Intro: Hi. Welcome to Dig In, the podcast brought to you by Dig Insights. Every week we interview founders, marketers and researchers from innovative brands to learn how they’re approaching their role and their category in a clever way.

Ian Ash: Welcome back to Dig In Today, we're talking to Paul Tashima. Paul is currently the Chief Client Experience Officer at Wealthsimple. In that role, Paul leads the client success operations and portfolio management and works with teams to provide an exceptional experience for all of Wealthsimple clients. Previously, Paul was co-founder and CEO at Nudge.Ai. Acquired by Affinity in 2020 and also led Eloqua Marketing which is an auto marketing automation software, as part of the founding team he took that company from $0 to over $100 million in revenue through the IPO and a successful acquisition for $957 million by Oracle. Thanks so much for joining us today, Paul.

Paul Teshima: Thank you for having me, Ian, excited to be here.

Ian: That was a mouthful. You've done a lot. You're a busy man and now you're at Wealthsimple. So can you kind of give us a quick overview of what it is that you're doing at Wealthsimple?

Paul: Yeah. And, you know, although it may seem like I’ve done a lot, this is only my third job in the last 20 years. So I kind of choose a place and stick to it. And I was lucky enough to join Wealthsimple about 15 months ago. And in my role as Chief Experience Officer, I helped manage all the front facing teams that engage with our clients across all of our product lines. And, you know, with every financial service product, there's an element of trust that's needed and we're there to help them, whether it's everything from how to get set up and onboarded all the way to providing you a financial plan and advice. So it's all those teams that have those different touchpoints that I run and work with today.

Ian: And how did you end up there from, you know, from founding two companies, bringing one all the way to IPO? How did you end up at Wealthsimple?

Paul: It's a great story. So I think, first of all, I was winding down my last company Nudge when I sold it, and this was in January-February of 2020. And the deal closed like two weeks before COVID hit. And I think two weeks later, I'd either still be at that company or doing something slightly different because of COVID.
So that was really interesting timing. And after selling that company, someone who I'd known for several years and stayed in touch with through the start ups, the CEO of Wealthsimple reached out and he presented a really interesting opportunity here. They really wanted to elevate the client experience function at Wealthsimple. He knew I didn't have a lot of financial service experiences, but he knew that I really, really cared about clients. And so through that process and meeting some of the fantastic people here, I fell in love with the mission and decided to join in November 2020.

Ian: Wow. And so, you join in 2020. You guys, have you basically been through, like, hypergrowth, right? Like, I don't know what the actual members are, but you're growing incredibly quickly.

Paul: Yeah. I have been part of a successful start before and the boards of other really fast growing startups. I have never experienced growth like I did after joining Wealthsimple. So just to give you a sense of it, we started with 73 people on the CX team and today we're well over 370 people 15 months later and it really kicked off with this whole meme stock phenomenon, GameStop in January, where a whole bunch of retail investors were flooding to brokerages and platforms like Wealthsimple to get involved and buy the sort of stocks like GameStop and Nokia and BlackBerry that were being run up with a lot of this activity.
And so as everyone was rushing to the market to get involved, we had a massive spike of clients and we've been catching up ever since.

Ian: Wow. So, you know, just joining a company like that. So, you know, you said you didn't have a lot of financial services experience and you joined during a hyper growth phase. And then the whole meme stock craze happened. I mean, those are all big challenges. What were some of the biggest challenges that you had to overcome when you first arrived so that you could keep up with that growth?

Paul: Well, I think there's a couple of things you know, having gone through two different startups with different sort of outcomes, I've developed a bit of a thick skin through adversity. So through this process, I try to break it down… and maybe it's on me, my engineering schooling, to break it down to the parts that we could manage and what we could control. And I think one of the hardest things is, and this is in all services type organizations, is this idea of how quickly do you hire versus maintain a certain quality process in getting those hires because it's that balance that really is going to make a difference for the client that they're talking to.
And for us, it was really challenging because we were so behind and there were so many clients on board. We couldn't hire fast enough. Everyone in the entire team, including myself, were doing front line single call interviews and then making decisions. So we get these people in the door and get them trained and get them helping our clients.
And I remember one time when things were getting really rough and we were not getting the clients fast enough. Our CEO was asking me, “Do we slow things down? Do we not let new clients join the platform because our service levels in responding to them are bad?” And I said to him, “You know what? The most interesting thing… And if you take a step back and think about context, only one in eight new customers ever call us. And so seven customers are getting the benefit of our platform without any problems. And then we need to talk to our support organization. And so why would we turn off the ability for them to do that?” And so that was kind of the guiding Northstar for us through that tough time.
And we managed to get through it by focusing on getting the right people in as fast as we could, but knowing that most of our clients were still having a great experience.

Ian: That's really fascinating. I mean, that just shows the importance of having those types of metrics at your fingertips and also of having great onboarding and great sort of product growth strategies in place so that people can use your platform without having to reach out to customer success or support, right?

Paul: Yeah. And that is I mean, the user experience is one of the real differentiators I think for Wealthsimple. And I'm standing on the shoulders of giants. I joined after a long time since they've invested in figuring that out and they made that a real differentiator in a tough market financial services to do that.

Ian: Right. So all of that, I mean, incredible story. But let's back up for a second to your previous successes because those are pretty massive as well. So if we look back before joining Wealthsimple, you've got two startups. Eloqua which you took all the way to IPO and Nudge which you sold in 2020. I'd like to talk about each of those quickly if you don't mind. I mean let's talk about Eloqua first. You know the percentage of successful startups is very low in terms of survival rate and just as a starting point. Let alone getting all the way to IPO which is incredible. I think you're probably the first person I've ever met who's taken something from startup to IPO himself or you know. I know you had a team, but what I mean is from the beginning. So if you were to boil down the lessons you took from that success, what are some of the top ones that you give to other people who, you know, have SaaS startups?

Paul: You know, there are some great lessons learned, I will say, and there's going to be some of them that talk about, you know, you have to hire a great team. It's all about the people. I won't go too much into that one. I think that's a self understood one.
For me, a couple of things that come to my mind are, one, I think the fact that we were bootstrapped at the start of Eloqua. So, you know, in 1999-2000 when it was founded, there wasn't a lot of venture capital in Canada, never mind, you know, SaaS startups in venture capital. And so we had to be profitable in the first 18 months.
And I think that DNA in us let us be really lean in how we approached getting the product market fit and then getting customers happy and successful. And that DNA I think allowed us to survive the downturn of 2008 and eventually become a business that looked attractive to the public markets in 2012. So the first thing is that the bootstrapping at the start I think forced us to start from a place that was very lean and focused on effectiveness really quickly.
The second is that we were really, really bought into customer success early because of being a SaaS product. And because of that we made two big pivots just because that's what the customers needed that we maybe wouldn’t have if we were focused more purely on sales or marketing. And that big pivot was moving from a chat product, which we thought was what the market needed, to a marketing automation product for marketers.
And today chats are prevalent everywhere. But back then, chat was not a prevalent thing on websites. And that change in decision we made really allowed us to become sort of the dominant player in the space.
And then I think the last thing for me… a lot of successful founders don't talk about is just some luck in market timing. You know, I think it's Vinod Khosla who says that success of a startup is just lasting long enough, but the company can till something happens in the market and I think that's fair. We lasted a long time in slow growth. And then when we pivoted and we started to get some traction in the economic turndown, everyone was carrying about these giant marketing budgets and how effective marketing was and really wanted them to be to be world, to be more focused on driving revenue.
And because of that market trend that started to happen, we became the glut of the hand that fit in that globe and really, really took off.

Ian: So you talked about getting to product market fit, which is I mean, it's a nerve wracking time because you're talking to customers and you're trying to figure out like, you know, not just is the product that I'm selling, is it fitting a use case for a key persona, but also am I selling it in the right way? So how long did it take you to not only pivot from chat to overall marketing automation, but then also feel really confident about your pricing model? Like I find that's a really challenging piece as well.

Ian: The pricing model is very very challenging and it's tied very tightly to productization, I would say, for sure. And we were in a different pricing model all the way into 2007, very much more of an agency style, like lots of different variables and you have a fee for this, usage fee for that. And around 2007 we had a new CEO come in, Joe Paine, and he asked me, even though I was running product at the time to actually come up with a simpler model and he came from the packaged goods industry like he came from, sorry, he was in B2B, but he came from like Coke, and he said I want basically a good-better-best model and they don't usually have that in software and it was pretty innovative for him to say that.
And I did the work and we put together this good-better-best model and it ended up being actually the default model. For now, the industry and market, everyone has it and they charge for context in the database and it was really a pretty interesting moment and important moment for us to actually start scaling sales even faster. And that's to your point on that matter. Before that, it was harder because it was so complex.

Ian: Wow. So you were one of the pioneers of good-better-best because that's everybody now. I think almost every SaaS page you go to now, you know, a few people have, you know, like a menu matrix type approach, but our modular approach, almost everybody is good-better-best. I almost think it's gone too far where, you know, sometimes now companies have a good-better-best when they really only have the feature differentiation to support two. But they forced the third one in, right?

Paul: I think we were like that too. So I think that that's a little bit of the psychology of it . But eventually you get that best model. But yeah, I hear you on that and I don't know, we were the originators of it, but we certainly pushed it the first into SaaS, B2B software.

Ian: Wow. So let's talk about Nudge. Let's contrast that a little bit with that. Just because you know, you and I, we have connected before. I asked you a little bit about Nudge. You were the one you referred to Nudge as more of a failure versus Eloqua, although, I mean, you still sold that. So I don't know how much of a failure it was. What did you learn from that experience versus what you learned from Eloqua?

Paul: I'll start by saying that, you know, one of the best things about building any business is the journey and the people you get to work with. And I always take that away no matter what. So I would say nothing was a failure. You know, we raised a bunch of money. We never got to escape velocity. And yes, we did end up selling the technology, but it was for a great outcome, for our investors. But I'm really, really happy that everyone got jobs again, like two weeks before COVID and moved on to something probably better.
But, you know, some of the key lessons for me… and so here's the interesting difference, is that we were very well-funded at the beginning. So myself and my co-founder just came out of the big winner, Eloqua. We raised almost 10 million US pre-revenue. And in some ways, although we were very frugal, like we'd never taken salaries except for one year out of the six and we just had a lot of time. And maybe if we had been a little leaner or raised a little less, there would be more pressure to drive to a product market fit outcome versus the one that maybe we thought was the right one. So the first lesson was that I'm not saying you still shouldn't raise capital, but you should find ways to really put tension and pressure and stress to move with urgency no matter what.
I think the second is that, again, back to market timing. I actually think we have a really great solution, and I think Affinity is actually doing really good stuff with it as part of their solution. I do think some of what we're doing will be used in every CRM system. And this one, we just didn't last long enough to get to a point where it started to take off.
And I would say the last thing for me on Nudge is… and this is really important for every founder out there, you know, we ended the company with money in the bank because we wanted to do the right thing for everybody and not run it into a wall. And I think that's really important that you're mindful that you have a fiduciary responsibility as a CEO and board member to treat your employees and your clients with the right process and right way.
And that gave us time to wind down things appropriately. I'm actually still technically on the Board of Nudge and have to deal with some things because there's some covenants that we're covering. But, you know, it's a real responsibility to start a company, but everyone should do it, but just know it's a real responsibility.

Ian: Yeah, no joke about market timing. I don't know how many times I've been to, you know, a web summit or another, whatever the one that they were holding in Toronto, starts with a “C”... Anyways. And you'd meet somebody and they were like, “Yeah, you know, I basically invented Pinterest before Pinterest, right?” Like there's so many of those stories where somebody went full bore on a great idea, right? And then they turned out to be MySpace instead of Facebook. Right? And so I think that's a common one.

Paul: I think it's a collision you're talking about, right?

Ian: Collision. That's right.

Paul: You know, a DC investor once told me and I always thought it was a great, great line that you know, there's only really two types of startups that make it successful. The first is one that finds the 30 best engineers in the world, and they lock themselves away for four years. And they invent the next Google. And that's rare, that's not a normal startup. And then the other one is a startup that's riding the coattails of a trend that's bigger than your startup that carries you along through the market as it grows, because you need that help because there's so many challenges. And I think it's choosing when and how to jump on those coattails. That's a huge part of being successful.

Ian: Yeah, that's really interesting. Let's bring that back to Wealthsimple first line because Wealthsimple is definitely riding high right now. I would think it's the combination of both, and there's definitely market factors that are serving as a tailwind for Wealthsimple. I think that's a fair statement to say.

Paul: Absolutely. Yeah. The rise of DIY investing, we have also a generation of people that want to be served in a different way. And then we have, I think, an entire segment of the market that just doesn't get access to financial services and tools that they're really going to need. And so it's those combination things that are really helping us get the traction and get the clients that are going to help make us successful.

Ian: So what is that vision strategy for Wealthsimple, the longer term goal there?

Paul: Well, you know, we want to make sure that we help everyone achieve financial freedom no matter who they are or how much they have. And it's really important. One of the proudest things I am at Wealthsimple is that a very, very large number of our clients on our retirement product or investment product actually wouldn't qualify to get their money invested because they have too little with us compared to other players.
But we invest in it because in my opinion, if you want to start a good habit, we shouldn't set a bare minimum threshold. Otherwise, how are you going to start that habit, right? And so I'm pretty proud about some of the things we do to help really provide that access.

Ian: That’s kind of starting with the “why” there. That's great. I mean, obviously there's an underserved market that needs to be served. So that's fantastic. And so this year, I mean, obviously, you know, over the last year, you've been dealing with that high growth, trying to get from seven to over 300 employees. What are some of the big things you're facing this year? What are some of the big challenges you're finding this year?

Ian: Well, I think the first thing that I think this is something that every business is facing is that you know, in a hybrid or mainly remote environment, especially in the client experience world, it's tough to keep the motivations high and the connection high. Sometimes some of our CX agents or support reps, they're working in a one bedroom apartment by themselves on long shifts. And it's hard to get them connected back with the team and the energy. And so it's something that's really top of my mind is how do I build more alignment, more motivation, more connection at a human level among my own team that continues to grow.
I think the other one is that, you know, we've raised a lot of money and we're a pretty big company and we're trying to do lots of things, not just one thing. And it's always just a challenge of like, how do we make sure we're putting the right amount of effort, bringing the right things at the right time across, you know, seven different product lines. Some of which are emerging and new, and some of them that have billions of billions of assets in them and, you know, have real responsibility and weight behind them we've got to manage. And so to me, the second is that constant prioritization process that we need to go through. Those are two big ones for me.

Ian: Those are challenges. Are there any other SaaS applications that you're using or that you think are helping, particularly in that sort of collaboration?

Paul: Well, you know, I know many people feel this, but like Slack went down the other day and we all were forced to go on Google Chat. And that was rough. That was a good reminder how bad Google chat is and how great Slack is. I think Slack for us has become a virtual office. No question, there're still challenges on Slack in terms of noise and busyness, but that's been a big one. We've also really, really rely on our own product a lot for a lot of what we do. And it's tied into a fantastic system we've built on the scenes.
And so I say between those two areas. We really try to bridge together this idea of being remote and how we work and collaborate with each other.

Ian: Right. I know at Dig and Upsiide, we've got a lot of fans these days for Notion. I think there's a lot of sort of superfans of Notion and also Miro. A lot of people are loving Miro these days, and so those are two that we've used effectively I think in the last couple of months to deal with the remote work challenges. But of course, Slack as well.

Paul: Yeah, Notion actually has been raised. We're actually on Quip and also on Google Docs, but I feel like since Notion’s the one that's been raised quite a few times and actually maybe, maybe we all even follow through after this and let's get a little more intel on it.

Ian: Excellent. So some of those things are new. So some of these challenges that we're all facing are completely new. This work from home challenge; there's not a lot of, you know, precedent for that and so we're all kind of groping and finding our way, trying to figure out the best way to maintain culture. But some of the challenges, I'm sure, are reminiscent of things that you've faced through your previous startup experience. And so what are some of the learning that you were able to bring from, you know, from Eloqua and Nudge, that right away when you stepped into the role at Wealthsimple, you were like, okay, I know a different way of handling this problem. I'm going to use the learning that I had in my, in my in my past of dealing with this.

Paul: I think there's a couple of things. I think the first thing that I really try to bring into as we become a large organization is, I really believe in the servant-leadership approach. So what I mean by that is, especially in the world of financial services, sometimes executives take more of … they’re a senior person. They only do certain things. You're here to serve them. And I take the approach and I think many at Wealthsimple do, that with our job as leaders is to actually support our people to be successful.
And so I spend a lot of time both meeting one on one with our frontline support reps or of course, talking to customers or having focus groups where we can find out what are the top three things that we're not doing well for our clients and hear right from the people who are working with them. And to me, that's like a huge, huge thing to keep doing as you scale and actually gets more important, not less important the bigger you get.
I think the second thing is, you know, we're really, really good at combining both, you know, the need for what I call some program project management to keep people in alignment and what's going on, but be really nimble. And I think that where I've seen challenges in the past that we've learned from is where you get too much into planning, too much into, you know, documents and documentation for everything and not enough doing. And so we really vector in my organization to like experimenting and executing, especially if there's little risk or no risk to the client. And so that's a big thing that we focus on as well right now.

Ian: That's great. Thanks. So thanks so much for your time today, Paul. I mean, I can talk to you forever, but, you know, I've taken up more time now than I asked for for this podcast. But hopefully we'll reconnect again soon. And I'd love to talk to you again one day because you have a really fascinating background and all your experiences and this is a great conversation. So thanks so much for joining us today. If people want to reach out to you, what's the best way to find you?

Paul: Well, Ian, thank you for having me. I really enjoyed it and really enjoyed being on the Dig Insights podcast here. The best way to reach out to me, is I'm pretty active on LinkedIn and Twitter. So Paul Teshima on Twitter and on LinkedIn, you can find me there. And I'll always be up for a good discussion or connection and some shared experiences.

Ian: Sounds great. Thanks, Paul.

Paul: Thank you.

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