Alison Gleeson

Cisco’s senior VP of U.S. commercial sales is bullish on the cultural evolution of  the workplace.

Any working mother knows that the secret to success—however elusive that reality may seem—is somehow managing to be at two places at once. Alison Gleeson, the senior VP of U.S. commercial sales at Silicon Valley networking giant Cisco, may be coming close to mastering that, at least on a couple of levels.

For one thing, the Michigan native and mother of two has managed to stay on her home turf her entire career. After graduating from Michigan State, she worked in sales at Unisys, and then, 17 years ago, moved to the Detroit-area office of Cisco.  Today, Gleeson makes the most of the video technology that Cisco sells to stay connected with both her Silicon Valley compatriots and her business network across the country. “There is a new freedom of workplace,” says Gleeson. “Seventy percent of white-collar workers today are virtual, and that’s changing the way we can do business.”

Gleeson has also distinguished herself by helping Cisco to evolve culturally. She advocates for what she calls “two-way mentoring”—the mentee also counseling the mentor—and she was the driving force behind Cisco’s Women in Action Network, which cultivates mentoring and career development among women at the company. She was recently chosen as one of Diversity Journal’s Women Worth Watching for 2013.

Katrina Brown Hunt, based in San Diego

Diversity Woman  spoke with Gleeson about taking a step back to move forward, the wisdom of millennials, and knowing when it’s wise to outsource.

DW: You’ve stayed in Michigan your whole career. How have you managed to stay out of Silicon Valley?

AG: I was born in Detroit, and I never left. I live about a mile and a half from the house I grew up in. My mom and sisters and I all live within a mile or two of each other, and my kids go to the same school I did. I am definitely a midwestern gal.

I have been asked on numerous occasions to move to San Jose. But as much as the company would like me in San Jose, that’s not enough for me to do it. Being here allows me to stay real. When you think of what Cisco is in the business of doing, our business is all about collaboration technology. By using the same tech that we sell, I am able to be so much more productive.

DW: Growing up, what did you envision for your career?

AG: I grew up with a mother who worked, so at nine years old, I was already making money babysitting, then I worked at a T-shirt store in high school. By my junior year I was responsible for the bookkeeping, and as a senior I was put on corporate accounts. [“Accounts” should be plural?] By college, I knew I wanted to be in sales, but I also had a passion for numbers, marketing, and finance. I interned at IBM and shadowed sales reps, and I knew this was what I wanted to do. Really, I’ve been in tech since I was 19.

DW: When Cisco first approached you about a position, you turned the company  down. Why?

AG: In ’93 Cisco asked me if I wanted to join, and I pooh-poohed the offer. I said, “You’re not quite a big enough firm”—which is really kind of funny. But a few years later I interviewed again, and it was electric—I could feel it—and I’m happy to say that 17 years later, it’s still electric. I even took a demotion. I went from being a VP at Unisys to being a first-line regional manager. I’m really proud of making that step, because so often ego can play into that choice. But I didn’t pursue the title, I pursued the opportunity—I knew then there would be longevity.

DW: How has Cisco changed since you started 17 years ago?

AG: When I started, Cisco then was very engineering oriented. I remember being in a meeting at first and thinking, “Holy cow, I understand the words but not the sentences. I’m going to hate this—I’m not an engineer.” And yet, Cisco has never operated like a huge organization. It has always been a very flexible organization, very adaptable, so culturally there is no question we have grown up.

DW: How has the company managed that?

AG: For one thing, we never lose the pulse of the customer, and you can’t go wrong if you let the customer help to guide and shape your strategy. We have checkpoints along the way as we develop strategy—where we bounce ideas off customers. They’ll say that’s right, that’s wrong or a bad idea. It’s very interactive.

DW: How has Cisco changed, culturally, for women?

AG: Ten years ago I was one of the first female sales directors to adopt a baby. When I told my boss I was going to adopt a baby, he was like, “Oh? OK?” There was no policy. I think I took two weeks off. It wasn’t that Cisco didn’t want to give me two months, but there was just no policy.  Then I had another baby, and there was no maternity policy for a sales director—because there had never been a female sales director. So we’ve come along way.

DW: You’re a big part of Cisco’s Women’s Action Network. How did that get started?

AG: Fifteen years ago the senior VP for the globe, Rick Justice, asked me if I would head that up, and it says something that he was attuned then to what the company’s needs were.

The idea was simple—to attract and retain female talent—and to have a supportive group that could create a professional network and be real with each other. It went beyond gender to create diversity of thought and culture. Today it’s literally on our badge that one of our key priorities is capitalizing on that diversity, because we have to—we are a global organization.

DW: How does the two-way mentoring support that environment?

AG: You want to look and operate like the customers you are selling to. These millennials—these young professionals—operate very differently, culturally.

They are expert users of social networks, and when they come to a company, they don’t want to feel like they’re going backward. We’ve seen this merging between what used to be social, and personal, with the professional. So these young professionals don’t want a desktop where they go and sit and write e-mails. We’ve found with recruits that the workplace environment is even more important to them than salary.

DW: Do you feel that, given that environment at work, you have a better shot at balancing career and home life?

AG: The technology lets me stay connected to my job, but also attend special events for the kids. That is in Cisco’s culture. But there is no perfect balance—and if anybody says there is, they’re lying.

DW: How do you advise other working moms?

AG: A few things: Don’t sweat the small stuff, or you’ll feel like a failure every day. Next, you have to get rid of your guilt. You can’t run around feeling guilty because  you missed a school play. My strategy has been to get a video of it and  then watch it together with my child. That way, I can enjoy it with them. And really, how times of changed! I ran track and played baseball in school, and I don’t remember my parents ever coming to see me. We have put this crazy pressure on ourselves and we have to put it in check.

But the number one advice to give is outsourcing—like when I took the lawn away from my husband, because the grass was up to my knees one day. He’s in tech, too,  and I said, “Mark, we’re outsourcing: no more mowing the yard at night with lights on.”

DW: What else have you outsourced?

AG: This was a tough decision, but I had to outsource the homework for my kids. I hired a tutor who could help them two hours a day. Then, when I get home, I spend time checking their homework, as opposed to coming home tired and fighting about their doing it, with the tensions on both sides, and my children feeling that squeeze because of it. It’s been such a relief to have a third party come in.

As I always tell my mentee, you just have to take it day by day. One day can be great, and the next is a train wreck. I like to look at my life in chapters, not as pages.

DW: What have you learned from your mentee?

AG: I have a mentee who is 24 years old, and I encourage all of my leadership team to have these two-way mentoring relationships. I met with her after a kickoff recently, and she said that she liked this that I said, but not that …  and then she said, “I liked the fact that you demoed it on an iPad.” They don’t like PowerPoint—it’s all about video for them.

My younger professionals often send quick video messages to their customers. But my mentoring back to her was, “Don’t forget who you’re calling on. If you’re calling on clients in their 40s and 50s, don’t forget how important a hand-written note can be—that shouldn’t become a thing of the past.”

She’s so great—she sent me a hand-written thanks for that.

DW: What great book have you read lately?
AG: There are two books in my briefcase these days. One is The Top 10 Mistakes Leaders Make [by Hans Finzel]; it talks about the failure to focus on the future. We can be so busy, gerbils on a wheel, that we focus on the short term, and the year, as opposed to peeking around the corner to set strategy for the future. I also have a Nora Roberts book because I am a hopeless  romantic—it’s good for red-eye flights on the way home.

Katrina Brown Hunt, based in San Diego, has written for Fortune Small Business and Smart Money.

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