Shopify Org Design and Why CROs Must Get Technical with Bobby Morrison

Hi, I'm Warren Zenna, founder and CEO of the CRO Collective and welcome to the CRO Spotlight Podcast. This show is focused exclusively on the success of Chief Revenue Officers. Each week we have an open, frank and freeform conversation with top experts in the revenue space about the CRO role and its critical impact on B2B businesses. This podcast is the place to be for CROs, sales and marketing leaders who aspire to become CROs and founders who are looking to appoint a CRO or want to support their CRO to succeed. Thanks for listening. Now let's go mix it up. Welcome to this episode of the CRO Spotlight Podcast. I'm Warren Zenna and welcome to the show. I'm really excited today. I've got Bobby Morrison, the Chief Revenue Officer of Shopify here and really excited to listen to all the amazing experience he has working at a company of that size and complexity. So welcome Bobby, and thanks for being here today.

Yeah, thanks for having me, Warren.

So as I was mentioning to you, right. The focus here is really how do Chief Revenue Officers survive today? Like, you know, the role has changed dramatically and I started this thing a while back. So I guess the first thing I'd ask you is, you know, when you look at your role as CRO at Shopify, like, how would you describe the scope of it? Like, what do you do on a day to day basis? Is it strategic, is it sales focused? How would you sort of describe the way you're, you're running the show there from a CRO?

Yeah, you know, first, first, in order to explain that, you have to understand that one, not all CRO roles are equal or the same.

That's for sure. Yep.

My, my time at Intuit was very different than my time at Shopify. And Shopify is very different than Microsoft in the way that we think about things. Maybe first context is, you know, at Shopify we have three main, main rules in the business. Priority number one is to make great products, build great products. Priority number two is to make money. And priority number three is to never reverse number one and number two. And it's important to have that context because the role of the CRO at Shopify is priority number two. So my remit across the business is across our marketing, our sales, customer success, post sales support, all the underlying operations that support those efforts, our pro serve, education, all of the other functions that sit, basically everything that's touching the customer sits in my remit. And, you know, understanding that our role is priority number two, not priority number one. We spend a lot of time making sure that we have deep interlock with our product teams, sharing the feedback we get from customers in the field. And my time is spent across the entirety of the customer journey. Sometimes I'm spending the majority of my time at the very front of that journey, helping to understand how we're connecting with different TAM opportunities in the market, how we're expanding that tam. Other times I'm spending it with our partners, not our direct teams, helping them build up their practices and acumen around our products and services and how they could fit into their existing go to market motions. And sometimes I'm spending with existing customers to get feedback on how are we doing and what could we do better. So it depends on the time of day, where we're at in the quarter. But I really try to make sure I'm living across all stages of our customer journey and then taking that feedback back and instrumenting behind the scenes with our Revops teams and our Rev Lab teams, which is like a dedicated AI function within the group to instrument our go to market to best serve those customers.

Good, that's very helpful. So your implementation of the role is consistent with what it is, in my view should be. And that's sort of like the objective I have here in my whole business is to make sure that that happens. But I'm fascinated by that because you too often I come across companies where that's not the case, where the CRO is running sales. So what's different about your organization? That they got it right and that you're running it a CRO role that way. What do you think it is that made you come to that decision?

You know, I'd like to give credit where credit's due. I. I actually had a conversation with Yamini, who's the CEO over at HubSpot. When she first came into HubSpot, one of the things that she did was she wanted to make sure that she didn't ship her org chart to the market. And I think the legacy traditional view of CROs is they're the sales team and then you have a marketing team and then you have a support team and everyone's part of their journey has hard handoffs. So for example, and generally marketing teams think their job is from lead creation to MQL wipe their hands. Now it's the sales team's job and the sales team thinks that their job doesn't start until MQL and they carry it down through the funnel. And one of the things that I felt very deeply about was that those customer journeys are Fluid all the way through. So my, my marketing team has hard objectives for closed one, not MQL's, which means they have to carry that business all the way through the pipeline. You know, we have the traditional, I'm generating enough demand, but field you're not closing it or field you're closing to, you're closing well, but we don't have enough demand. There's none of that. Those groups are aligned to the same outcome, which is the revenue objectives of the business. And they have to do it within a guardrail based profitability that we set out at the beginning of the year and we're constantly playing with that. So I think, I think I give Yamini credit for the inspiration. And when I came to Shopify, it was one of the things I was, I was happy at Intuit. Things were going well. Great, great team. That team continues to do very well. But when Shopify said, hey, look, we're willing to put together all the pieces into one remit so you can orchestrate across the entire customer journey from beginning all the way through referral and post sale, that was intriguing to me. So that's one of the reasons I came.

Gotcha. That's great. Because that's the model. I think it's happening more. I'm seeing more of a shift. Started this conversation myself around 2019 to take the CRO role and, you know, maybe expand it to where it should be. And you're. What you said is precisely what I'm trying to do is make sure that the role, that the organization is less fragmented and bring more alignment across all these things. Right. And it's not just, you know, handoffs, it's also data and process and KPIs. Right. Everything. So how did you set that up? Like when you. Was it already done that way when you got there or did you have to kind of create those things? And if so, I'd love to hear more about how you did it.

I'm sure if only they were here when I got here.

Here.

Yeah, no, we were, we were in build mode. I, I have a great team of people that came along my side and that was part of some of the first moves where we needed. We lack some operating discipline, go to market discipline, just some basics, fiscal discipline. Jeff Hofmeister, who came in around the same time I did, he's our cfo and I sat down together and said, hey, look, let's put together some basic constructs, guardrails that we can operate the business within. Let's make sure we have the Right incentive structures in place, the right segmentation in place, most of that was loosely there at best. And then some underlying operating principles that we thought would actually help us drive the business forward. And we brought in some leaders that knew what great look like but needed to pattern match it for the uniqueness that is Shopify. So we spent a lot of time rebuilding a lot of the back end. A lot of times I think organizations look at Revops for example and will think of compensation systems as an independent thing. I actually think about them more in flywheels and I think when you structure them the right way, they become anti fragile. So yes, compensation systems are one component, but your performance management needs to be aligned with that as well. And then your reward systems, your incentives around whether it's trips or whatever else you may do, need to be tied in. So technically all three are working together, not one as three separate independent things, just one each one. So we spent a lot of time on what are those flywheels, which ones do we need to instrument first and how do we set them up structurally so that they don't become rules based. I think that's the traditional approach that I've seen in the business is and when you start to apply rules you lose speed and agility and that that Shopify had in spades. So how do you balance founder mode, super fast, super aggressive, super agile with operating maturity? And so it's the reason we moved away from this notion of hard sets of operating capabilities or cadences and more of a connective input output, flywheel orientation. It's allowed us to stay agile and still provide structure to our go to market. And that's. And you know, I think the other thing is I had shared this with the board. You know, I think most companies start with do you have the right people in the right places doing the right thing? You know, if in the hierarchy if you could draw a triangle, you have people, operations and then systems on the bottom and everyone starts at the top. We actually I flipped that I started first with systems because I really do believe deeply that the systems that you deploy will become the creature of habit that you ultimately build in your operations and in your people. If you start with people and work the other way, you're going to clash with your systems at the end of the day. So we spent a lot of time at the systems layer developing the right systems so that first you shape your tools, then your tools shape you. If you shape the tools the right way, you can get the archetype of the organization you want as A result. So that's, that's where I spent my time and focused in the beginning. And we worked our way up the stack.

How long was that before you got that together?

You know, probably the first six months we started to get the systems in place. Took three months to understand what was going on, what was working, what wasn't working. We started off with incentives. I think that's the single biggest lever you have. I believe in extreme accountability and extreme reward. We have an uncapped compensation system that's rare in this world. We have a regression multiplier schedule. You overachieve, everything multiplies back to the very first deal. So the next deal up that you close is worth exponentially more than the last deal that you close. But there's also an aggressive decelerator. If you miss a certain number, there's a deceleration. And we hooked our performance management plans to that. So that was, that was like the first flywheel system that we put in place was incentive structures and accountability. Segmentation went along with that. We were missing segmentation, proper segmentation. So we, we worked through that and then over time we built on top of that. We did a lot with our data. I still think we're in that process now. You know, we can maybe get into AI a little bit later, but a lot with our partner channels, part of our distribution was almost exclusively direct. Our partner ecosystem was a referring ecosystem, not a co selling ecosystem. So we had a lot of work to do to convince the partner world that we were enterprise worthy and that they could build a practice on us. And there's a long story around that. So we started first with systems, shifted a little bit to channel. That was probably another 6 to 12 months around channel and then dynamically just updating systems as we go.

Hey everybody. First I want to thank you all for listening. It's really important to me that you know how appreciative I am of the people who tell me they can't wait for the next episode. It's really remarkable. Actually started doing this just on a whim. But I also wanted to share a little bit. You know, if you're an aspiring CRO, if you're a head of sales, if you're ahead of marketing, maybe you're head of Rev Ops and you're listening to the show because you're interested in being a CRO, you should really consider the idea of taking a look at our CRO Accelerator program. The CRO Accelerator program is a executive development program designed specifically to help revenue leaders become chief revenue officers. In fact, the CRO Collective was the first company to create a CRO education program. I'm very proud to say that, you know, we sort of saw early on, six years ago or so, that the role was completely unsupported. Very few people really can define it, and as a result, the role is being misused and misappointed across all organizations. And the CRO Accelerator program was designed specifically to fix one side of the equation, which is to deploy people into the marketplace that were really competent about what the CRO role is, what CROs actually do, and the right way for them to start winning in the role from day one. So if you're a head of sales, you're a head of marketing, you're a head of rev ops, you're a revenue leader that runs a team, and you feel like a CRO role is next for you, but you sort of feel qualified or you want to put your best foot forward, or most importantly, you want to gain the confidence of what it means to be able to go face to face with people who maybe have had the title before and still get the job. But most importantly, not just get the job, but succeed in it. We give you the tools, the frameworks, a program specifically designed for incoming Chief Revenue officers to win and know exactly how to handle all the trepidations that come with this role. This is a very complicated role, and the first 90 to 150 or whatever days are critically important to succeed in. Matter of fact, that's where CROs win is. That first pre acceptance letter during the interview process and after you get the job. So if you're looking to ensure that you succeed in the role and learn more about the role and frankly, walk out of the course, in some cases being the smartest person in the room about this role, consider taking the CRO Accelerator course. It's easy to find. You can just go to our website, the CRO Collective.com that's the CRO Collective.com and look under the course page and you'll see the brochure has all the information and then you can apply. I get all the applications myself. I vet each person and I'd love to hear from you, so check it out. Thanks. So that's interesting because, you know, that's a lot of time and it's the. It's the appropriate amount of time to do what you're saying. But was that all you were doing was building systems or were you doing other ways to sort of, let's say, justify your compensation while you're doing Those things like how did you get the latitude to do the strategic work while money need to be made? But how'd you.

Yeah, yeah, yeah, yeah. You know, segmentation and incentives do a lot to motivate behavior tactically very early on. So I mean our growth rates in bookings, I want to say in 2023, we're north of like 60% year on year. Growth rates in 24, over 23 were also around 60%. So like when, when that started to flow and you saw a shift in the revenue streams and bookings and then also in build revenue like that that earns trust. We talk a lot about the trust battery inside of Shopify and you come in with a trust battery and autonomy. I remember the conversation I had with to, you have a sledgehammer and you can knock down any wall you want. Just know some may be load bearing but go break things. And it's just, it's an amazing empowerment and like a great feeling as a senior leader, a CRO or otherwise. When you know you have the remit for change and when you have that remit and you walk in the door with that level of autonomy, that's just a wonderful thing. It's, it's all the things you've always wanted to do but haven't had the ability to do in the past. At Shopify, you know, the role is a builder role, it's not an operator role, it's a builder role. And so we spend a lot of time on building and you know, if you have the right incentives in place, you start to then stack on top of that. People who know what great looks like and can pattern match in a Shopify unorthodox way. And you know, momentum begets momentum. And so then we've just been building on that momentum over the last three years. It's been pretty fun to see.

Yeah. So you were able to take the machine, make it more efficient and pull more money out of it early enough to get the kind of latitude you needed to continue to do those things and satisfied whatever other needs, financial needs that the company had. So my question then would be, you know, you're in a unique situation at that company because of its size, so you've got a rather large, you know, exponential group of people whom that lever would result in a lot of resulting income because of that, you know, that, that, that size. If you're starting out as a CRO at like a 30 or $40 million business, you don't have a salesforce. That one incentive is going to flip things enough so you know, remember, the people listening to this in many cases aren't going to be getting a job like yours, right. They're going to get a job at like a 50 or 60 million dollar business as a CRO and they're going to be asked to do two things. One is come in and like you said, you know, be Bobby Morrison and give us a system and a machine that works. But at the same time you got to make us some money and you got to do it quick because I got a lot of people worried about the fact I just paid you 750 grand and they're worried if it's your worth or not. So make me that money. Prove yourself. The problem they have is they make that money and they're like, you know what, keep making that money, that's pretty good. And then you never get to strategy because you're too busy making money for the company. How do you suggest someone that doesn't have the sort of resource and size and scope of the business do both at the same time when they're trying to actually do what you're suggesting, but also have short term goals they have to hit at the same time?

Yeah, I sit on a few boards of firms that are in the size you're talking 100 to 500 million in revenue and they're trying to seek it out. I try to keep things super simple. I think about a simple math equation of rate times volume divided by friction. And so the friction side is the system side. Right. If I have a business that has high friction, my number one thing is to defriction that business. And that's where the systems and tools come in. If I, if I don't have a lot of that friction because maybe I'm smaller, I'm looking at the rate and the volume side. Do I have strong volume and I need to move up market and increase average deal size? Do I have good deal size but I don't have enough reach? Volume isn't where it needs to be. So I break those problems down into those three sections and then by the way, the end if we put all of that into an equation, then I multiply the output of those things times leadership because I do think leadership matters key in that equation. Like you can't, you can't exclude, it's my career over the last 30 years. I will tell you, I, I. So I sometimes still get surprised and every time I do it's a reminder of this lesson that a strong leader will always outperform and deliver higher results than an Average leader. And I know that sounds like, of course that's true, but when you, when you replace someone who's been complaining about the inability to do A, B, C or D with a strong leader, that has just a slightly different perspective on the market, all of a sudden that exact same team outperforms. And so leadership matters in this equation. But if I, but if I was looking at a scenario where, hey, I've got decent direct go to market, but as I think about all of my tools at my disposal, I don't really have a strong channel, the first thing I'm gonna go do is go get channel activated so that it can come alongside. If I don't have any of the above, the very best place for me to spend my time is in front of my customers. Like, make no mistake, you wanna move the needle quickly. Go all the way to the front line, pick off your 10 biggest deals, make sure you're in the room, you're doing a quality assessment of the client engagement, whether it's you or a partner, and you're, you're exerting your influence into those deal cycles to get wins on the board quickly.

Great. I love it. So now I wanted to understand the way you got things set up there. So I'm assuming from the way that you describe things that you've got someone from marketing reporting to you, someone from sales reporting to you, some of the customer success reporting to you, et cetera, et cetera. How is that correct? That you have sort of like people that ladder up to you and then you ladder up to the CEO?

Is that essentially how it's functional in. At a level? So my enterprise leader, Josh Rice, leads across enterprise globally. Underneath of him he has the customer success, the sales, the solution engineering function, all in one group.

Gotcha.

Professional services is a dedicated line. North America outside of enterprise is a dedicated line. Europe and apac, dedicated Rev Ops, dedicated Rev Labs, kind of a dotted line scenario. But for the most part that's. You're, you're right. It's a series of roles. Some geographic, some segment, some function. But all functions exist. Just depends on what, at what altitude. And I did that on purpose, by the way. I really wanted to. You always have this debate. I saw this actually at Microsoft quite a bit. And they've since changed by the way. If you have a craft owner of call it the solution engineering team and that functionally reports all the way up to the CRO as a single organization, then you have this orchestration tax on the business between the sales function and this Solution, engineering, function. And in reality they're in the same room together with the customer. So I really pushed the opposite direction and it was informed by a past experience. I'll share it briefly with you. At Microsoft, they had a product called Workplace Analytics. I love it. It's now called Viva. I would tell you to any of your Microsoft shops, if you have Viva in house, you should be using it. The insights you will get are amazing. And one of the insights was that you could see kind of where people were spending their time. And we found that more than 88 different contacts were required internally at Shopify or at, at Microsoft to actually go to market in any given quarter for an account executive. And that was this ticketing system of, hey, I got a deal, I need to go pull in this expert or that expert. And I worked closely together with my team and we said there's got to be a better way. So we created pods that bring those resources together structurally and the incentives are 100% aligned so that the AE and SE manage the same exact territory at the territory level. And so I pushed the SE organization very close to the front line. We still manage it at a craft or what we call group or discipline level broadly across the company. But structurally we felt like the best place for these, these different roles to interact is at the moment of truth, of where they touch the customer. So same same thing for my enterprise team. My customer success solution engineer and account executives have the same book of business that they are responsible for with the same performance outcomes. They just have different primary, secondary and tertiary roles across that podcast. And so they're all working together in concert to deliver value for those customers that are already with us and then creatively find ways to tap into those customers that are in that book that are not yet with us. And it makes the business fast and it eliminates a lot of the finger pointing my organization's doing. Well, what's going on on your side? I really believe a lot of the friction in that calculation I just gave you comes from org design and incentives. So again, it's another reason why we focused on unifying those incentives at the most granular level.

Yeah, but we're aligned on everything here. So, you know, the big thing I'm trying to help solve for my clients is what you're you did is amazing, is, you know, the problem with the organization is people. You know, when you have people that have all have C suite titles, you created a problem for yourself that people don't really recognize until down the road because as you already Know, you have revenue misalignment where you have a bunch of different objectives and you know, all sorts of motivations happening at the sea level that make it impossible for anything to happen without that friction. And if you remove that friction and you put the CRO at the seat of the orchestration, it makes it a lot easier to build the system because now you've made everybody on the same boat. They all carry the same oar, they're all rowing the same water. And you know, I think it just seems like so logical what you're saying and you know, this is what I'm talking about every day. But it's amazing like how many companies are still sort of the muscle memory they have to get off. That sort of C suite architecture is incredible to me and it's just so much more efficient to run it the way we're referring to. I think the problem I see, and I'm curious to what you think about this is the marketing part seems to be something that's a challenge because a lot of my clients, they could become a Chief Revenue Officer, but there's already a cmo. And that CMO sort of has like, as you already said before, you articulated earlier like this whole problem with the KPIs around, you know, MQLs, et cetera. And when you try and shift that, you're threatening that, that marketing leader's existence because they've been, you know, they, they kept their job based on those MQL KPI's. Right now all of a sudden they're being rolled into somebody else's and that sort of cooperative environment put is a big threat to that person's survival. And the friction is many times the CEOs like, you know what, I'm just going to leave this one alone. I don't want to get in the middle of these two. You guys work it out and they work it out by just having nice meetings. But the KPIs are still not really aligned.

Yeah.

And so it's, it's amazing that, that, that making that change is tough. And I'd be. Your thoughts are, let's say, you know, before you got to Shopify and there was maybe a little bit more of that bifurcation there, what would a founder do to switch things up and become more of a systems builder as opposed to like maybe more of a, a fractional builder when they're doing that sort of thing.

Yeah, I, I still, I still think it, this is going to sound like I'm being repetitive and I hope, hopefully I'm answering the question. I, I think about these types of things more in terms of principles than I do or design or funct. And it's a lesson I've learned a lot from Toby Here at Shopify we don't debate metrics, we don't have an uber success criteria. We debate principles. And so what's the principle? The principle is you have customers who are not yet with you, you have customers who are in the process of considering you and you have customers who have said yes to you that you need to make wildly successful. And if you think about your responsibilities that are required to help customers through that decision process, yes, we call this thing where customers haven't yet made that decision marketing. But remove the name just for a second. I need someone who wakes up every day speaking to an audience in a way that resonates with them about a set of value added services and capabilities that they are likely lacking today that we think we could provide as a benefit and help them accelerate and grow their business or transform their cost or whatever it may be. Remove the name marketing. My goal is to one talk to that audience, elicit a response and then help educate them along the way until I can get them in front of somebody who can have a one to one conversation with them that continues to help educate them and we identify if there's a there there for them to move forward. We don't have a CMO at Shopify to be very clear. We have VPs across the business that have very specific functions brand. We have a growth group that focuses exclusively in payback guardrails. We have programmatic pipeline generating pipeline teams. Like we've broken it out into different, different role responsibilities a very untraditional way. But it's because we don't think about marketing as a dedicated craft. We think about it as a series of customer engagements that that someone is responsible for in developing and nurturing that journey. I know that sounds a little bit weird, but it's not weird at all.

It's exactly what I agree with you. And in fact I don't think marketing's job is to get sales leads. I think marketing's job, if you want to call it that, if you want to say marketing is a thing like you said, it's just to get people smarter about something and curious about something.

That they want to have a conversation.

With you about something curious.

And curiosity has different stages of curiosity. We call them lead scoring, but it's just a different stage of curiosity and interest. And once interest reaches a particular stage, my job is to make sure that I get you handed off to someplace else that can help you nurture that interest until that interest becomes a commitment. And then once that commitment happens, then my job is to nurture you forward so that you realize the benefits that you had thought that you were going to get in the first place and then you tell other people about it so that we can help others begin that journey. I think sometimes we have our labels that we put into our go to market are not overly helpful because again, they tend to speak to org design and less about the customer. And at the end of the day, if you just pivot, I think for founders, if you pivot your thinking to just that customer journey end to end and not necessarily the org design that maybe you see in a blueprint someplace, I think you'll end up in a better spot.

100% agreed. So I love it. So I wanted to switch gears a bit, talk a bit about revenue operations. You mentioned it before. You know, I wouldn't say it's a new thing, but it's a newer thing. Right. And it's evolving, you know, it's becoming a really massive part. So you mentioned Rev Ops and also uses Rev Labs. Rev. Right. So I'm just curious, like how does that function work in your organization? How did you structure it and what does it do and how does it sort of spread itself across the way that you map that customer journey? Revops. I'm curious to know your thoughts on how you've constructed that and how the.

Way you manage it revops lives from using the nomenclature we just said we shouldn't use lives from marketing all the way through support.

Gotcha.

And so that common layer of instrumentation, they manage the compensation programs, the systems, the tools, the reconciliation, the audit and control of compensation. They, they lead the segmentation strategy, go to market, they do the sales play orientation and design. So as you define certain plays, you want to run in a market and map it to a set of customers and then pair it with a set of partners, they. They do a lot of that back end orchestration. There's obviously a reporting function, I think that's very traditional in that space. There's a series of others that kind of ladder up. We have a systems and tools group that wakes up every single day thinking about how seismic sales loft and salesforce all interoperate and feed each other. What are the unique insights that come out of that that maybe guide us as we go forward. But I do think this is one of those roles, one of those functions I should Say that is going to go through a pretty radical transformation right now, I would tell you. And, and we haven't gotten to the AI topic, but I'll just share it.

We'll get there. We will. Yeah, it comes up.

But like this is, this is one of those places where AI, AI is absolutely going to be an exoskeleton around this part of the business. I even think, for example about our systems and tools. Go back to first principles again. What is a CRM? A CRM is a database that has a set of rules that sit on top of it that help you gauge where you are with a particular customer at a particular point in time and a repository of the interactions with that customer. Those interactions are traditionally an earlier in career, generally speaking, doesn't have to be, but generally speaking, earlier in career, individual who is having conversations with the customer, interpreting those conversations, summarizing it and dropping it into a note. And we all know, you know, most CRMs are garbage in, garbage out, but let's just say directionally that goes in. So then what's the system that wraps around that. The system that wraps around that is then a manager sits with that account executive that AE once a week, once every two weeks, whatever it is, and they reconcile that pipeline. Tell me about this account. Where are we at? It should all be in Salesforce, but it's not. So then I have to have a dialogue around it. Then I do this tap dance thing that says okay, now based on all that conversation and what I've seen in the past, let's go to do this forecasting part of the business that I mentioned, that product at Microsoft Viva. 11% of the time people were spending forecasting like what are you doing? Management team spending 11% of your time forecasting. It's not. So now fast forward, we're in an AI first world. If I have the call transcripts, which I like to think of the interactions like the one we're having right now, those transcripts are the new source code for AI. They are with the correct prompt engineering, the ability to query and assess quality of engagement. Objection. Handling technical brief and design. All of that can be derived from the actual transcripts themselves. So now I don't as a manager have to which typically sees less than 1% maybe of all the customer interactions. Now I can get 100% of the customer interactions reasoned over in real time with probability of close derived directly off of that. Like there is a world and we're working towards this. I would tell you in six to nine months, Warren, I won't have a traditional CRM. It'll be all AI enabled.

It'll be like almost a cloud based set of data that you query and.

It just gives you that, that I query has a bot that sits on top of it. Maybe a, maybe a front end UI for traditional kind of reporting requirements. But, but now, but now as a, as a leader, I have all the information I need at my fingertips.

Yep.

I have all the coaching requirements that I need for that individual to grow in their craft. Not pipeline, manage them, but developing the skill that's required that, you know, improves the pipeline and overall performance. The jobs all change and at the forefront of that is revenue operations, is building out that infrastructure, that's making sure we have the right listening post and solving for. Yes, it works great when you and I are on teams or Zoom or one of whatever my core platform is. But what happens when I'm not on that core platform? What happens when I'm face to face in meetings? How do I, how do I, when some are in a room and some are outside of a room, how do I associate who is speaking in a group of nine people in a room that has a single designation and mic going into the conference? So like Revop's job is changing from being reporting analytics, pipeline segmentation, forecasting, compensation to building this new way of going to market. And that's, that's a pretty big shift for them. But I will tell you, it's very energizing.

Thanks again for listening to the CRO Spotlight Podcast. We're excited about all the great guests we have and more importantly, we're excited mostly about you for being avid listeners and supporting the work that we do here. Feel free please to share the CRO Spotlight Podcast with any of your colleagues. We just think there's a great wealth of information here and we want to get the word out to as many people as possible. And your support of the show is really appreciated. I wanted to share information about a program that we offer called the CRO Masters Council. The CRO Masters Council is a bi monthly group of six seasoned Chief Revenue Officers who are looking for a Chief Revenue Officer Board of Directors, so to speak, that they could share what's going on with them, collaborate with ideas, get some feedback on what's going on in their current role. And these are great conversations. I facilitate them. The CRO Masters Councils, again, they're twice a month and they last for at least six months to a year. So if you're interested in having your own CRO suite, your own Board of Directors of Chief Revenue Officers. It's a private, confidential conversation that we have. It's infinitely useful. Imagine having a room full of other Chief Revenue Officers you can talk to and say, hey, I'm working on this. Or have you guys figured that out? Or, I'm having this issue right now with my business or my results. These are just invaluable conversations with Chief Revenue Officers. Chief Revenue Officers have a very, very unique role. It's a very lonely job, and only other CROs understand what you're going through. So that's why we created this program. So if you're interested in being a member of the next CRO Master's Council, which we have a number of them being put together right now, just go to my LinkedIn and DM me masters or masters Council, and I'll follow up with you and set up a call or send you some more information about it. Looking forward to seeing you there and thank you. It's amazing. I mean, it is. I'm working with a lot of people on all the things you're talking about in various ways, and I'm amazed at what's happening, how quickly it's happening. And yes, I do agree. I think RevOps is going to be at the forefront of these things. And the RevOps competency is changing because of it. People have to be different types of people, understand different types of tools.

Yeah. We've made it a requirement in my org for both market marketing and if you've heard people like Kasna Jashin say this online, I was, I took it as a term of endearment. He's our. One of our. Our C suite. He's a CEO, COO at Shopify. He said, we have the nerdiest salespeople on the planet. And I'm so proud. And I love that because, you know, we just, we just finished hack days and we had, I think over 800 people with cursor downloaded for the first time using it, and another four or five hundred of them using Gumloop, which is a mcp. And we have other MCP servers in house. Everyone was vibe coding, so our ops team and our marketing team must be able to write SQL, must be able to use. Must have cursor and some MCP that is part of their overall core responsibilities. It's almost like proficient in office back in the late 90s. You know what I mean? Like office proficient.

I agree, I agree that that is.

The role of the future is you have to be. You have to be AI native and AI first in your thinking or you're just going to get left behind.

Yep, totally. So what does that mean for the CRO then? You know your role. Are you. I mean, I don't think so. I think that CROs, because you, you said it before earlier in this conversation, which I completely agree with you, that the leadership part of the equation is, it's just, it's, it's, it's, it's on, it's unmatched. You know, you need people to do these sort of things unless we just all become a bunch of robots, but we're not. And so I think the CRO, the leadership competencies of the CRO are going to become some of the more vital competencies because of the requirements they have. And if you have good ones, it's going to be easier for those to be seen. But how technical do you think CROs need to be to do their jobs similar to RevOps? I mean, do you have to be a nerd to be a CRO or can you be a leader, systems builder CRO and rely on other people to run without being threatened that your job is going to be taken away?

I think you, I think you're going to have to start to become a nerd.

Warren.

I really do believe that systems thinker, systems design, great salesperson, all of those are good. But if there isn't a deep embracement of technology and a curiosity about like the CRM conversation, if you're not thinking that way, you're running the exact same playbook, the exact same systems and tools as everybody else. And the way you get a competitive edge is you have deep domain expertise that is different than those that are in the market and you want to apply it uniquely in your circumstance that you think gives you a competitive. That's what we're doing at Shopify. We are building tools. We are builders, not operators. We are building tools that help us show up differently than another company that has to follow the same rigor structure, third party software that helps governor drive their business. Whether that's from the Martech stack, the lifecycle management, Lifecycle management is going to be all one to one AI enabled. But let me back out. I do think there's a place for deep domain expertise commercially. One of our board members, Kevin Scott, said this in a podcast and I hope I get it right. Something along the lines of like the, the, the role of the pm, a product manager is going to be very different in the future. And at the end of the day it's the deep domain expertise that you bring to the table that is uniquely valuable. And so commercially, if I think about that, what do we do uniquely? Well, what's. I always used to say I would dream about this. I've said it for 30 years and I'm finally thinking I might be able to see it before the clock runs out on me. My dream is this, that our teams never have to have five separate screens open, fill in 13 different documents, update, forecast five times and have meetings all day long. Internally, I dream that all I do is go have great conversations with customers. That's all I want to do. And we've never really had the software to do that. We've had increments of it that helped us get better in our productivity. I think AI unlocks that and actually makes it a legitimate reality. But the CRO leader needs to be capable enough to add a minimum Vibe code. Teach yourself Python. I'm going through Python. You have to be able to write your own SQL just to be able to have the fundamentals of how data is structured and how it works. Like you have to be able to do basic Vibe coding and MCP connection and a little bit of QA work and just know that AI is going to get better over and over time. So your dependency on your knowledge to make that output exactly what you want will become less and less. But I think it's a bias in your mindset that says, look, the world is changing. The technical commercial leaders are the ones that are going to win versus those that are not. And start doing the investments. Take the time on the weekends, go watch a handful of podcasts, get your hands dirty doing the things that you have asked others to do for you, your data science team, so that you can be more, not only self sufficient, but now you can exert your domain expertise into the systems that are being built to help your team go in. And if you're not technical enough to understand data structures, if you're not technical enough to understand which MCPs are the right MCPs to use, which AI engines are the right AI engines for, for different tasks across your business, then you're going to use a wrench when you should be using a hammer and you're going to get a very different outcome. And so I believe deeply that AI should be democratized and put into every person's hand. It doesn't live just within the ML data science and engineering orgs. And you saw that actually in Toby's post, that very bottom we got in priority number two, made it in as a blurb hashtag revai use cases is the most active channel we have in Slack in all of Shopify. And I was just, just saw something Jamie Dimon was talking about where I think JP Morgan Chase had like 600 new point task solutions that they had built inside. I think we have more than 700 just in the revenue organization inside Shopify so that you. I think the future of commercial is an AI. I don't want to use Copilot because it gets overused, but an exoskeleton that is built both at the frontline and institutionally across the business that help our teams go to market and win. So yes, I do believe you have to be more technical.

Got it. I tend to agree. I'm playing around with everything right now too. And it's like I'm a kid in a toy box right now. So let's talk about like some of the different tools and technologies that you currently use to, you know, accelerate your business. What are some of the various tools and let's say technical or even AI products that you're finding you're are useful to you and how are they being employed? Because like there's so many out there, it's crazy. Like just how many services are coming into the market and what, what you like and what you find you're using a lot.

I'll start, I'll start on the AI side. MCP Gumloop. I love it. There's nothing like being able to easily stitch together workflows.

So most people are zapier type thing.

In a way it's like Zapier N8N like very, very similar. But what you're doing is most teams and this is what we found when we democratized the ability to go start vibe coding with some of these things is your teams will when empowered. And that's a big choice by the way. Most organizations don't do it this way. But I felt pretty having seen this pattern before with mobile and 2G, 3G, 4G. Like the people that win are the ones that tinker early. Feels like you're playing with the new technology but then play comes to like an aha moment and then there's real use case that's born out of it. And I've seen it over and over and over again in my career. And so that's what we started. We want people to tinker and play, but what gets produced are point solutions. I'm automating a task. Maybe it's a. I want to write a technical brief for a launch case for a particular client and I'm going To build an agent that does that. Well, for me it's a point solution. It's really just an LLM. It's not even an agent, it's an LLM that's building that for me. Great. But then I still have to give IT inputs to do that and I have to take the outputs and I have to go do something with that and I have to do it for each customer. What if it did it automatically for each customer? Linked to my Outlook calendar four days in advance of the meeting and the inputs were automatically ingested from the right sources and the output was logged into Salesforce as a dedicated artifact that now I have it in my CRM and it's already produced for me so that when I walk in it's already done. Like that's what MCPS have done, is allowed to take various point solutions and pull them together and I think it then changes how work happens. So like that would be a set of tools that MCPS really helped. We use every AI engine you can think of. We use 4O 3O 3 Pro on the anthropic side. Opus, I think it's 4O Opus was 3.7 Sonnet. 4O Opus is really, really good. And you know, we have taken an approach that the goal is to use whatever the latest and greatest, most powerful AI tool is. Some organizations have bias to the most cost effective. So you'll be operating on maybe a legacy version. If you're still running GPT3 because you're trying to manage your token cost, I will tell you, you're a penny wise and a pound foolish. Like you're way off, you're way off on what needs to happen. You should be biasing towards the high end. In traditional SaaS we spend a lot of time getting from 53 systems down to about 7 to 8. So we're a full Google shop in house. We run Seismic Salesloft, Salesforce as kind of my three cores. They write in and out of each other. I don't use Seismic as a learning enablement tool. I use it as my orchestration layer. And each one of those are being revisited to say what's the value that they have in kind of an AI first first principles world. And so some of them will, will be retained, others, you know, I think you'll see a sunset over time. But those are, those are the key key systems. And then we have a bunch of third party data that we bring in to help us be more knowledgeable about each one of our clients so that we're talking to Them in a way that matters uniquely to them, including not just the industry and what we know about their business, but their tech stack that they're running. We can see a lot of that. So we know what ERP you have in place, we know what CDP you have in place, we know what your Martech stack looks like. And that helps inform both the partners that we will go to market with to talk to you, because we want to bring in domain experts with your archetype as well as our value prop. So that level of specificity and that investment is actually pretty substantial for us.

How about like data cleaning and data enriching and data management and all the stuff that goes with that?

Yeah. So we have a core data set, zoom info, just like everybody else we enrich with like in Lyft does some really good work on the data estate. I used them at Microsoft when I was there as well. Use them at Intuit, have used them here. There's a bunch of others that are out there. The further you go east, the more specialized your data needs to be. I believe deeply also in the enrichment from your team. So you're having conversations with customers, you're getting intel. Either your SDRs or your AES are making direct engagement. They need to be able to refresh. And I will tell you, it's one of the most often missed data enrichment efforts that I see across my peers in the industry is not tapping in to those organic conversations that are happening and using that to enrich your data. They typically blow by it, especially if you're running it in the third party like a sales loft. And it never ends up in Salesforce, nor does it end up in your data enrichment. So we've built a feedback loop there that has really helped us go fast. I had a conversation with the. Well, I probably, now that I think about it, I probably shouldn't say who it was, but it was. It was fascinating how they use their gig economy drivers to enrich their data whenever they show up at a place that they hadn't been before, which I thought was fascinating. It's like, wow. So, not. Not elegant, but super effective.

Hmm. Amazing. So this is great. I really appreciate all this. This is so insightful. What do you think is gonna happen with the sdr? Are they gonna stick around or is it gonna be a roll?

I think they are. Look, I know people. I am, I am a minority in this point of view. I know a lot of people think the SDR function is going to be automated. I don't think that's the Case. I think the best place for AI to go work in the pre sale is all of those clients who didn't score high enough in their intent to get to an SDR to have a conversation. I personally think the SDR role is super valuable in the conversations we have with our customers. I think it's the first place where they get to talk to a human in your business. And make no mistake, human interaction will always matter. Human interaction will come with trust building. I think it's a part of trust earning trust, especially in the pre sale process. And look, who knows what the future is going to look like. But you know, I have these conversations with my wife all the time. Is what I'm looking at an AI thing or did a human actually create? I think you're going to see that in music, you're going to see it in other entertainment venues, you're going to see it in your, in your emails. Like, is this a today? It's pretty easy, you know, when you're getting hit with a bot or a form letter. Sometimes I even get ones for SDRs that are listening. Please do not send me stuff that says that you forget to put in, fill in name. And it just says name on the form letter. Like just stop.

It's amazing.

Amazing videos. Videos, fine, if you want to use AI to help around the edges. But one to one conversations still matter and I think they're going to matter quite a bit in the future as well. So what we're doing is we're building, we're building tools to help our SDRs take the administrative parts of their job off the plate so they can just have more of the conversations like you and I are having right now.

Yep. And then also like outbound, you know how messed up that is right now and how that's changing. And I'm fascinated to see where that goes because, you know, customers have been completely changed in the way they want to buy things, the way they're responding to this stuff. And that's a big problem I'm seeing my clients are having is just how do they get attention from people that are kind of overstimulated with crap like.

You just said, by the way, I think it's, I think it's surprise and delight. One of, one of the best tactics. I'll tell you what, I always think about myself as customer number one. Like what would I answer when I get pinged on LinkedIn? Please don't. Hopefully your audience doesn't start just barraging me with the exact same tactic when you shoot A video. You're like, hey Bobby, I watched this podcast with you and Warren. I really enjoyed it. This isn't an LLM by the way. I literally watched it. I like the thing you had in the background. And by the way, there were three things you said that I thought were fascinating. I think they're similar to what we're seeing and there may be a light connection there. If you have five minutes, I'd love just to grab time and if you're not the right person, please let me know. My name. Hi, my name is so and so. I've even seen people show up at offices dropping off donuts, videoing them walking in to drop off donuts. Hey, I was at your Shopify location in Toronto and I dropped off these donuts at the front desk. I just wanted to let you know, like genuinely appreciate what you guys do and would love to spend just a few moments. I know you probably don't have a lot of time, but would love to talk to you just for a few moments to see if there's a.

There.

There's like that. That is how you connect with people. It's doing things that are unexpected and not just email spamming across the board. I think that type of one to one communication is dying.

Yeah, it goes to show someone took an extra thought, extra effort and made it special. Sometimes what I do in LinkedIn is instead of commenting, I make a loom and I put the loom link in the comment because I have so much I got to say about this particular post. And you know, it really, it's just a way to, like you said, be a little bit more intentional about the way I want to respond to something. I think video is huge, personal videos. Anyway, I know we're zipping up near the end of time here, but I really appreciate you being here. So what, what's next? Like what's going on with Shopify right now? What are some things that maybe you want people to know about or things you're working on and because we're all customers of yours at the end of the day in some way or in some shape or form, what's happening in your world that is exciting and is coming up?

Yeah, I mean we're just really passionate about helping our customers win. You know, this is a really important time. I think in our, in our. But it's not an unfamiliar time. You know, we've seen uncertainty in macroeconomic and geopolitical scenarios multiple times. 98, 2008, 2020, 2025. And so we feel like our Responsibility is to come alongside our customers and make sure they have the tools required for them to be able to win in these uncertain times. And so far since we've been public, I think Harley talked about this on an earnings call. I think it was 38 out of 39 quarters of cohorts since we went public of customers on Shopify have outperformed the market. And so whether it's good times or bad times, we'd like to think of our platform as being anti fragile and fairly easy to deploy, operate, scale and then when required, make changes. And just what we're hearing a lot from customers these days are these shifts. Even tariffs alone have dropped an unexpected shipping date into their, into their calendar and they're realizing just how fragile those existing systems are and how hard they are to make change. So like the language I've been using, and it came from one of our customers and it's come from many of our partners, is they're starting to realize their legacy system or platform, maybe even custom build that they had isn't helping them win, it's actually holding them hostage. And so we feel like there's an obligation there to show them there's a better path. We're going to remain committed to building and shipping every six months over 100 new features. That's what we do with our additions to future proof the business. We still have the best tco, the best converting checkout. These are things that have been well documented and you know, we're just trying to make it easier for customers to make an alternative choice. And so that's where we're spending our time, is finding partners who can come along our side and build practices around that to help customers win and be trusted advisors to them as they think about the choices they have to make going forward.

Thank you for listening to the CRO Spotlight podcast. The CRO Collective's mission is to help CRO succeed and help founders and CEOs build CRO ready organizations. You can find out more information about our services@the crocollective.com that's thecrocollective.com and we look forward to having you join us next time.