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Unlocking Amazing Opportunities: The Power of Taking the Unconventional Path

Writer: Jessica ReevesJessica Reeves


While raising capital during fundraising activities throughout my career I was often met with comments like “your background is interesting” or “most COOs take a different path” ...


Hustling for 15 plus years I never really took a moment to think about the journey that got me to the point of running a company as COO. I write this in hopes that if you also have aspirations to grow into a role that may be unconventional to your current path, don’t be discouraged. 


Firstly, I am thankful for the years of deep Human Resources experience I gained earlier in my career. Frankly, I think I’m a better executive because of it. When it comes down to it, business is people. You can’t have a business without people. It taught me how to manage conflict, build empathy, influence without direct power and how the criticality of how people feel about their work and impact directly connects to business success. 


Was becoming a COO intentional? No. What was intentional was to continue to learn and stay uncomfortable. As projects or strategic initiatives came up that didn’t exactly “fit” into one specific domain, I raised my hand. That grew into more scope and eventually more expertise the more I saw and experienced first hand. 


How to chart your own path?

  1. Start small and adjacent to your current core competency. The first thing beyond HR for me was legal- HR has many legal components so by taking over simple legal documents (as an example) seemed like a natural step as we needed someone to sub in. That grew to commercial contracts and so on. One thing builds off another. Being close to commercial contracts had me become close to sales and negotiations. I then became integral to GTM. This is just one example and there are many more.

  2. It's ok to fail: Fail small and quickly, run experiments to test your assumptions. Iterate from there.

  3. Find mentors: You don't have to go it alone, or pretend to know everything. Network and connect with subject matter experts to ensure you have a mentor to learn from as you venture into new areas. This can be internally (super helpful as they know the conext of your organization) but also externally. Generally, people want to help other people, it's ok to reach out cold!


Growth happens when you’re  uncomfortable. Let’s all get uncomfortable in 2025.  Feel free to reach out if you'd like coaching!


 
 
 
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