Chapter 9 - Fail Forward: How I failed my way to the C-Suite and The Gift Wrapped in a Reorg

The gift wrapped in a reorg

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 9: The Gift Wrapped in a Reorg

When I left TiVo, it wasn’t by choice. If it had been up to me, I’d probably still be there. I loved that company so much. But in 2009, after nearly a decade of service, my time there ended in what I now refer to as the “reorg of one”—me.

It was a 400-person company, and yet somehow, the only role that got restructured was mine. My department was folded into IT and handed to one of my peers—a man we’ll call TinkerTim.

TinkerTim had been hired years after me by an SVP named “Dick”. Dick was brought in to run IT. For reasons unknown, Dick simply didn’t like me. Maybe it was something I said. Maybe it was just my personality. Who knows? Not everyone is going to like you in life.

My boss, we’ll call him Ace, reported to him as VP of Operations. Ace, who came from a Sales background, had no real operational experience, but he was a genuinely nice guy—laid-back, always tan, and almost surfer-like in his demeanor. While reporting to him, he mostly let me do my thing. He trusted me to run my department efficiently, and I did.

But when Dick came in, something changed. Ace became, for lack of a better term, tense. His easygoing nature gave way to frustration. He grew short-tempered, raised his voice in meetings—behavior completely out of character.

Then came the “one-on-one” meeting that wasn’t really a one-on-one. Ace and the VP of HR (whom I respected and admired deeply) pulled me aside to deliver the news: my role was being eliminated.

I was in shock. And in that moment, the only thing I could think to do was stand up, shake Ace’s hand, and thank him for the opportunity. “It’s been a pleasure working with you,” I said. I could see the surprise on his face. He hesitated, then stood and shook my hand and wished me luck.

As soon as he walked out of the room, I broke down in tears. I was sobbing, you know the kind of sobbing where you can’t catch your breath.

I had given nine and a half years of my life to that company. I helped launch the original DIRECTV + TiVo DVR. I led the Rewards loyalty program and the gift-giving initiative while running the full operations, project management, partnership, and service operations teams. I trained AT&T and Comcast installers out in the field. I had been a high performer. I had survived the dot bomb layoffs not once but twice because I was such a valuable player. And now I was being escorted out like a criminal.

Even the VP of HR teared up as she walked me to my desk. I managed to pack some personal belongings in one box, and they said they’d pack the rest for me to pick up the next day. My team watched silently as I walked out. It was, to say the least, one of the more humiliating moments in my career.

The next day, around 30 colleagues—my team, developers, IT partners, all took me out to lunch. Everyone was confused. No one saw it coming.

This was the second time I had been fired in my life and this time I couldn’t understand what I had done wrong. At least when I was fired from the truck stop at nineteen years old it was crystal clear on why I got fired. But this was a mystery.

Because I had invested so much of my soul into that company, it took me years to make peace with it. Eventually, I realized I might never understand why it happened. Sometimes the new people coming in just don’t like you for whatever reason. So I just learned to let it go.

But if I reflect really hard, the signs were kind of there, I just didn’t see them in the moment. Here’s what I mean:

Six weeks earlier, Ace had lost his temper with me in a one-on-one over something trivial. Not long after, he suggested I work with an executive coach, one that was company-sponsored. I agreed. Free coaching? Why not? I met with the coach a few times, and even she seemed blindsided when I was let go.

When I look back now I can see it for what it really was: a slow, silent performance plan without the paperwork. I was being managed out. And when that didn’t stick, the reorg became the excuse.

Lesson learned?

Honestly, this was not just a lesson, but in hindsight, the greatest gift ever given to me. I got a career reset, which we often never get in life. We graduate, we start working, and then we keep going—decade after decade, with only the occasional vacation or parental leave to catch our breath.

This moment gave me space to breathe. To reevaluate.

It made me realize I didn’t want to be in operations anymore. I was good at it. Actually, I was great at it, but it didn’t motivate me and make me feel like getting out of bed in the morning every day.

Once I had a chance to reflect, I realized what I actually enjoyed were the adhoc projects I’d done with the marketing team. That was where I felt creative, energized, aligned.

And that’s when I made the decision to switch careers from operations to marketing even if it meant starting at the bottom.

Sometimes failure doesn’t feel like a blessing in the moment. And sometimes, you have to be pushed off the path to find the one you were meant to walk. This was how I wound up in marketing.

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