Ep 64: Holly Rollo: Turning Uncertainty Into Transformation

Diva Tech Talk was thrilled to interview Holly Rollo, Senior Vice President and Chief Marketing Officer of RSA (www.rsa.com ), a Dell Technologies (www.dell.com) company, offering business-driven security solutions, designed to detect and respond to advanced attacks; manage user identities and access; and reduce business risk, fraud, and cybercrime. RSA protects millions of users around the world and helps more than 90% of Fortune 500 companies thrive in a high-risk world. 

Like some other Diva Tech Talk interviewees, Holly said: “You never know what’s in store,” since she did not originally set out to be a technology leader. The daughter of a Marine who was taught the value of determination and hard work at a young age, Holly’s journey began with a passion for investigative reporting. With an undergraduate degree from Santa Clara University (https://www.scu.edu) in journalism, “I had two job offers, right out college.  One with a paper, and the other as a PR person for a high-tech, semiconductor company.”  She chose the PR job and has no regrets since “what is amazing about marketing is that you’re constantly chasing a story. It’s a creative job. It’s a quantitative science job. It’s a technology job since marketing has gotten more technical.” Her philosophy is that journalism concentrates on telling the truth, and “that’s what we try to do as marketers. In technology we are trying to find the true things that really help people solve problems.”  One of her strengths is her “curious mind.” As Holly got started, she “asked the dumb questions”, including ‘what does this mean for customers?’ and ‘how do they buy it’….” The answers she received helped her ”understand the whole picture” and weave the right stories to promote and strengthen brands, products and services. “As I would drive the discussion to a more strategic level, I became a better marketer” since it helped pinpoint the right customers, the right segments, the right channels/methods of product distribution.

From National Semiconductor, (purchased by Texas Instruments (http://www.ti.com/)) Holly moved up through a variety of marketing jobs, building a substantial career and a wide perspective. “Early on, I was thirsty for as much experience as I could get.” She said that her path, which encompassed stints at Young and Rubicam, IBM (www.ibm.com) Sanrise (www.sanrise.com) Symantec/Veritas (www.symantec.com), Sybase (www.sybase.com), SAP (www.sap.com), Cisco (www.cisco.com) , FireEye (www.fireeye.com) and Fortinet (www.fortinet.com) , was forged by “focusing on what I was good at; what I was interested in. 

“What I am really interested in is major shifts or transformation.” So rather than working in status quo situations, Holly was motivated to take on “big, hairy problems.” Some of those included repositioning companies or older brands to take advantage of new markets, effecting full company turnarounds, positioning organizations for hyper-growth, or rationalizing and organizing hodgepodge tech product portfolios.  “I like jumping into the middle of chaos and making order out of it!”

Her career has also morphed, as her priorities changed. Holly said that life stages can surely affect your career choices.  For instance, starting out, she said, “the brand that you work for, ‘speaks’…” and choosing it wisely can determine your career trajectory.  “After that, there are different things that are important,” she noted. One of her career changes was inspired by a desire to “work with a woman who could mentor me.” Then, “later, as I had children, flexibility was more important,” she said. “Now, what I have learned is that I want to work with people who are amazing, people to have fun with, every day.”   

In making mission choices, Holly thinks that what instinctively drives decisions can be different for women than men. “Sometimes, what’s important is the money. I think women are sometimes uncomfortable with that idea.”  Holly also stated, “there are tradeoffs.” She cited the example of choosing a startup with exciting potential, great experience and an impressive title versus working for a larger, more established company at a higher compensation level. “You have to be your own advocate.  And you need know what you are advocating for…” When making key career decisions: “do the introspection; understand what’s important for you, at any point in time. Get as much information as you can; know what you want; know what your boundaries are.” She recently finished reading Never Split the Difference: Negotiating as If Your Life Depended on It by Chris Voss, a book germane to this topic, as well as other areas of business mediation, and then gave it as a gift to her daughter.

Holly also suggested, for personal peace of mind, “there has to be a conversation, at home, about tradeoffs.  You have to know what you can balance, at home, in that workload,” to construct the right career road. In collaborating with her family and children, she also tried to be transparent; “when you must miss something, it’s important to explain to them what’s going on. They’re going to be faced with the same challenges in their lives. They are going to have to make tough choices, too.”  Her daughter is 22, and her son is 20. “He’s going to be a husband someday. My expectation is that he’s going to do half,” so she has been setting an equity foundation and example for her children through her actions, conversation, and counseling.

To achieve balance, in times of stress, in addition to yoga and hiking, Holly reminds herself “it’s one day at a time, one work week at a time.”   The tech industry is unpredictable so “this can all change tomorrow. The best I can do is just focus on what’s right in front of me and take it in bite-sized chunks.”  She uses the same approach with her team, when facing gargantuan, challenges, and then they “do things they never thought were possible --- amazing, epic, incredible things.”

Holly is grateful to be in the security field. “There’s a bigger mission. Particularly in the current environment, you can really understand how what goes on in the digital world impacts us all. It’s about how you detect and respond, managing risk to your bigger business mission.”  The security issues are so massive according to Holly that “I constantly feel like we are behind.” To address the quickly-rising level of crime and malicious activity, “we have a lot of catching up to do. It’s not just information technology’s job. Everybody has to think about risk to the organization.”  She notes that the rise in security breaches is also affecting marketing technology, an exploding field. “There are over 6000 martech companies,” she said. “And half of those companies are less than two years old. Complexity is the enemy of security. So, marketers now have a role in opening up companies to data privacy issues and data risk.” She recommends that people read: Future Crimes: Inside the Digital Underground and the Battle for Our Connected World by Marc Goodman, for a better understanding of the future  security issues potentially facing our world.

Holly noted that there is “a massive issue in technology employment,” and “everyone is going to be needed. We need all kinds of talent.  We need more women in engineering; we need more women in leadership; we need more women in storytelling positions.” With the advent of the “Me, Too” movement and more progressive societal influences, she thinks that “a lot of behavioral changes are going to happen” to assist in breaking down diversity barriers. “We have the power to vote with our feet, and choose not to work for a certain company, or a certain manager, leader or CEO.”  The biggest issue in Holly’s mind that needs to be addressed is “the pay equity piece.” She noted that each individual manager can change that. “Every year, we go through reviews. We have the power to address the pay gap” then. Her perspective is that pay equity is solvable, “if we chip away at it, little by little. Everybody can play a role.”

Holly can be reached on LinkedIn at https://www.linkedin.com/in/hollyrollo/ and on Twitter at @HollyRollo.

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Diva Tech Talk Team

Podcast Divas