#ScaleStrategy is produced by DX Journal and OneEleven. This editorial series delivers insights, advice, and practical recommendations to innovative and disruptive entrepreneurs and intrapreneurs. Read the in-depth Q&A with Teshima here.
“One of the most important aspects of scaleups is figuring out how to transition sales – from a founder to a larger sales team. It’s also one of the hardest,” says Paul Teshima, CEO and co-founder of Nudge.ai, a relationship intelligence platform that helps sales teams to access new accounts, analyze deal risk, and measure account health.
And, he knows what he’s talking about.
Teshima is a Canadian-born serial entrepreneur and a rare breed too. His previous company, Eloqua, achieved unicorn status.
As part of Eloqua’s executive team, Teshima grew the company to more than $100 million in revenue over 13 years, through two economic crises, its IPO and its eventual acquisition by Oracle for US$957 million in 2012.
Today, from Nudge.ai’s office in OneEleven, Teshima and his co-founder Steve Woods (also a co-founder at Eloqua), are hoping to scale up again. Since launching in 2014, the company has grown to 22 employees, several major enterprise clients and over 20,000 B2B users on the platform. And they were recently featured in the Wall Street Journal on how AI is changing sales. It’s no surprise they’re gaining momentum given the growing need for digital relationship management support. After all, Google, Salesforce, Microsoft, Cisco, and more tech giants are moving into the space.
As Nudge.ai builds out a sales team, Teshima is leaning on lessons from his past and learning new ones about who, how and when to hire, what founders forget about when training newbies, and the art of cracking an enterprise deal.
From One to Many
When it comes to the first few sales hires, Teshima believes they should be entrepreneurial. His approach to building a high-performance sales team is what he calls a classic best practice: hire people in pairs so that you can start removing variables. For example, if both salespeople are having trouble, it may mean that it’s not the right time to transition. If one is successful and the other is not, then it could mean you didn’t hire someone with the right skills.
Nudge.ai is in the process of transitioning its founder-oriented sales team to a larger group. “We’ve got some salespeople working on that delicate transition period now,” he says. “I can tell you that I’m already overestimating how much I think they know because I take my knowledge for granted. I mean, of course they don’t know what I know, it’s in my brain still.”
As a company scales, Teshima urges founders to pause and appreciate how much they know about the business, and how quickly they can make decisions at the drop of a hat in a deal cycle. Those skills are not always things salespeople can do right away.
“It’s really important to simplify,” he says. “Understand what can be translated to a salesperson that he or she can then repeat over and over again.”
To support their success, Teshima focuses on being as methodical as possible throughout on-boarding and training. In addition, he brought someone in to help simplify the sales process to determine what can be scalable.
Hiring Sales People
Should you hire a Director of Sales or build the team from the bottom up? Teshima says it depends on where you sit on the revenue curve as well as the capital and talent that’s available to you at the time.
He definitely sees the value of of hiring a Director of Sales first who can “carry the bag” and help to scale that initial phase, but also agrees with the approach of hiring a hands-off VP to go build up the entire team.
“Both require early evidence of some form of scale. You have some sort of process that defines how the sales process works today and also key metrics about it,” he says.
Teshima acknowledges that finding sales talent can be a challenge. “Are there less seasoned salespeople in Canada who have gone from $0 to $100 million than in the Valley? Yes. Do we need to solve that problem? Absolutely. But you are seeing a lot of seasoned people coming back and as that continues you’re going to see those people train others to get to the next scaling point,” he says.
Closing Enterprise Deals
Enterprise deals are coveted targets for scaleups for the revenue, for the credibility, and for the learning that they offer.
“The hardest part of closing an enterprise deal is finding it,” says Teshima. “Getting involved in the sales cycle itself is challenging because decision-makers are so inundated with a barrage of outbound outreach. These buyers shut down and avoid dealing with 20 or 30 vendors.”
He says that if you’re going to play in the enterprise space, you should understand what you’re getting into. First, it’s difficult to get in. Secondarily, startups can’t wait out a 44-month sales cycle knowing the deal may not close. “You can, but you’ll be losing a lot of sleep,” he says.
Teshima’s scaleup strategy is to show pocketed value right out of the gate. “Lock them in and then go from division to division quickly. And do it more cost-effectively than the competitor. Try that approach versus just the top down approach.”
When it comes to offering freebies or deals to close a deal quickly, Teshima believes low-paid pilots can be risky.
“Enterprises today actually have slush funds to experiment with technology where they didn’t before,” he says. “You could be in a small little pilot where they throw money at you and you wouldn’t even know if it’s a real deal or if they’re throwing real resources behind it. It is absolutely true that if they put some skin in the game, you’ll have a more successful pilot. You need to be pretty disciplined about qualifying, and if you invest in the cycles then put a price on it.”
What about when enterprise customers who scaleback during the renewal process?
Teshima says he hasn’t experienced this yet at Nudge.ai, but in the earlier days at Eloqua, there were times when customers pulled back.
“It’s only a death cycle if you don’t learn from it for the other existing customers. You should never forget that customers can always come back and champions can always move jobs. You always want to do right in those situations because you never know when you’re going meet them next in the ecosystem,” he says.
Channel Partners Sales
In B2B sales, channel partners can be a tempting avenue to explore. While there are good synergies on the tech side – on the cloud and services side – it can be more challenging to have channel partners depending on the nature of the product, says Teshima. In fact, he warns against channel partners in the early scaling stage.
“If you think training your first salesperson is hard, try training channel partners on your product when they have 20 competing products to sell and they’re making a small margin on your product,” he says. “You can get lucky and find one strategic partner and go big, but more often than not, you’re going to find that they’ll get all excited, get trained, and not sell anything. Even if they do close something, it may not even be the right fit,” he says.
Instead, Teshima recommends, clearly establishing that you can directly sell your product in a repeated way before you think about channel partners.
Scaling a sales team isn’t easy. And it won’t happen overnight.
“My one piece of advice is that it’s never one thing,” he says. “It’s a million little things you need to do every day. That’ll make you more successful than trying to figure out the one thing that will help you hit the jackpot.”
Want more? Read the in-depth Q&A with Paul Teshima for more insights on scaling sales.
Q&A: Paul Teshima, CEO & Co-founder, Nudge.ai, on how to build a sales team that scales
One of the most important — and hardest — aspects of running a scaleup is figuring out how to transition sales from being founder- to team-driven.
One of the most important — and hardest — aspects of running a scaleup is figuring out how to transition sales from being founder- to team-driven. Paul Teshima, CEO and co-founder of Nudge.ai, knows how important it is to growth.
Teshima is a Canadian-born serial entrepreneur who, as part of Eloqua’s executive team, grew that company to more than $100 million in revenue over 13 years before it was acquired by Oracle for US$957 million in 2012.
In 2014, Teshima launched Nudge.ai, a relationship intelligence platform that helps businesses find and build the right relationships to drive revenue. He secured an office in OneEleven and along with his co-founder Steve Woods (also a co-founder at Eloqua), and they have grown the company to 22 employees, landed several major enterprise clients and more than 20,000 B2B users on the platform.
Bilal Khan: How did you manage the transition of startup to scaleup when founders go from being the primary salespeople to building out the sales team?
Paul Teshima: One of the most important aspects of scaleups is figuring out how to transition sales from being a sales team of one as a founder to a sales team. It’s also one of the hardest. Founders often overestimate how much they actually know that no one else knows, decisions that they can make in their brains at the drop of a hat in a deal cycle. It’s really important to try and simplify and understand what could be translated salesperson that they can then repeat over and over again.
I also think that first hire is super critical to be much more of an entrepreneurial sales person. A classic best practice as you continue to scale is hiring them in groups of two so that you can start removing variables because it may not be the right time to transition it you didn’t hire someone with the right skills. That stage is really delicate and you will need to be patient.
Khan: Have you transitioned Nudge.ai into a sales team approach as opposed to the founders?
Teshima: I’d say that we’re still in founders plus a bit of hybrid sales teams. So we’ve got some salespeople working on that delicate transition period now. I can tell you that I’m already overestimating how much I think they know because I know and take it for granted. I mean, of course they don’t know, it’s in my brain still. It’s about being methodical. We just brought someone in to help us really try and simplify the sales process to determine what can be scalable.
Khan: When do you start thinking about finding a seasoned sales leader? Do you immediately find someone who can start building a sales machine or is this further down the road once you hit your stride?
Teshima: It depends on where you are on a revenue curve plus the capital you have and the talent that’s available at the time. There’s definitely an argument that you hire the Director of Sales first that can carry the bag and helps to scale that initial phase. But there’s also an argument about hiring a hands-off VP to go build up the entire team. Both require early evidence of some form of scaling. You have some sort of process that defines how the sales process works today and there’s some of the things that we know in terms of the metrics about it.
Khan: What are some of the key metrics for a sales success that you think are important?
Teshima: There’s obviously the output of generating revenue in the growth program. For us, we’re in a product-led model so it’s a little bit different and a little newer. We look at early stage interest as signing up for a user, finding a cluster of users account — is it qualified product lead? — and then we ask if we can turn that into a trial that converts to a paying customer. We look at those stages which is a little different than the classic B2B funnel.
Khan: In Canada, we talk a lot about whether we have the sales professionals with the deep skill set to be able to scale companies and do B2B sales. Has finding sales talent been a struggle for you?
Teshima: Are there less seasoned salespeople in Canada who have gone from $0 to $100M than in the Valley? Yes. Do we need to solve that problem? Absolutely.
I’ve been lucky that I’ve been part of the business that has gone from $0 to $100M in revenue (Eloqua) and we didn’t have anyone to rely on but ourselves. I think it’s just a matter of going in and doing it. You are seeing lot of seasoned people coming back to Toronto and as that continues to happen you’re going to see those people train others to get to the next scaling point.
[Sales] is really about the discipline of keeping in contact and helping others in your network, knowing that it will pay back over the long term. We did a study where we showed that the average head of sales has a strong network at work that’s three times the size of an sales development rep, which makes sense.
Khan: I wanted to talk about B2B sales cycles. Those are really challenging time frames in cycles to manage when you’re starting a company. How have you hacked in on the early stages of the sales cycle from a simple cash-flow perspective?
Teshima: The hardest part of closing an enterprise deal is first finding it and then getting involved in the sales cycle itself because they’re so inundated with a barrage of outbound outreach from all these customers. The strategy I recommend to scaleups is this: You have to show some pocketed value, lock them in and then go division-to-division quickly. And do it cheaper than a competitor. Try that approach versus just the top down approach right out of the gate.
Khan: Would you do that at the expense of generating any revenue?
Teshima: Enterprises today actually have slush funds to experiment with technology where they didn’t before. It is absolutely true that if they put some skin in the game, you’ll have a more successful pilot. This opportunity allows you to qualify those deals earlier. I think you need to be pretty disciplined about qualifying and if you invest in the cycles and then put a price on it.
Khan: So you’ve landed the customer and they are paying for the product offering. You’re coming to a renewal cycle and they scale back their offer. How do you address a situation like that?
Teshima: We haven’t had that happen at Nudge.ai. If I think back to me earlier days at Eloqua, there were times when customers pulled back. It’s only a death cycle if you don’t learn from it for the other customers that are existing. You should never forget that customers can always come back in and in champions can always move jobs. You always want to do right in those situations because you never know when you’re gonna meet them next in the ecosystem. Maybe they’ll evaluate it differently.
Khan: How do you think through channel partners strategically?
Teshima: In cloud software, it’s more challenging to have channel partners because of the nature of the product. On the technology side, there is probably good synergies. On the service consulting side, I think it’s harder. If you think training your first salesperson is hard, try training channel partners all your stuff, when they have 20 competing things to sell and they’re making a small margin on your product.
You first need to establish that you can direct sell your product in a repeated way before you think about channel partners. You can get lucky and find one strategic one and go big, but more often than not you’re going to find that they’ll get all excited, get trained and they’re not going to sell anything. Even if they do close something, maybe it’s not exactly the right fit. I’d say be careful with channel partners in early stages.
Khan: Are there any books that helped you in your scale journey?
Teshima: I am probably less of a book guy than I should be as a CEO. There are two books, however, that I found helpful:
- Jim Collins’ book “Good to Great”. I especially liked chapter five about managers and this idea that the best managers, CEOs and executives don’t even want the spotlight. They’re much better being extremely streamlined and determinedly humble, inwardly focused on driving change.
- “Switch” by Chip and Dan Heath. One thing that came out of that was this idea of focusing on the bright spot in your startup. As a founder, you’re geared towards focusing on what needs fixing. It’s actually better and more uplifting for the business to focus on the bright spots.
How Wealthsimple grew to more than $2 billion in assets in less than 4 years
Founder and CEO Mike Katchen on the crucial balance between steady growth and creative innovation when scaling a financial services company.
#ScaleStrategy is produced by DX Journal and OneEleven. This editorial series delivers insights, advice, and practical recommendations to innovative and disruptive entrepreneurs and intrapreneurs. Our in-depth Q&A with Mike Katchen can be found here.
It’s February 2017 and Wealthsimple is woefully unprepared for tax season.
“We didn’t anticipate this huge spike,” says Mike Katchen, Co-Founder and CEO, Wealthsimple, which got its start at OneEleven. “The industry talks about taxes being super seasonal and it’s the busy time of year, but we never experienced that before. During last year’s tax season, we were wholly under-resourced on our customer support team, which led to delays. People were working 120-hour weeks for a couple of months straight to try and dig our way out of that hole.”
Since its launch in September 2014 with 3 people, Wealthsimple has grown to over $2B in assets under management, 175 employees, and raised $165 million in capital from Power Financial Group. In 2018, it landed on the 2018 Narwhal list, a University of Toronto report that highlights Canada’s 50 most financially attractive tech companies. The story of its scale up is filled with moments of challenge where Katchen and the Wealthsimple team learned on the fly how to best balance steady, consistent growth with innovative leaps forward.
For tax season this year, Katchen wasn’t going to make the same mistake twice. It was time to innovate.
“Rather than hiring an army of customer service people, our technology team tried to figure out if there was software we could build that would both support our customer support resources as well as eliminate the need for customers to call in,” says Katchen.
It worked. In 2017, there were more than 35,000 interactions in the month leading up to the RRSP deadline. In 2018, despite tripling their customer base, there was only 5,000 more interactions and no additional customer service people. “People were working harder than they normally worked, but nowhere near 100-hour weeks and it was a very manageable process,” he says.
Gardening vs Planting
Tax season 2017 is a stark reminder for Katchen that Wealthsimple must ensure it is two things: robust and scalable.
“Historically, we like to do a lot of things,” he says. “We get really excited about big ideas and don’t always see the ideas all the way through.” Katchen realized that they needed to be selective in what they pursue because “real technical debt accumulates if you build things you’re not going to commit to, and it becomes more difficult to manage as you scale.”
In the last year, Wealthsimple has refined their product planning process to better activate the great ideas within their team. Now anyone in the company can pitch their ideas, but with a process in place to determine what actually gets built and what gets killed.
In an effort to balance growth with innovation, Katchen recently introduced a new framework for thinking about how teams can be more disciplined about allocating resources: “gardening” and “planting”. Gardening is about tending to the current business. Planting is about new ideas.
Katchen says 75 percent of team effort is now spent on gardening in order to grow their market share, optimize on delivering a better experience to customers, and to continue improve the business fundamentals.
The other 25 percent is reserved for planting new ideas to support Wealthsimple’s much bigger aspirations.
“We want to build a business around the world that truly transforms the landscape of financial services. And to do that requires some big bets,” he says.
Whether gardening or planting, Wealthsimple teams are empowered to build processes and develop solutions to get work done. Plus, some of Katchen’s favourite moments are when his team accomplishes something he has no involvement in.
“The ethos of building a team is to find people who are way smarter than you,” he says. “If I feel the need to exercise control, then I’ve hired the wrong people. If I am exercising control over people who are much smarter than me, then I am not letting them reach their potential and I’ll never know what they could possibly bring to the table. I want the company to do great things that I have nothing to do with.”
Power of Transparency
One key way Katchen supports his team to get work done is with practices that promote and support transparency.
Consider the company’s long-standing weekly all-hands meetings; not only does everyone on the team get to hear at the same time how the business is doing that week, along with priorities and challenges, each of the members of the leadership team also take turn leading the meeting. This allows for different perspectives to be openly shared.
Another example is a practice from within the weekly meetings called FUD (which stands for fear, uncertainty and doubt). The practice invites anyone in the company to publicly or anonymously share an “an existential concern” — aka a fear, uncertainty or doubt — that they have about the business. Katchen was inspired to adopt FUD by Stripe and believes it re-enforces that it’s okay to have tough conversations at the company.
The last transparency practice is a bit unorthodox: Katchen makes Board documents accessible to the whole company. Again inspired by Stripe, Katchen says that when smart people are given access to information, they make better decisions. Katchen would much rather err on the side of transparency than hiding things from people, or labelling documents “privileged information.” The only thing he removes is highly sensitive content such as compensation, but company financials are available to any employee who wants to see them.
As a first-time entrepreneur Katchen readily admits that Wealthsimple has more work to do around building a scalable process. “[Good process is] something you can’t even see. It’s just a way of operating that makes everyone better, but not something you pay attention to or gets in the way of work,” he says.
As he continues to grow Wealthsimple, Katchen welcomes the unforeseen challenges and remains committed to his larger vision.
“I’m on a personal mission to build a Canadian champion globally. I want to see more companies in Canada take on the world and build long-lasting global institutions,” he says. “The only thing that’s true is that if you’re scaling a business, every six months it’s going to be a different business. In order for you to be successful in your role, you just have to keep learning and stay one step ahead of where the business needs to be at the next journey.”
Up next: Learn more about Wealthsimple’s ScaleStrategy story in our Q&A with CEO Mike Katchen.
Q&A: Wealthsimple CEO Mike Katchen talks process, culture and scale pressure
In three-and-a-half years, Wealthsimple has raised $165 million in capital from the Power Financial Group and scaled from three employees to 175. And in early 2018, the company announced a milestone of more than $2 billion in assets under management and cemented itself in the vanguard of Canada’s new breed of financial services businesses.
“I’m on a personal mission to build a Canadian company globally,” says Co-Founder and CEO, Mike Katchen. “I want to see more companies in Canada take on the world and build long-lasting global institutions.”
Wealthsimple’s scale-up story is the stuff of legends (you can read our piece on their journey here). As part of #ScaleStrategy, Katchen spoke with Bilal Khan, Managing Partner of M6ix Ventures and the founding CEO of OneEleven, about the pressure, pain and pleasures of growing rapidly.
Bilal Khan: What has the experience of scaling your business been like?
Mike Katchen: I think the hard part for me is that we’ve never done this before. We didn’t really know what good process looked like. I like to think that good process is something you can’t even see. It’s just a way of operating that makes everyone better, but not something you pay attention to or gets in the way of work. Today, we’re trying to introduce structure to make people more productive, but we still have a ways to go on that front.
Khan: And you’re happy to let team members build the processes themselves?
Katchen: I’m very hands-off. I’m here to support our people to do the best work of their lives.
Katchen: If they need my help or support, they want to problem-solve things, come to me. But I am not going to drive the agenda for each individual team as to what they’re supposed to accomplish, what they’re working on, what their goals are. I’ll encourage them to push their thinking, but it’s not up to me to set each person’s ownership over their parts of the business. That’s a key point of our style.
Khan: Was there a time when you realized a certain process or system that you were using was starting to become disastrous and you had to introduce something new there?
Katchen: On the people side, I led HR and recruiting for the first 50 hires. It was really important on the recruiting side, but a terrible idea on the HR side. Quickly after that, our first HR leader came in and helped to structure some of the “people process” that we have here, which made a big difference. At some point you transform from being a small, scrappy family-like team to building a company where things like career paths, trajectory, titles, salary and benchmarking become really important. As soon as you hit a certain size, you have to think about what the company starts to look like rather than just a group of folks trying to will something into existence.
On the product side, in the early days, you go by your gut. You build the things you want. That’s still is a part of our ethos because we are clients of our products and we love to build things that we want to use. At the same time, you start to pay real technical debt if you build things you’re not going to commit to, and you become much less nimble as you scale. In the last year, we really tried to implement a better product planning process where anyone in the company can pitch what we build, but we have a process in place on how we decide what to build, what to kill. This is important to help us stay focused on building the right things.
Khan: Tell me about a scale pressure that was a hard nut to crack.
Katchen: Last year we were unprepared for the enormity of tax season in Canada. The industry talks about taxes being super seasonal and that tax season is the busy time of year, but we never experienced that before. We didn’t anticipate this huge spike. During last year’s tax season, we were wholly under-resourced on our customer support team, and this led to some poor experiences and delays that we had to crawl our way out of it. People were working 120-hour weeks for a couple of months straight to try and dig our way out of that hole.
This year, we tried to be a lot more thoughtful about it. Rather than hiring an army of customer service people, we threw a technology team at our customer support operations and tried to figure out if there was software we could build that would both support our customer support resources as well as eliminate the need for customers to call in.
What we found is that last year, there were something like 35,000 interactions in the month leading up to the RRSP season deadline. This year, we have more than three times the amount of customers but only had 40,000 interactions. All without a bigger team.
Khan: How do you continue to be innovative, test new product offerings without impacting the business at scale?
Katchen: We get really excited about big ideas and probably throw too little resources at them and don’t always see the ideas all the way through to where they need to be: robust and scalable.
We need to focus on maintaining our positioning and growing our market share, keep optimizing to deliver a better experience, keep improving to make the fundamentals of our business better. But our aspirations are much bigger than just that. We want to build a business around the world that truly transforms the landscape of financial services. That requires some big bets and not all will pay off.
So, one of the new things we’re introducing is an analogy from one of our team members: Garden and Plant. This describes those two activities of growing market share and making big bets. We need to be smart about how we resource between those two activities. To do that, we’ve decided that 75 percent of the company resources should go toward gardening activities that support business growth, and 25 percent should go toward planting or cultivating new ideas. I think it will bring some more discipline to allocating resources.
Khan: How do you manage culture with 165 employees and growing?
Katchen: We’ve done a few things right with culture at scale.
Katchen: We still have an all-hands meeting every week, and we’ve iterated a lot on the content of that meeting and who leads it. I used to lead them all the time, and then my co-founder and I started sharing the responsibility, and now it’s everyone on the leadership team can run them. I think people enjoy that different team members from other parts of the business get to share how the company is doing. It adds perspective on how things are going that I think is valued.
And at that meeting, we try to do things that ensure that people know where we are going. We remind people of the company priorities and how we’re doing moving against them. We talk about metrics.
Specifically, we have a concept called FUD, which we stole from Stripe, who we really admire for their culture). It stands for Fear, Uncertainty and Doubt. It is a chance for anyone in the company to publicly or anonymously share what we call “an existential concern” that they have about the business. It’s a pretty jarring thing for people the first time they hear it. But I think it inspires a culture of transparency and enforces that it’s okay to have tough conversations here.
Khan: Have you had the conversation around potentially bringing in people who have done it before.
Katchen: Ah, the grey hair question. We’ve been fortunate and managed to grow very quickly. Boards are happy when you grow fast. For me, I’ve always had the mindset that there might come a day where it makes sense to bring in someone. To me, there’s no ego about it. I’m here because I believe in what we’re building at Wealthsimple. I believe in the team. I want to see this through to building a truly transformative company that makes people’s lives better. Right now, I am probably the right person in this role. If that changes, that’s cool, so long as it’s for the right reasons and it’s the right person.
For Wealthsimple, we gave up control as a business. We sold the majority stake to Power Corp., which is a really unusual thing to do for a business of our size. And the reason why it’s okay is because to take a company all the way to IPO, you’re going to have to do that at some point. For us, hanging on to control is less relevant. It’s a question of “how do you set up your business for long-term success?” We tried to find a partner that we trusted and believed could be a long-term partner to help us get there. It made that trade-off a lot easier. They share that trust with us and our management team.
Khan: What books helped you in your scaleup journey?
- “Why Mexicans Don’t Drink Molson” By Andrea Mandel-Campbell. This book was a huge wake-up call on the need to think big and do things differently. I talk about the book a lot because it informs a much of my thinking around Canada and how we need to build global companies.
- “The Lean Startup”. By Eric Ries. How many businesses get built where people spend years of their time on products and projects that don’t have fit because there’s no market for it? They never test it. Everyone has to know that.
- “The Hard Thing About Hard Things” by Ben Horowitz. In the first year of scaling, I remember reading what he wrote about hiring friends who have been a part of the business from the beginning and how much that sucked. And it does, it’s heart-wrenching.
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