Tiffany Kaminsky co-founded Symend in 2016. Headquartered in Calgary, the company now has operations across Canada, the US and Latin America and has helped nearly 90 million people to date—and growing—with its Behavioral Engagement Technology™ that makes difficult conversations a more positive experience. The founders have successfully raised $187 million in capital and lead a team of more than 185 people. 

Tiffany grew up in rural Saskatchewan in the small town of Preeceville of 1200 people. Her dad was a farmer and mom was a teacher. In their household, “do your best”, “helping others” and “profitability and sustainability can co-exist in business” were core beliefs. 

How did you start down this path?

I’ve always been intrinsically motivated by learning experiences, roles and companies that have a strong social good. When I entered university, I applied to business school, to be a social worker, and to be a teacher—pretty broad options. But what was consistent then, and still is true today, was my desire to help people. 

I spent my early career with a startup, TinyEYE Therapy Services, providing technology that aimed to bring equal access to speech and occupational therapy to students in schools. When I started with them there were about five of us, and by the time I left, we offered the online solution in five languages to 12 countries. That journey instilled a lot of the passion I have for entrepreneurship with a social mission, and I continue to have a ton of respect for the CEO, Greg Sutton, who played a pivotal role as a mentor to me. 

Did you always want to found your own business?

Before starting Symend, Hanif and I had been friends for many, many years. I actually consulted for his last company, Aimsio, and we discovered that we had a very similar high intensity work style. He’d come to me with so many business ideas for months, but none of them had the right hook for me to decide to get involved—a strong social ‘why’. 

It wasn’t until the idea of what is now Symend, and the concept of helping people who fall past due on their bills, that we felt we had something. I think back to my first student visa and how easy it was to fall through cracks and what a negative experience that was. Financial literacy just really wasn’t taught in schools and still continues to be a gap. Hanif came to Canada as a refugee from Iran. Coming to a new country where you don’t yet have access to credit and English is your second language, his family experienced the stress of collections calls. That was our ethos and why we started Symend. A personal mission to make a difference for people like us, and at the same time, make it a sustainable, profitable and successful business that also helps enterprise companies achieve better financial outcomes while improving their customer experiences. 

Was there a moment where you decided to make the leap to start Symend?

Hanif and I spent a lot of evenings and weekends researching whether it was a viable business. Is the market there? Do we have a passion for it that will sustain the effort? Were we actually going to quit our jobs and start a company? 

I had an offer for a CEO role with another company I was consulting for, so I had to decide quite quickly whether I was going to step into someone else’s organization that already had some momentum and great founders, or whether we were going to do it on our own with more risk. The idea for Symend was captured on a napkin sketch after a few too many Old Fashioneds at Hayden Block bar in Kensington. And there was a moment where we just knew we deeply wanted to do it.

Then Hanif and I personally led our first million fundraising along with friends, family, and angel investors to get off the ground. That wasn’t a heck of a lot of money given the vision that we had so we both still consulted on the side and moved in together to save on office costs, transforming our kitchen table to a boardroom table—really your modern day garage startup. 

When did you know you really had something with Symend?

When we won our first client who then became an advocate, it became very real. We started to see the first results, see how many people we helped and the amount we could deliver in ROI to the business. It worked! Everything we had been talking about for so long was coming to fruition—that was a pretty incredible moment for us as founders. 

Even now, we just launched our new platform that we spent 18 months building to really automate our offering and take it to the next level. We wouldn’t be here if those first customers hadn’t seen the transformational power of our vision.

What are the accomplishments that you feel most proud of?

The one I’m most proud of is that we’ve stayed true to our social mission, our North Star from day one. You’ll see it in our values, you’ll see it in the people we hire and the solution we provide with our technology. That ethos for our business has not wavered. 

In 2021 we helped the equivalent to the population of Canada. Last year, our goal was to bring that total to more than 65 million people, and we helped over 75 million people. In 2023 that number continues to grow. If you would have asked me how many people we could help when we started that would have been a dream. It’s a bit surreal that we’ve had such a profoundly positive impact. None of that would be possible without our incredible team of Symenders that lead with empathy and make it happen every single day. 

What have been some of the hard moments?

Like every business, we’ve experienced the ups and downs. In the early days, every contract is a make-or-break for a business. Then you have to calculate when to scale and risk hiring before things come to fruition. 

And like many tech businesses, we’ve recently had to pare back our team. We just finished going through a restructure and I think those are some of the hardest decisions to make. On the one hand, you must do what’s best for sustaining the business. But on the other hand, it’s letting go of people that trust you with their livelihood. I hold deep responsibility for those choices. So I think a lot of those changes—those have been really tough.

When you are asked for advice from other founders, what’s something you share most often?

I’m still learning. A couple things have served us well though.

First, I highly recommend finding a way to build a solution with product-market fit really quickly. For our first six to eight months, we didn’t build anything. All we did was reach out to every telecommunication company, every financial institution in North America and said, “Hey, we’ve got this vision to start this business, you’re an expert in the field, we would love to hear from you.” And we really went through learning the pain points of the industry, asking “does this make sense”, and validating what we should build to ensure a PMF before developing the platform. We actually found our first customers through that process. 

Second, you don’t have to have all the answers, just hire well. It’s quite unusual to start a tech company without a tech-first founder. We did. Our founding team was really honest about the skill sets we had or didn’t have and we hired to fill those gaps. Learn how to find incredible individuals who are aligned with you and your vision for the future. 

For us, we have many hard to fill roles in behavioural science and AI and technical spaces where it’s incredibly competitive for talent. We often go up against Apple and some other really big players. To compete, we draw upon relationships we have with A100 and C100 members, and our investors and advisors to tap into their networks. They know us, know our mission, can connect us with like-minded individuals, and can vouch for the opportunity we offer.

You’ve talked about the importance of picking the right funding partners. Were there any really hard no’s along the way?

We’ve done quite a few rounds now, and at each point we have had different strategic intentions that guided who we wanted to work with. What’s remained consistent is the importance we place on having partners really aligned with the impact we’re aiming for and our values. We’ve made decisions to take lower valuations for the right alignment and it’s truly made a difference. I couldn’t speak more highly of our investors and our board, they’ve accelerated our growth. They’ve added a ton of strategic value that we really trust. As I think back, if we made different choices, I don’t know that I would be saying the same thing, or that Symend would be in the same place.

When you first started Symend, you were in a chief strategy role. Now you’re in a chief impact role. How do you handle that change as a founder?

I think that’s an often overlooked reality for founders. In the very beginning, you need a founder mindset to take on whatever is needed in a day where you can drive the most impact and value. And you need to take it as far as you can. 

But then as you grow and go through different stages as a business, you need to be humble enough to ask, “at this new point of growth in our business, is someone who’s got 10 more years of experience in our critical technology, or who has built an organization from our size to five times that—are they better in this seat?” 

I think being able to take a step back and look at the bigger picture and what’s best for the business is really important. Founders have to muster the courage to always go where you are needed the most. 

With all you’ve learned so far, is there any advice you would have given yourself back at the startup start line?

You know, I think one of the things is just be really confident in your decisions. For every founder, there are so many things in the early days that you’re doing that have never been done before. You’re learning on the go, and sometimes reinventing industries. Just trust your decisions and move forward fast while learning from your failures. 

Which brings up a second thing I would have loved to learn sooner: don’t be afraid to turn to people and ask for help. As you build a company and grow your customers, so many people are turning to you and depending on you, you want to have all the answers. But you don’t need to. 

You’d be surprised at the lengths people will go out of their way to support you, including the really seasoned entrepreneurs in the A100. I’ve also experienced that generosity of wise support from our investors and advisors. I can call them up and say, “Hey, this is the challenge we’re facing. Here’s a few options I think we could do. What’s your take?” When you don’t know what to do, you’re not falling short. It’s just time to reach out to others and learn from their experience. It’s taken me a while to get comfortable with that, but it’s key to take the next smart step, faster.

Is there anything that you’ve learned as a woman founder that you think is particularly important to share with others?

I think back to some of the big learning lessons throughout my career and a standout observation is that men commonly ask for more. We see tons of studies on men asking for more salary, more promotions, or better financing terms and there’s a common sense of deserving. Women need to cultivate that.

I think back to a scaleup program that early in the business, one of my mentors suggested I look at. We didn’t check all the boxes as a company so when he asked me if I applied, I said no. He pushed back at me and said, “If you were a man, you would not have hesitated to even though you didn’t check all the boxes. Go apply!” I took the advice and we actually got into the program. There have been many moments like that throughout my career. Those moments of hesitation can hold women back when they really shouldn’t. We all feel those moments of hesitation but put yourself out there, the worst thing you’re ever going to get is a no—and you’ll be learning.

Is there a book you would recommend that’s had a big influence on you?

I am a big, big Simon Sinek fan. His “Start with Why” book on how great leaders can inspire others to take action really nails how it’s not what you do, or even how you do it that matters. It’s why you do it. That is really core for me.

Tiffany Kaminksy is an A100 Charter Member and member of the A100 board. The A100 is a non-profit, member-funded organization of experienced tech founders and executives. Formed in 2010, A100 members are dedicated to growing the next generation of tech and innovation leaders through advising and mentorship, providing deal flow pathways, peer knowledge sharing, and connecting and expanding networks.