Jessica Cullen Goes Pro

Jessica Cullen is a rookie professional triathlete, podcast host at Endurance Icons, and Managing Partner at Regenerative Capital Group. She’s also a previous champion of Ironman Canada and Ironman 70.3 Tremblant. We spoke with her about some mega life changes including a switch to professional racing and leaving her 9-5 job. 

You recently made a huge career change. What was the catalyst for leaving your job to turn pro? 

Going pro and leaving my job lined up a bit serendipitously. I had begun thinking about going pro in late 2022 and spent 2023 training and racing at a higher level to see if I would like it (I loved it!). 

I had found another job opportunity that I took at the same time as taking my pro card which is a lot of exciting change all at once. 

What was the scariest part of making the change?

I think all the scariest moments of any change come more from your thoughts than anything life can throw at you. Because I gave myself a runway to really think it through, I haven’t felt much fear. The triathlon world is just such an incredible world – people have been supportive and welcoming, and I am treating it as an incredible adventure. 

What’s been the biggest surprise of your new lifestyle? 

How much more training I can absorb. For the past few years, I wore heels and went to the office every day. I loved what I did but carried more work stress than I was aware of at the time. Making the change to be in control of when I work, waking up without an alarm, adding training hours and swapping heels for toe spacers means I can increase hours and intensity and recovery quickly. 

What does a dream season look like for you?

I am just in awe of how the sport has grown and levelled up over the past decade. I am honoured to be able to race in this new field and am so excited to grow and learn. Without any experience racing as a pro, my dream season as more to do with my own growth and development than how I place (for now!) My dream season is to do 3 Ironmans and 1-2 half Ironmans and post my best time in all disciplines. I also would like to begin to hone my racing skills and strategy as that element is newer to me but coming from bike racing, I know how much I love it. If I can end the year with personal best times, injury free and having given each race everything I have, that’s a dream season for me. 

How does your daily routine look like without the traditional 9-5?

It varies but I keep it structured as I match the cadence of my key training partners – Mark Cullen (husband and coach) and Allison Jacob (fellow pro rookie).  Community is such a critical element of what brings sustainability and joy for me in triathlon. I wake up without an alarm (except for the extra early morning days – then my husband puts a cup of hot coffee on my bedside table to bribe to me to wake up!). I’m often up by 5:00 am and will do one or two training sessions within an hour of waking up. 

• After training, I will spend until lunchtime doing some work. I often do another session around mid-day and spend the rest of the afternoon working. If training requires, I might add a nap to my day.

I eat dinner with my husband and these days, we spend the evenings prepping our house for sale! When we are not doing that, we will either spend it with friends, do another training session, or record a podcast together. I’m a voracious reader so in my spare time throughout the day, I will often read a book.  

Are you dedicating all your time to training? Or do you have any other professional pursuits on the go?

I view training as the energy and focus that fuels everything else I do. I took a new role in 2024 as Managing Partner at Regenerative Capital Group which means I am an acquisition entrepreneur. My day-to-day work is searching for a lower mid-market Canadian business to acquire and the flexibility of the work ties beautifully into my training. 

My husband and I also have a podcast called Endurance Icons. (Matt’s episode is #X!) We interview the best athletes and experts in endurance sports. 

I love everything I do, but the balancing act calls for a structured approach.

What advice do you have for other triathletes looking to invest more in themselves and their athletic pursuits? 

Surround yourself with a like-minded community to allow your pursuit to be a lifestyle and not a goal. You spend 99% of your time training and 1% racing so focus on enhancing that 99% to get the most out of yourself with positive, driven people. It will make perceived exertion lower, you will pick up good habits (I call it an upward spiral), you will have accountability and you just might push yourself that tiny bit more to keep leveling up!