Head of Revenue Automation, Tooling & Enablement at Shopify + Founder of Jameson Strategies
21 Insights · 7 Questions · 21min Read · 25min Listen · Connect with Craig on LinkedIn
Take a long, long, hard look at your go-to-market process, not from the perspective of what you're currently looking at, but put yourself in the shoes of your colleagues. If you're in sales, take a look at the marketing side. If you're in marketing, look at customer success. If you’re in customer success, look at sales. All of those things, if you want to be successful as a business, it's not about I, it’s about we. It means you need to learn, understand, and really look at what is the entire journey and get really buyer-centric from that perspective.
Here’s what Arthur Castillo said about Craig:
Sometimes we are too obsessed with our ICP. I heard Craig Handy talk about this where he looked at the ICP qualifications for previous years, Closed Won revenue for a client of his. He found that 60% of the Closed Won revenue technically would have been disqualified because it didn't meet their ICP qualifications. So a lot of the time, again, let's ask about where they're trying to get to? Or, maybe what they tried to do prior to reaching out to us, because often it could just be a simple switch or a tiny little product feature now that can expand an entire new industry and TAM for us, yet we’re disqualifying them. So, let's talk to those people, understand not necessarily where they're at today, but where they’re trying to get to. —Arthur Castillo, Senior Manager of Field Marketing & Community at Chili Piper →
3 ways that your team converts your
market into revenue?
1) PLG (Product-led growth). This is a big part of my role at Shopify. We, in a RevOps perspective, talk about “right person, right time, right way,” and I don't think there's a better “right person, right time, right way” than someone who's already engaging with your product to a certain degree—whether that's from a free trial perspective, whether that's from a basic plan, or even a big plan—and going with them and growing with them, providing that value for them when they need to see it or additional add-ons when they need to see it. The beauty of product-led growth is you have the visibility to what they're doing. You have the visibility to their performance, their challenges. You see other customers that have similar experiences. So being able to not only reach out to them in a very meaningful way, or the right time, but then also for them, in many cases from a self-serve perspective, say, “Oh, Hey, I want that, and I could get it, and I'm going to do it. And I don't need to have a million meetings to engage that way.” So that's a big piece there.
2) Referrals. From the Jameson's Strategies perspective, referrals. Huge driver for us. I only once went outbound. The real thing for me is: in a market where I think I'm coming with it with a product that is not common, we call it RevOps as a Service, and you're seeing a little bit of pop up, but it's not super common, and there some skepticism in that. So, having a warm referral, where someone's like, “Hey, this changed the game for us. So this really helped us. How do we pass that off?” And so we're really adamant to say that's meaningful for us, but we provide that value, and we naturally provide that value, so that people want to talk about it, and want to share it. That stems over to the third one.
3) Upsell / Cross-sell. This is prevalent in both Shopify and Jameson Strategies perspective. Sometimes the best barrier-to-entry is a little one, or one that is low-risk, or one that is a no brainer. And though, you believe deeply that the value is there, and I firmly stand by this, is that you don't sell something and believe it, you know the value is there, and sometimes you need to walk before you run. And so that entry-level where, “Okay, let's come in on a low plan if it's Jameson or let's come in on a low plan for Shopify,” and then you start to see, “Okay, these people care about me. They value me. They're providing me with value constantly, and they have a path for me to grow as I grow.” And so, I think to the question of how you turn your marketing into revenue, the micro concept of your market, as in your customers, how do you grow that? That is something that, if done right, is a safer, more consistent, and a more human approach to growth.
3 hard problems that you
I struggle with this question a little bit, because I was thinking, “What have I overcome?” It's always a constant struggle.
1) Making a tight budget tech-stack run like a sports car. I was playing around with this term, it’s like an engine swap of a Ferrari in Honda Civic. But the reality of this is that, especially from a smaller business perspective from the Jameson Strategies side, you have a budget, and especially in an approaching downturn, I don't want to throw into all these licenses, and all the op services, and is this the right tool? Is this the right tool? So the asks are huge. We want all of these things. But, the budget is like, “Ah, I can only buy a quarter of it.” So one of the challenges that is always a roadblock, but something that we've been very successful in overcoming is, “Okay. Can we make this and squeeze as much value as possible?” It's not always pretty, and I'll be upfront about that, but the bottom line is you're trying to achieve something. How do we help you to do that? That's been a consistent thing with a lot of clients. We get them to that particular point and then they prove that value in that, in that business case, and then they continue to grow. But sometimes, we've got to stretch a little bit outside of our box at the beginning. So that's a big one.
2) Forming a super alliance. This is from the Shopify context. There's a lot of things going on. There's a lot of investments happening. What are we building? When are we building it? How are we we doing this? There was a really interesting topic that my team and another team both had a lot of skin in the game on, so at first, well, who owns this? We want to drive with our direction. They want to drive with their direction. It took a few deep breaths, really thinking, “How do we put our merchants first? How do we put our customers first, and come together with a meaningful relationship?” And what that basically formed is, and we talk about it as like our step-sibling, this alliance between we call the project something, they call it something else, but it’s the same goal, same objectives. We just have different lenses on it. We always approach it with, “How do we win together?” That aligns us, which has been really strong and really powerful. So, that's been a huge one.
3) Growing a team really quickly. And so from the software perspective, towards the end of 2021, we restructured a little bit. So, a good portion of what my team was responsible for, my team moved to a new group, but then we inherited a lot of new requirements and new expectations, plus the revenue growth of the company. In that scenario, we need to fill these seats, so huge push. Thankfully we had a fantastic recruitment team, but doing hundreds of interviews, and engaging on a meaningful level, while also realizing, “Hey, I need to double in size, but I also want to add to the culture. So that was very challenging, but I'm happy to say we successfully did it. It's phenomenal. I'm loving all the new people that we have working with the group.
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3 roadblocks that you’re
working on now?
1) Time. I'm sure you probably hear this all the time. It's a constant struggle. Juggling that, not only within work, but also within your personal life, your personal life balance. I can get really like laser focused on something, but as someone who embodies my work life, finding that balance is incredibly tricky. The other thing, too, in our perspective, in a digital world, where neither of the businesses am I in-person, that whole sense of, “Let’s just hop on a hangout.” I've heard this many times from people, “I don't want to get on a meeting without agenda,” or, “This didn't need to be a meeting.” But, on the flip side, it's like, “Well, why couldn't it have been for the perspective of some human interaction? There's a way for us to not get mixed up in the way we're typing and read into things. Let's just get on a call and have that chat.” But in doing so, the calendar looks really, really nasty. So, that roadblock is, as expectations and everything started to grow and change, how do I have to adapt that without losing that human connection with a growing team, and a growing client list, and so on and so forth? So that's a big one. I don't know if there's an answer, but I'm certainly not going to stop. I'm too stubborn to stop searching for one.
2) Prioritization. This is especially true across the board. I call it separate from time, in the sense that you have a lot of things that are out there that we could do, a lot of ideas, a lot of projects that could produce value. You have a finite amount of resources in a certain set period of time, and, of course, you ask marketing, “Hey, what's the most important thing?” In sales, “what's the most important thing?” And sometimes, there are different things. Of course, to them, their thing is the most important thing. And so, how are you objectively, and collaboratively, identifying the priority? From my view, and my fear, where the roadblock lies is that by systemizing this into a really concrete process, you lose the human level of this. You talk about what the average number of kids people have is 2.5, but you and I both know you can't have 0.5 of a kid. So when you're talking about prioritization, it's like, “Oh, this is prioritized because this score was slightly higher.” But, does that make sense? Is that a human approach to the business? We're serving humans as our clients, and so in that case, it doesn't always work like that. That’s a big struggle. What's the balance between those two things?
3) Tech debt. It almost needs no explanation, but the reality is, as businesses grow, whether they're big companies or small companies, they grow very, very fast when they're on the right track, and they end up buying technology to solve problems. Without a really good long-term strategy around that, that stuff starts to build up, and we like to joke around and call it a Frankenstein system, but that's, in essence, a bunch of different parts that were never really meant to work together. Then, you start to investing time in decoupling that and rethinking that, and in the early days, it's no problem, but as you get bigger, and as you want to pivot, that weight makes it incredibly difficult for you to do things. The minute you start, and this is a big one for me, the minute you start making decisions not based on what the best decision is for the business, but based on the amount of effort it would take to make that change, you've gone down the wrong path. So, that's a big thing. How do you identify that early on? If you rack up a big financial debt, likelihood is you're not going to just try and go pay it off all at once, which is unfortunately how tech debt is associated. Instead, you get yourself on a payment plan, and you start to pay that debt off. And so, I encourage you to think about tech debt in that same way, where just because it's not a problem now, it’s best to believe that exists, so how are you effectively, without having to like rethink everything, slowly getting yourself in a better position over time?
3 mental models that you use to
do your best work?
1) I think of myself as an artist. This irritates so many people when I say this, but I say it nonetheless, I think of myself as an artist. I approach things from the perspective of an artist. This probably could be totally inaccurate, but this is what I say. This is why I'm going to say it again. Pablo Picasso, famous for his abstract art and everything, one could say, “Oh, I can do that. I can throw some paint on the painting and be like, I'm an artist.” But the difference being is like, can Pablo Picasso make a hyper-realistic, I-thought-this-was-a-photograph painting? Yes he can, but he chooses not to. So in this case, could I do that? No, I cannot. I can throw paint on the thing, but I can't make it look like you. That perspective, to me, is, when you understand the book, you understand the science behind it, you understand the process, going into a perspective of, “Okay, is this actually the right thing to do? Or can I make some creative decisions, or creative directions, that go outside of what you would expect and create something beautiful?” And that almost is like a mutation, but I like to call it art, in this case. It irritates some folks, but the mental model is, I'm not trying to be rigid. I'm trying to be artistic in the way that we approach revenue operations.
2) Big vision. Again, this one probably gets me into trouble all the time, but I'm always thinking about the next thing. I'm trying to think about the big thing. I just despise mediocrity, and that perspective is, “Great. We've done this now. How do we do it a million times? Like, how do I million times X this thing?” I'm always onto the next idea.” For me, that means, and not in a negative way, don't settle, but for me that means, don't get comfortable in what you're doing and keep thinking about what's next, what's next, and drive yourself there. That, for me, is this constant thing when I wake up in the morning, to say, “Okay, what am I going to do next?” And I'm excited for it. I don't know what I'm going to next, but I'm excited for it.
3) A human approach. Anytime someone asks me how you build a team, I say, foundationally, it must start with psychological safety, and that means that people feel comfortable to be able to make mistakes, have failure, whatever those cases may be. All of that stems from the fact that in business, it's very easy for you to objectively say to someone else like, “Oh, I can't stand them.” Or, “I don't like them.” Or, “They're doing X or Y,” and you can totally take the human out of them, and that's awful. From my perspective here, you have to realize this is a person in front of you. Someone loves them. They have children. They have parents. They have friends. People care about them. When they go to an interview, they go home and maybe their, their son or daughter says, you know, “Hey, how did the interview go?” They deeply want their parent to be successful. Or, the parent asks, “Well, how was your day?” And like, “I had to argue with this person.” It's a human. And so whether it’s selling, marketing, internally building things, I always remind myself, there's a human in front of you. Speak kindly, speak softly, speak in a way that is putting them first. That's a big one for me.
3 techniques that GTM teams
need to try?
1) Build adaptable foundations, not scalable solutions. I hear the term scalable, like, “Is this solution scalable?” It's coming from a good place, but I deeply believe that it's wrong because if you build something scalable for now, you are compromising what the best thing is for right now. And quite frankly, I think you're arrogant to the fact that you think you can predict the future in a level of detail. That means your solution you made today is going to suit yourself two years down the road. Instead, what I would then say, and I think is a better term, is adaptable foundations, which generally starts from the data. So thinking, “What is the best thing I can do right now? And how do I future proof it by meaning that I will need to change this? It's inevitable in a year, six months, two years, I will need to change my approach, but how do I engineer it now that when I do change that approach, it's built to be able to allow that to happen.” So in this case, one of the things I always say is footnotes kills funding. So in a company that's growing Seed, Series A, Series B, you report on something a certain way, and then you're like, “Oh, well, we had to change all this, and so we don't have year over year, but we're trying to…” No, that's messy. So, how do you, again, from a granular perspective on the foundation, create something that says, “We know this is going to change.” So think of it, but you don't know how it's going to change. So just do your best to predict that, but it starts from the data side of things. You need to spend more time and attention on that one.
2) Embrace the multi-armed bandit. This is where Arthur Castillo was mentioning about your ICP, and getting too focused on that. And so the term, the multi-armed bandit, it's a statistical model, and it's basically the balance between exploiting and exploring. The assumption is that if you continue to exploit something that you know, so, in essence, your ICP, you're just capitalizing off of what you know today. But the reality is, in the world and in business, your product is an adaptable piece of the market as it continues to change. And so if you don't spend time on exploring what that is, AKA speaking to people who, right now, are not a fit for your product, then you don't know what to build. You don't know what's coming down the line. Yeah, you don't want to put all your time in explorer because those deals are probably not going to close, but by having a healthy balance between that, the most profitable, most successful direction, is fluctuating back and forth from that because the explorer will mean that your exploitation down the road will be infinitely higher. Otherwise, if you just continue to exploit, your known world remains your known world. That's a really important one. And that's where you hear the term, “Build for where your clients are going. Not where they are today.”
3) Tension metrics. I've had some great people in my life also really focus on tension metrics. The assessment here is if you measure an individual thing at a point in time without taking into consideration, what came immediately before, and what comes after, what you're doing is you're only seeing one little picture of the story. So this is really common for sales saying, “Oh, our win rates are really high.” Okay, but are you losing things from the initial lead qualification stage? For example, are you being really super critical where you’re having waste, where you're saying, “No, I'm not going to work this deal.” But really, it could have been a great deal because you're obsessed about that win rate. Or maybe, you win rate is really low, but, “I'm just pushing things through the pipe.” But then, you have a huge churn rate. So it's like, “Okay, well, why is that? Are you overselling?” So the really important thing is a holistic picture of your entire go-to-market process, and for every thing that you measure, part of that measure should be what good looks like from the measure before and the measure after it, and it all comes into balance. If you're not doing that today, you should be doing that because that's so important for creating a healthy business overall.
3 questions that you
love to ask and why?
Questions are so important. I love that.
1) How do you define success 1 year, 5 years, and 10 years, for yourself? This is an interview question that I ask, but I also will ask people in general. I think it's a really good one. Some folks will say this is not a good question, but hear me out with this. So the first one is I generally say, How do you define success 1 year, 5 years, and 10 years, for yourself? There is no right answer to this question. You can be like, “I don't know. I haven't thought about it.” And what it tells me is you're living in the moment. You're not worried about that stuff. You're not worried about success for yourself. You're satisfied there. Some people come out with, “Ok, one year, I want to do this. I want to have a car. I want to have this. I want to have a house. I'm going to be married. Five years, 10 years, whatever.” I love to ask people that question because, A) if they say things and I know what matters to them, what's important to them, then we can continue to talk about that. But B), it's just interesting to see the perspective that folks have on short-term versus long-term and like, where are they looking right now? That's really important.
2) What motivates you? I think understanding on a level of what people are motivated by is the biggest driver of how to work best with them. When people are open and honest, and that comes from psychological safety, and they tell you what they're motivated by, then you can work in such a way that’s great with them.
3) What important truth do very few people agree with you on? A Peter Thiel question, which comes from Zero-to-one, which is my favorite book. For example, I answered that question with, from a RevOps perspective a lot of people say, “We're trying to break down silos.” I don't think so. I think silos are great. I think silos help build your craft, get people really good at what they do, but it's been the RevOps person's job when we actually ship and speak to our buyer and our customers, we don't ship those silos. We take all the best thinking and brainpower and processes out of those silos, and we put those together and create that holistic process that the customer's like, “Oh great. I'm speaking to this company.” But that's one of those examples where, if someone really thinks about like, “As an expert in my field, what do I know that other people won't agree with me on.” Tell me about that. I love that because it's such a window into someone who's put thought into something that's just taken as a given. I love that question.
3 operators that should be our
next guests and why?
1) Fahd Alhattab. He's the Founder of a Unicorn Labs. A good friend of mine. He's built this business, bootstrapping it himself. He got his start in motivational speaking and transitioned to leadership and leadership development from a corporate standpoint. He's absolutely brilliant, unbelievably engaging. I think his big focus is, is that if you had more Fahd in the world, if you had more Fahd involved with corporations and whatnot, then you’d have a hell of a lot better leaders out there. So from that perspective, but also from the perspective of like he's gone as a solo person, building a team, building a business, and really working well in his go-to-market strategy. It's a really impressive story.
2) David Andrews. This guy I think is the human embodiment of a machine learning. And I say that from the fact that, I don't care who you are, he will at out-work you. Absolutely brilliant account executive, unbelievably methodical about how he goes to market and how he sells, and does so with a smile on his face. So, if you want to think about how do you create discipline from an account executive perspective and how do you contribute to the overall business, not from a very intrinsic perspective, but someone who's like the definition of team player, you’ve got to speak to him.
3) PJ Goupil. He is a serial entrepreneur and founder of Agency Fox in Montreal, Canada. PJ really impresses me because he's a big thinker. A big, big vision kind of person. And he's disrupting the way that the real estate rental market is going by providing these like really interesting marketing, go-to-market experiences. What intrigues me from him is to as twofold is that I think you, you would see his company as like a marketing agency, but the reality is, is it's more like a think tank. They just approach problems with such unique and interesting perspectives. And the other side of it is that he is not a win-at-all-costs kind of person, but he's the kind of person that is willing to try just about anything. And so he's had many failures, many successes, and just a really interesting business perspective on how you go to market.
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Jameson Strategies and
May 2022 · Interview by Chris Morgan, Host of Market-to-Revenue
Market-to-Revenue Podcast ⚡️ Lightning-fast interviews with GTM operators in sales, success, product, and marketing.
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