I had the extreme pleasure of getting to know the person featured in the latest installment of the “My Day” series at a Fireside Chat on she co-led called “How to Manage a Remote Team” at the recent Canadian Rural Innovation Summit. She was there alongside another incredible woman who I had interacted with a bit before meeting in person at the Summit, Cheryl Himburg, the founder of Key Element Solutions. They are both so welcoming and real about the challenges faced in their industries, as well as so positive and caring. I really wish I was better at keeping in more consistent touch with both of them!

Kaitlyn McCullough, a Shopify Plus Academy Lead based out of the Bay of Quinte Region, to me based on the few conversations and email exchanges we’ve had, truly is how she describes herself below: curious, strong, and caring. When she found out about Youth Beyond Enterprises (then known as Bay of Quinte Young Entrepreneurs), she wanted to know more about the site and how she could help out. Naturally, I asked if she would participate in the “My Day” Interview Series, as well as she could send me a list of “hot topics” for young entrepreneurs so that I can make sure that I am speaking about relevant topics in my upcoming blogs. No surprise, she said yes!

Let’s get to know Kaitlyn a little bit better together!


Question 1: Describe yourself in 3 words only.

  • Curious;
  • Strong, and;
  • Caring.

Question 2: Tell me more about your business(es)? What kind are they?

  • I work for the SaaS (software as a service) company, Shopify, which is a
    complete commerce platform that lets you start, grow, and manage a business
    by creating an online store, selling in-person, and through multiple online
  • Specifically, I work within Shopify Plus, a department that helps enterprise
    businesses. My team created Shopify Plus Academy, an exclusive online
    resource centre. We provide self-guided courses, in-depth how-tos, and industry insights across key business areas.

Question 3: Where does your entrepreneurial drive come from? What are your sources of inspiration?

  • I’m drawn to businesses that create positive change, where people saw a
    problem as a challenge to be solved, instead of a defeating end.
  • Since I started with Shopify more than 4 years ago, I have come across some
    truly incredible entrepreneurs and brands trying to make a difference in the world. That’s what gives me inspiration — entrepreneurs with compassion for others and passion to leave the world a better place than they “found” it.
  • *I also fangirl a lot over Marie Forleo and get inspiration from the stories she
    shares 🙂

Question 4: Considering how fierce competition is among your industry, what are your business(es) competitive advantages? What makes you stand out in the crowd?

  • Shopify is a company that truly cares about making commerce better for every
    person; regardless of where an entrepreneur is, their business model, whether the person is looking to start a side hustle or actualize their dream. We provide the tools and services entrepreneurs need to start, run, and grow their businesses.
  • We empower independent business owners everywhere; we support starting their business journeys, empower them to use one platform to sell everywhere, help to market their businesses, and enable them to use a single dashboard to manage everything—gaining the insights and knowledge entrepreneurs need to grow.

Question 5: No two days are often the same for an entrepreneur, but what does a typical day look like for you?

  • This ebbs and flows depending on season—Black Friday, Cyber Monday, and
    around the end of the year is a totally different whirlwind!
  • I have a morning routine that works well for me (more on this later) and helps to start my day well. Generally, once I sit down to start work, I review my schedule for the day and start with creative work, as much as possible (no emails!) or I’ll have a block of meetings about different projects I’m leading and helping with.
  • Since I have a dispersed team (spanning from Europe to the West coast), we’ll
    often meet the hour before lunch, so it’s not too early or too late for anyone and
    we can brainstorm, connect on goals, opportunities, roadblocks, and other areas for collaboration.
  • I’m still working to get better at this, but I often eat lunch at my desk, while
    catching up on administrative tasks or Slack messages and emails (author’s note: I’m terrible for doing this too!). I try to read an article after lunch—usually something that has landed in my inbox or has been shared by a colleague (the Pocket app has been a lifesaver for this).
  • In the afternoon, I often have more meetings or work periods. On certain days, I block off time for deep work on projects or tasks that need to move forward and are under my “important and urgent” section.
  • I finish my day by scheduling an activity so I actually take a break from work,
    often scheduling myself for a workout class at the gym, meeting up with a friend, or planning a specific recipe for dinner.

Question 6: What do you do daily to grow as a person?

  • I heard a quote once that really resonated with me and impacted the habits I’ve
    instilled to set myself up for success: “Don’t let people pull you into their storm.
    Pull them into your peace.”
  • To ensure I stick to this, I’ve started a number of things, but what has had the
    biggest impact is my morning routine. Everything I do during that time is to help me start my day on the right foot…truly the way I want to, rather than in a
    reactionary way.
  • From the time I get up, I don’t use social media, check my phone, or look at
    personal email until usually around late morning or lunch time. I take time to
    meditate. I think about my day, what “big rocks” I want to accomplish and how
    I’m going to get there. I read (Pocket is a great app for saving online articles you
    come across throughout your day). Sometimes I write (I have a goal to get more
    consistent with this). At the end of the day, I write a few lines about what I’m
    grateful for to help reflect and learn from that day.

Question 7: What tricks have you discovered to keep you focused, productive and achieve a decent work/life balance?

  • I’m still honing and changing this all the time, as I haven’t quite found the perfect mix. I would say I’m closer than I was 4 years ago!
  • Throughout the day, I make a point to keep moving (sitting all day makes for a
    very clouded brain!); I stretch and when I need inspiration or energy, I’ll move to another space (either another room or go to a coffee shop).
  • For productivity, I use Noizio to create background noise that helps me focus and I leverage the Pomodoro Technique. This is an efficient way to maintain focus for lengths of time without distraction (no phone, email, instant messaging), so you can get into a flow of working or creating. Research has shown that the most effective lengths for these are 57 minutes of uninterrupted work, balanced by 17 minutes of break. Focus Booster is a great app—with a freemium version—that can help keep track of your time and give you reminders when you’ve finished a pomodoro.
  • For work-life balance, it’s been helpful to have a regular morning routine to start my workday (as outlined above). At the end of the day, I also make sure I have something scheduled so I don’t end up working until 10pm without stopping. Recently, scheduling a workout class at 5:30 has been working well (shout out to the amazing community and trainers at the Fitness Guild!). Because I “book” the class as an appointment, I’m more likely to hold myself accountable to going and I have a great reason to get out of my office, get moving, and get my blood

Question 8: What popular entrepreneurial advice do you agree/disagree with?

  • “Learn through failing”. Although it can be such a scary thought, in theory, I agree wholeheartedly with this. In practice, it can be challenging (especially for a closet perfectionist)! We often learn the most when we fail or “miss the mark” on something; if we truly take the time to reflect, we learn from our mistakes.
  • The great thing is, we can learn from the mistakes of others, too! Failure provides us feedback on what didn’t work, or what could have been done differently in a way that allows us to “fail forward” to make better decisions or think differently next time.

Question 9: What’s your favourite metaphor to describe entrepreneurship?

  • This is often a phrase used when talking about Search Engine Optimization
    (among many other things), but I love the idea that being an entrepreneur and
    starting a business is a “marathon, not a race.” There are often ups and downs
    when it comes to being a business owner. Keeping this metaphor in mind helps
    when there are tough days, weeks, or months that seem to have no end…that this time or challenge is not everlasting, but an often temporary roadblock in the journey that will ultimately lead to a stronger you and a stronger business.

Question 10: What was the toughest moment you have experienced in your business practice? How did you succeed to get over it and move forward?

  • Although this isn’t in my business practice, I would say the toughest moment I’ve experienced in the e-commerce/SaaS business was when I first started! I was so new to this industry, having just come from a career in teaching…I had very limited understanding of the world of online retail.
  • I had some great colleagues who helped me onboard to Shopify and train me to
    understand the product and ways it could help business owners. There was so
    much out there that I had to learn about when it came to technology and
    business (both online and offline). I’d still say there is much more I have to learn, but I can attribute my early achievements at Shopify to the amazing learning team who helped ensure I was set up for success.

Not included in question count: If someone wants more information, what is the best way to contact you?



If you would like to participate in an upcoming “My Day” interview, or just want to know more about the site and/or me in general, please send an email through my Contact page.- Rachael