Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)

Brett: Maybe a place to start that that might be particularly interesting to hear your take on is, uh, you bring, you've been bringing software to market for a while. You click, you sort of had a huge chapter, um, call it pre-chat GPT or pre LLM as we know it.

Then post sort of chat GPT in one of the leading companies that's bringing, um, cogen to market. Now you're joining another company that's at the forefront of this technology. What's like your observations in, let's start with kind of new world, old world of selling these two different forms of software,

Do you think it, it tends to be more different and you're relearning your job or Most of it's like 90%.

Graham: identical. I think one of the funny things about this generation of, of companies and of sales is that it feels like the playbook companies of like the cloud era, the, like Mongos, Datadog snowflakes have kind of become, there's like backlash against it. And now there's a lot of very like anti playbook sentiment.

And I think the reality is that I've found that it's very much in the middle where like windsurf cognition.

Brett: In the sense of, in this generation of founders and companies, we gotta reinvent everything and go back to first principles kind of.

Graham: Yeah. My sense is that there's just like a lot of like pride in PLG. . And I'm like, we want the product to carry the sales motion forward. And there's like less around this like very structured, measurable sales process and more about meeting companies where they are and injecting sales at the latest possible point.

And that it feels like in a lot of these companies that have been super successful, there is, uh, maybe like a negative ethos around the word sales. . And what I found on like what we bet on at Windsurf was. In AI natives, you have to sell completely differently. The amount of information out there is is much larger.

They do a lot more research before coming in. People can try products and so there it is. Have a conversation, figure out where they

Brett: the end customers.

Graham: Correct. So like the newer companies that have been founded call it like post 2020, um, where they come in with a pretty strong perspective, often having used a bunch of tools in the market and like what you're having to do is figure out what they believe relative to what they're trying to achieve and like do some education around that.

But there is probably a very different motion there than like an older school, like what made HubSpot famous, for instance. . Um, I think in the enterprise it's very similar and it moves faster, but like you still change, management dictates success in the enterprise more than technology. And so companies still want people to come out and deliver services and do trainings and spend time with the, in the, with the team.

And like when we were doing large rollouts at Windsurf, we would send people. On road shows, like two reps in particular I remember went to India, Europe all over the US to sit with different offices for different banks. And the feedback we got was, since we've been buying AI tools, there's not a single company that has actually sent teams to go and do this.

And like part of why we're going with you outside of belief in the tech is that we think that you guys actually understand how to partner with us as an enterprise because it's not just our tech is amazing, release it into your marketplace internally and it'll spread like wildfire. . There was like a willingness to sit and to do discovery on current workflows, propose new ones, align on what the actual answer was, and then go and like spend time driving it.

Because six months in, companies that did structured rollouts were a lot more successful and we ended up collecting a lot of data on this because it became part of how we sold. Then the companies that said, Hey, I've got tool A, tool B, and tool C, we're gonna throw them into a marketplace and just like let the market decide that wasn't six months out.

Super effective. There was, in a lot of cases, minimal measurable change. People had done the wrong things because instead of having trainings, they had just messed around with it and figured out their own workflows. Um, and so I think in that way, the like old generation of sales is still very much applicable.

Graham: Where I think people want opinions, they want clarity, and in a lot of cases there's interest and excitement about something because they have an idea of how it can be effectual in their business. But I think companies lose an opportunity to become more than just a vending machine for software when they're not willing to say, Hey, we are really strongly opinionated about the best way to do this and why.

And look, we're gonna take the time to get to know your business, but then we'll read that back to you, apply our perspective. And if that is the thing that you believe is a viable option, then we'll work with you to make it successful.

Brett: Why, why do enterprises wanna be sold in this way?

Graham: I think companies that have large scale organizations, and certainly the executives at the top of that chain understand that getting large groups of people to do anything is really hard. And that if you can provide a step-by-step guide, get in the boat with them and work on how to apply that and how to execute it, execute, and then are constantly able to, because everyone, like get they gets brought into a training, is wondering why they got pulled away from work.

So you have to have a really strong upfront value prof on, Hey, at the end of this two hour session here is what you're gonna be able to take with you and how we expect it to impact your work in week one and week four and week 12. Like, this is the, the carrot at the end of the stick if you spend in two hours not doing your primary job.

But if you do that really effectively and you're able to come back and do. Ongoing training and enablement and you develop relationships, then like the ultimate change management across thousands or tens of thousands of people is more effective. Um, because on top of there being a systemic piece to it, there's a human piece where like if someone doesn't trust you or doesn't know you, less likely to listen.

If someone is making the effort and there's a team that shows up and is willing to work with you, and over the course of a year you see the same people a few times, you begin to develop relationships. It's why systems integrators, var as have multi-decade relationships with these companies and are so effective, like ww t ahead emphasis doing tens of billions in revenue.

A lot of that is because there's executives that have been there for the entire span of the relationship and there's like a deep amount of trust that if someone says, I'm gonna deliver this, they'll,

Brett: Do you, do you think that's gonna change in any way? If you're a betting man, you would say in the next few years that's that's how it's gonna be.

Graham: I think that at. Any large scale organization, large, those foundational principles will continue to exist. Like Parallel is the first company I've worked at that I would say is truly AI enabled. And what we do internally with Claude and Notion and att and like all of these different tools is amazing.

And like Claude Cowork is in a month, three weeks of being at this company, it changed how I work because I can now go into cloud and have all these different systems hooked up to it. . And say, help me build a slide deck. Help me build a doc. Like, Hey, I'm looking to prep for the forecast tomorrow.

Can you gimme a readout of all of this stuff? And so I think I have a much better command at the data that I have within the company. But if I were doing a large scale rollout, especially if I had a team of a few hundred or a few thousand, I still think I would default to wanting to be able to work with a vendor on how to make that successful.

And like, yes, incorporate that into our workflows, or teach me how I should change the workflows. But I don't necessarily see. I even see this in my team of like 10 people right now. How we all use clogged flow work is pretty different. . And so if you scale that across thousands of people, I think you probably end up with a lot of redundant work inefficiency.

And that absolutely would lead in, in that situation to wanting to work with a vendor on how to make sure that we're getting the most out of something versus just being better than we were,

Brett: What is, if you think about large enterprise and your experience with windsurf and then cognition and you think about excellence in sales., a lot of the core components are similar. Are there really important differences with this, this type of technology and bringing it to the enterprise over the last 18 months?

Graham: yeah. I mean, I think one of the things that at Windsurf and cognition we did really well was, the way I describe it is like great sales is like squeezing an orange or applying pressure from both sides. So on the one hand, do you want to go. Talk to engineers and like have a strong dero practice and really get in and like understand on the ground the way that people are working, thinking what they want to be doing.

Absolutely. That's really, really critical. But at the same time, these executives that are managing huge budgets have projects and increasingly have CFOs saying, oh well, like that company over there, cut head count 40% and increase productivity three x. How are you gonna do that? Like if you're not involved in the conversation with them, then you're just hoping there's enough of a flywheel at the ground, like at the ground level to pull your product up.

I think what we did really effectively was how to strong practice around going out and meeting developers where they were. And that was both like being active on Twitter, being active in meetups, having like a strong devra practice about trying to bring together a community of people that created a conversation that was ongoing around how to use the tool to the best of its abilities.

But then also we had a really strong practice on. Executive events, making sure that we were plugged into the CI C-I-O-C-T-O and being able to go and basically translate what we were hearing from their people, which in a lot of cases they weren't getting direct and giving us the opportunity as we were going back and engaging with the developers to say, Hey, we spent some time with, you know, Mr.

And Mrs. Executive, here's how they're thinking about it. And I actually think that great sales organizations understand that in a lot of cases, they are the vehicle that both developers and executives use to get a clearer insight of what's happening in other parts of the org. Because if there's six layers, if you're selling to a major bank, like CIO of JP Morgan is nine layers between an engineer and she's not necessarily hearing from engineers on a regular basis.

But if you're a vendor who can say, Hey, we just went and did a huge training at your Ohio office, like here's the feedback, here's what we're hearing. And then like able to integrate that into. How they're thinking about AI strategy. That's a huge value add for that business that goes beyond just the tech.

And I think we were super intentional early from like the very, very early stages about how we chose to do that. Because when I got into windsurf outside of hiring sellers and deployed engineers, the three things that I told our CEO that I wanted to go do was hire a Worldclass partner person, a Worldclass enablement person and a data person.

And my premise was, we're at single digit millions in revenue right now, but by the time we get to 50 a hundred in a product like this, it is more important that our enterprise customers are able to get consistent services and ideally from a place that they trust. And that is through partners. Like being able to go and build credibility and build belief in the big partners and systems integrators was something that we started doing probably $40 million in revenue before most companies, but by the time we hit 50 a hundred, we were in.

Some of these centers of excellence that we wouldn't have been in until we were at 250, otherwise. And that was a huge force multiplier for us because it meant that if a bank said, Hey, on short notice we have this event in Singapore, can you come out? We could probably send one or two people, but we could call the partner that we knew they worked with, that we also were close with and say, Hey, can you, can you flex 30 people to come help us deliver this?

Um, and I think for us, knowing early on that we were going to be more enterprise focused, that was a really high leverage way to spend time. And then from an enablement perspective, I think

sellers in some cases get a bad rap because they're not necessarily credible able to come in and provide information that their, their customer might not have without them. And so by investing a ton and creating a sales team that was well drilled, well educated, was able to speak not just to our product and to our competitors, but to the market as a whole.

And to do this in a way that was programmatic. Like we measured the outcome of enablement and we're able to look at like, Hey, how did the first four weeks of digital onboarding go? Like, how are people performing in these sessions? How does, like at bootcamp, there's different measurements that we have and we could then look and say, Hey, like this cohort that hit 75% on average became productive in the field three months before previous cohorts.

And so I think just being very intentional and programmatic early on, things that at 10 sellers like doesn't necessarily seem important, but that meant that at a hundred, we had that completely dialed in in a way that at other orgs that I've been at, we were scrambling because we realized too late that we should have done it a year before.

Brett: What about, what does excellence look like when you're selling to AI native customers?

Brett: How different is it?

Graham: That's, I think, the most different thing. Uh, and it's been really fun. I think AI natives a like. In a lot of cases, a good percentage of their employees started using chat GBT in like college or high school. . And so you have this group of people that are just like born to it in the same way that like our generation might feel about an iPhone.

But it means that the education curve is completely different. 'cause it's not like, hey, here are the rudimentary pieces of like what an agent is and how you get the most out of it. But it's okay. Like show me what you're doing, show me your workflow. Okay, cool. Like you are miles ahead of someone that I might be working with who picked this up when they were 45.

And now it's about like optimizing for the outcome you're looking to create. Ideally giving you like two or three pieces of information or two or three things about how to use the product or get the most out of a workflow. Having you go back, do it, provide feedback. Like I think the way that we communicate at parallel with those companies is like a lot in Slack, a lot over like text.

There's just like a lot more constant communication. And it feels more like an ongoing conversation because I think a lot of this generation is just used to async, first of all. And also just like having a pretty constant narrative going on. Because even if you're talking to chat GBT, that can be an ongoing conversation.

And so there is this much more like continuous exchange of information and then you get on a call every couple of days to like go through the most recent stuff that's happened. But we're coming into those conversations with way more context because rather than, Hey, here's an email recapping what we talked about,

Go do this and then we're gonna read it out.

You're coming into a conversation with like three days of just like constant communication. . Which is cool because I think in a lot of ways it's allowed us to get a lot more embedded in the outcome they're looking to drive and like that's really fun. Um, but I also think that it's just been a completely different, uh, challenge and set of things to think about from like a not even sales process.

The sales process is similar, but the time interval of the sales process is very different. Or like an AI native, a process that might take just naturally six to eight weeks in enterprise is like five to eight business days. . Um, because there's just so much continuous exchange of stuff that otherwise you'd have to extract over a period of time, just like naturally gets compressed.

Brett: What, um, what are the implications for what the sales org looks like selling into that end customer, based on sort of that observation. Is there, like, could, is there a different seller persona or way of going about the work to be successful for that customer base versus, um, you know, traditional business enterprise, mid market, whatever?

Graham: I think really good sellers tend to over communicate no matter what. Just like, depending on what that, what that means. And so like an enterprise, it might be you're sending like project management emails weekly to recap everything that happened to talk about expectations for next week.

And ideally you're texting some of the people that are involved. And I think if you took a great enterprise seller that does all of those things naturally, it might take an adjustment to like being in Slack all the time or being in text communication as much as we tend to be. Um, but I do think the basic like personality traits that make people good at AI native existed in enterprise, they've just never had to communicate that much.

Um, so to be fair, I really haven't experimented yet with taking like a great enterprise seller and being like, Hey, I'm gonna pull you off of the big banks and like stick you into the right, the tier one San Francisco companies. But I suspect that, uh, the adjustment could happen and I actually like from a personality profile perspective, no.

I think if anything. Companies overcomplicate hiring of sellers like you hire smart people that are good at problem solving. Uh, something I say all the time is you can't fake giving a shit. . Like people that care deeply and are very human oriented will go above and beyond to make customers happy and won't be really sincere and authentic about trying to understand like not just what the company is trying to achieve, but like, Hey, I'm talking to these three people every day.

Like, what do they care about? Like, who are they as people? Um, and I think that that personality profile is exactly what we look for in AI natives and an enterprise. I think the, like hard skills that come with it are different because the a native reps that we're hiring are for the most part, younger in their careers, often grew up with GPT and just some of the like, communication styles that they have are pretty different.

But if I look at from a behavioral perspective, what makes our a native reps really good versus our enterprise reps really good, it's almost all of the same things. Just usually across different technology stacks.

Brett: What about in terms of the way that an AI native company makes these decisions build verse by how they evaluate competitors, um, ROI or differentiation or like sort of those type of things?

Graham: Yeah, I mean the, the interesting thing is that where I have sat in ai, I feel like there's less of a build versus buy conversation. Like pretty quickly people realized that they weren't gonna build copilot or cursor or windsurf uhhuh. And so it became a what do we prefer? . And in a lot of cases, again, this is where I think there is an opportunity to like bring back some of the old school, which is that, uh, if all tech is, if you're working with one of the top three vendors in every, in any space in AI right now on a four to six week cycle, the tech is probably within 10% of equal.

So there is like a taste human preference perspective, but I think there is also this like, trust is this person, or is this company gonna show up for me and help me if I run into an issue? And I think. Where we've had a lot of success in AI native and in enterprise. Back to the showing up, like are you willing to go on site and do work with the team?

Are you willing to fly out and like do a training session? Are you asking about, uh, hackathons or like major milestones where like the engineering team gets together and like asking to participate in it? And the consistent feedback, and this was true at Wind Exon at parallel, is the way that our orgs operate, felt different to them.

But when we said, Hey, why is this really good feedback? Can you tell us why? The answer almost always was like, you guys show up a lot. Like you guys are very present, very willing to jump in and help and like ask for trades. I don't think that like fundamentals of like, Hey, if you're gonna go invest a ton of time, it's okay to say, Hey, we'll send people out.

We wanna make sure that if we do that we're gonna like get the right amount of FaceTime. We're gonna be able to meet with the right people, but we're happy tare nuo do that. Like for most, for the most part, people are very comfortable with that. But I think there's a lot of companies right now that have defaulted to zoom and defaulted to slack.

And I think that being willing to like put in the lead work and develop relationships, like one of my favorite stories is, uh, one of my, the best reps I've ever worked with, uh, during COVID found out that his, what champion at one of his company's sons had been taking guitar lessons and couldn't anymore because of COVID.

So we ended up teaching this guy's kid guitar over Zoom during COVID.

Brett: Because he knew how to play guitar.

Graham: So like, this just like came up in the course of them getting to know each other and it was like, oh, you know, my son was, he was like, hi, you know, how are you guys managing COVID? And he was like, oh, like, you know, my son was taking guitar lessons and it's kind of been a bummer 'cause he hasn't really been able to, and my rep was like, oh, like I'd play guitar.

I've like taught people, I'm happy to give him lessons. . And he also didn't tell anyone, like, no one found out about this for a long time. And then the, the champion at this account brought it up on a call with me like six months later. It was like, oh yeah, Isaac has been like teaching my son how to play guitar.

And I was like, what? Um, but it's like that. And it's like, I think the thing that people miss is yes, like sales process is important. Having the right stages, the right gates, the right operational rhythm so that everyone in go to market knows where to be at any given time is helpful. Not because that's what makes success or failure, but because if you can create that in a way that is aligned with your customers, it creates a lot of clarity for everyone involved and what they should be doing at any given time.

But the thing that actually makes special or special is the kind of person that you have then running in this process. And at no part in our process doesn't say teach someone guitar. Right.

Brett: So, so then if you pull at that, how does it make you think about, what do you want to standardize as you begin to scale a go-to-market organization versus kind of like, what do you wanna push to the edges, which is, hey, you're a smart, capable, passionate person. Yeah. Go use your own best judgment to help us build our business.

Graham: The CEO of parallel said this to me recently where he said, Hey, like I want us to have a super measurable, predictable sales process, but I want what we do to raise the floor. Like I want the floor to be really high. What I don't want that I feel like does happen in some of these very process heavy orgs is for us to cap the ceiling.

So how do you create something that creates like a bare minimum as far as people's operational expectations, how they're gonna behave every day? That means that we know we're never gonna go below 90 without creating so much structure and so much process that it doesn't give people the opportunity to go do something kind of special and unusual.

Um, and a lot of that is, I think simplicity is important. We don't want to have too many sales processes, too many sales stages. It's important to be really clear on what they are and why, and to have a really clear set of like three to five, never more, and probably not less than three things that happen in each of them.

So it's like, hey, as you're moving through the process, do we have these things to move to the next stage? Did this meeting occur where someone said, yes, I'm gonna do this with you. Do we know that that person has the power to do it? Great, move on. But by keeping it very simple, everything else is pick your own adventure.

I generally think that if we've created the right expectations in the field, someone else's judgment on why to deviate or how to do something that is like nonlinear is gonna be better than mine

Brett: Because they're just closest to the customer to the problem.

Graham: closest to the customer and, and like I hire people to be better than me, there's not a single person in any of my, in any of the orgs that I've been a part of building that I didn't think was better than me at the thing that we hired them to do.

I think that that's really important because also if you create a culture where people, because there's two ways this goes. Either leaders want to validate their existence by having input on everything and by having input on everything, you actually create a culture of people being frozen and unable to act because they feel like if they don't get your sign off or don't get your input .

There will be some penalty. Or you create a culture where everyone knows that as long as you've thought it out, I'll ask a couple of questions, but they come in knowing there's an almost 100% chance I'm gonna say yes, which actually makes them accountable for the outcome. . Like if you're in an environment where someone's gonna say no to you, you actually don't feel that accountable because you threw out a suggestion, they rewrite it, and then you just go do that.

If you're in an environment where someone is gonna be like, all right, tell me why. And as long as there's a coherent thought behind that, the default response is, yeah, do it. Let's see. And if it works three times, we'll enable the fuel on it. And if it works once and not again, then like we learned.

Um, but I think the way to create autonomy and or orgs of any scale is to hire, like, every time someone goes to hire for me, like one of my leaders, I'll say, Hey, like, do you, do you feel like you are going to be able to say yes to this person? The vast majority of the time they ask for something? 'cause if not, we should talk about that.

But if yes, then like that's a good signal that we want that person here.

Brett: Why does it not work as you're scaling to have such a good system and process, this is a genuine question, such good system and process that you can kind of hire relatively mediocre people and have them thrive and deliver for the business. Like why, like embedded in what you're, I'm articulating the opposite of what you're saying.

Yeah. And you obviously have a belief that that's not the optimal way to sail a Go to Market org scaling. Go to market org.

Graham: I actually think the optimal way to scale go to market org is probably to have a system that is, 'cause again, like the three to five things that that should exist in each of these stages should be enough to run a consistent, healthy cycle.

And so I think at scale, like if someone walked in tomorrow and said, Graham, hire a thousand people in the next year.

It's not gonna look the same with this at Hire 50. But what you need at that point is to have that process that you've articulated be correct and opinionated enough that someone who. Does the training leans into enablement, leans into developing the muscle memory to go follow the steps. Maybe they never operate above the floor, but if the floor that you create is high enough .

And they can follow the steps, maybe that is the person who is a consistent like 95 to 110 of quota. . But what is important is that the people that are gonna come in and go teach people guitar lessons or go and like have a cooking class for a few of their prospects that they found out really love cooking, still feel empowered to do that.

And I actually don't think that those things are at odds. I think what tends to happen is orgs either are like, we only want the greatest people, and like great people, great people are unstructured. Mm. And you end up with these sales orders, it's like a bunch of artists just kind of like throwing paint at the walls.

And it's not that those can't be effective, but it's really hard to measure.

Brett: What? Talk about why, what the problems are with that.

Graham: Um, I think if you have a bunch of people that are all really good at problem solving, but all do it in silos or do it in different ways, then when you go to create predictability in the business, there's not actually really a baseline to be forecasting off of because you have person A over here who is like an amazing technical mind who can walk into a room of engineers and just like absolutely enthrall 'em and get people very bought into their technical brilliance.

You have the person over here who is great at executive level conversations and doesn't understand the tech at all, but can go and like connect deeply to the business problems and then bring the right resources to bear. And they have totally different ways that they go about validating the tech and totally different lengths of time that it takes and different deal sizes.

And if there's all of these different objects that don't look the same when you go to the VP and you're like, all right, you have a hundred of these people tell me what's gonna happen next. . That is a pretty challenging kaleidoscope of behaviors to be looking through. And I think the important thing is if you create that floor and you have this system that is clear, concise, measurable, you can hire people, not to say mediocre, but like who maybe aren't, don't flex in that unusual way, who can come in, lean into the system, follow the process, and be super successful.

What you don't want those to create a system that is so rigorous, it's only people that are looking for that level of clarity and certainty who gravitate to it. So it's like how do you create a process where we can bring people in who might not just naturally be that kind of like artistic nature, but who are diligent, hardworking, smart care, and will follow the process.

And you'll get 95 to 110% of them, and I'll take 900 of those people if the remaining a hundred. Are the people that are out there teaching guitar classes or doing cooking classes or like, whatever that might be. . And so it's like, how do you create a process that allows people of differing skill levels at a baseline to be more successful than they could have been otherwise without working in that system and create enough flexibility in the system.

But if someone is like, Hey, I wanna like flex and do this thing, that's really unusual. You can still say, hell yeah, let's go do it.

Brett: What you think true excellence is leading the GoTo market function.

Graham: I think, I think excellence at leading the go-to-market function can, you'll see I love this number, probably be broken into three things. I think it is. It's, it's easy. Yeah. Yeah. It makes you sound smarter than it. There's only two, but not so difficult that you have to keep four in your brand at the same time.

Um, I think as a leader it is how are you predictably driving revenue? And that is both like net new logos. How are you thinking about expansion programmatically? Like when my founders come and talk to me, I need to be able to tell them, Hey, from a new logo perspective, like here's how we're operating.

Here's what it looks like in AI native. Here's what it looks like in enterprise. Here are the things that are going really well. Here are sticking points related to how we're selling. Here's product feedback we're hearing. And then from an expansion perspective, are we before close? Like if, if you are not talking about how to successfully deploy the thing you're selling, basically from the moment the eval goes well, then you're completely missing the plot.

Like the plurality of revenue that exists in most organizations happens after the first deal. So how are you going in and saying, and this is another thing, like an example right now is at parallel we have so much, the market is coming towards us so intensely that the team is overwhelmed. There's like not enough people to respond to the demand that we have.

And so like that's a good example of just having to simplify it where it's like, all right, if the eval went well, have we agreed with our champion and with the economic buyer on the kickoff date? Which then applies pretty direct pressure on like how quickly we get paper done. If we agreed on what the first 30 day milestones are, first 90 day like we have to create a lot of clarity for what success looks like.

So the customer's not wondering, did I get something out of the investment? Like it's your job to take that on. And so revenue's the first piece. I'm gonna put talent development in the same bucket, but I think one of the biggest like tragedies of the generation that's coming into go to market right now is that a lot of organizations have become so focused on responding to demand.

They've really heavily moved away from development. And like for anyone, for anyone looking at getting into sales right now or go to market sales to put engineering post-sales, like finding an organization that's still puts enablement and developing of people like primary among its responsibilities, I actually think is really critical because, and I don't remember which executive gets credit for saying this, but like there's a lot of people that talk about how if you don't love yourself, it's hard to love other people.

Well, I think if you're not like actively investing in. The development and careers of the people that chose to entrust their career development to you, then you're like missing the mark as a company. And that probably says something about how you're handling your customers. . And so like I, the woman who built along, which, so Jeremy Powers and Nicole Redinger built Mongo was an enablement program, which was legendary and had every reason to be.

Nicole came built out Windsurf, um, and brought similar to like Nicole and Jeremy worked really closely together at Mongo. Nicole came in and was like, I'm bringing in Danny McCabe, who is every bit as good as me. And so we had, in my opinion, the two best enablement people operating at Windsurf, uh, for about a year and a half.

And we built an amazing enablement program. But what that meant was because there was so much pride in how we were able to develop people, and whether you're like an SDR AE leader, this is the other thing, like a lot of people get into leadership and everyone's just like, all right, you're never gonna develop again.

Congratulations on being a leader and like. That isn't how that should work. If anything, it is super critical to be intentional about saying, all right, look, who are my cohorts of leaders who are in the first two years of leadership? . Because like the lessons and development that they probably need to be hearing are different than someone who's in years three to seven.

And I think being very intentional about that both makes you more attractive to top tier talent and makes you able to take risks on people who are kind of like we were talking about, or maybe someone doesn't come in knowing the process, but if they're smart and willing to learn and have all these unbelievable other characteristics, you can bring them in and develop them.

And so like for me, revenue is the big piece people, and enablement is the second piece that I think is unbelievably critical. And then like, how are you aligning everything in the organization, both today and six months out to reduce friction for everyone internally and therefore for customers? Because if you are hiring great people, enabling them and making them better on a continuous basis, delivering revenue to the business, that is also delivering measurable value to your customers.

And. You're being intentional and programmatic about, Hey, how does what we're doing in sales connect to marketing? How does it, are we communicating with Auto Point engineering colleagues? Am I communicating with the engineering team? Like is our, is our legal team being appropriately protected by the sellers?

Do we know how to have the conversations around limitation of liability and all of this stuff? And like a huge part, I think of any, any executive of any business unit should be making sure you're spending appropriate time with your peers. Because if you get that connective tissue built appropriately, it's awesome when like legal is being appropriately protected.

Finance isn't calling me being like, how on earth did we approve this term? And they can all go focus on things that are like value added to the business and not trying to create fences around sales. So sales doesn't do idiotic things. And like better yet, if you're able to develop rapport where you know there's gonna be times that you ask for help.

And if you have done the like legwork and put in the, the sweat equity to build trust and to show people that, like you will show up proactively when something does happen and it will, where you're like, Hey, I need, I need an assist here. Like, generally that is like a, a good moment to kind of like band together and get closer.

Whereas where I've been in ORs where there's that tension, like people help, but there's a huge difference between like, yeah, I'll help and like, hell yeah. I would love to like get in the boat in a row

Brett: I would say the natural path, which is that functions grate against each other, or most likely blame each other. You know, marketing conventionally blame sales for not hitting a number. Sales says we're not getting the appropriate. Yeah. Leads or, or coverage from marketing or sales is blaming.

'cause they're not delivering a product that's saleable and like you have this normal sort of cadence where I think the functional leaders often blame each other as opposed to truly coming together. And you know, it sounds like you have this customer centricity with your counterparts, which is like, Hey legal, let me sit in your shoes a little bit.

Yeah. Not let me scream at you because this deal term is blowing up this $5 million enterprise deal. And you know, sort of those types of things that can happen in scale

Graham: Yeah, I mean if you, if you have like the particular mental illness where like running go to market teams is fun for you. Then like everyone is your customer. Like the other organizations that are like part of your company are very much your customers, your reps, and like the people that work for you who like trust you with their careers and trust you to be able to give 'em a path to success of your customers.

And obviously the people paying us money as a business for our technology or your customers. And I think, like again, you, when you said this at the beginning, there's different ways. There's not one right way to do it. . Um, and man, like Amazon has been so successful with this, like we don't want agreement, we want conflict.

Like this is part of who we are and they clearly attract personalities for whom that is like motivating and galvanizing in a way that's really good. Uh, I don't have the world's most like healthy relationship with Ger. And so like I default to wanting, I do my best work and I'm able to make mistakes in a very productive way if I'm in an environment where the people around me, assuming I don't make like a ridiculous mistake, trust that I had good intentions and they're willing to like talk to me about.

What went wrong? How do we fix it? And I go fix it. And like things are good. And I think that assumption of positive intent and that assumption of like, we're gonna figure this out together is the environment that I react really well to. So I try to create that. . And like if someone is like, I really want a lot of conflict, like they probably shouldn't come work for me.

But I think something that we did really well at Windsurf, and this was like semi accidental, is rather than creating an organization where there was like inherent conflict, and again, Amazon is an example of one that did that intentionally and was super successful. What I tried to do was find people that led different organizations, whether that was like post-sales or deployed engineering or partners who were 80% aligned on almost everything we were doing.

Like I want the foundation to be, we agree on most of how to do this, and then that 20% is debate and that's fine as long as there is this like general. Affinity and trust where like, you know that at a fundamental level, everyone in the room with you is part of solving this problem, or building this machine has your back, wants the same thing.

Is it gonna like Empire Build to try to step on your shows or play political games? And I think by having that comradery at the top level, not only were we able to solve problems, like one of the things I used to say at Windsurf, and we haven't had to do this yet, a parallel, but I would say I don't ever, like, I don't ever want a debate or a conflict between my directs to come to me, because if it does, I will intentionally make a decision that's designed to annoy both of you.

I will just like try to find the exact middle.

Um, but generally speaking, my expectation is that like we're all adults, we can put our egos aside and that, like the right answer is pretty apparent. And in two years there were only two things that got escalated to me. And in both cases it was just like silly, like the ego

Brett: Interpersonal.

Graham: just like, like people's egos got ped, but like, we like sat down and I was like, guys, if you like.

Put your egos back in your backpacks and like take a breath. Is the answer to this question actually hard? Yeah. And in both cases we sat there for a second and they were like, no, I got it. And I don't actually think in either case we anyone said out loud what the answer was because it was very obvious and they just went and did it.

Um, and I think that that is super important. So like by creating that ethos though at the top, it then meant to the point of like companies mimicking founders values, it meant that the teams saw that the leaders got along well. Mm. And so for the most part it was like just natural, like people bumping into each other.

But I think by having that like ethos of an assumption of we are all in this together, we're gonna build together. And that doesn't mean you don't call things out when someone's not. Like if someone falls below a standard, call it out, but ideally do it one-on-one. . Like if you choose to do it in a room, to me that's performative.

That's not actually being a good peer, being a good partner, being a good leader. Like that's, that's a conversation where you pull someone aside and you're like, Hey, not at all trying to blow you up or come down your street, but like, I'm observing either you doing this or like, what I'm feeling is your team is dropping the ball here and we've seen it a couple of times and here are the specific examples and here's why I feel this way.

Um, and I think it is a lot easier to move fast when you're not looking over your shoulder.

Brett: What do you think the downsides or tradeoffs that you're making to behave in this way and, and create an organization that behaves in this way? If.

Graham: I mean, man, now I, because I, you know, like the two other examples I have is I was in org, I was in an organization that was really high performing, uh, so combative. . So like a bunch of people from New York and Boston. Um, and I think the negative side was that you could get into meetings that were like just 20 minutes of people yelling at each other that had nothing to do with soften the problem.

And it just became like egos. Um, but in a lot of cases, some of the most, like ignatious difficult people that I've worked with were often a right, and b thought in different ways, and so would get frustrated and vocal because they had this like, different way of thinking about things. It was really valuable and it is probably good to like, inject in a conversation.

Um, and I don't like, you know, again, I I

Brett: You're saying you can lose that if there's

Graham: too much agreement harm it. Yeah. Yeah. And so I think you, like, ideally you try to find that person who is still able to be, uh, you know, the stick in the, the stick in the mud or whatever. Uh, but for the most part can do so in a congenial way because also, like I am someone that will try to call stuff out, but I generally try to do it in like a playful seeming way.

But I think that's a risk, like if you default too much. 'cause there's also like agreeable, fake agreeable and there's like agreeable, aligned, agreeable. . And so I think I like, generally I joke that.

Brett: Fake agreeable is you're agreeing for the sake of agreeing even if you don't agree or it's something else,

Graham: I mean, I think in the, uh, is it ruinous empathy, but like, I'm not, if I gonna say this Yes. Fucking people just like saying yes for the sake of avoiding conflict. Yeah. And like, that's not ideal. But for me, the way that you have the most productive flavor of conflict is if you have built a foundation of trust so that conflict isn't threatening.

Like ideally, if you have people that foundationally like, and trust and care about each other, that actually creates a platform, right. For productive conflict.

I think in enablement, if one of the things, and this is like crunchier than I was planning to get, but like I think one of the things that like some pieces of America is missing right now is that a lot of cultures that have really strong identities have like natural cultural touchstones.

So like whether it's like a bar mitzvah or quinceanera, there's like shared experiences that people have that like bond a group over a shared identity or a shared thing. And I think that's actually where enablement's really powerful.

Where if, and like, I'll, I'll give a Mongo example, but like at, if you have bootcamp, everyone goes through three to four weeks of like onboarding, online training, and then you get to bootcamp.

And you take it seriously. It was like you dial in, like you take a test coming in, there's winners, like it's competitive, it's fun, it's fun to make you better. But this is like an opport,

Brett: A test like that.

Graham: uh, what we would do. The Mongo one was more intense at Windsor if it was like, not quite this intense, but it was literally just like, Hey, over the last four weeks you've worked through these training modules and now we're gonna give you like a, in some cases multiple choice.

In some cases fill in the blanks. But it's like 20 questions. It was meant to take like 30 minutes, but just to make sure that you've absorbed it, that you weren't like watching TV and doing laundry and just had it on in the background. . And it's just like, we want to make sure that as a foundation for doing, for investing a week in bootcamp, that you have absorbed the information that we were hoping you would to make this valuable.

And so, like really the intent is just did you do the free work? Um, but it was a way to make sure that the reap would be valuable. And then you go through, like, there's competitions and that range from like trivia games, just like stuff that is meant to create, to force recall at the end of a long day or like, uh.

Mock discovery calls and you'd do 'em in front of the room and people would rate it. And like it was just a way to like both like build a reputation and make friends and like build this community. But across, you do once a month across 12 cohorts of people, like everyone. Years later, ATMs would be like, oh, well what bootcamp class were you in?

And it was like, oh, I was with like Matt McClennan, who's now the CEO of Augment, or Graham Siemens, who's now the CRO at XII. And like it became this thing that oriented everyone because it would be like, oh, like did you guys do this training? And they were like, oh no, we had scraped that by the time I was there, but like they'd introduced this one.

And it becomes this common cultural touchstone that also becomes a really big source of pride for people about like who they came up with and like how hard it was. And it just becomes this rallying point. And it also sets the tone early that like being excellent and being elite is A, an expectation.

Also be can be really fun Like I think right now in AI especially, there is this like glorification of misery where people are like, we work 11 hours a day, 500 days a week. And you're like, uh, okay. Um, and I didn't read the part of the book that said that you can't have fun and like at every, whether it is music or art or sports teams, like most of the greatest examples of all of those were people that appeared to be having a pretty good time doing it.

And I think that that is like an important thing.

And if you talk about like instantiating an idea in a culture, enablement is the best way to do that early. And then like the way that you make that an ongoing part of pride is great.

Brett: Do you think enablement's changing a lot with sort of the type of knowledge a seller can have at their finger, uh, fingertips?, do you think you run the risk of if you don't actually learn it? There's a certain feel and taste and judgment. Um, instantiated in a person when you're actually going through training, that if you're just relying on an lm, give less.

Graham: Depends on the kind of sales you're doing. I think if you're out there selling like a basic application, it's probably fine. Also, those are the sales jobs that are gonna get AIed. Yeah. Um, I think if you're doing like real enterprise sales though, it's really hard.

There's not like an LLM that can tell me about organizational change management and like, I, like, I just, my, a lot of my favorite customers, but also my scar tissue comes from like financial services and then insurance companies. A lot of what you're navigating in those organizations is political. .

And there's not an LLM that can tell you that now. Like, do I, do I see, not even do I think, do I see sellers that have information at their fingertips, like abdicate the responsibility to understand that. Yes. And where that kills 'em is in person.

Because on a zoom call, you can have, right. The little AI bot that's like slinging you information.

Right. Um, but those are the people that you have to like, send into a rocket and shoot into the field because they won't go willingly.

I also think this goes back to just base hiring, where if you're not hiring someone who is naturally curious and like, wants to be good 'cause they want to be good, not because you're making them then you run that risk. But I also think that that goes back to like, who you let in the door matters a lot because if you're not, uh, creating, you're not cooking with the right ingredients, no amount of knife work is gonna change that.and so I think yes, there's a huge risk that on the one hand

though, I think.

What I'm seeing with AI and like again, parallel, most AI advanced organization I've worked with and Danny McCabe showed up two weeks ago and like already is like all the way in on being able to figure out how AI can not just enable ourselves in live conversations, but also from like a practicing and enablement perspective.

Yeah, yeah. You can do a lot more. So I think the cool thing about AI in enablement is it actually allows you to have like to go significantly deeper on your own. So by the time you get in a room with other people, you can be much

Brett: In terms of like simulation and all that kind of stuff?

Graham: Simulation like the, the ability rather than like single shot calls to mimic complex situations, even if it's not in like a simulated conversation, but you're like having a conversation with a bot that is like forcing you to like string concepts together and to connect ideas.

And we're just like, the synapses that are firing are more complex and different. And like if you're trying to like build myin and like create the underlying nerve matter that allows you to build skills like complex movements is how you do that. . And like transitions are a really important part of that.

And so I think that that is a really cool part of AI enablement. But yeah, totally. If you're gonna let people hide behind a computer and just read snippets of like other conversations that sound smart. Yes. Dun. Like I would recommend you not let those people go on site. Yeah.

Brett: What are the other things in this bucket of enablement in your mind? If you're operating at a world class level?

Graham: When we were selling MongoDB, we effectively had to know the database industry.

And that was kind of it. Like I had to be able to talk about different relational databases. I had to be able to talk about the like different no SQL databases that were out there.

But I didn't really have to be able to talk about like big data systems or like anything to do with Kafka or anything to do with Kubernetes.

It was like pretty confined to that industry. And I think now if you really want to be elite, because not only are you selling against direct competitors, you're selling against implied competitors. Like you have to actually have a pretty good grasp.

Brett: interesting.

Graham: like you have to have a pretty good grasp on not just your competitors, but like the entire infrastructure layer, the app layer, right?

A bunch of stuff that like is a little bit of everything and like not, 'cause not only are people saying, okay, like why can't I do this with Claude? Or why can't I do this with GPT?

But like every company on earth that was an app company, like tried to crash into developer tools to avoid getting obliterated.

And so now like randomly people will be like, what about this company? And I'm like, did they even have something in this space? Like Google it? And I'm like, oh, they do.

You have to be able to clarify and simplify for customers why things matter. 'cause people will come in and be like, all right, we're doing this with Claw and this with GPT and like we have, you know, cognition for this cursor for this.

Yeah. We have like 15 other dev tools. Notion has started doing a bunch of stuff that is like not necessarily what was in their initial remit, how do I tie this together? And like, I think the hardest thing for sellers, A, you have to be able to speak about it intelligently because if you can't, you don't even earn the opportunity to simplify.

So like you do actually have to be able to play ball across all of these different products and be able to have a coherent narrative and a coherent opinion. But I actually think one of the things that the best sellers and the best organizations do is help to clarify things.

Brett: In sort of the top bucket of driving predictable revenue? What are kind of the input drivers to excellence there?

Graham: I mean in a, like take people out of it because I think that's like the big one, but from a process perspective, it's okay, you're gonna go do pipeline generation, uh, we call that stage zero targeting. So it's like, hey, these are the companies that we're trying to engage. And a company can only be in targeting if it has been actioned on, reached out to in the trailing five business days.

Reason that we're so strict about that is we wanna see from the time that we engage and there's two buckets. There's leads, there's like people that came inbound and there's people that we're proactively reaching out to. Yeah. We wanna see how much time does it take in each of those buckets to get to a first meeting.

And then from a first meeting, we have a set of qualification criteria. First meeting goes into use case evaluation. So if the meeting goes well, we're like, yep, there's something here. We're gonna have a larger conversation. We're gonna move into use case evaluation meeting doesn't, that doesn't go well.

If it's not the right fit right now, might push that towards self-serve, might push it towards a drip campaign, might disqualify for the time being. There's a number of reasons you could do that. Then use case evaluation, could be two conversations, it could be 20. Just depends on the organization, depends on who you're talking to and where you have to get.

Then you have a POV initiation conversation that is, hey, this is all the stuff that we've talked about, everything we've covered. Do you agree that we're gonna go take this hill together? Yes. Great. Moving into evaluators, move into a value or move into scope. That is clearly measurable criteria that we're gonna go test against.

We all agree that if we do these tests and achieve these results that we're gonna purchase, go have a conversation with the executive. And at each of those stages, we're looking at conversion rates. So you're instrumenting the entire process. So it's like, all right, we know that in cold outreach takes us three weeks to get a first meeting.

We know that 40% of first meetings convert into use case evaluation for US qualified pipeline QP is starting at scope. So once you get to scope, we expect the close rate to be 60% or greater. So we know 50% of use case evaluation conversations move into scope. We know that 60% of deals in scope close and like you're instrumenting each stage of this pipeline.

So what should happen over a quarter or two is you are able to create a heat map of from. A warm lead or an outbound prospect through close. This is the amount of time it takes. This is our conversion rate. And then suddenly you have a map of all the things that you can go coach to that allows, shows you all the leverage you can pull, and so you develop a baseline for the company.

You look at AI native, you look at enterprise, and then you look at individual reps and you can effectively show someone like, this is the company baseline, this is the baseline for your segment, and then this is where you are relative to that. And that should make coaching conversations like pretty non-confrontational.

It's just data-driven.

By having this heat map, you're able to basically take the entire revenue cycle and demystify it so that at any given time, a, there's like maximum accountability on me. Like I can never say I have no idea why something is happening because at any given time I have a heat map that I know have to go look at.

And the same is true of post-sale because like honestly, especially, especially it feels like right now an AI companies aren't doing three years. They're not doing huge upfront commits. They're like dipping their toe in the water and then like just gradually consuming more. And so a lot of the work is done in post-sale.

Brett: Do you think that post sales should always roll up to the revenue leader?

Graham: Yes.

In general it is really important to have surprise clarity on like what the overall direction of the org is. And so like where I've seen there'd be struggles, I'm like, I, I worked at a company that, that had unbelievably good people, but we split the go-to market org into like three separate pillars.

And in theory, all of those people were equal. And the way that I used to describe it to people is it is like you took three people, spun them around for like two minutes and then tied their legs together and said, walk straight. Mm. Where everyone is just not intentional. There's not like any malice to it, but everyone is just like kind of leaning this way or leaning this way and there was just like all this tension.

And so generally speaking, I think you want to confine the greatest amount of direction, setting clarity to the smallest number of people possible, like generally speaking, not a fan of authoritarianism. I think in businesses it's actually really important where you need one person who is responsible for owning the strategy of go-to market.

And like for me that is like basically anything revenue generating or customer related ideally is under a single person. Now that person's obviously accountable to the founders and to the board and to all these other things, but like there should not be two people that the Gordon Market Organization looks at for direction because that's the only way that you can have the appropriate level of clarity and the appropriate level of ownership.

And I think post-sales is like an unbelievably critical function, but so is deployed engineering, so is sales and like you want post-sales to be a really clear mirror of the product and of the sales process back to sales and then also to engineering. And so it's super important, like we talked about with the cross-functional stuff earlier, to do the right type of enablement to make it so that people can communicate cross-functionally effectively.

. But ultimately if there's an organization that is responsible for the success of customers that have invested in us and for earning the right to expand beyond that, I don't see another way that I don't see who else I could report to. And I know there's a lot of other opinions on this, but like this specifically is something that I think all the other opinions are wrong.

Brett: Is your sense, it also just stops all the normal issues you have when, um, sort of a traditional sales org is throwing a, a signed op over to a success team and like accountability and ownership and like, are they jamming somebody in, into the funnel that is not gonna retain for whatever, you know, and all of those like subtle things that end up popping up.

Graham: I mean I'm, yes. So like, first of all, yes, I think having that go to a singular place, like creates the opportunity for clarity. I also think that this just goes back to like the people you hire, um, and like stuff happens. Yeah. Like someone is always gonna, there's gonna be a deal that blows up like that.

That's inevitable. I don't know that I've ever been somewhere that that didn't happen, but I think if you hire the right kind of person who is high ownership and like, I want reps to feel. Like a sense of like ownership and accountability to their customers. 'cause ideally you've made these people your friends, like .

If you have connected with what they care about, who they are, you like, have done the legwork to like build trust and to connect with them there. Like it shouldn't be an option to that seller . To hand off the account and be like, yeah, good luck with your life. Like I have sellers who I have pulled accounts from just because they were too busy.

Where it's like, Hey, you're covering three of the Fortune 10. Like I need you to just go like live there. So I'm gonna pull these other accounts back from you. But who still like, actively communicate with the people that they develop relationships with and like are telling the existing account team. But I think in like a healthy org, if you've hired the right kind of person, like it shouldn't just end there.

. Um, and I think another, and this is hard, this is not like an easy thing. Getting the swim lands right for sales and for post-sales is super important. And like I am.

Brett: Given the way that you describe the type of sellers that you want in your org Yeah. Which is, um, smart, curious, customer first, customer obsessed.Why do you think that sales commissions make sense?

Graham: I think the sales commissions make sense because it's, well, it makes sense. Maybe. I think you're looking for people that are really competitive and I think you're looking for people, not in all cases, like they're, I know some amazing sellers who like, who grew up very privileged and I, but ironically everyone has this, a different flavor of the same chip.

So it's like either you grew up with not a lot or like in like varying versions of situations that like created a lot of adversity.

Brett: Yeah. Or you don't want to, you wanna prove that you're not a silver spoon kid or some other version of

Graham: or you're like the, the runt of the litter in a very like, talented family. And like I probably skew more that way. Like my parents grew up super blue collar, but like, I didn't necessarily, but I am from a family that is like really frighteningly accomplished.

And I was the athlete. I was like the one that was very obsessed with soccer while everyone else was at UChicago. Um. And so for me it's this like incredible drive to not be

Brett: I am smart enough.

Graham: Yeah. Like to do, to not be the loser of the family. Totally. Um, and I think that, that, I think that that personality profile, like if you're looking for, 'cause the other thing sales impact is so measurable on the business.

You can justify like a different sort of pay because you're able to say, Hey, like our margin is this total cost of servicing the business, like engineering infra all in is this. Yeah. And then like the rest of this we have that we can build a comp plan around. And like the reality is that if I can go write a comp plan that at the top tier, and like in AI right now, the top tier is like 30 x your OTE.

Like, you know, like I remember in the days where it was like, oh yeah, if you're doing like five XOT, that's like spectacular. And now quote is like 10 XOTE first accelerator tiers 20. Second is 30, and at that point that person has paid themselves back. . Paid themselves and like everyone else back so many times over.

Then I'm happy to give them that, that upside. Because the reality is that, like I've done this now, I've seen it recently. When you give people healthy accelerators, not only does it attract a different kind of rep, but like as much as everyone is driven, kind, compassionate, all this stuff, every poker game anyone has ever played, it gets a little bit more intense when there's money on the table.

. And I do think that even though you're hiring these people that embody all of these traits that I think exist with or without that carrot, uh, the competitive fire that comes up when you can like go make a life changing commission check or you're trying to compete to be number one and it's not just to be number one is really fun.

And like I have that I like to. Would go do the right thing for customers no matter what would go do the right thing for employees no matter what. Like I, I know in general, leadership is for you if you get more excited when other people make money than when you do. And like the best day of my career was when, uh, cognition acquired Windsurf.

And I like saw what the 200 people who for like 96 hours I had been having a panic attack that I failed we're making. Like that was the coolest moment of my entire life. It was unbelievable. Um, and I think if you don't have that perspective and like leadership probably isn't for you, but as much as I get fired up and like we're paying our commission checks, it's also really fun to like try to run up the score.

And I think that like the natural tendency to hire people that come from competitive backgrounds and it's not just sports. I think like the sports thing gets beaten to death and there are great sellers Mm, that play sports, but I also know great sellers that were like very good at music. . And had to like compete in

Brett: chess are all sorts of things,

Graham: mean, shape music, chess, acting. . Like theater is not, I've learned, not like Right. An easy thing to necessarily get the roles that you want to go get. And just like, I think anyone that did something that was based on passion and obsession, and that was inherently repetitive for long periods of time.

So you could string it all together in a game or in a play, like that's a good profile for sales.

Brett: Um, last couple things in, in the way in which companies are scaling right now and the environment is changing. When you think about leading the go-to-market org far, do you think you should be thinking and working on the business six months, 18 months? Like it feels like it could be anywhere from one to three years In the previous

Graham:

Yeah. so I'm gonna give you the, my current state today, and then like, I think how that evolves over the next few quarters right now, like, just getting in, it's observing, watching and trying to like, figure out what we're doing today, how we're doing it, what to, and then like, you boil, like you, you know, you boil the frog, right?

You don't wanna just come in and be like, here is all the process we will ever have at the same time, because people's heads would explode. So it's like, all right, we're gonna introduce a couple of like light concepts. Hey, we're gonna send, we call them w emails, like weekly emails to our customers that are just like project management recaps.

But it just helps us all stay aligned. We're gonna set a set of expectations for like, how we interact with customers and how we interact with each other. We're gonna like start to make certain things a requirement depending on where we are in the cycle, like little things. And then you introduce sales process and sales stages.

And then like, once the team is patterned into doing that, and like for operating a forecasting rhythm, like for a lot of people at these early stage companies who've never really had to forecast before. So like explaining how to do it, like how to create ranges, like how, and, and just saying, Hey, like this is gonna be messy for the first four to six weeks.

But like the goal is that in a quarter we haven't dialed in. Um, and setting expectations like, Hey, I don't, six weeks out I need to be within 5% of the forecast and like never down. Um, but once you have that pattern, and that's probably six months in where you have sales process, sales stages. You have the right level of inspection, like the reps know what to expect, the leaders know what they are expected to be digging into.

You have the funnel instrumentation that I talked about where everyone can see where they are relative to expectations, where the company is like all of this stuff. 'cause it's really only once you have absolute clarity about how people are expected to operate today, that you can or should spend a lot of time on the future.

So like let's say it space six months to build that level of like clarity, consistency, and the right amount of capacity. 'cause the other thing is like early stage companies, everyone is on fire. So like no matter how much you put great ideas in place, it's hard to, yeah, if someone's running 30 deals, like they're not gonna follow the sales process to, they can't.

So I think it's like getting that to a healthy state. And then once you do, like you as a leader, again, have to, but also should be in a place where you trust. You're enablement leader, your sales leaders, your deployed engineering leaders, like all these different people to like operate the business most of the time.

And like at that point, your focus should probably shift to still a lot of recruiting. Think 80% of the job of most very senior, like go-to-market leaders is, is still recruiting. And that will never change. Um, but then the rest of it is, okay, how do we evolve? What does this look like? What does the org look like?

Like hey, we built, I think you do have to build capacity models 12 months out. I know some people don't like that, but like I think if you don't have a bottoms up model for how you're going to build success, especially looking at like time to hire current ramp time, like

Brett: where you're working backwards from what.

Graham: correct. And like, and that can be from a revenue perspective or we can say, Hey, we actually think in the next six months.

Given some of the stuff we have coming on the product side, we're gonna flex and we're gonna hire way more on enterprise. Yeah. Like we have whatever, we have X, y, Z things coming. So we're gonna scale enterprise in preparation for this big release hitting in 90 days. Um, but I think you have to start looking at that because like back to the idea of like alignment cross-functionally.

It's like, all right, well what, what's coming on the product side? Uh, what are the expectations of the business? What are we seeing now that we can like, extrapolate out and make a reasonable bet on? Or maybe it's, hey, like we are at a scale of revenue where we have enough inputs to know that we have very specific plays in insurance and healthcare and in banking.

So maybe we start to experiment with verticalizing. Like, you don't do that mid-year. It's a great way to piss a bunch of people off and cause a bunch of chaos. But like, you start planning for that change 90 to 180 days out. So like, all right, at the turn of the year we're gonna verticalize. And like, if we're doing that, what are all the breaking changes?

What content do we have to create? Like what. Collateral do we have to spin up like field marketing teams that are specific to these different things and like, so you're going and putting all of that scaffolding in place while at the same time running at the back half of the year. And like I do think once you've built the foundation to start of the scale of the team, if you're not spending, uh, 70% of your time, like if not more, 70 to 80% of your time, three to six months out, then like I would then I would be curious to know what you're spending your time on.

Because certainly at Windsurf, like a huge amount of my time was spent on like, looking at the capacity model relative to product stuff, relative to like the, like how does that, what does legal have to go do if we do this? What is, how does customer success change? How does the deployed engineering team change?

And like beginning to put all of that stuff in place so that when you go to make the change, it's there. Like, the worst thing that can happen is you gotta make this big structural change team gets a bunch of whiplash and gets there and like. It's basically the FY Fest version of an org change. Um,

Brett: So, so then how does this ladder into, call it your six or nine months in, a business is starting to scale. You're maybe in the tens of millions in revenue.

What does like a normal week look like if you're really maximally productive in the seat?

Graham: so actually I think for me, what I found effective, like this is a sample size of one company, so I'll probably have a different answer to this over the next few years. But it just became like, what are the things that if I spend time on are the most force, force multiplicative? So like at Windsurf, which is where I have that context, it was the partner organization.

So like we made the decision to run a hundred percent of our revenue through partners. And so I spent a ton of time with my partner leader and his, his directs in front of. The systems integrators in front of the VARs, like building those relationships because being able to get non-linear revenue throughput as well as like services and all of this different stuff, like building the relationship, building the belief, figuring out what, like a Indian systems integrator, how, how are they going to incorporate our offering and like the services attached to that, into their existing AI playbook.

Like if you're working with like a head or WWT or some of the bigger US options, like what does that look like? How are we enabling their sellers? It's like going back to enablement. If you just like develop these relationships with people, show up, putting all hands and you're like, yeah, you go sell ai, it's great.

Like it's not gonna happen. So you have to invest a ton of time and resources and enablement and training and building relationships and being super intentional about going out and getting three to five wins that you can then go take internally to my team and internally to theirs and going and publicizing that.

And like for me, I knew that if I could get, if I could spend a ton of time with our partners and they leaned in with us, so like that from a revenue perspective. Was more nonlinear than almost anything I could do with an individual seller here. Likewise, uh, enablement. So like we were hiring, you know, 10, well, like 10 people a week, so you're looking at like 40, 50 person classes of bootcamp.

And so it's like, okay, well that'd better be dialed in. Like if we're looking at what is the ramp data from the last six months and had like, and now with 50 people going through a bootcamp class, pulling ramp forward by a week is meaningful. And so like, how do we like pull apart what we've done before, like figure out where to tune the knobs, knowing that it's gonna take us six months to see if it worked and go and like do that again.

And so for me it became what is the most forced multiplicative place as I can spend my time. And I'll try to spend probably 50% of my time total in those two or three. Then as we've heard, big alignment guy, uh, I spend a lot of time in one-on-ones. I probably spend two to three full days a week, even at like max output.

On one-on-ones. And like some of that is scheduled and a lot of it too. And like my wife is a saint for putting up with this, but like my team knows that I'm available pretty much all the time. And so like the worst thing is I put blocks on my calendar for gym and the smart people have figured out that I'm available then.

And so I will just

Brett: While working out.

Graham: yeah, they're like, oh gram's at the gym. He's not on a scheduled call. So I'd get like 30 calls while I was at the gym and I'd come home and my wife would be like, how's your workout? And I'd be like, I didn't do it. I paced around outside for two hours and then gave up and came home.

Um, but I think that's important. Like again, I think if you're gonna spend your time on something that's force multiplicative for like the impact of the field is really great. That's a good use of time. Same thing with being cross-functional. Like I would spend a lot of time with peers or with like different groups that were meant to support the overall revenue infrastructure.

'cause I knew if that broke, especially as we got bigger, the like immediate impact of that across a hundred sellers is really high. Um, but also like you don't ever want to be, and not that this is preventable at a certain scale, but like, you don't for as long as possible, you don't want to be a leader who's just like out there in the clouds.

Brett: Yeah, you wanna stay close to work?

Graham: Yeah. Like you wanna be someone that like will just pick up and like call a rep that either is like doing really good work on a deal or that, you know, is like fighting the good fight on a renewal. That's tough. Like, how are you being intentional about like, oh, all right. Like I should probably go call this person and like, check in with them, see how they're doing.

Or like, call this person running this big cycle for us and see if they want me to fly out. But like, putting in the legwork, I think to create the right culture, like has hugely multiplicative benefits if like you do it correctly and you've hired the people around you who are doing the same, because you kind of have like concentric circles of people that think that way.

Like you end up having something that is like supportive and fun and dynamic and challenging and hopefully like really lucrative. Great. But even more importantly, like. Give someone a network and a set of skills that they can take with them for the rest of their career. . Um, and like never gonna be a doctor, never gonna be a lawyer.

But for me, if I can like be a part of building revenue organizations that can like materially change people's lives, like that's cool.

Brett: That's a good place to end. Thank you so much. This was great. I really enjoyed it. Thank you for spending the time.

Graham: of course.