How Experimentation and Pivoting in Your Career Makes You a Stronger Executive
By Jenna Gaudio, Co-President at Vydia
Jenna Gaudio listened to our podcast episode with Jen Taylor of Cloudfare and these are her takeaways.
The path from product manager to executive is usually a winding, unpaved road without any clear signs or guides to make sure you’re headed in the right direction — especially for women. Sometimes if feels like I had to learn every lesson the hard way on my journey to VP Product Management, Chief Operating Officer, and now Co-President of Vydia.
Listening to Jen Taylor, Chief Product Officer at Cloudflare on the Women In Product podcast provided me the insightful comfort that my own experience is not that uncommon. Hearing Taylor unpack the lessons that shaped her perspective resonated with me deeply, validating that growth is not linear and it is also never-ending.
Taylor takes us through her early career experimentation and attributes her agility to landing where she has today. I appreciated how she spoke about trying different roles and working for different types of companies, which allowed her to more confidently calibrate who she was as a leader.
I like to call this the process of building your own Executive persona profile.
Taylor walks us through the discovery process required of arriving at the right role at the right company. This requires asking questions such as:
- Do you thrive best in the B2C or B2B space?
- Do you best collaborate with technical or visionary founders?
- Are you energized by talking with clients or internal teams?
- What is the chemistry of the existing executive team and how do you fill the gaps?
- What is the vision and are you aligned?
When talking about challenges, Taylor advises that you should be prepared to take on complexity, scope, and responsibility outside of your core domain expertise.
How do you prepare for this?
She shares something I tell all my mentees — you almost always have to do the work before the title and be willing to take the risk. Also, the unspoken secret is that there is no manual for how to become an executive and do the job well. This is why it is so critical that you start building a supportive community and network of executives right now. This will be your place to turn to ask the tough questions or just compare notes on how do YOU lead as CPO?
The challenges she touches on are areas where I often see people get caught up as well. A few career moments to focus on overcoming may include:
- The transition from IC to a Manager. She walks through the importance of learning the skillsets of people you’ll manage (i.e. Design, Tech, Marketing, etc) so you’ll have that as a foundation and become a good communicator and coach to your future team.
- Learning to make decisions without all the information.
- Being able to work with diverse perspectives and productively disagree.
Where will you spend most of your time being an impactful executive?
Taylor and I both agree on the investment of architecting and scaling a team is where you spend a lot of your time. The payoff is enormous though. Not only will this dictate the success of your company, but these are the people you will learn from as much as they will learn from you. Be vigilant in hiring the right people. Your company culture and the success of your product depend on it.
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