Aileen Lee interviewing Amy Chang

Wednesday night, at a StrictlyVC event in San Francisco, venture capitalist Aileen Lee took the stage to interview Amy Chang, a former eBay product manager turned head of Google Analytics turned startup founder.

It’s a transition that has introduced Chang to night sweats, she readily admitted.

Chang’s three-year-old startup, Accompany, received one of its first checks from Lee’s firm, Cowboy Ventures. And Lee asked Chang about what it’s like to leave behind a cushy paycheck to launch something new, even with her former Google colleague, Matthias Ruhl a large-scale systems design expert by her side as her cofounder.

For one thing, Chang said, getting the company to the point where it could launch publicly took far longer than either she or Ruhl imagined it would. Though they now claim that they’ve built the second-largest database of people behind LinkedIn. Accompany basically creates cheat sheets for folks who need to get up to speed quickly on the new people and companies they meet every day. It took them 2.5 years.

They’ve also had to raise a bunch of money, $40 million altogether so far.

“It was a much bigger data challenge than we expected,” Chang said. “We had to build this whole data platform ourselves. Though once you have textured understanding of how a person’s network lays out. . . you can serve them a lot better.”

The native Texan, who nabbed her electrical engineering degree from Stanford and stayed in California, has also learned the pleasures and pain of working with 40 people, compared with the hundreds she managed at Google.

“When you’re at Google and it’s more a GM role, you’re managing to a mean,” explained Chang, “On any given day, maybe 20 percent of people are performing at a 5 [level] out of a 10. They’ve got stuff going on or are distracted by something. That 20 percent who aren’t operating at a 9 or 10 level of intensity is okay, because in the grand scheme of things, you’re [still in good shape].”

“When it’s 40 people, every person matters. I know now whose child is sick whose cat is sick. I have to make sure people’s emotional needs are met because if they aren’t, they can’t focus and perform at the level required to move a startup meaningfully forward every day.”

The good news for Chang: her leap out of Google appears to be paying off. Though she declined to get into granular detail about her business, owing to competitive concerns (Accompany is far from the only virtual assistant game in town), she was recently pursued by Cisco, which invited her to join its board.

She says that plum role came about because recruiter Jim Citrin, who leads Spencer Stuarts North American CEO practice, began using Accompany last year, got excited about it, and told Cisco CEO Chuck Robbins to try it, too. He was like, “Who makes this?'”

It helps that Cisco was looking for a digital native who’d grown up with mobile and with analytics in particular to add to its board. “I kind of fit the profile, and there was good chemistry,” she said.

The position which pays her a $75,000 annual retainer and gives her a grant of restricted stock worth several hundred thousand dollars, says a recent New York Times article presumably offsets much of the financial pressure that many other company founders face.

But Chang says she still wakes up in a cold panic at 3 a.m. oftentimes.

She has resigned herself to the fact that it’s the new normal. But she did have some advice to other aspiring founders in the room: Do not wake up your spouse every time it happens.

Read more: https://techcrunch.com/2017/02/10/ex-googler-and-ciscos-newest-board-member-amy-chang-on-her-leap-into-startups/