The Go-To-Market Maturity Model Part II With Highspot's Stephen Hallowell

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This is a podcast episode titled, The Go-To-Market Maturity Model Part II With Highspot's Stephen Hallowell. The summary for this episode is: We're back for Part 2! The playbook for success is one that’s hard to come by. In hypergrowth companies, you are often running around so much that it can nearly impossible to stop and articulate the evolution you’re a part of, what's working, and what isn't. Unlike so many of us, our guest on today's episode has taken the time to write it all down. That guest is Stephen Hallowell, VP Strategic Services at Highspot. He’s seen what happens when companies like Mulesoft and Snowflake go from tens of millions in revenue to hundreds of millions, and luckily, Stephen has written the whole playbook down for the rest of us to follow. That playbook is what he calls the Go-To-Market Maturity model, and he published 4 pillars to that model in a series of LinkedIn articles. On our previous episode, we covered Pillars 1 and 2. On today’s episode, we’re going to cover Pillar 3, The Sales Process, and Pillar 4, Accountability. Stephen's GTM Maturity Model: Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @HYPERGROWTH_pod

Sean Lane: ...Hey, everyone, welcome to Operations, the show where we look under the hood of companies in hyper- growth. My name is Sean Lane. First things first, if you haven't listened to our last episode, I definitely recommend going back and listening to that. This is part two of our conversation with Stephen Hallowell. So, it will be really helpful to go back and listen to part one first. For those of you who have listened to part one, welcome back for part two. As a reminder, Stephen Hallowell is the VP of strategic services at Highspot. Over the course of his career, Stephen has led sales enablement, sales productivity and sales ops teams in some of the fastest- growing companies around. Companies like snowflake and MuleSoft and Responsys. In our last episode, we introduced you all to his go- to- market maturity model, a playbook that Stephen has written for all the rest of us on the evolution from the earliest stage companies to best- in- class. In part one of our deep dive into the model, we covered two of the four pillars. Pillar One, targeting the right accounts and Pillar Two, messaging. Today, we're moving on to Pillar Three, the sales and buying process and Pillar Four, accountability. As we go through each pillar, I want you to visualize a spectrum. A spectrum that ranges from those early stage companies to best- in- class. Try to place your company along that spectrum. Where are you in that evolution towards best- in- class? Let's jump right in with pillar number three, the sales process. Stephen explained to me that it's not really about your sales process or your sales stages. Instead, it's about the buying process, the buyers. How are your customers making decisions? How you move the buying process along can be very different, depending on where you are at in your company's go- to- market maturity.

Stephen Hallowell: You know, what I really think about there, and I mean, listen, I think sales process can be a really loaded word. A lot of people think of it as," What's my CPQ process? What are the steps I have to take to get sign- off on something? What hurdles are you going to make me jump over to get resources?" I mean, listen, some of that stuff is certainly necessary, but what I'm really focused on, with sales process, is understanding," How does a customer look at the world before you engage them, or before you enter a certain stage of the process? In that stage, where do I need to shift them to, to be able to move forward?" Going back to this idea of, if my customer looks at the world as," I need this widget, I know I need one. I hate everything else that's out there. I just need to know, can you do A, B and C? If you can, I will buy." That's a very different situation and requires very different things from the sales team, than somebody who says," I've heard of you guys, everybody's talking about you. I'm curious, I want to learn more, but I'm really not quite sure if I need it yet." So, when you think about what the sales team needs to do in those situations, are very, very different things. I kind of think of the sales process as, if you're going to cross a river and you're hopping from rock to rock and you say," Okay, well, I'm not going to get across this river all in one go. I need some things to stand on along the way. What's the first rock I need to get to? How do I get to that one? Then, what's the next one? And then, what's the next one?" If you can make it really clear for your sales team, like," This is the path that, in our experience, based on how people buy, these are the things that they need to be able to move through. Here's how you get from one rock to the next, to the next." Now, you set up a really easy, repeatable way for them to navigate and get across that river.

Sean Lane: One of the things that I really liked about the way you broke this down and, certainly, starting by just getting these rocks that you're jumping from documented and getting people aligned around them is the key, in terms of the starting point. But, a part that I hadn't seen before, that I think could be helpful for people, is you talk about this concept of kind of two halves of the selling process or the buying process. You basically say the first half is all about getting the buyer and maybe a group of buyers to agree that, if you can do what you do or what you say you're going to do, it would create value for their business. That's the first half. Only when you get to that, can you move into the second half about actually delivering those things. I'm curious, as you've set these sales processes up at different companies, where do people typically fall down in that first half? Because it seems to me like everyone really, oftentimes, wants to jump to the second half.

Stephen Hallowell: 100%. The place people fall down is they simply skip over it. Again, it is that classic," How fast can I get an SE in here, we go do a demo?" I want to just get into talking about technology. In fairness to a lot of the A's out there, if they've been selling at a company for a while, that's what those innovator and early adopter customers want. That's what they need, because they get the first part already. They don't need the first part, but not all customers have that situation. In fact, as you get bigger and as you now have, let's say you've got a more defined book, you've got 40 accounts and these are my accounts. Probably, the lion's share of those accounts are going to need to go through that process. It's a natural reaction, but it also isn't one that actually gets companies where they need to go.

Sean Lane: I want to underline Stephen's point here. His proposal is to break your sales process in half. The first half is all about getting a buyer to agree, that if you can do what you say you can do, it would create value for their business. Getting a buyer to agree that if you can do what you say you can do, it would create value for their business. Then, the second half is about proving to the buying group that you can actually deliver and aligning on commercials, right? But, put more simply, the first half is aligning on a vision and the second half is proving the vision. Stephen's way of simplifying this is super useful, but I often find that, once you start adding more nuance and complexity to your sales organization, things can get less simple really, really quickly. All of a sudden, you've got sales methodologies versus sales processes, sales versus qualification criteria. Some people use these terms interchangeably, but they can mean totally different things. Let's take one that we use at Drift as an example. We use a qualification methodology called MEDDIC. That's M- E- D- D- I- C. There's some slight variations, some people have another C in there, but MEDDIC is an acronym that basically represents all of the key components of a B2B sale. M is metrics then E is economic buyer. Decision criteria, decision process, identify pain and champion. The idea is that, if you have a handle on all of these key components, you'll win the deal. With all of that detail, I asked Stephen how I should think about a methodology like MEDDIC, in relation to his third pillar of go- to- market maturity sales processes.

Stephen Hallowell: If you think about the components of MEDDIC, you've got metrics, economic buyer, decision process, decision criteria, identify pain and champion. Thing I've always found a little funny about MEDDIC is I'm not really sure how they decided that the order should be that order, other than inaudible acronym.

Sean Lane: I think it probably was just that it made a nice acronym.

Stephen Hallowell: But, as you break that down, most of that, it actually hits what you need in the first half. Metrics, what are they? How are they going to measure success? Who's the economic buyer? How are they going to make a decision? What's the pain? Who's the champion? Those things really all go in the category, maybe a little less the how are they going to make a decision, but, but everything else really falls in the category. The M- E- I- C of," Do I need this thing? What problem am I solving? Is it a big problem? Do I understand how this company might create value for me to solve that problem?" It's actually only the decision process and decision criteria, if you're really getting into, depending on how you define those, but are we going to do a POC? How are we going to frame that POC? What are the success criteria? Those pieces that are much. Who needs to sign? Who needs to approve? Those things that come much further downstream. All the other M- E- I- C, at a minimum, have to happen early. So, what I think is really helpful here in a MEDDIC environment, is having a checkpoint where you're not saying," Do I have all of MEDDIC?" Because, again, some of that stuff is going to come later, but," Do I at least have four big buckets of MEDDIC early?" If I don't, I've got work to do. I've got to really polish that up before I worry about what exactly the decision criteria, the decision process are going to be.

Sean Lane: By the way, there's even more tactical detail and recommendations from Stephen on articulating and implementing your sales processes in his LinkedIn articles. So, not to worry, the link to those in the show notes for you after. But, right now, it's time for us to look at Pillar Four, accountability. Stephen writes in his articles that the pillars are multiplicative, not additive. They need to evolve in lockstep with each other and reinforce one another. To me, when I think about Pillar Four, accountability is both the by- product of all of the other pillars and at the same time, it's the one that enables the other three. According to Stephen, understanding this pillar of accountability starts with defining it.

Stephen Hallowell: Let me be clear, first, on what I mean. I think accountability is a word that almost can feel like it has a negative connotation to it. What I don't mean is that you need somebody who yells at all your salespeople all the time. That's not what I'm focused on. What I am focused on though, is that people have an understanding of what they need to do to be successful. They know how they stand against those things. The simplest piece of accountability is," Am I achieving my quota or not?" Obviously, you need that, in most most companies that's easy enough to figure out, but that doesn't tell me anything about," If I'm not achieving my quota, what do I need to do differently?" As you get more granular with accountability, you can say," Hey, am I doing the right things at the top of the funnel? Am I progressing things the right way?" There could be things like," Geez. Am I engaging partners?" If that's an important part of your sales motion, but as you identify what those most critical things are for people to do, it's just giving them feedback on, for the things that really matter, are you doing them? Are you not doing them? Obviously, that should correlate strongly and if you have somebody who can be really successful without doing any of the things you say are important, you probably haven't picked the right things. But, if you have those things and everybody kind of agrees," Yeah, these are the things that matter." I've certainly seen cultures where nobody asks any questions about those things. It's a real disservice to any layer of management. That may be a senior sales leader who isn't asking the right questions of a frontline sales manager. Maybe a frontline sales manager who's not asking the right questions of their frontline account executives. But, wherever I am in that organization, if I don't know if I'm doing the things I need to be doing, it robs me of the chance to get better. I firmly believe that coaching depends on good accountability.

Sean Lane: You also talk a lot about the fact that that expectation setting kind of has to come from the top, right? It takes something as simple as the questions you were just mentioning. If you're probing someone about a specific deal or about a forecast, there could be totally different types of questions asked in different parts of a sales organization. I always worry about someone on our team getting promoted from one team to the next and having a completely different experience with their manager when it comes to some of those things.

Stephen Hallowell: Yeah. To me, I mean, listen, I've worked in a lot of places where the APEC guy and the EMEA guy and the North America guy or gal all do things in a very different way. Listen, innovation is a good thing, but if there are things where everybody's agreed this is what best practice is, and then somebody's not following that and is not demonstrably better than best practice, then it's worse. That just kind of says the organization hasn't invested in really driving the right alignment. To the extent that you have made investments in figuring out who to target, how to message, what your sales process is, you say," Hey, we actually know what good is." You're off doing something that's not good, if I don't bring that to somebody's attention, I'm wasting all that other investment. I think, just to kind of push on the coaching point a little bit more, good coaching, in my experience, is very dependent on, if you're my manager, my willingness and ability to come to you and say," Hey, Sean, I know I need to work on X, I'd like some help." Me, as the person being coached, opting into that discussion and being self- aware about what I need. The accountability is the piece that creates that self- awareness, and allows me, gives me the reason to ask for help. Helps me know where to ask for help, and then can make that experience much more purposeful than otherwise it might be.

Sean Lane: I honestly think that the accountability pillar is my favorite pillar. It's my favorite for a bunch of reasons, but the biggest reason is that anyone in your organization, regardless of where they fall in the org chart can make a difference here. Stephen explains that if you've done all of this work to align your go- to- market, inside of any of these pillars, and then you see some behavior that doesn't align with all of that work, it's your responsibility to call that out. If you simply turn a blind eye to it, or just allow it, you're essentially wasting all of the time and investment you've made on that alignment in the first place. Also, we can contribute to the level of accountability and the level of good coaching, by simply seeking that out ourselves. We can seek out coaching from our own managers and be open to it in the first place. In fact, us opting into that coaching and showing that level of self- awareness means you know what you're supposed to be accountable for. You're seeking help in that specific area. That is so, so powerful. Accountability is also about focus, though. You can't blame people for not holding themselves accountable for their responsibilities, if the list of their responsibilities is a mile long and a mile wide. So, how do we maintain that focus, both for the coaches and for those being coached?

Stephen Hallowell: Listen, I have been guilty of, I'll have the," Geez, I want it all." You know? I had," Man, all these things are so important." I think I've learned the hard way over the years, that you got to start with, if you can actually get people to consistently pay attention to one thing, even, but they're actually doing it consistently, that's a much bigger victory than 20% of the people paying attention to 20 things. Really sharpening up on, if we had to just get people to focus in a couple areas, what are the things that matter? Let's get really consistent about that and build that muscle of learning how to be consistent. Once that muscle's in place, if you say," Okay. Good. Now we've got this piece down. Now, we want to add another layer or another wrinkle to it." Now, you can start to fold in more, but I think that allows the organization to sort of adapt to it over time. I mean, I think it's like anytime you learn something new. Think about whether it's a golf swing or whatever your sport is. Somebody gave you," Hey, think about these 25 things." And that's going to help you get a good golf swing? That's not going to be helpful. On the other hand," Look at the ball and don't move your head." Okay, that's a place to start. Once you get that down, now you can add other pieces in.

Sean Lane: I keep thinking about that, as one of the ways that we've kind of tried to solve for that at Drift, is we have picked certain components of the funnel, right? Said," Okay, we're going to, let's say, just to keep things simple, we're going to work our way down the funnel. We're only going to focus on this specific part of the funnel for, I don't know, this month or this quarter. Then, once we've seen what we want to see there, it's time to move on to the next part of the funnel." Similar to the golf swing analogy, I can imagine a world where it's easy to backslide or lose some of the things you did early, right? To go back to the golf swing, you get really, really, really good at keeping your head down, but then, as you start to focus on the way your hips move, you forget to keep your head down, all of a sudden. You're on step three and all of a sudden, step one is failing. Inside of folks' businesses, you talk about these pillars being multiplicative instead of additive. And so, I'm curious. How do you make sure that you don't backslide in some of these areas, after you've worked so hard to progress?

Stephen Hallowell: Well, I think we're kind of zooming back out again, now, to the whole framework. I think the good thing is that they should relate to each other. I guess, just kind of as an example of, if I want to make a shift, if I'm making this shift from selling to innovative customers who are mostly coming inbound, to I'm now going more outbound. I need to be able to create more urgency in my sales process and I'm really trying to overcome no decision more often. That, first off, I've got to be talking to the right person. If I'm talking to somebody who's really deep in the organization and doesn't have any business context, I'm not talking to the right person. That comes into my targeting. Who am I engaging? Who my ideal customer profile is. But, obviously, I need messaging that works with that person. At MuleSoft, when we started shifting our message to take in to focus a more senior audience, is, what worked for an integration architect was not going to work for a CIO. That message has to come along with that as well. Similarly to now, the sales process is also going to be different. The sales process that worked with that more low- level person isn't going to be the same process or what works for somebody more senior. Then, in the accountability, if I'm starting to look at," Hey, how is my conversion rate from opportunity to midpoint in the funnel evolving?" That inaudible to wrap that up. The good and bad there is, if I try to make that transition and I just say," Hey, sales team, stop focusing on junior folks, focus on people who are more senior." You'll get a lot of eye- rolls, because you're not actually helping them do that. If you say," Yes, we need to focus on a different audience and here's how to do that. Then, we'll build in the ways to measure and see if we're actually doing it well and see how we're progressing." That actually kind of wraps all that up in a bow. You can move forward on that piece and then take the next leap, all in all. I kind of think of it as these four pillars are four guys chained together, trying to get down a football field. One guy can't run to the end. They all have to move a little bit and then they move a little bit more and then they move a little bit more.

Sean Lane: Well, that's what I was going to say, right? It's easy, because we're talking about these in such a zoomed out context, but, in reality, the work that it takes to make the incremental progress on each of these four pillars is really difficult. They really are, to your football field analogy, all happening in parallel. But, some of them are going to be just more naturally based off of internal priorities, or different people who are working on them, stronger than the others. But, you can't just go, it sounds like, from what you're saying, you can't just go way ahead on your messaging, if your targeting isn't figured out first, for example.

Stephen Hallowell: Totally. Yeah, yeah, product marketing can't say," Hey, we've got a new message guys. We're going after this new audience. Go to it, we're going to certify all of you." If that doesn't fold into a sales process, for instance that supports that.

Sean Lane: ...Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months.

Stephen Hallowell: Sorry, I'm not going to be as rapid- fire as I'm supposed to be. Okay, I'll give you one. Peak Performance. This is a really interesting book, co- authored by a former McKinsey consultant and a world- class running coach. It draws a ton of parallels between the world of athletic performance and business performance and how do you optimize both over the long- term?

Sean Lane: Love it. That's Brad Stulberg, right?

Stephen Hallowell: Yep, that's the one.

Sean Lane: Awesome. I just read their other one, Passion Paradox. That one was good as well.

Stephen Hallowell: Yes, yes. A good one too. Yeah.

Sean Lane: All right. Usually, I say to people, your favorite part about working in ops, so I'll say to you, your favorite part about working on go- to- markets?

Stephen Hallowell: Oh, man. I just think it's so interesting, because it's at the heart of the business. The reason, what pulled me into this space, was it just felt like the biggest lever for impacting the performance of the business. I continue to believe that. That you're designing the machine and you're helping that machine run and hopefully run really well. When you get those things right, it can be such a powerful impact.

Sean Lane: Least favorite part about working on go- to- markets?

Stephen Hallowell: I think that the thing that can be challenging, is you've got to align a lot of people on a lot of things. You're often doing that with, whether it's an obstacle or an enabling role, or what have you. You often can't just, you're not in a position to declare," Hey, this is the way you must do it." You've got to get people to buy in. Listen, sometimes that's easier than others, but, I think, with the right investment, you really can bring people along.

Sean Lane: Someone who impacted you getting the job you have today?

Stephen Hallowell: I'll go to just what got me into this space. So, I started, when I was at Responsys, coming out of business school, I started in a product marketing role. We had some interesting performance challenges and then some needs in the business. I'll give a lot of credit to some leaders there that both saw that I had some potential for doing this. Frankly, were willing to say," Hey, go for it. Go see what you can do." Gave me room to run. Allowed me to really figure this stuff out. It's a career path I wouldn't have predicted. If you asked me, 15 years ago, what I was going to be doing, it wouldn't have been this, but it's been a great fit.

Sean Lane: That's awesome. Last one for you. One piece of advice for someone who wants to have your job some day?

Stephen Hallowell: I think the biggest piece of advice I would give anybody in the ops or enablement or product marketing space, is to really look for leadership opportunities and don't be afraid to take them. I think when people see themselves as," My role is purely a supporting role. I'm here to do what other people ask me to do." It really limits what the job can be. When you come in doing a lot of listening, but, being close to the data, understand, use that as a way to bring some unique insight to the business. Have unique perspective, use your skills at structuring, breaking down problems, making things clear for other people. You can really have a powerful leadership voice. I just say to use that.

Sean Lane: Thank you, thank you, thank you to Stephen Hallowell for taking us through his go- to- market maturity model for our show. Thank you to all of you who stuck around and listened to both parts one and part two of our conversation. I think there's a ton of really helpful and insightful information in these two episodes that people can refer back to, as you are building and evolving the go- to- market models at your companies. Also, if you would prefer to see the written version of this model, all of the links that you need to Stephen's LinkedIn articles are included in the show notes. Go back, read those. There's a ton of insightful stuff that we didn't get a chance to cover in either of our conversations. So, plenty more value to be had there. Also, if you enjoyed what you heard on this show or any other episode, please, please, please leave us a six- star review on Apple Podcasts and please subscribe. Thanks so much for listening. That's going to do it for me, we will see you next time.


We're back for Part 2! The playbook for success is one that’s hard to come by. In hypergrowth companies, you are often running around so much that it can nearly impossible to stop and articulate the evolution you’re a part of, what's working, and what isn't. Unlike so many of us, our guest on today's episode has taken the time to write it all down. That guest is Stephen Hallowell, VP Strategic Services at Highspot. He’s seen what happens when companies like Mulesoft and Snowflake go from tens of millions in revenue to hundreds of millions, and luckily, Stephen has written the whole playbook down for the rest of us to follow. That playbook is what he calls the Go-To-Market Maturity model, and he published 4 pillars to that model in a series of LinkedIn articles. On our previous episode, we covered Pillars 1 and 2. On today’s episode, we’re going to cover Pillar 3, The Sales Process, and Pillar 4, Accountability. Stephen's GTM Maturity Model: Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @HYPERGROWTH_pod