“Being Sensible” — with Corey Gross, Co-Founder & CEO Sensibill

Today, we’re speaking with Corey Gross, Co-Founder & CEO of Sensibill. We discuss what inspired him to create Sensibill and why starting your own company may not be as hard as you think.

Today’s episode of Journey Map is brought to you by MindManager.

Journey Map listeners know that with the right map you can take your career anywhere you set your mind to. MindManager work management software puts your ideas, plans and projects on the path to success by transforming them into dynamic digital maps, charts, diagrams and more. Mind Managers flexible visual format makes it easy to capture, organize, understand and evolve critical business information and with powerful collaboration sharing features it’s the perfect tool for keeping remote teams aligned, on track and headed in the right direction.You can take a free thirty day no commitment trial today by visiting www.mindmanager.com/journeymap.

Welcome to Journey Map, the audio experience that deconstructs the career paths taken by some of the world’s most interesting people. Today’s guest graduated from Western University with a degree in History. He then went on to receive his Juris Doctor in Intellectual Property Law from the University of Windsor. After graduation he started his first company Smart Slips a company that enables retailers to issue electronic receipts to customers. In 2013 He goes on to help found the company he is now CEO of Sensibill. For those of you who don’t know Sensibill is the leading provider of everyday financial tools like digital receipt management and SKU-level data that helps banks and credit unions better know their customers.

Today’s episode of Journey Map is brought to you by MindManager. Journey Map listeners know that with the right map you can take your career anywhere you set your mind to. MindManager work management software puts your ideas, plans and projects on the path to success by transforming them into dynamic digital maps, charts, diagrams and more. Mind Managers flexible visual format makes it easy to capture, organize, understand and evolve critical business information and with powerful collaboration sharing features it’s the perfect tool for keeping remote teams aligned, on track and headed in the right direction.You can take a free thirty day no commitment trial today by visiting www.mindmanager.com/journeymap.

DH: Today we’re speaking to Corey Gross, CEO and Co-Founder of Sensibill.Corey, welcome to Journey Map!

CG: Thanks so much for having me really happy to be here!

DH: So Corey I wanna start actually not at the end of the journey some slightly more recent in the last 5 or 6 years anyway. I didn’t get into it in the introduction but you have actually done quite a bit of guest lecturing at places like the Schulich School of Business, Ryerson University, the University of Waterloo. What are the subjects you cover when you do those guest lectures?

CG: I usually get brought into entrepreneurship, starting businesses, sometimes I will speak about fintech, but usually into how do I start my company? How do I raise venture money? And all that kind of stuff. It tends to be top of mind for people looking to start their own business coming out of school or join a fast growing start up which is obviously now all the rage here in the ecosystem of Toronto.

DH: When you’re doing these guest lectures what do you think is the piece of content, wisdom, advice, or experience that you share that is least obvious. In terms of like there’s lots of stuff on the subject of entrepreneurship that people can learn nowadays, what do you think it’s like the one nugget that you bring to your lectures that might leave a person in the audience thinking I never really thought about the world of entrepreneurship that way?

CG: I think these days of course in the technology ecosystem in Canada and in Toronto in particular there’s a lot of hype around raising money and building these venture backed, venture scale technology startups. People I think believe that that’s the way, like that’s the way you have to build a company with an idea, you pitch investors about your idea, investors give you money, money hires people, people build the product, you sell the product and maybe you raise more money and on and on it goes until a billion dollar valuation happens. What I usually start talking to people about isn’t the path to raising money, it’s what do you want to accomplish out of your career?What do you want to build? What drives you? What are you passionate about? I think most people forget that most businesses don’t go the route of raising tens of millions of dollars to break even, or even earning tens of millions of dollars just to burn cash, an IPO, and try to take over the world with these transformative technologies. Most of it originates with people being passionate about a particular area. Maybe it’s starting a food truck, it’s a great business for people who are passionate about food and sharing their gift and passion for food with others. It might be starting a retail store because you love designing gift cards. You might be a contractor or an artisan and you want to share that you want to be passionate about building homes. So I really challenge people before you go down this path of raising money which is what a lot of people’s thoughts revolve around, just start with what you want to do and that may not be close to a company that needs to raise millions of dollars in capital. So I think a lot of the times people are taken aback and they’re like “What do you mean I can start a software company and I don’t need to raise tens of millions of dollars, and it doesn’t need to be a business that generates millions of dollars in revenue to be successful?”. The answer is no it doesn’t, and all of that money usually adds up to a whole lot of pressure and stress and that’s not what a lot of people want out of their life. They want to be able to take greater control of their working hours and their career, so I would say that’s the thing that sparks a lot of discussion after I’ve spoken that you don’t have to go the venture route to build a great company, or build a great business, or a great life for yourself.

DH: Right well thanks for sharing. Funny enough you talk about what your passion is, you have a great many letters behind your name in terms of degrees and other academic pursuits that you have done. What do you think drove you to spend from what I can see the better part of 8 or 9 years in academia?

CG: I don’t know I think at the very beginning of university I thought that I was going to be a lawyer. I was trying to think of all the things that I did well and that I liked to do and what might I pursue was a major in university. I knew that I loved solving problems creatively, I knew that I liked history, and political science, and I liked random stuff like travel, movies, the arts. I knew what I didn’t like, I was not a math guy, I wouldn’t say I’m not a numbers guy because I actually can really get into the weeds in a spreadsheet or a financial statement with really anyone which is more of a function of being in the business. But that wasn’t the thing that excited me, I didn’t care to go to business school, I didn’t care to pursue a career as an accountant or anything. So I applied what I thought I was good at and where my skills lied with potential careers. So research, critical reading, writing all that seemed to line up with law, I was also a big Jerry McGuire fan so that kind of sealed the deal. So yeah throughout undergrad I took a lot of stuff, a lot of legal studies, a lot of political science, a lot of international relations, a lot of history you know a lot that I can apply my core skills at. So law school was just a natural extension of what I thought was going to be my career. In particular I was a big sports fan growing up, I wanted to be an entertainment sports lawyer. Then through law school I learned that being an entertainment sports lawyer is maybe not awesome. A lot of these people who I met who were agents in the U.S. did not seem to be having great lives, and were investing a lot of capital into a business that could go awry at any chance, because these were businesses dominated by a few agents. Some are able to suck up the top prospects before they are able to sign their big contract, it doesn’t matter how much effort you put into building a relationship with these people ultimately these guys want to get the best deals and the big name agents end up getting the best deals for their clients. So that didn’t seem like an awesome business, and I became disillusioned with the culture and the politics of being a lawyer at a firm. So while I did get a little bit of the firm life I looked at a lot of different practice areas working in different law offices. I realized that maybe that life wasn’t going to be one that would give me joy. Whether the thing that I want to do ends up building a digital receipt company startup or not, I just knew that wasn’t the livelihood that would interest me over the long term. So I decided that although I had invested a lot of time and money into education into being a lawyer that didn’t mean that not pursuing law was a waste. I do think it developed me in other ways.

DH: If nothing else you’ll win the legal sports trivia any day of the week in terms of name dropping but the top entertainment lawyers.

CG: I have a good friend of mine who was a lawyer who is now corporate counsel for a technology company mind you. He interviewed for the NHL PA and so we were talking prior to his interview about what interview questions could be, and actually his interview was around who could negotiate a better deal on arbitration Nik Zherdev or Joffrey Lupul. I kept swaying it’s Lupul, he just scored 4 goals in a Stanley Playoff game and this guy went with Zherdev and ended up losing the interview. I was right so maybe if I applied to the NHL PA maybe my career path would have been different.

DH: That’s great. Listen I’ve got so many questions and there’s so many different angles I could go but you know I just wanna jump into it. So you have done two startups back to back all based around the idea of helping either on the business side or the consumer side better managed receipts. What was the impetus? What was the idea? What was fascinating with that specific technology niche or consumer need niche that you thought you’d be best suited to tackle?

CG: Yeah I mean I could tell you that when I was 14 years old or 13 years old but I think I was gonna solve the world of receipts and digitizing receipts the answer would be no. But I think where the early inspiration came from was that I was that kid who would do a lot of shopping at HMV, Future Shop, Best Buy, EB Games, and hockey equipment at Sport Check. Places where they were all big ticket items that cost a lot of money that ultimately were prone to breaking or prone to needing to be returned or prone to needing a warranty claimed on them. I remember when I was in my teens I would have in my top draw to the right with my computer and my desk this file folder of receipts with sticky notes with the name of the product and the date it was purchased and where it was purchased from, so that if I needed to make a return or a claim on a warranty this made sure that I didn’t lose track. This predates apps, this predates even online web apps so this was my way of keeping track of important purchases. I think maybe the thing that triggered me was I was in first year university Trinity College at the University of Toronto and I bought a universal remote control from HMV on Bloor between Young and Bank, and it broke! I went back, it’s a walk from Trinity and they didn’t let me return it because I didn’t have the receipt. I’m now at residence and my receipt system broke down I guess.

DH: It must be maddening to have gone your entire adolescence obsessively collecting these receipts and then the one time that you need it you don’t have it.

CG: My old system did pay off for sure there were many times where I would go back to Best Buy and would get a new graphics card because the old one got blown away or something. So I marched down to HMV and I’m like can you track my purchase in your point of sales system or something? And they said no. So I was like this needs to be fixed and that kind of really inspired me to really think through what products or what a solution for this would look like. Would it mean building my own point of sale system and selling it to every retailer in the history of the world? Well that wasn’t going to happen. Those really were the seeds that inspired me to learn more about retail, point of sale, loyalty card programs because I tried to imagine that maybe this would be something embedded in Air Miles, you could swipe your card to get points and maybe it would allow you to track your purchases across all those retailers you got points at. So those were the early seeds of inspiration for what would eventually become SmartSlips.

DH: Like I said we should have booked a special two part episode for this because there’s so much I want to talk about but skipping forward to Sensibill is that the model (without trying to butcher it while I explain it) but primarily you are working in a B2B to C model. Sensibill has partnered with over 85 financial institutions like Natwest and Alterna as well as

some of the leading core and digital banking providers like FIS and NCR. What was your process to pitch your first major financial partner on forging a partner with you to provide this technology?

CG: So in the early days of Sensibill there was no Sensibill there was no business, no intention to start a business offering the solution or a solution at all to financial institutions. It was a series of meetings through my network and people interested to talk to me about “Hey you know you’re the digital receipts guy, what would it look like if we paired digital receipts with banking?”. That was a conversation that was happening off and on for a little while, and then eventually they came to me and said “Hey listen we’re innovating in mobile payments, which is going to be this immensely transformative world” this of course predates Apple pay,Google pay, Wii chat pay etc. Every company on earth has a pay now right? Back then it was banks who wanted to deploy their own mobile wallets and own the end to end experience, and own the brand relationship as they ought to believe they should. One of the big banks in Canada brought me in and said “Hey we’re working on this mobile wallet, it will let customers use their mobile phones to make payments” (This was non iPhone it was only Android at the time, and only a select few Android phones). They wanted to surround this with other value added services, that was the phrase that started to become top of mind buzz word for Senior Executives at banks at the time. So what would make payments mobile payments value added? Well if you allowed customers to add gift cards in their mobile wallet and make payments with them virtually they might find interest in that. If you allowed customers to store coupons, and store loyalty cards that would be value added. If you allowed them to track and manage all of their purchase receipts for warranty tracking, and return policy tracking, and ultimately for expense management for small businesses and customers looking to manage their household expenses that would be value add. So I was a receipts guy, they brought me in to talk about this and you know many months later our first few banks that we were validating this with pilot it for brand proof of the concept. So customers, their branch locations and getting feedback from users and they determine that yes this would be a value add to customers. It actually tested very highly as a concept, and that ultimately it inspired us to raise some money and build this into a business. So that’s really the way that Sensibill got off its a**, was having paying customers validate the value proposition and justify that this could be a business that could work. From that initial validation from tier one banks , that you don’t really expect to be working with as a first customer. Most people who are smart end up working with smaller companies where there is less bureaucracy, less cycles of discussions before you reach a deal, and less time to market because starting out you want to get it to market and get it to revenue as quickly as possible. We kind of did it backwards, but the benefits to that is that we have major organizations saying our name out of their mouths so that helped us get some early credibility and put some points up on the board.

DH: I’ve got time for maybe one or two more questions before we have to let you go. So the future of Sensibill and your career, if you take your emotional timeline and extended it out five or ten more years from now what do you hope is the highest point on that emotional timeline for yourself?

CG: That’s a really good question, and it’s probably something I should confront more often to give me a sense of light at the end of the tunnel right? I honestly think that I have a high bar for myself, and I have a high bar for what I’d like Sensibill to achieve. I think an emotional high for me is less of an event and more of a feeling, and I think that I am trying to be a leader, and as a company build our business to a place where it is a flywheel. It is a self sustaining machine that is resilient to changes, it is resilient to somebody who you might have historically called an individual with critical skill leaving the company, it is resilient to me it can survive and thrive despite me being in the chair, it’s something that can go on. I know that’s probably a tall task and a lot of pressure to put on myself for a company that is still very much in the early stages of the business. I admired companies that are resilient to changes of leadership, or changes to functional accountability, and changes to market trends. You can’t be in a kind of business where covid-19 happens and disrupts travel and your business goes in the tank, you’ve got to be multi threaded, multi disciplinary, you’ve got to have people independent of senior leadership coming up with amazing ideas to pivot the business if need be, and to be able to execute on those pivots and not just have them be thought experiments. So I think as we achieved milestones of team growth, and obviously business growth it makes me feel like we’re closer to getting to that point. So that’s a long winded answer to ultimately I want to make sure the company can replace me and survive with great success, but yeah I think that’s the sign of a resilient company.

DH: What a great answer so I don’t have any problem that you took the extra words to communicate it, really great. Last question for you and then we’ll let you go. What is the Corey superpower?

CG: That is also a good question. I would say my power can sometimes be a weakness but I am an optimist and I’d say realist too because it’s not like everything is roses for me. I really try to dig in and understand what something means before I get overly excited by it, but I feel like I can be very personally resilient to adversity. This covid stuff came, and I’m really proud of the way my leadership team handled it, and I know having to make challenging decisions as a business through garbage times is not fun and nobody certainly looks forward to making choices that might be affecting other people. But to be able to roll with it and just say well this is a crappy hand to be dealt but we’ve got to steady ourselves as the leadership team, evaluate what needs to be done for the company to survive, and then focus on what it needs to do to thrive, and then just execute that. So I think that I’ve always been resilient to the tidal waves of crap that can be thrown any founder of entrepreneurs way as your building a company, because if you can’t handle those it doesn’t matter what else you’ve got you could be the smartest guuy in the world but it’s coming for you and you better be ready for it. I feel like despite challenges I’ve always been able to take a moment and steady myself through them.

DH: Well you’re living through a great test of that super power right now, and it sounds like you’re passing the test thus far and I hope you continue to do so. I also hope that we don’t have to live this life much longer, but listen thank you so much for taking the time to join us for the interview today with some really great stuff. Like I said as I was preparing I was like this could easily be a two or three part episode, but then you’d have to give up an hour and a half of your day and you’re a busy guy. So with that being said in the show notes we will include links to where people can learn more about the business and learn more about you, and let’s try to do this again in a few years to see if that emotional high has been hit it would be great to do a follow up.

CG: For sure thanks so much!