Tracy Sestili: “Surround yourself with positive people”

Surround yourself with positive people. You have to fill up your own cup, so to speak. If it’s empty, you won’t have anything to give to others in your life. Positive people feed your endorphins, and on days when things aren’t going according to plan, you need those people in your life to lift you […]

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Surround yourself with positive people. You have to fill up your own cup, so to speak. If it’s empty, you won’t have anything to give to others in your life. Positive people feed your endorphins, and on days when things aren’t going according to plan, you need those people in your life to lift you up. My best friend since the ninth grade is one of those people.


How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love and life as a powerful woman.

As a part of this series I had the distinct pleasure of interviewing Tracy Sestili.

Tracy Sestili is a tenured marketing executive leading teams at Fountain, SparkPost (acquired by Message Bird), Cisco, and TiVo. She has previously served on the board of Women for WineSense, and co-founded a nonprofit for lung cancer, for which she received a Bay Area Jefferson Award. She has also been an adjunct professor in digital marketing and social media at UC Berkeley and San Francisco State University, and has authored Taking Your Brand from the Bench to the Playing Field.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I grew up in an all-Italian household in Northeast Philadelphia before moving to Silicon Valley in 2000 to work for then DVR startup TiVo. My father worked in a steel mill and then for the Philadelphia Housing Authority before retiring. He also did masonry work as a side hustle for as far back as I can remember. He was always working multiple jobs so we could have a better life. My mother worked part-time jobs and then, once we were old enough to look after ourselves, she went back to work full-time, first processing claims at an insurance company and then in accounts receivable at a nationwide lighting company up until her death. Neither of my parents went to college. In fact, they didn’t even graduate high school initially, although my mother did go back to get her GED. My brother and I were the first in our families to go to college and graduate. I remember really wanting to go to college in California, but we couldn’t afford it. We both took out student loans and had part-time jobs during college. It was nothing unusual for us to work: I had worked since I was 13 years old as a waitress in a neighborhood Chinese restaurant and he had worked since he was 11 years old starting out with a paper route. Work ethic was ingrained in us since we were kids. We learned: Work hard and it will pay off.

Can you tell us the story about what led you to this particular career path?

At TiVo, I started out as a project manager and worked my way up to Director of Operations, often servicing the marketing and customer service departments with their needs. After nine-and-a-half years I decided it was time for a change, so I left TiVo to figure out what I wanted to do next with my career. I thought I might want to be a writer. I took some freelance writing gigs and wound up ghostwriting for a CMO on his company blog. That experience led me to believe I, too, could start my own blog and my own consulting business, so I did. What I hadn’t realized was how much work consulting was when you are doing all the work yourself, plus marketing and selling your services and maintaining a website. After six years of consulting at companies like Cisco and CA Technologies, I decided to seek out full-time employment to contribute to my 401k, and that landed me a full-time job as a social media manager at a B2B SaaS company. Even though I was overqualified for the role, I just wanted to be doing something that I loved. Shortly after I was hired, the CMO decided I was too valuable to work on the sidelines and quickly promoted me to Director of Digital Marketing. My career flourished from there.

Can you share the most interesting story that happened to you since you began your career?

If I had to choose one, I’d say it was getting a six-foot LEGO structure built of our “flame” logo for a developer conference. It was super stressful because we didn’t have an events manager and I came up with the idea of the LEGO about 10 weeks before the event. I didn’t know anything about getting massive LEGO objects built. I quickly learned that there are only 40 Master LEGO Builders in the world and they all work for LEGO. Well, all but five, who started their own company in the UK. I contacted them and they said they could do it but it would take eight to 10 weeks. I decided to go for it. After it was stuck in U.S. Customs for a few days, it arrived at the event the day before the conference started.My goal for this event was to elevate our brand, drive people to our booth, and do it all within the small budget I had. I worked with my team to come up with a “Tweet It to Win It” contest with the hashtag #FindTheFlame that was used on everything from staff shirts to swag and social media. On the last day of the conference, a camera crew came by and handed me a weightlifting belt and congratulated us on winning Best Integrated Marketing Campaign — beating out over 300 other vendors, many with much larger budgets. I had no idea there were any sort of awards!

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Persistence. I believe persistence is the key to success in everything you do. After I was promoted to run a department, I had a founder once say to me, “Congratulations. You wouldn’t have been my first pick, but I support the decision made.” I didn’t quite know how to respond to it. Internally I could hear my mom’s voice saying what she always used to say when you told her you were going to do something: “Pretend I’m from Missouri, the ‘Show-Me’ State, and show me what you can do.” I’m a big fan of actions that speak louder than words.
  2. Curiosity. I have found that truly taking an interest in what others have to say and asking questions, getting to know them on a more personal level, helps you uncover possible untapped skills in your organization. For example, once I learned in conversation that a team member was bilingual in a market we were trying to break into — a handy skill indeed.
  3. Gratitude. You have to remember to thank people in your life. At one company, I used to give out greeting cards that were in the shape of a guitar and called it the “Rock Star Award.” Each month I would give one out along with some company swag or a gift card to a team member to recognize them for something they did well.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

It’s true, strong women are not the norm; however, I think as a society we have a real opportunity to change this perception. Boomers and Gen Xers whose values are often rooted in stereotypes are aging out. Gen Z and even Millennials are more inclusive, open, and respectful of opinions that differ from their own. It takes a conscious effort to question values you grew up with and that you thought were true. But after careful examination, you may find these are just stereotypes.

Without saying any names, can you share a story from your own experience that illustrates this idea?

You have to be direct about the change you want to see. At one company, a senior male leader came up with the idea to give out a “Woman of the Year” award for best achievement by a female. What was fundamentally wrong about this, as some of us pointed out, was women don’t want to be recognized in a special category. We want to be recognized equally for our achievements among all of our peers, including men. While the initial idea came from someone who was trying to be helpful in recognizing women’s achievements, sometimes the best intentions are unconsciously biased. Thankfully, there were enough powerful women in the room to quash that idea.

What should a powerful woman do in a context where she feels that people are uneasy around her?

If you notice it, then it’s probably true. To be sure, you could ask the person if there is something you said or did (or didn’t say or didn’t do) to make them feel this way. Usually we assume it’s what we said or did, but it can oftentimes be something we didn’t say or do that made them feel uneasy. Opening lines of communication and showing you are receptive to feedback can help open doors. Communication is the key to success in every relationship.

What do we need to do as a society to change the unease around powerful women?

We should always take opportunities to educate others when we can and encourage others to be curious, to ask “why.” Powerful women are not afraid of the tough questions. However, it goes far deeper. Men need to recognize their unconscious or conscious biases and fears toward powerful women. Equally, women need to recognize men’s fears. As a society, and I’m no expert here, but all of our issues seem to stem from inside the home. Growing up, children look to the matriarch and patriarch and family dynamics to understand how men and women interact. If you grow up in a household where your father constantly verbally abuses your mother and you notice her self-esteem takes a hit, then you may think this is the normal way men and women are supposed to interact and speak to each other. You take those lessons with you and although you don’t realize it, you unconsciously develop biases from them. The truth is, whether we want to admit it or not, we are all exactly like one of our parents, emulating values we admired, or exactly the opposite, which usually stems from bitterness or resentment.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

Long before the days of rideshare services and before I came into my own skin, I once found myself stranded with a group of co-workers and managers after a meeting. I thought we were going to a bar for a quick drink. When we arrived, it turned out to be a strip club. I had no way of getting back to the hotel so I forged ahead and went in. Within 10 minutes of sitting down, one of the guys whispers to another guy, and the next thing I know I became the recipient of an unsolicited and unwanted lap dance. It was humiliating. The next day at work, all I could think about was that they were picturing the lap dance every time they looked at me. The funny thing is they probably don’t even remember this incident. But I’ll never forget it.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?

There are a few. First, it’s lonely up here. There aren’t a lot of boardrooms or executive off-sites I’ve been to where the number of women outrank the number of men. When it’s team-building time, you usually have to go with the flow and put your big girl pants on rather than your skirt. On the flip side, you never have to wait in line for the bathroom.

Second, pay parity is still an issue. Women just are not great negotiators. Every female who has worked for me and has asked me for a raise, I’ve taken the liberty of coaching them on how to better ask for it next time around. As powerful women, we should coach other women on how to navigate the waters.

Third, how we express ourselves is always under a microscope, especially with video conferencing. From our facial expressions to the way we’re dressed to what we say. If a guy shouts in a meeting, “That’s [insert f bomb] ridiculous, there’s no way we should do that,” he’s considered forceful, insightful even. Whereas if a woman said that, she’d be considered “emotional.” If she doesn’t say anything, she’s considered weak or stupid. If a man is quiet, then he is “actively listening.”

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

In 2005, my mother was diagnosed with lung cancer. The doctor told my brother and me that she had about a year to live, give or take. I wanted to spend as much time with her as possible but I lived and worked 3,000 miles away and had just started dating my now-husband of 16 years. It was one of the hardest crossroads in my life, trying to balance a job where I was working 70-plus hours per week, a new relationship, and a dying parent. TiVo allowed me to work remotely one week a month for the entire 15 months before my mother passed away, which back then was considered very generous. During this time period, I got engaged. At one point it looked like she might recover, so we were quick to plan our wedding. However, unfortunately she passed just five weeks prior to our wedding. During this time, I had been managing a large team and we were giving out salary increases and stock grants. One of my direct reports received a larger raise and grant than I did, and when I asked why, my manager told me that I had been “out a lot” even though I had been working remotely. I explained that people can’t plan when people die and that our wedding was already planned so we would have lost so much money had we cancelled. But there didn’t seem to be any empathy. My absence, even though I was working and orchestrating things from afar, was hard for him to justify. It was almost like I got punished for trying to make everyone happy.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

The death of my mother and meeting my husband both taught me that some things in life are way more important than work. Work is always going to be there, but the people in your life may not be. I think as women we get caught up in the climb to the top and forget about what actually matters most. I think COVID-19 has really forced people to be alone with their thoughts, reflect, and evaluate their lives. It wouldn’t surprise me if we see more people living their lives rather than climbing the corporate ladder. There’s an old Nike t-shirt quote that said, “Everyone who lives dies, but not everyone who dies has lived.” After 25 years, I find that more relevant now than ever.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

There’s a higher scrutiny put on women but it’s put there by societal norms, not necessarily by the workplace itself. I’ve always been a big believer that to get the part you have to look the part as well as act the part. Once I became an executive, I always wore a power blazer and jeans or slacks. You never want to look disheveled for fear someone may think your work is as unorganized as you appear to be. But I don’t think there is a need to try too hard here either. You have to find some middle ground where you don’t look too flirty, yet you don’t look like you just rolled out of bed. It has to be somewhere in between.

I have worked with women who get up two hours earlier just to do their hair and makeup. That is way too much effort for me. Besides, isn’t that what Zoom filters are for?

How is this similar or different for men?

If you think about it, the expectation is fundamentally lower. Most men don’t wear makeup. There’s a lot of time you need to budget as a woman to get ready. Also, women are just fundamentally judged on our appearances and that’s long due to the representation of women in the media. For decades women were depicted as sex objects. While many brands have made a conscious effort to be more inclusive and have diverse representation, we still have a long way to go in society.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

  1. Integrity. Brené Brown says, “To be clear is kind, to be unclear is unkind,” and you have to be true to yourself and your own core values. Your values drive every decision you make, from family to dating to critical decisions at work. Be aware of what they are and hone them if you need to. You have to look at yourself in the mirror at the end of every day and be happy with what you see.
  2. Surround yourself with positive people. You have to fill up your own cup, so to speak. If it’s empty, you won’t have anything to give to others in your life. Positive people feed your endorphins, and on days when things aren’t going according to plan, you need those people in your life to lift you up. My best friend since the ninth grade is one of those people.
  3. Seek to understand. I often find when conflict arises, there is always a miscommunication or misunderstanding that causes it. Ask questions, be curious. Ask for feedback about yourself or an interaction. Even if you disagree, understanding how someone perceived your words or actions can help you modify it next time you’re faced with the same situation.
  4. Lift up others. Always take the time to recognize others and say “thank you.” Being successful is less about what you know and more about the relationships you’ve built along your journey. You don’t have to be liked by everyone, but you should always be true to yourself.
  5. Family first. There is no job on the planet that is more important than your family. Period. When you live to work, you’re not working to live. Life is short and sometimes shorter than we planned. You don’t get time back so make it count.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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