Alexa Kilroy got her start in eComm after getting thrown directly into the deep end in 2018, managing massive ad budgets for multiple DTC brands. At the same time, she was studying digital marketing data, developing growth strategies from the ground up, and building performance marketing teams for brands.
Today, Alexa is the Head of the Brand at Triple Whale, the Smart Data Platform for eCommerce owners & operators. She works across the company and directly with some of the most profitable brands in the industry on all things strategy. You can catch her crafting killer content, throwing awesome events, and leveraging lots of amazing data to figure out how to scale eComm brands to the moon.
For more details, visit Triple Whale’s website here.
Today, we sat down with Alexa to learn a bit more about her journey as an entrepreneur.
Q. Tell us a little more about your journey as an entrepreneur – how did you get started? What inspired you?
Alexa: Crazily enough, I started my career as a high-school English teacher. But I always had an entrepreneurial spirit. I remember being a little girl – in the single digits – and my mom helping me to set up a faux fashion company called AMK Designs. She even went to an office supply store and bought me all the real invoice slips, bits to build clothing catalogs, etc.
I graduated from Boston College in 2018 with a dual major in Secondary Education & English, and a cross-disciplinary business minor. I thought I was going to be a teacher forever; I had no idea what was in store for me.
After teaching for a few years, I realized I was seeking more. I got a foot-in-the-door job at an edTech company, and shortly thereafter was recruited to work at my first eCommerce company. They sold superfood supplements, and I think I was hired #4. I started by processing returns, and chargebacks, and winning back folks who were trying to cancel their subscriptions.
I kept asking for more responsibility, and dialled my creative energy into product photography and videography for the brand, in addition to copywriting. Within a few months, I was leading their advertising team. That’s how I truly fell into the “deep end” of all things eComm!
So much of my inspiration comes from my parents. My dad was a built-from-nothing type, raised effectively in poverty to later go to college on scholarship, drudge through the ranks, and become a successful tech executive. My mom was a respiratory therapist and literally saved lives. They’ve both always pushed me to always get an A+ rather than an A. So much of my intrinsic drive was instilled by them!
Q. How do you market your business, and which tactics have been most successful?
Alexa: Triple Whale has made such a splash in the past year – and I wouldn’t dare credit all of that success to myself. Our Marketing Team is led by a killer CMO, Rabah Rahil, who pushes us to take our crazy ideas, build a business case for them, and make them happen. Our marketing philosophy is structured around 3 core pillars: content, community, and education.
Content comes in just about every form possible, from our expansive podcast network to the crazy DTC Reality TV Show we filmed in 2022. We seek to be the trusted source for all things eCommerce, so you can come to Triple Whale when you need guidance building your DTC business. Plus, we like to provide fun stuff too, which helps keep the hard days light.
Additionally, we produce collaborative content that’s closely linked to our community. As such, we’re not just circulating our own ideas, but also those of the true key players in the game. Community is SO central to all that we do. You may have recently heard about The Whalies, a 3-day mastermind/community event/awards show we hosted in Austin, TX. Bringing people together not only for education but also just to grab a bite/drink and talk about life, has been integral to our growth and brand advocacy.
Finally, our team works diligently not only to provide thorough product education, but also general education on how to effectively grow and scale eCommerce businesses. We release guides, host webinars, host IRL masterminds, and the list goes on and on. Marketing is so much more than providing value through your product and I think this is one of the aspects where Triple Whale really shines.
Q. What has been your most satisfying moment in business, and why?
Alexa: Gosh, there have been SO many! Often the moments that bring me the most joy are sharing in others’ joy. When I get to work on case studies with clients, and they share how much Triple Whale has impacted their business or life, that is so rewarding for me.
If I think about my own personal moment, I think it’s a moment I have every day. I wake up every morning and think about how I’ve built this crazy path for myself to marketing leadership at a rapidly growing SaaS company. Just a few years ago, I was teaching high schoolers why they should care about Shakespeare — and while I still think that’s important, knowing that I’m working for a company that helps people’s side hustles become their full-time, profitable job is priceless to me.
Q. Where do you see the future in your niche/industry 3-5 years from now?
Alexa: It is very hard to make predictions on the future of eCommerce because it’s constantly ebbing and flowing. The changes that occur within the space are drastic and it’s an industry that’s heavily impacted by the world at large.
As we’ve seen with TikTok advertising in the past few years, I expect new digital marketing channels to continue emerging. Each time this happens, younger brands have the opportunity to get up on the competition, be there first, and build something incredible for themselves. It’s hard to say what the future of TikTok in the US will be as of early 2023, but if it does disappear, there will definitely be a new player to take its place.
At Triple Whale, we’re investing heavily into AI/machine learning, so owners and operators can focus more of their energy on the things that make waves in their business, rather than tedious tasks. Especially with the rise of ChatGPT and AI creative, I expect a lot more seamless automation and incredible creative brainstorming coming in the future.
Lastly, I think shoppers are craving more and more personalized experiences. Personalization tech is on the rise for a reason, and I’m not just talking about changing the name of the recipient in the emails that brands send. For example, fashion brands are currently leveraging high-tech tools to provide better predictive sizing for apparel to reduce the volume of returns and exchanges. I expect more neat tools like this, as well as super customized predictive upsell/cross-sell/post-purchase flows for consumers.
Q. What is one of the best or most worthwhile investments you’ve ever made?
Alexa: I think my most worthwhile investment has been the time I’ve dedicated to learning and skilling up in the e-commerce industry. So much of what I’ve built in my career has been self-taught: watching Youtube videos, listening to podcasts, taking people to coffee whose work I respect… all of that has been invaluable. But it takes a lot of time, and that means sacrificing doing “fun stuff” sometimes to keep building your brain.
Q. Which social media platform are you most bull-ish on in 2023, and why?
Alexa: Hot take, but Google and YouTube. Google’s new advertising rollouts continue to get better and better, especially after their refinement period. Insider reported in 2022 that Gen-Z alone spends 3+ hours a day watching YouTube videos, and I’ve seen brands scale to 300-500K USD per day on profitable ad spend on a single video advertisement.
Google PPC/brand terms definitely hit a scaling wall, but there are so many other valuable tools within the ad suite, especially via YouTube, that have massive profitability. There are few brands that lose after dedicated investment, creative strategy, and strategic partnerships there.
Q. What business-related book has inspired you the most? Or, What is your favorite book?
Alexa: This probably sounds like such a cop-out, but the book that really got me into eCommerce and helped me to thrive in my career is Drew Whitman’s Cashvertising. It’s a classic for most marketers. If you haven’t read it – just do it; it’s a fast and easy read.
The only way to market effectively/profitably is to have a strong understanding of your customer. I’m not just talking about persona, I’m talking about the core desires that drive them to purchase, and how you can really tap into those. Advertising kicked off my passion for consumer psych. It’s been critical to my growth in marketing leadership, and I refer back to it often.
Q. What is your ‘one-sentence’ piece of advice you’d like to give to someone who is just embarking on their entrepreneurial journey?
Alexa: Move forward each day with authenticity, kindness, generosity, adaptability, and vulnerability.
To keep up to date with Alexa and her journey, connect with her on Twitter.
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