving away from his family. They had only shared one previous job, when Ben was a high school product testing engineer at a company called Codonics, where his father spent 16 years and became vice president of engineering.

PREVIOUSLY: Immigration Startup Boundless Raises $ 25 Million, Seeks Opportunity With “Pro-Immigrant Administration”

Ben was not directly involved in launching Boundless out of PSL in 2017, but has since gotten to know co-founder and CEO Xiao Wang and supports the company in any way he can. When Wang brought up the need to hire a VP of Engineering, Ben thought Alan would be a long shot.

“I emailed and stayed completely out of the way from there,” Ben said. “At one point I was like, ‘I kind of want none of you to talk to me, everyone to make their own decisions independently, and then approve of me if it works. “”

It worked.

Alan said that while he was looking for a few more opportunities, Boundless has always been the favorite. He first heard about the company through PSL when it was founded and said, “It always seemed like a great concept and a great mission. He jumped at the opening.

“Boundless’s mission and culture was really where I personally wanted to learn and grow,” said Alan.

Wang said Ben was quite familiar with Boundless and the startup’s needs as it grew, and that they had a list of “superpowers” ​​they looked for in their senior vice president of engineering. The fast-growing start-up, which has raised $ 45.3 million to date and employs around 150 people in multiple offices, sought out the experience of someone who has already been through the adventure, from the initial stage to the release of a billion dollars.

CEO Without Limits Xiao Wang. (Photo without limits)

After interviewing over 40 applicants, Alan was the guy.

“I think it was really one of those fortuitous times when the stars aligned,” Wang said. “I think Ben was a little sheepish about suggesting his father as a candidate, but I have always considered saying yes to be the genesis of everything that goes well in life.”

While some might worry about how things could go wrong between Ben, PSL, and Boundless, Wang is focusing more on how employee connection networks increase the chances of things going right. And he emphasizes that Boundless doesn’t sacrifice its commitment to diversity, with a team made up of more than 50% women and people of color, at all levels of seniority.

The fact that a Seattle startup has hired an engineering manager based in Columbus, Ohio, is a testament to the changing dynamics of remote working in the wake of the pandemic. Wang, who previously firmly believed that in-person collaboration was essential for team building and productivity, changed his perspective and, like all businesses, they were forced to adapt.

“I would normally have focused our search for this role in Seattle,” Wang said. But opening up many roles to distant candidates has given Boundless access to a much larger and more diverse talent pool. “The ability to hire top talent from across the country has created a high performing and more diverse engineering team than our pre-COVID team. “

Boundless has also recruited New York-based Chief of Staff Ann Souza; VP of People Heba Williams, based in San Francisco; and the company is currently looking for a vice president of products who can also be based anywhere, Wang said.

Alan had never held a remote position for almost 40 years since his first job as a robotics engineer at IBM. As the trips opened up, he recently made his first trip to meet his colleagues in person. It made him realize what he lacks when he only meets on scheduled Zoom calls.

“For example, when someone wants to subtly point out 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. “This type of communication needs to be a lot more deliberate when you have a screen full of faces and no eye contact.

“I also miss the happy coincidence of a shared lunch or cup of coffee without an agenda,” he added. “I think overall it’s worth being able to hire from anywhere, but you also have to have time in front of you every now and then. Startups are tough, and you have to build relationships to get through the tough times. “

A relationship with her son, rooted in part in technology and business, was a good place to start.

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