Founder Stories: GROUPBY – Mastering your own destiny

Our Director of Marketing, Katie Paterson, sat down with Roland Gossage, Founder and CEO of Groupby, to learn more about his startup journey and what being people-first means when building a great company.


KP: What inspired you to start Groupby?

RG: Two main elements. One, I like to solve really difficult problems, and obviously, search and relevance was one of those. The other is working with amazing people. A lot of the original people here at Groupby, and the ones we continue to hire, are just that.

KP: Tell me how you went about starting Groupby?

RG: I phoned six of the best people I’ve ever worked with and said – ‘I’m going to start this company called Groupby, I’d like to know if you’re going to join, and, by the way, can you start in two weeks?’. The first question everybody asked was ’What is Groupby going to do?’ to which I had to reply I didn’t know. But I am a believer in the principal that people come first, then you decide the chairs they sit in. That idea has contributed significantly to our success.

KP: So then my next questions is, what does Groupby do?

RG: Groupby is an e-commerce platform that looks after retail distribution, telecommunication and financial services. We provide a user experience platform where people can put the right pieces of content relating to their product or information in front of the right user at the right moment.

KP: As a founder, what obstacles do you face?

RG: I always say if it were easy to start a software company, everybody would do it. We are a people-first company and finding the right employees has probably been the largest challenge, and it’s critical because if you find great employees the journey becomes a lot easier. The other thing is we built Groupby in a slightly unconventional way. We bootstrapped versus going through a traditional institutional round to get a big cheque. It was the more difficult way but ultimately it ended up being much more rewarding and successful.

KP: You mentioned that you are a people-first company. Can you tell me what it is like to work at Groupby?

RG: Our corporate culture is a people-first culture. We like to be inclusive and allow everybody to have a seat at the table. I think that’s something most companies don’t do. It means being very transparent, whether it’s rounds of funding or what’s happening in the current sales quarter. It’s a very communicative and team-oriented sort of environment.

KP: Tell me what it has been like to find the funds you needed to grow Groupby.

RG: A lot of us who did join originally had exited another company. So we all had some money from that exit. We then realized we needed a little bit more money to help accelerate our growth and that’s when we had our first experience with Espresso.

“What we wanted to do was build out the company to a point that we were still the masters of our own destiny.”

After we paid Espresso back, we did a small friends and family round. This was probably better for us, versus a VC round, as it was less dilutive.

KP: What skills would you say drive success as an entrepreneur?

RG: I think to be successful, you have to be ambitious and have drive, but you also need other traits like empathy, and skills around helping others become successful as well.

KP: What has been the biggest takeaway from your experience building Groupby?

RG: My biggest takeaway is that if you’re going to start a software company, you have to have very, very thick skin. Be prepared for a lot of challenges, very hard work, and dealing with a little bit of crazy.

Keep a look out for our next edition of the Founder Stories Series, which we will be releasing in the next few weeks. If you know a great founder who should be featured, contact Katie at

Espresso Capital Joins Elevate Toronto Tech Festival

Espresso Capital Joins Elevate Toronto Tech Festival

Earlier this week, Elevate Toronto announced their plan to host a 3-day tech festival which will showcase the Toronto tech community and focus on three values: Diversity is our Strength, Disrupt Together, It’s Our Time. In front of a crowd of over 250 people at the Horizons Restaurant atop the CN Tower, Mayor John Tory shared his support of this new initiative. “Toronto is becoming a global centre for innovation and technology,” said Tory, who believes the city should be the home of disrupters.

Espresso Capital is excited to be the producing sponsor for the King West Social. Elevate attendees will experience the King West district and connect over cocktails and conversation during the Wednesday night event.

“Creating a social space along King Street West is the perfect platform where we will continue conversations from the day, connect with the community, and celebrate innovation here in Toronto,” said Katie Paterson, Director of Marketing at Espresso Capital. 

“Toronto is an amazing city and is incredibly well positioned to capitalize on the current wave of emerging technology,” said Razor Suleman, CEO of Elevate Toronto.



Get an Early Access Pass – for FREE!

Elevate Toronto is offering complimentary passes for those who demonstrate the Elevate Toronto values. Learn more here.

Get Involved!

If you want to get involved in Elevate Toronto – please reach out to Katie Paterson at – all ideas are welcome! Let’s work together to make Elevate Toronto the biggest Tech Festival in North America.

About Elevate Toronto

Elevate Toronto is a non-profit organization led by TechToronto, MaRS, #movethedial, OneEleven, Cossette Communications and the Spotlight Awards, in partnership with the City of Toronto. It is a collaboration between 17 technology organizations which came together to create a three-day festival. It aims to be a world-class innovation festival where people from around the globe can discover, connect, and be inspired by the individuals shaping what’s next in Toronto. The conference is set to take place from September 12th to 14th in Toronto.