A Startup’s Journey: Getting to Know the Entrepreneur Katherine Regnier

Women in technology has been a hot topic in recent news.

So why is it that whenever we picture successful technology companies, our traditional image of leadership has not changed?

Astonishingly enough, in nearly a $1.8 Trillion-dollar industry, only 5% of startup tech founders are women.

That is why in following the celebration of Global Entrepreneurship Week and the amazing women we have had the pleasure of working with in this space, we wanted to catch up with technology whiz Katherine Regnier, Founder and CEO of Coconut Software.

This is her story.

Where it all began

Growing up in a farming family Katherine was exposed to an entrepreneurial lifestyle and understood from an early age that she wanted control of her own time. In fact, those values of hard work and accountability for her time and actions was something she aspired to attain.

Yet when speaking with Katherine about her early aspirations, I am not sure she would consider herself to be the ‘budding’ entrepreneur, but rather very passionate about solving a problem.

What was the problem you may ask?


How was it easier for someone to book a flight across the country yet she had to jump through hoops to make an appointment down the hallway?

There had to have been a better way.

That accidental path to discovery led her to grow the extremely successful enterprise grade customer engagement platform that we know today – Coconut Software.

Getting off the ground

Katherine best explains her journey with Coconut Software as the 5-5-5 story, beginning with a $5,000 loan.

This small, yet essential amount of money aided her in launching her company. With a fellow female programmer by her side, Katherine got her dream off the ground and they quickly signed on several companies. Ecstatic, Katherine dove into all aspects of marketing and sales.

Her idea was growing.

Until it wasn’t.

Hiccup in the foundation

She found a local agency that shared her vision with her. They shook hands and Katherine was off. Her dream was rolling… until it wasn’t. They refused to sign her legal agreement.

As an entrepreneur just beginning to evolve, the news was crushing.

Yet she decided to start her journey once more.

This time, Katherine was determined. She found a firm; they signed the agreement and it was time to shine. So much so, that they got an incoming lead from a major telecommunications company.

Making it work

With TELUS on board, Katherine worked day and night for months to bring her promise to life.

And they did.

The product was launched in the fall of 2010 and was bringing in enough capital to allow her to quit her full-time job. It was an entrepreneurs’ dream.

Of course no dream comes easy, and in Katherine’s case, along with the challenges of starting her own business was the fact that she was also expecting her first baby. So, working through the hardships to get Coconut Software off the ground, Katherine was doubly determined and could not have done it without her right hand, Romeo Iula, now CTO of Coconut.

Through long hours, hard work, and constant improvements, they bootstrapped her company for 5 years, while still attracting high profile clients. And in the end, they made her dream come true.

Venture into the unknown  

Flashing forward in Katherine’s journey, we reach 2016 — a year that an exciting opportunity would change her life. Invited to an elite technology mentorship program in San Francisco led by Mr. Neal Dempsey, Katherine was selected as not only the only North American, but also the only female participant.

It was this incredible honour that opened her eyes to the possibilities for her fast-growing company. And as the final 5 in her story, it was there that she decided to take on Venture Capital. The first raise was for 710K and the second investment was a year later for 4.2M to bring Coconut into its next phase.

Facing the failure

As anyone in business knows very well, failure is a large aspect of what drives entrepreneurs into their next notion of success. So, while Katherine’s journey was certainly a difficult path, it was those difficulties that led to her current success.

Since facing those early challenges, Katherine has led Coconut Software through venture capital funding, strategic partnerships and rapid growth. Yet none of this was possible without the clarity of knowing what she wanted.

Having respect for your failures while still continuing to envision your goals is how to know that these failures won’t stop you.

Lessons learned

When speaking with Katherine, there was a lot to her story that resonated with the life of an entrepreneur, but the biggest learnings were this:

  1. It takes a village of support. You must prepare yourself to seek out these opportunities and have the right coach and mentor on your side. You might think you can do it on your own, but your company won’t scale.
  2. You never know who you may meet along your journey. The value of relationships is number one. Invest in them – whether it be employees, investors or mentors.
  3. Work-life balance is not a part of a startup. So, setting boundaries might be more appropriate.

Giving back to the community

Above her success in her own entrepreneurial journey, Katherine is passionate about giving back to future entrepreneurs. She is a board member of Co.Labs, (Saskatchewan’s first technology incubator) and is a regular advocate for women in technology. And of course, as someone who knows the value of strong mentors and inspirational voices, she is a regular contributor at events aimed towards providing support and guidance to those just beginning their journey. A journey that, for Katherine, is a continuous path of both self-improvement and increasing value to her team and customers.

About Coconut Software

Coconut Software provides digital scheduling solutions that have redefined how customers interact with organizations. An enterprise system that has modernized how banks and credit unions engage and streamline the experience for staff and customers.

A sincere thank you goes out to Katherine Regnier, Founder and CEO of Coconut Software, for taking the time to speak with us at LaBarge Weinstein LLP for this piece.


Start typing and press Enter to search