Ep 63: Jill Maiorano: Sales Leader, Blessed to Find Tech

Diva Tech Talk was thrilled to interview Jill Maiorano, Director of Strategic Engagements, Americas Division at Cisco (www.cisco.com).  A leader with robust sales and new business development background, Jill discussed wide-ranging topics from team management, startups, strategy and learning, to balancing home/family with a busy career.

“I was not a ‘technology tinkerer’ “ Jill said.  “From a relatively early age, I decided to be in sales.  My entire family were salespeople. If you wanted to get a word in edgewise in my household, or my extended family, you needed to sell your idea!” After graduating Eastern Michigan University, where she specialized in organizational communications and marketing, (focused on communication, public speaking, negotiation), she felt “really blessed that I was able to find tech.  And to this day, I use what I learned.”

Jill’s first tech sales job was with Allnet Communications, a division of ALC that provided long-distance services to business customers. She was only there a few years when Frontier Communications acquired the company in a bid to compete with telecommunications giants.  Frontier was later acquired by Global Crossing Inc. (www.globalcrossing.com), now morphed into Level 3 Communications (http://www.level3.com/en/).  Her first product portfolio grew from long distance services to “the Internet and selling Internet pipes; and that became frame relay, and other data networks.”  At Allnet, Jill progressed from frontline sales, to sales team management, to opening and managing markets throughout Ohio (Toledo and Cincinnati), to management of the entire Midwest.

Jill then changed jobs, in the heyday of telecommunication divestiture, to join the startup team at USN Communications, a CLEC, where she opened and managed 13 offices across Michigan and Ohio. “It was really a fun, innovative experience,” Jill said. But “it ended with a phone call from the president saying that we had run out of money, no more VC funding.”  That happened in November, and Jill’s wedding was in December (“it was interesting timing,” she laughed). “I spent the next two months running what felt like ‘resume clinics’ and writing referral letters” for the 150 people working for her. Then Jill moved to Qwest Communications (now CenturyLink, www.centurylink.com) as a director, running several states.  After she had her second child, she migrated to Sprint (www.sprint.com) and  “the easiest job I ever had” as a sales manager. “After climbing the corporate ladder, I wanted a little life/work balance, so I intentionally took a step back. It was fun. I had a great team. I spent two years working directly with customers.” Her next decision to plunge into greater technology depths drove Jill’s decision to join Cisco, 12.5 years ago.  “I went from the easiest job I ever had to a really fabulous job. There was an intensity shift.”

Jill is a Cisco enthusiast for a variety of reasons. “We take our investments, our future, very seriously,” she said. “We call it a ‘buy/build partner model’. We just completed our 202nd acquisition. We innovate. We have a lot of R&D and do a lot of internal innovation. We also partner with other ecosystem companies, to really provide our customers complete solutions. “ She also loves the fact that Cisco deploys a “work is something you do, not where you go” philosophy to help team members achieve life balance.  At Cisco, like many fast-moving tech companies, “we change every year,” Jill said. “For 11 years, I ran sales organizations. Each year was slightly different. For two years, I had 10 states; for a couple of years I had 2 states; bigger teams and smaller teams. I ran commercial for a few years; then I managed SLED state government, local government, K through 12 education, and universities.” Jill really enjoyed this latter assignment, because “there’s a sense that you’re making a difference. Education was taking on tech in a more meaningful, classroom-centric way. It was a really interesting time.”  

Then in 2016, Jill “took on a role that never existed before.”  Reporting to the Senior Vice President of Cisco’s $28 billion Americas (Canada, Latin America and the U.S.A), she was asked to “help with the way we engage with our customers, our partners, our employees.”  In that communications position, Jill said “it’s been a fabulous change. After 25 years of leading sales organizations, I am doing something totally different, and in many ways making a much bigger impact. It’s about how we engage. I have a small team of 7 fantastic women – first time in my life that I have an all-female team! –we are making  a difference in the way we (at Cisco) listen and communicate. “Jill’s busy team handles internal and external events, speaking engagements, public relations, internal and external communications of all kinds. “My team also captures the ‘stories’ “Jill said, both within and outside of Cisco, and “elevate and share them.” They have created very impactful Advisory Councils and “do a lot of survey” work to really listen to the field employees to hear more about what is happening in the market, with customers and partners.  Her team then sifts and analyzes the data to extract meaning and drive additional results. Ever action-oriented, Jill said: “I’m in the ‘then, what?’ business, and enjoying it!”

At this juncture, Jill feels very comfortable in her skin and has learned, along the way. For one thing, she has developed a strong appreciation for “mutual mission.” Jill said that to feel fulfilled, “most people need more than a number” for which to strive. “They need to feel they are making a difference.”  She believes that much of what Cisco offers truly makes a difference for customers. She is also intent on promoting unique treatment for each team member at the company. “While we rally around mutual mission, individual attention, understanding what makes that person tick” is a strength she uses, daily. “It takes time,” she said. “But until that connection really happens, I don’t think leaders serve their people as best as they can.”  She also candidly noted that patience is not an intrinsic part of her personality. “I have patience for the people, but not for the result.”

While comfortable now, Jill harks back to an earlier time in her career when she “felt defensive” as the only female leader in organizations. “Gaining results took some of that away, but part of it was simply deciding not to live in that ‘head space’ – to not allow myself to feel like I wasn’t welcome” among her male peers.   She gives back to the Cisco community by spreading that message and trying to help through an internal affinity group called Cisco Connected Women, a community for all women at Cisco, all over the globe. “I started the Michigan chapter. Then 2.5 years ago, I was asked to take over the Americas chapter of Cisco Connected Women.” It has grown to 4000 members in the Americas, with a 14-member managing board, and a 30-member Advisory Board.  “Connected Women’s role is to help attract, retain, develop, and celebrate women as part of Cisco’s competitive and diverse workforce,” Jill said. “We’re making a difference. And I have met amazing women; women I would never have met in my normal job!” Like other tech companies, Cisco is concerned about diversity, and so is Jill. “We are 23% female,” she said. “We’ve got a math problem here!” Jill decries the fact that while science, math and engineering are part of middle school and high school curricula, technology in many regions and school systems is noticeably absent. Jill’s rallying cry is “where’s the T????”.  She also notes that in film, and on television, female technologist role models are noticeably absent. “We don’t have a single film showing women doing meaningful tech,” she lamented. Cisco’s Connected Women, 7000 strong globally, implements outreach among adult women and in schools to encourage girls to pursue STEM curriculum and vocations.

In terms of her current personal situation, Jill’s children are thriving teenagers, so she is now “at an interesting place where I am trying to get back to things I enjoy” which includes tennis, a sport at which she has always excelled, working out regularly and socializing with friends. “Ultimately what makes me happy is having a blend. When things get out of whack, I really feel the stress. There is no perfect. You have to look at balance, long-term.”  She points out that dependent on the time in your life your priorities change. “We all need to have a little perspective; and let ourselves off the hook,” she exclaimed exhorting women not to be too hard on themselves over not achieving perfection every day. While work might take precedence one day, and family the next, each month and year are just the chapters. Jill also admits that she has an “unnatural fear of failure,” but has become much more comfortable taking risks, and learning from them.  “At today’s pace, you must be willing to be out on the edge, and then retreat, regroup and relearn.”

As an experienced sales manager for quite a while, Jill has several sales mantras.  One curriculum she developed started with a clip from the movie Tommy Boy, that emphasized intentional, focused listening in the sales process coupled with body language and other “buying signs.”  She also is a believer in what she terms “the sales fundamentals:” discipline, a process for contacting prospects and cultivating them, and the magic of face-to-face relationship building.

Key leadership and life lessons that Jill shared were:

  1. Be yourself. At some point in her career, she relaxed and “stopped trying to be one of the boys.” (Although she did learn to golf, “as opposed to drive the cart, which was suggested a couple of times.”)  When she mentors people, she advises them to be their authentic selves.

  2. “Go for it; be a pioneer.”  Try something new. “Do it different.”  

  3. “Embrace change.” The pace of change is intense, so keep up with it.

  4. “Be real with who you are.  Know your strengths and your weaknesses. Match your skills with your career.”

  5. “Create a woman friend network. If you have the right ones in your life, they will ‘high five’ you better than anybody. They will hug you when you need a hug.  They will nudge you when you need a nudge. And they will ‘call you on it’ when you need that!”

Jill Maiorano can be reached via Twitter at @jillmaiorano or via email at jmaioran@cisco.com.

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