Chapter 6 - Fail Forward: How I failed my way to the C-Suite

Failure to make a career pivot

Hi 👋 , I’m Tracy Sestili. I am a 4x CMO, 1x CRO and have built a career in SaaS. My path was not linear, but I wanted to share with you my path to the C-Suite in hopes you may find it helpful along your journey. I originally was going to turn this into a book, but decided I didn’t want to gate the content with a paywall.
I will be posting each chapter weekly here.

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Chapter 6: Failure to make a career pivot

Sometimes you’re not ready to make a change, and that’s okay too. Even if it is what you’re meant to do in the long run.

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As a Sr. Manager of Operations at TiVo, my new boss decided I didn’t have enough on my plate. At the time, I was overseeing Operations, Project Management, Partnerships, Business Intelligence, and Service Operations. Naturally, he thought I could handle one more thing—so he volunteered me to lead a new project for the marketing team: developing TiVo’s first ever gift-giving program.

TiVo truly revolutionized how we watched television. No more commercials. Pause live TV for a bathroom break? Genius. But the company was straddling two worlds—hardware and software. While you could buy a TiVo box and give the box as a gift, there was no way to gift someone the service itself. The box came from our hardware partners, like Philips and Sony, but the TiVo service had to be set up separately. The goal of this project was to bridge that gap and create a seamless gifting experience.

Even though I was already working 70–80 hour weeks, I genuinely enjoyed this project. I loved working with the marketing team. They were sharp, collaborative, and had a certain glamour about them—sending TiVo boxes to the Ellen Show, gift baskets to the Emmys®, and always buzzing with fun, high-visibility campaigns.

As we neared the project’s launch, the SVP of Marketing invited me to lunch. I figured it was a casual check-in, but partway through, she asked me a pointed question:

“How do you want to grow your resume? Wide and varied, or narrow and deep?”

Wide and varied meant I’d want to learn more about areas other than operations. Narrow and deep meant I wanted to still learn more about operations, and I was young and in my thirties – I also wanted a director level title and didn’t think I’d get that by hopping around from department to department.

In hindsight, it was a pivotal career moment—and I didn’t see it.

I wasn’t sure what I wanted, but I felt like I had to answer with something definitive. So I said I wanted to continue deepening my skills in operations. What I didn’t realize was that if I’d said “wide and varied,” she was ready to bring me over to the marketing team. That single response could have changed the entire trajectory of my career.

But that opportunity wasn’t my only missed career pivot.

Shortly thereafter, I was feeling ready for a new challenge. A friend at DoubleClick referred me for a role with their SVP of Marketing. He liked me immediately, and a few weeks later, I flew out to their New York office and met with one of his VPs. They offered me a manager-level position.

At the time, it felt like a step backward. A week later, I was promoted to Director at TiVo—the title was something I had been working toward and really wanted before I hit thirty-five. So I declined DoubleClick’s offer.

Weeks after that, DoubleClick was acquired by Google. And yes—I kicked myself. Hard.

What’s the lesson?

In my experience everyone goes through the same phases in their career:

• In your twenties you want to make more money than you have experience for.

• In your thirties you want the title that you’ve worked so hard for.

• In your forties you want the bigger title and ability to make the bigger decisions – you want a seat at the table.

• In your fifties you care about being employed, having health care coverage, and 401k contributions are an upside.

• In your sixties and beyond, if you financially planned properly, then you only care about healthcare. Any paycheck is considered a bonus.

These phases often influence the decisions we make regardless of the opportunities presented to us.

Also, opportunity doesn’t always show up with flashing lights like a blue light special at Kmart. Sometimes, taking a step forward means taking one sideways—or even backward.

Would I have loved working at Google? I’ll never know. Had I answered “wide and varied,” would I have gone down the path of direct-to-consumer marketing instead of B2B? Possibly.

The truth is, we can’t always see how each decision will shape our future. But we can learn to evaluate not just the title, but the potential. Ask ourselves what happens if I do take this role, or don’t? We can learn to trust our gut without letting fear or ego get in the way. Both require serious inward reflection.

Every decision changes our path. And while these choices may have altered mine, they also gave me clarity—and taught me to listen more closely to my gut the next time an opportunity came calling.

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