🎨 Craig Handy: Shopify, Head of Revenue Automation, Tooling, & Enablement + Jameson Strategies, Founder

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 → Listen

What are 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.

What are 3 hard problems that you recently overcame?

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.

What are 3 roadblocks that you’re working on now?