Being CIO at Charles Schwab meant that Dawn Lepore would get vendor solicitations from top executives at tech companies. So it was not unusual for Microsoft’s Steve Ballmer or Steve Jobs, when he was head of his computer company NeXT, to sit in her office and pitch their software products.

Lepore, who is CEO of drugstore.com, said she used the opportunities to quiz those top tech executives on how they ran their companies, how they dealt with problems and what they saw as the most pressing problems in the industry.

Lepore said Jobs, Ballmer or Sun Microsystems co-founder Scott McNealy may not have known it, but they were mentoring her.

“Because they were trying to sell me, they had to answer my questions,” Lepore told an audience of about 350 people, mostly women, who attended Thursday night’s Women in Tech event presented by TechFlash.

Lepore’s efforts to learn how to run a company didn’t stop with peppering CEOs on vendor calls. Early in her tech career as a computer programmer, when Schwab hired a new CTO, Lepore said she started keeping a notebook as he spent his first day on the job, jotting down what he said were his priorities and how he made decisions.

Here are some more details from Lepore’s talk, which was moderated by TechFlash and Puget Sound Business Journal Publisher Emory Thomas Jr.:

On expanding her mentoring network:

Charles Schwab had a rule about his executives serving on other company boards. They couldn’t do it, Lepore said, because he figured if his people had any spare time, he wanted them to focus on Charles Schwab. But Lepore convinced Schwab that she could grow professionally by serving on boards, and he gave in. Her first board seat was with Times Mirror Co., publishers of the Los Angeles Times.

“It was a wonderful opportunity to see firsthand how CEOs ran the companies,” Lepore said.

She joined other corporate boards, including eBay, where she met fellow board member and Starbucks founder Howard Schultz. He told her that she really needed to run a company.

Today, she also serves on the board of The New York Times Co.

And she said encouragement from people like Schultz helped her overcome the negative voice in her head that told her “I cannot do this,” referring to seeking major leadership roles.

On being a woman CEO of a tech company:

She said being a woman CEO or CTO in an industry that doesn’t have a lot of top women leaders can feel like “being in a glass house.” She said things have changed a lot for women in recent years. She remembers that when she was named CTO at Schwab, investors asked Charles Schwab why he put a woman in charge of the company’s technology department.

One piece of advice from Lepore: It can pay off to join a fast-growing company early. Lepore was employee No. 444 when she was hired at Schwab, a company that grew to have more than 25,000 employees.

When she almost failed, and a dark day at drugstore.com:

As CTO, Lepore helped build Charles Schwab’s successful online trading service. But at first, making the transition to CTO was a struggle.

“The first 18 months were very rough. I almost failed,” Lepore said. “I felt like I had to be perfect.” The low point was when she discovered she was having a negative impact -- she felt she could not show emotion in the office.

“I found out people were calling me the ice queen. I was devastated,” she recalls. Lepore said she hired a coach who helped her relax and be herself, which made her a more effective leader. Still, she said, “That was a very rough year.”

She has had many high-water marks at drugstore.com, including being a part of the deal to be acquired by Walgreens for $429 million. But it has been a challenging six years running drugstore.com, which is a low-margin public company that is highly sensitive to reaction from Wall Street. One low point was when Medco Health Solutions, a company that drugstore.com built an online store for, missed its revenue projection. Drugstore.com claimed revenue from the store as part of its revenue, and Wall Street did not like the missed revenue target.

“We lost 70 percent of our market cap that day,” Lepore said. Luckily, she said, she had the support of the board.

On her experience moving to Seattle from San Francisco:

In San Francisco, Lepore said, if you tell someone who knows a lot of people that you are a newcomer, the person will introduce you around. Seattle was a different experience, she said, describing the “Seattle Freeze” culture. If you tell someone in Seattle that you are a newcomer, the person will reply, “That’s nice.” One person even said, “We already have enough friends.”

“It’s a beautiful place,” Lepore said. "We are happy to be here. But it was difficult to fit in at first.”

What’s next for her after drugstore.com:

Lepore said Walgreens plans to merge the two companies' e-commerce divisions into one. She said Walgreens made a talent purchase and plans to keep operations going in Seattle, where drugstore.com has about 250 employees. Lepore said she has agreed to stay on for three to six months after the transition is completed. But then, for the first time in nearly 30 years, she will be out of work and seeking a new opportunity.

“It feels a bit daunting,” she said.

Photos from the event will be published on our Facebook page.

Thanks again to our sponsors for their support of TechFlash: BDO, The Seattle University College of Science and Engineering and Whitepages.com.

We'd also like to thank our "Friends of TechFlash for supporting this event: Medio Systems, Microsoft, The AK Group, TW Telecom, and UW Professional & Continuing education.