5 questions for 5 years with our Founder and CEO, Ashleigh Vogstad

5 questions for 5 years with our Founder and CEO, Ashleigh Vogstad 

Transcends Marketing is turning 5! As we raise our glasses to the journey so far, it’s not just about the numbers on the calendar; it’s about the stories, the challenges conquered, the victories shared and the people.  

To mark this milestone, we sat down with our Founder & CEO, Ashleigh Vogstad, for a heart-to-heart chat. Picture this as a cozy fireside chat (this time, a virtual one) where we get the inside scoop on the last 5 years at Transcends Marketing. So, grab your front-row seat and let’s dive into our 5 questions for 5 years.  


5 questions for 5 years 


  1. Why did you start Transcends Marketing?

“Startups are really hard. But I was incredibly passionate about creating a values-led workplace, both for myself and for others.” This passion is reflected in Transcends Marketing’s 5 core values, but it is our value of #DigitalFreedom that Ashleigh dug into.  

Following a jet-set career in male dominated industries, Ashleigh created Transcends Marketing in 2018 when she was living in a beautiful and remote corner of New Zealand. “I had this aha moment when I realized that my fully male team were being compensated twice, if not three times in some cases, as much as me… the pay equity gap.” This realization fueled her determination to create a workplace where not only herself, but everyone could strive for financial abundance and freedom from anywhere in the world.  

As well as being values aligned, creating a diverse company was important to Ashleigh. “I’m also passionate around technology and helping others on their journeys of growth, especially women and other diverse and underrepresented populations working in tech.” As testament to this, Transcends Marketing has been a WEConnect diverse certified business since 2020.  


 2.What advice would you share with young Ashleigh?

Young Ashleigh was wildly ambitious. Although this Ashleigh is still very ambitious, she is wiser and understands the importance of being compassionate to yourself and others, even in the hectic start-up world. “Done is better than perfect,” and “have the confidence to be yourself because only in embracing your true and authentic self can you accomplish your life dreams,” she passionately states. Taking a pause, she finishes with, “There is always someone better, faster, stronger… comparing yourself is an exercise in futility. Take a deep breath,” she concludes, advocating for self-compassion and resilience.  


3. What has been Transcends Marketing’s biggest achievement been in the last 5 years?

Reflecting on the journey so far, it is clear there have been many incredible and meaningful milestones, but there is one that Ashleigh feels shaped the last five years the most. “We secured Microsoft New Zealand as our first-ever client, a momentous step that set the tone for our trajectory,” and we continue to work with Microsoft teams and partners across the globe.  

She beams with pride as she recounts a more recent milestone, “we doubled our headcount in the last 6 months, a testament to the amazing team that makes Transcends Marketing what it is today.” “And let’s not forget the wins! We won our largest-ever contract in 2023, plus, working with HUGE companies when we were still a smaller team was no small feat.” 

Outside of our client work, Ashleigh comments, “a personal highlight for me has been increasing my own brand, taking the stage at #ShiftHappens and Ultimate Partner, joining the Fast Company Executive board, and becoming a member of Entrepreneurs Organization,” she shares. Plus, “building a successful remote work culture before it became a global trend was groundbreaking.”  


4. What has been the funniest or most memorable moments of the last 5 years?

There have been many – you need a good sense of humor when running a start up! One that quickly came to mind is Transcends Marketing’s 2022 RISE conference. “As a fully remote team, we make a tremendous effort to get together face to face at least once per year. And the activity that rose to the top of that list: downhill mountain biking in Whistler, BC, the world’s mecca for downhill mountain biking.” 

“It was an interesting choice as a leader. I don’t know if I would make the same choice again. We had a team member go over the handlebars, several falls, and one of our team came back so black and blue…. I didn’t even know that bruises could get to that size! Not a repeat activity, I don’t think. Lessons learned.” 


5. What’s in store for the next 5 years? 

“The next 5 years are about expansion,” Ashleigh declares with enthusiasm. “We’re looking to expand our values-based culture to a larger team and global community, incorporating diverse languages, cultures, and backgrounds.” She envisions stepping into new markets around the world, and “our expansion won’t just be numerical but through meaningful partnerships, embracing an ecosystem that allows us to work more deeply alongside our partners.” 

“As we grow, our thought leadership will also expand,” she continues. “We aim to have a stronger and more confident voice on diversity, remote work, channel partnerships, and go-to-market strategies. The next five years will be about making an even greater impact and leaving our mark on the industry.” 

The milestones achieved over the past five years are not just checkmarks on a list; they are the tangible results of a team dedicated to pushing boundaries, doubling down on values, and embracing challenges with open arms.  


As we take a pause to mark this moment, we extend our heartfelt gratitude to every team member, client, and community member that has been part of this journey. Here’s to the last five years, to the lessons learned, the growth experienced, and the laughter shared. But more importantly, here’s to the next five years – an exciting chapter waiting to be written. Cheers to the adventure ahead! 

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