12 Questions with Holly Rollo

Chief Marketing Officer at RSA

As Chief Marketing Officer at the cyber security company RSA, Holly Rollo leads the global marketing organization and guides its market transformation.

Over the past 25 years, Holly has led successful transformational initiatives that have driven growth, established global brands, and built operational scale. Holly joined RSA from Fortinet where she served as Chief Marketing Officer.

Prior to that she was at FireEye, where she served as Vice President of Corporate Marketing and played an instrumental role in the cybersecurity company’s explosive growth by building a scalable marketing engine, driving brand awareness, and transforming field marketing in partnership with sales. Holly has also served in senior marketing roles at SuccessFactors and SumTotal Systems, and marketing and strategic planning roles at Cisco, SAP, and IBM/Tivoli. Holly holds a Bachelor of Arts degree from Santa Clara University.

  1. When did you decide that you wanted to work in the tech industry?

In college, I wanted to be an investigative reporter. I loved writing, the pursuit of truth, and solving complex problems that involved people instead of math. I graduated from college with student loans and two job offers, one for a newspaper and one for a semiconductor company in public relations. The PR job allowed me to pay my living expenses and loan payments so it made the decision pretty easy. What I discovered is that being in marketing in tech uses the same ideas and skills as a reporter uses; seeking truth, investigating facts, finding and plugging holes in the story, and revealing the big idea.

That led me to jobs on the agency-side, and for some time I crossed over to strategic planning. I found that often marketing drove strategy because when you have to write down what your company stands for, there are often big decisions that need to get made that are way above marketing’s pay grade. I think curiosity leads people to strategic roles because they can’t stop asking questions.

The day I made the transition in the mid-90’s, I was leading the marketing planning process for a company and the business plan wasn’t well understood. No one wanted to go up to the executive floor to find out what it was, so we were stuck. I went up the elevator to the top floor and knocked on the door of the new VP of Strategy’s office (he was the big important guy), and I asked him what the business plan was. He told me to close the door and said, ‘Here’s the thing, there isn’t one, but do you want to help me figure out what it should be?’ I learned a lot working for him over the next year doing research, segmentation and go-to-market strategy.

I went back to marketing after a number of years in strategy because I liked creating brands, telling the story, and building high-performing teams. As opportunities presented themselves, I tried a lot of challenges on for size. I think the secret to figuring out what you are good at and what you like is exposing yourself to as many different situations as you can. I learned I wasn’t a great fit at big companies because I was too impatient with the pace, though I did fine in incubated or subsidiary divisions of large companies because they acted more like startups. I discovered I was really good at leading major transformations, which had really aggressive goals and time constraints. I found that I thrive when there is a sense of urgency, chaos that I can help make order out of, and an opportunity to create or rebuild something from the ground up.

2. When did you first realize that you are a leader?

In hindsight I’ve never been shy about making decisions or stepping up for things. I don’t particularly have a desire to be in the spotlight or a need to be in ‘charge’, it was more about me wanting to move things forward when there was a situation that needed attention. Patience is a virtue, I’ve heard, just not one of mine.

As my career progressed, I had the privilege to try different things and help different brands transform or turnaround situations where there was a complex set of problems. I discovered I was really good at pulling in different people and rallying them to work together to overcome or accomplish things that on the surface look too hard or goals that others would say are too aggressive. I’m a hopeless optimist and have this passion for the underdog to win, so when there is a big mess, I can see what it could be and a path to get there.

This is also a weakness of mine because I have gone into challenges, eyes wide open, and have given it a herculean effort but some things are just too broken to fix. However, I don’t regret any of those adventures because I always learned more for next time or more about myself in the process.

3. How have you navigated through career changes?

Someone told me very early in my career in tech, ‘You don’t work for a company, you work for the Valley.’ This is such a true statement. There are some good principles to apply. First, be honest with yourself about your career goals and what’s important to you. No one else is managing your career so it’s important to take a look at this every once in awhile and be sure you are staying true to your goals. Sometimes it’s about flexibility, sometimes it’s about getting experience, sometimes it’s about the money. It’s just important to know what that goal is. This is an easy thing to get confused because we often define success by what other people are doing, rather than by what we want in the short-, mid- and long-term.

Second, be open with your manager about your goals and check in at least twice a year to see what you can do to improve in areas to help you achieve them. It’s important that your manager, and other people, know what you are striving for and what you are working on because you can get good feedback and support along the way.

Third, don’t feel guilty about making the best decisions for yourself and your family, if you make a decision to leave. Loyalty is important in relationships and those relationships will last beyond individual jobs and can last a lifetime. People are loyal to people; we are all in the same industry.

Finally, be a good leaver; everything comes full circle. Backchannel references are how people get jobs. I’ve interviewed people that I used to work for on more than one occasion. In business, and in navigating changes, it’s good to remember the notion of Good Karma. What comes around goes around, so keep your side of the street clean.

4. What’s a challenge you’ve faced in your career journey?

The biggest challenge, beyond anything else, is being career-minded (not just working, but being a women who wants a career that progresses) and the trade-offs that go along with that as a mother. I’ve experienced two major trade-offs: time and guilt.

Let’s talk about time. For some couples the father stays home, or there is more of an equal split of responsibility at home. In many cases most of the responsibility of the day-to-day logistics and running the home falls on the mother. I’m talking about all the parenting technicalities and tactics: organizing carpool, getting homework done, keeping up the house, groceries, meal planning, doctor’s visits, dental emergencies, teacher conferences, open houses, vacation planning, weird school schedules or half days, paying the bills, PTA, getting the carpets cleaned after a kid was sick with the flu, and on and on and on.

It’s a second job — forget wanting to exercise or read a book. The problem is that it’s a thankless job. The father can take the kids camping one weekend and they remember that for the rest of their lives, but no kid remembers the million things we did and the endless hours it took to just keep the engine running over the years — while also trying to progress a career. It’s the hardest thing I’ve ever done and it’s a job that starts when your children are born and doesn’t taper down until they can drive themselves. On the other hand, being a mother makes you dig deep and show what you are made of, which makes you a better leader. You learn how to delegate and outsource, manage time, expect people to own their part. I think staying career-minded also makes you a better parent. I expected my kids to be self-sufficient and independent, learn when to ask for help and when to knuckle down and figure it out, and learn how to respect other people’s commitments, responsibilities, and time. This is how real life works. I took that approach early on; I wanted them to understand the concepts of personal responsibility, accountability, and real life consequences.

“Being a mother makes you dig deep and show what you are made of, which makes you a better leader.”

This is where guilt kicks in. They are your kids so you want to be the mom that makes them heart-shaped sandwiches for lunch or shows up at the school pep rally with a poster with their name on it. You miss those things. When my son was in preschool I missed a birthday party invite that was shoved in the bottom of his backpack. The teacher called me from school because he was crying that he was the only kid not going to the party. Bad mommy!!! (He ended up going with another mom, as I was bawling my eyes out the whole drive home from my office to meet him there — without a gift.) Maybe because of a business trip you miss games or meets. It’s just the way it is.

What I learned to appreciate is what I was teaching my kids. I was showing my daughter what it would be like if she chose to have a career and a family, that it would be hard but not impossible. I was showing her what’s possible. For my son, I showed him what it took to have a career and kids, and talked a lot with him about how he could step up to help. As he reached 14, we had talks about how important it was for the man to step up and do his part. In this way, I felt like I was helping the greater good, both with my kids and for future working women in a small way.

5. Describe a time you were proud of yourself.

I wouldn’t use the word pride, I would use the word grateful.

I’ve overcome a lot in my life, many of people have. I am truly grateful to have been given the opportunities that I’ve had, which were initially disguised as barriers. I came from a family who had nothing and struggled on many levels. I grew up in a tiny log cabin in the back woods of Maine with a dirt floor and no running water or electricity. My father was a disabled Veteran who struggled with PTSD. In middle school and high school we moved many, many times switching schools almost every year, going on and off of welfare. Through all this I knew I wanted a college education (I would be the first in my family) and was accepted to a great university and was grateful to be given scholarships and financial aid. That opportunity changed my life. I overcame some personal challenges in my 30’s that were unexpected, but helped me to further develop.

I think, however, that the proudest day of my life is yet to happen. I’m pretty sure it will be on June 17th of this year when my daughter graduates from college and will be pursuing a career in tech. She worked hard for it for sure, but I’m already bursting with pride with the idea that I was able to raise such a strong, independent woman who gets to take on the world and make her dreams come true. I know people raise kids everyday and thousands of kids graduate every year, but honestly, it feels like a tiny miracle.

6. How have you seen women differ from men in the tech industry?

The following is an absolute general statement not true in every case, but generally true.

I think the biggest difference is men don’t feel the need to be fully informed with facts to speak from a position of confidence. Women don’t do this. What I’ve observed over the years, time and time again, is men take a conclusive position and fill that in with evidence, then look to others to find solutions. Women like to gather evidence and facts and then take a position, then offer solutions, which include how to collaborate to be successful.

When women do this, men will ignore it, move on, and then restate it as their idea or pick the idea apart until the woman backs down, which she usually does. I honestly think that women just want to get to the best answer, don’t have pride in it being their idea and are quick to assume they missed a meeting or piece of information.

Here’s the problem: in tech, the world moves fast. We can’t always have all the facts, so when men do this, there is a tendency to move rapidly, getting behind the man to move forward, though he may not actually know the solution. This is often confused with leadership, so men like this get promoted where women appear to be followers because they are the ones solving the problem. What I’ve also seen is a quick decision made based on how confidently the position was delivered by the man. Women rally to solve the problem and it fails, then the women get blamed for failure to execute when the true problem is that it was a flawed decision in the first place.

A man gave me a great piece of advice early in my career. He said, in tech as a woman, always ask yourself ‘what would a man do in this situation?’ I must ask myself that question at least once a day. It’s a really weird and controversial piece of advice because I don’t believe I should need to act like a man to succeed in this industry. What it does do is force me to think through the situation and sometimes that pause gives me the courage to either confront or approach it differently than I would have otherwise and so because of that, it’s a great piece of advice. It also makes me think through the person I have to negotiate with or escalate to which is usually a man, so it helps in that way too.

7. What are tangible actions we can take to make tech more inclusive for women?

I’m not convinced the issue is inclusion; inclusion is coming because women are smart and focused, so the talent gap will start to solve this. It’s pay equity that I’m concerned about; it’s taking too long. It’s not right that we make 70% less for the same work. Short of all the women in tech going on strike until our pay is fixed, this change will only happen through meaningful mentoring. You can read more about this on my blog ‘One Woman at a Time’.

8. Can you share advice for women who are working mothers in tech?

Many young women won’t remember this, but when I was growing up there was the commercial that perfectly captured what we were being told at the time. “I can bring home the bacon, fry it up in the pan, and never let you forget you’re the man.” You have to watch it, it’s ridiculous.

The big lie at the time was that we could do it all successfully. We can’t, something always gives. I don’t know a single working father who feels like they do everything at the same time and still feels like they are falling short. Maybe they secretly do, but for all the women I speak to, this plagues us. The design flaw is that we require sleep.

The advice I would give is twofold. First, remember that everything has trade-offs. It’s been my experience that you actually can’t do it all, so lower your expectations for yourself and you’ll quit feeling like you are failing everywhere — give yourself a break. Second, guilt is a wasted emotion. I realize not everyone will agree with me on this. It doesn’t mean you are a bad mom because you miss a game or forget a birthday party. Our kids need to learn that we are individuals with goals and dreams of our own outside of our role as their mother, and we are human, just like they are. This is my personal opinion, but not only is it good role modeling, it’s good for helping them learn to be respectful and independent as they grow into adults.

9. What keeps you up at night?

Pay equity for women. My daughter is graduating from college this year and starting in tech. It aggravates me to no end that she will ultimately make 25% less in this industry for the same work — which will some day include all the extra work required at home when she decides to have children of her own.

“My daughter’s great-great-great-great-granddaughter may see equal pay for equal work around 2186. This is not acceptable.”

The World Economic Forum estimates it will take 170 years for us to see gender pay equity at the pace we are going, (see the US Gender Gap ranking for the US). That means my daughter’s great-great-great-great-granddaughter may see equal pay for equal work around 2186.

This is not acceptable.

The second thing that keeps me up is gender bias and what to tell my daughter about how to handle condescending misogynistic people…who control your career. Early on, you have fewer options to call foul because it’s so subtle and nuanced. We take the high road and grow thick skin but the problem is people confuse tolerance with acceptance, which just perpetuates the problem. This is where we need the help of our male peers, we need and we appreciate their support — we need them to be part of the solution and have our backs. It’s not the best solution by any means, but it’s one solution.

As I’ve gotten older, my tolerance is much lower and now I have my own boundaries about who I will and won’t work for and with. I no longer interview with companies, I interview bosses and the executive teams. It’s all about fit, over money or anything else. As more of us refuse to work for these kinds of people, ultimately they will just quit attracting good talent because in the Valley word travels fast and you can find out everything you need to know about someone in two phone calls and again, it’s the team that decides success or failure.

10. What gets you out of bed in the morning?

The sun and the smell of coffee. I love to sleep and am not a morning person.

11. If you could try another job for a day, what would it be?

This changes every day. I would love to try lots of new things, but I think I would like to try being a CEO, a CIA agent, a journalism professor, a trauma surgeon, a National Geographic photographer, and a DJ… or a drummer in a rock band.

12. If you could give your eighteen-year-old self a piece of advice, what would it be?

I think when my career started to get more meaningful as a leader was when I realized the hidden truth about business — no matter how experienced or smart people are, leaders are still making things up as they go along. People are making the best decisions they can, with the information they have, making choices and learning as they go. I think when you are young you have this idea that wicked smart people sitting in the boardroom, with special data and models or fancy degrees making highly quantitative evaluations and coming up with super scientific strategies and plans for their business. I’m sure that is true in some cases but it’s been my experience that business leadership is the ultimate equalizer. No matter how smart any one person is, there are so many dynamics in making choices to lead change or growth, so many unknowns and unintended possible consequences, that the best people can do is put as many ideas on the table as possible and collaborate together to narrow to the best, most effective option; rather than searching for the individual idea that’s perfect.

Early in your career you sort of feel like this imposter, like you don’t know enough or have enough information to contribute, or maybe missed important conversations that everyone else seems in on. I’ve done this myself and I observe women especially do this a lot. It’s a very self-centered point of view, thinking so much about your own deficiencies that you choose not to share your ideas in places where it might be helpful. We mostly do it because we fear being judged. My turning point was realizing it has nothing to do with my insecurities and if I contributed enough to the whole collaborative process at some point something I contributed would be helpful. That’s how it happens; good ideas come from unexpected places.

The best day of my career was the day I put three things together. First, I quit caring about my own deficiencies and what people thought of me. If I have a true north and make suggestions or decisions with integrity, all people can expect is my best possible thinking and effort. I felt like I took a 100-pound weight off my back. None of us control what other people think of us anyway so it’s wasted effort caring about being judged if you really think about it.

Second, I realized everyone else is learning as they go too. Every leader feels like an imposter at some point and wonders if they are making the right decisions. The trick is to make the best ones you can and either succeed or fail fast and recover.

Finally, I changed my thinking about contributing. It’s just selfish to keep ideas to myself because I don’t think they are good enough; who am I to judge? To someone else they may be brilliant or trigger someone else’s idea that’s even better. There are really big problems to solve and they can’t be solved if everyone is looking at the problem the same way. That’s why we need many different perspectives at the table and more wild and crazy ideas to drive innovation.

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