career choice

Lessons from a Triathlete: Small Startup to Large Enterprise – Which is right for you?

Editor’s Note: This is the tenth and final article in a 10 part series on how an elite athlete applies the lessons she’s learned from Triathalon training to her role as a Fortune 100 marketing executive. Read the rest of this series here.

Recently, a recruiter and a friend asked what it takes to successfully navigate from a small startup to a large Fortune 100 company. A few items came to mind immediately – from my own experience as well as what I hear echoed from leadership circles:

  1. Stay focused on the business goals (revenue targets)
  1. Define more distinct KPIs for your team or functional area (marketing, engineering, customer success) and clearly articulate up and out how those other measures will positively impact revenue.
  1. Balance thinking fast and slow. In a startup, it’s easy to just go do and in a large enterprise, you may need to take a few more moments to consider how a program or strategy change will scale across 100+ countries and multiple languages.

As I started to think about the journey from small startups to a large enterprise, I realized my professional path mirrored my triathlon trajectory from sprint distance races straight to Ironman. Maybe what I learned from increasing my triathlon race distance by more than 3x (5k to marathon, 15 miles to 112 mile cycling) taught me how to handle the leap from a fewer-than-100 person company to 380,000-person company.

Climb the ladder or Leapfrog?

Most people build their way up to an Ironman distance – and typically over a few seasons of racing. You might tackle an Olympic distance race, then train for and complete a Half Ironman race. Some people may even throw in a marathon or two before deciding to race an Ironman. This would be analogous to climbing the corporate ladder – with each role, you’re building a larger team and becoming responsible for a wider scope of work and higher business targets.

Or, you could skip the logical, progressive approach and dive right in.

I love a challenge that’s fairly daunting and a bit unconventional. It makes me nervous and excited. I can’t stop chatting with friends about my “crazy” plan. That little bit of fear pushes me to commit to all the things I need to do in order to be successful in making the leap. In order to make the leap from Sprint Tri to Ironman, that meant finding new training partners, adapting to early morning workouts, reading about nutrition and changing my grocery shopping and food prep accordingly (read more about making preparation a habit here).

So, perhaps what made me most successful in leaping from small startup to enterprise was that willingness to take on a challenge, be a little fearless, and the do-it-yourself attitude inherent in most startups. Whether you get acquired, grow your company significantly, or jump into an enterprise, you’ll find there’s a surprising amount of room in a large enterprise to change the way things are done – as long as you’re willing to do the work.

Can you be great at companies of all sizes? Could I be as strong a triathlete at all distances?

Triathlon has taught me a lot about adaptability. You need to modify your training schedule to account for work, injury, travel and so forth. You need to learn new ways to motivate and figure out how to keep a cadence. On race day, you never know what the weather will bring – and you may need to modify your initial plan thanks to excruciating heat or a relentless downpour.

Startups teach you the same lessons about adaptability. You need to pivot your model, wear multiple hats from sales leader to tech leader, and build a company culture while you also build a profitable customer base. At one point during my time at Cleantech Group, I was the head of customer success, leading product development for our database tool, and the executive producer for our annual conference – the Cleantech Forum. It’s that adaptability and resiliency that will enable you to not just survive, but thrive.

We may not all be like Ester Ledecka who won two gold medals in two different sports (snowboarding and skiing) at the 2018 Olympics, but we can probably all learn to apply our professional athleticism across multiple company sizes and industries.

I’m proud I’ve tested myself at the Ironman distance. I love the communities I’ve built from coast to coast. And, I’m thankful for all the lessons I’ve learned from Ironman training and racing, which I can apply to my work life.

But, if you look at the data (and anecdotes from family and friends), Ironman is not my best triathlon distance. For the past 5 Ironman races, I’ve placed in the bottom third of finishers. On the contrary, if you look at my performance across sprint and Olympic races, I do much, much better – often finishing in the top third of all women and sometimes even in the top 10 of my age group. Why not lean into my strengths? How much faster could I get at a shorter distance? How much more balance would I have in my life if I wasn’t training 15 to 20 hours a week for 5 months of the year?

Finding your perfect-fit company

Honing in on the right triathlon distance is not that different from finding the right company fit. It’s worth taking a leap, experimenting with a big challenge, minding the data, and being honest with what brings you joy.

How can you find your best company fit? Here are my recommendations:

If we return to the start of my Ironman adventure in 2008, my goal was crystal clear: Cross the finish line with a smile. By my fifth Ironman race in 2014, I got caught up in improving my performance – and left the race feeling disappointed and unfulfilled when I did not hit the marathon goals for which I trained. This year, I’m excited to return to Lake Placid one more time – for one more Ironman. I’m going back to my roots – to accomplish this challenging race with a smile on my face. Then, I’m going to throw an Ironman retirement party for all of my friends and family at a fabulous Adirondack mountain house. The end of Ironman racing will not be the end of triathlons. I’ll spend the next seasons focusing on my niche in Sprint and Olympic triathlons.

Re-examining the Ironman distance fit is nudging me to rethink my role within a large enterprise as well. If I perform better at short races, does that parallel my professional performance? Would working on another emerging business within an enterprise bring me even more joy and success? Could I apply what I’ve learned from an enterprise to a fast-growing startup?

No matter the size or growth of the business you’re in, remember that, just like my journey to Ironman, you’ll have many memorable moments to apply to every part of your professional path.

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