Chapter 10 - Fail Forward: How I failed my way to the C-Suite
Hi š , Iām 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 didnāt want to gate the content with a paywall.
I will be posting each chapter weekly here.
Making it to the C-Suite: Transition, Growth, and Reinvention
Somewhere between burnout and reinvention, I stopped being afraid to change lanes. These later years were about climbing higher, realignment, resilience, and learning how to lead on my own terms.
Chapter 10: Interlude: The Career Pivot
After TiVo I wound up consulting for six years before I figured out where I really belonged. I worked at Cisco and CA Technologies on their marketing teams doing various digital and social media projects. I also consulted with various organizations B2B, B2C, nonprofit and became my own CEO of my own consulting business. It was 2010 and social media was the hot topic and everyone was just figuring it out, kind of like they are right now with AI.
After six years my husband tapped me on the shoulder and said it was time to find a company who would contribute to my 401K. Iām 45 and as I explained earlier, I did a shitty job on planning for my retirement.
I applied to a few jobs in San Francisco because I wanted the luxury of walking to work after a fifteen years of commuting 75-90 minutes each way for TiVo and Cisco. So I applied for a social media role at SparkPost. It was so low level for me but all I wanted was a job that paid a certain amount and one in which I could walk to work.
My cover letter went something like this, āDear recruiter, I am overqualified but thatās exactly why you should hire me.ā It went on to list my credentials but I wanted to put it out there that I knew I was overqualified, but I just so badly wanted to be able to walk to work. It was a mile from my house. (For the record, that would never fly in todayās market.)
The recruiter called me and acknowledged my cover letter. I told her the truth, which was I was just in a different place in my career right now and walking to work is important. I was hired and I worked at SparkPost for over five years.
At first, I kept my head low. I honestly wasnāt sure if I could handle going back into an office, reporting my time, requesting time off to go to the dentist, etc. This was a big change from consulting and running my own show. I had one foot out the door at all times for the first nine months I was there.
Then, the CMO at the time, Steve, promoted me to Director of Digital after nine months. Unfortunately, Steve didnāt stay long and was replaced by a friend of the founder, who knew the industry really well but knew nothing about marketing. He knew so little about marketing that he gave me my own office and promoted me within a couple of months to VP of Growth.
I remember arguing with him about my title. It seemed inane. Why wasnāt it just VP of Marketing. He said I would thank him for this in the future because growth was really hot at the moment. (I just want to go on the record and say, that the title of VP of Growth has never once helped me land a job).
The reason he gave me that title is because I mostly did Demand Gen and Growth at first. I managed content, events, lifecycle marketing, customer marketing, digital, social, and any and all advertising. We had another woman who managed brand, product marketing, graphics, the website, and analyst relations. She was there first and she got the title VP of Marketing.
Within a year, we got a new CEO. She was let go and I inherited all of marketing.
The industry CMO still existed on the org chart in name only. He was mostly absent the entire time, due to substance abuse issues. That left me as the most senior person in charge of a satellite office of 55 people. This was when I learned the importance of a title.