Chapter 7 - Fail Forward: How I failed my way to the C-Suite

Failure to put myself and my family first

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 7: Failure to put myself and my family first

In 2005 my mom was diagnosed with lung cancer. She died 15 months later and five weeks before my wedding. At the time I was working at TiVo. My boss, Stephen, who was incredibly kind, suggested I work remotely one week per month. This was long before the pandemic when remote work became a thing. Remote work was virtually unheard of then.

I took him up on the offer. For the next 15 months, I traveled back and forth to Philadelphia from Silicon Valley, balancing work and caregiving. But every time I left, my mom would look at me with her soft, doe-brown eyes and say, “Can’t you stay a little longer?”

Those words hung in the air a few seconds and then fell on me like a ton of bricks – every time.

I was conflicted. At the time I had just started dating my now husband. Juggling a new relationship, working 70 hours a week at a startup and trying to be there for my dying mother was a lot weighing on my shoulders.

While the offer TiVo gave me was quite generous, looking back, I should have applied for the Family Medical Leave Act (FMLA). It would have meant taking a 33% pay cut and going into debt, which at the time, I didn’t think I could afford given my rent and bills, but in hindsight it would have been worth it.

During those 15 months, my manager changed. The new one didn’t quite understand the arrangement—even though it was explained to him. In his mind, I think he wanted to know what made me so special to deserve such special treatment of being able to work remotely once a month. Every time I came back from the week with my mom and we had our one on one meetings, I always felt I was getting grilled even though I was actually working the whole time.

I knew what a gift and privilege this was and I never took it for granted. I worked around the three-hour time difference, taking my mom to medical appointments during the day, running errands, then logging on from the afternoon until midnight. I was working just as much, if not more, than my colleagues.

After my mom passed I met with my new manager to pass out stock grants to everyone. This was when my loyalty to the company smacked me in the face.

One of my direct reports—a younger, prettier woman—was awarded significantly more than me.

When I questioned it, my new manager didn’t hesitate.

“You were gone a lot last year. She stepped up while you were out.”

I was stunned. I had never been “out.” I had literally been working and directing her from afar.

In that moment I realized favoritism was at play and more importantly, face-time mattered.

Up until that point I never regretted my decision to not take Family Medical Leave. But in that moment? I regretted it more than anything.

Lesson learned?

You don’t get time back. You can’t go back in time to get a do-over. This was an epic fail on my part. It cost me time with my mom. And in the end, it didn’t even help me at work.

A year later, I was let go in a company reorg after nearly ten years of service.

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