התמלול המלא של Zig-zag your way across GTM roles | Chapman Swaine, Ashby

some of the what what first of all, what role were you doing? What role did you move into and what were some of the motivations there? Chapman Swaine: Yeah, for sure. maybe just quickly before I joined Slack, I had actually applied for a role at the company I was at that was going to be kind of working with and leading frontline salespeople. And I didn't get the job, and some of the advice that I was given was go get time and see selling to customers because it's a pretty irreplaceable skill and irreplaceable experience. There's no way to pretend what it feels like to be negotiating or getting to the the end of a deal or going through discovery. So That's kind of what led me to Slack. and I joined as an account executive or account manager at the time. And then we, as we grew, I found myself in enterprise sales and really enjoyed it. But definitely my favorite parts of the job was spending time in the product and helping customers understand the impact and the change that it was going to bring to their organization. And so yeah, I spent four years or so selling into enterprise companies with Slack. And I always took a very value-focused approach to the sales process. So really spending time understanding what made the company tick, what was important to them as a business, and then aligning the product to those things as opposed to showing off different feature sets and that sort of thing. So it was a really successful approach for me as a salesperson. And then there was an opportunity to build out the value consulting team at Slack. Which really felt like a dream roll with a lot of the different experience that I had had. and I spent about an hour and a half or sorry, an hour and a half, year and a half, building out that team and and figuring out the VC motion with that product, which was a ton of fun. Chris: Yeah, amazing. And a lot of SEs listening in will find it refreshing to hear a salesperson who was really focused on the value side of things. That's often something that, you know, as an SE you feel like you really need to push that into the deal. Chapman Swaine: For sure. Yeah, you're kind of pulling teeth sometimes. The question I always used to ask was, how does this company make money? And the number of times people wouldn't have a solid answer to that heading into a business case or the the end of a sales process was always a little surprising. So that's something I've tried to to influence as much as I can on any sales team I've been a part of. Chris: Yeah. Interesting. And so did you feel like beyond the sort of understanding of the b business value, was there anything else that you felt was transferable moving from that AE role into the value consulting role or like what did you feel was net new that you had to learn? Chapman Swaine: I think what was really transferable was like the empathy for the AE role and like what it was like to carry a quota and be the person that's kind of where the buck stops on a lot of these opportunities. Like it's a high pressure place to be. So that was really helpful. and just understanding what it was like for the partners that I was working with. But I also think the the business understanding of like how organizations work, how they make purchasing decisions, what often influences those types of decisions. has been was really helpful as a value consultant, of course. But as I was kind of standing up the SE function at Ashby, it really helped me think about how we would shape the nature of SEing with that particular product and that customer base. So really understanding what went into the purchasing process was key and how we oriented the way we showed the product off. Chris: Interesting. And I I love the point that you made around that empathy for the seller. I actually had another guest on the show who was in a sales role and then moved into solutions engineering afterwards and they said they had so much respect for the work that needs to go in to get that f first meeting. You know, sometimes an SE can be so dismissive around like, this is hardly qualified, why are we spending time on this? But actually doing a stint in sales, even if that's not where you end up, can be really helpful for for pre sales or SE. Chapman Swaine: Yeah, I I think so for sure. And I I think like the the best AEs that I've worked with, the empathy goes both ways and they understand like how much work it it takes to set a S E up for success as well and how important that early discovery is. So I think I don't know, throughout my career I found empathy to be a really important thing, kind of regardless of what side of the the table you're on. Chris: Yeah. So you start building out this value consulting team at Slack, and just to give everyone an idea sort of timeline wise, this was during the pandemic, right? So it was Slack was sort of red hot in terms of demand, this amazing company. And then you made the Chapman Swaine: Yeah. Chris: decision, like you said, to to to move to Ashby and back into a an IC role and a sales role. Like to talk us through how that came about and the motivations there. Chapman Swaine: Yeah, for sure. So after spending about a year and a half building out the VC team, I made the decision to leave Slack for personal reasons, burnout, however you want to describe it. and I actually went and did a coaching certification through the University of British Columbia and spent some time coaching people and and teams. I also got plugged into a number of different startups just helping with like go to market positioning, how to sell with value, how to bring that into the AE skill sets within their business. and then someone I've worked with at Slack and who I've become good friends with, Mike Clapson moved to Ashby and called me up about two months after he joined and said, Hey, like if you're interested in moving back into full-time work, we've got a great product with a great team and great customers. and I spoke to a few recruiters

and all of the things that I wanted in a job were there. Like I said, good people, good product, and customers that were excited. And so I joined when we were about 30 people. I was the second sales hire and was selling, you know, startup deals and working with founders. and then very quickly we found that kind of upmarket trajectory. And a lot of the skills that I honed at Slack became really, really relevant as we moved further further up market and started getting involved in more and more complicated purchasing decisions. Chris: Amazing. And and what did it feel like because you were at Slack, You were leading this team, you had gone down that leadership path. How did it feel moving back into an IC C role? Was that something that bothered you or you were looking to stay back on that track or t talk us through that a little bit? Chapman Swaine: Yeah, it's an interesting point because It's something I've gone through a couple of times now where I've made a a bit of a zag some people would think, when it comes to a a career decision. When I made the decision to leave Slack, when I made the decision to join Ashby, when I made the decision to move into building up the SE team at Ashby, I spent a lot of time working with a coach and like really making sure that the decisions I were was making were like rooted in my values and what I wanted out of my career. And so None of this was an unintentional stumble into a position. It was all quite thoughtful from my perspective and in what I was moving into. There's definitely an ego thing that shows up. that, wow, I've moved to a leadership position, into an IC position. And I think that's where that work was extra important, was to just make sure that when I was having those doubts, and I have them every day, I can look back at the work I did and the reasoning for it and feel good about that. And when that reasoning stops being true, that's when it's time to kind of reevaluate and think about what the next move should be. So definitely there's like ego things that show up there and it can be kind of a jarring transition. But I think as long as you're doing it with your eyes wide open and you're being thoughtful about that decision, it can it can be quite quite relieving in some ways and really opens some different doors that might end up in there. So yeah, I like I said, if it's an intentional decision, I don't see any issues with making that type of jump. Chris: Yeah, absolutely. And it's one of the things actually I found really refreshing, the AI labs have sort of set this standard or trend for doing away with titles or at least having these really ambiguous titles. You hear a lot of people like the famous example, CTO of Workday, move to Anthropic to be a member of technical staff. I had Krishma, you'll remember from Slack, was on the show actually talking about her experience and she moved from a leadership role back into an IC role there. And you know, sh her advice was really don't get hung up on the title, look at the role, look at the opportunity to learn and have impact. and Chapman Swaine: Yeah. Chris: I feel like that's something that maybe the industry is a bit more open to than historically. Chapman Swaine: Yeah, and I also think like having the right I've kind of said this already, but the right intention behind the move. Like when I moved from internal strategy and product management at a Canadian bank and jumped to an account manager role at Slack, I was doing that because there was a gap in the experience that I had that I wanted to be intentional about closing. Same sort of thing when I moved to value consulting, it was like the culmination of a whole bunch of stuff that I had done. And then when I moved to Ashby, it was wanting to get back to full time work. working with an incredible team, all that sort of stuff. So there's always intention behind those decisions. And I think as long as you're sure of that intention, you can't really go wrong. it's the kind of blind reactionary, like rage quit into a different role that I think can sometimes not go so well. But thankfully I haven't Chris: Yeah. And before we get into your current role, there was one other transition that I thought would be worthwhile covering. So you mentioned when you moved to Ashby, you started out in a in a sales role again, but then ultimately you built out the S E function there. Chapman Swaine: Yeah. Chris: Yeah, talk us through like how that came about. Chapman Swaine: Yeah, so I think what we started to recognize was the need for more technical, like deeper product knowledge in the sales cycle. And so w at Ashby we've always been really big on hiring highly technical account executives that can get into the product and know how things work and can can go deep. And we found as we started to scale up the AE team that there was like kind of a A speed run we could do if we were giving account executives better technical resources on the call. So rather than having them learn everything and be their own SE by layering in that resource, it it was really helpful. So I kind of raised my hand as we started to move out of the five to ten thousand dollar deals and into the like, you know, sub 100 grand, but still like pr pretty, pretty meaty deals. I raised my hand and said, like, I I can do this SE thing, it's how I I sell. I maybe underestimated the complexity a little bit as I jumped in. There was a lot to learn and a lot to refine, and many whiteboard sessions figuring out how do we talk about this product in an effective way. but it was one of those things where There was probably a lot of business need for it and then I had a skill set that I thought I could apply and bring a really solid perspective. and as we proved that out, we added in more and more SEs and kind of built the team up to seven or eight across the globe. all kind of Selling and approaching their interactions with a bit of a value lens, you know, a bit more of a like a business lens than

purely product and really trying to make sure we're connecting to what makes those businesses tick. So yeah, it was a strong business need, something I was interested in doing. I've really enjoyed building and figuring out. there's probably some people that would say I'm less good at the like operational scaling aspects. I get a lot of joy out of figuring things out for the first couple of times. Chris: Yeah. Yeah, interesting. That definitely seems to be a common theme. You mentioned building out the value consulting team at Slack and then building out solutions engineering. Funnily enough, I was listening to another podcast and it was about a a labs team in Google and they have even within the lab people that they feel are really good at zero to one, then one to ten and ten to a hundred. And yeah, yeah, Chapman Swaine: Yeah. Chris: it's people find their niche right and there's like a particular stage of development that people all gravitate towards. Chapman Swaine: Totally. And I even found, you know, I was at Slack from 200 to a couple of thousand. And the most fun phase for me was when we were small. And as an individual, I could have like a pretty big impact on the trajectory of things or the shape of projects or the way things that came together. And as you get bigger, it becomes harder and harder to have that impact. So for me personally, I like I love being in that stage where a couple of decisions or a change in process can really change the way that we're doing something in a super positive way. And it's Super fun now seeing a lot of the things that we did early days at Ashby kind of being cemented into the sales process. so it's been quite fun. Chris: Very cool. So let's fast forward now to your role at Ashby today. If you could give the audience just a an overview of sort of what that role involves and then maybe we'll get into how it came about. Chapman Swaine: Yeah, for sure. So mostly like right now, I think one of the ways you would probably call it is like a special projects role. So what are the things from the sales leadership perspective that we need to be working on or focused on? and I've been able to jump into a couple of those types of projects over the last year and a half or so. everything from enterprise messaging to surprise, surprise value selling to how we're leveraging AI in the sales process to general sales enablement. kind of been a bit of a a Swiss army knife on the different projects that are needed across the team. So my my boss now, Mike would probably has called me an expert generalist. And I think that that skill set is is pretty powerful when you can point it at important projects and and see what happens. Chris: Yeah. And I imagine with AI you already talked about applying AI to different parts of the business, but with that emerging the same sort of time, you moving into this role, it seems like the perfect sort of time. There's so much rethinking around how business processes work, how AI can be used to to to disrupt them and change them. Chapman Swaine: Totally. Yeah. And it it's interesting, like there I found a a real need for applying my own context experien and experience when leveraging AI. So it can be really powerful in as a kind of one person team building out something, you can have a lot of scale with it, but also just wanting to be aware of making sure that it's your own thing as well. So spending tons of time in the weeds on the topics that you're building things for to make sure you truly understand how and why it's gonna work. and then AI can be great at giving you the scale to support the rest of the team for sure. Chris: Yeah. And you had alluded to some of the projects that you've worked on in this role and it sounds like the role has a a a quite open or a fluid scope for other people who are thinking about a role like that. Is there anything you could share in terms of how is it that you define the projects that you you do work on? What what are the things at the top of mind or what's the process there? Chapman Swaine: Yeah, it's kind of been a mix of what I see within the business. So I think like in order to be in this role, it's been really important for me to have a ton of context on our product and our customers and our sales process. so I can kind of see some of the gaps or some of the areas that we might be able to put some time into and see an improvement. also being closely connected with the sales leadership has been really important. So if they're seeing numbers that aren't moving the way that they should, or there's things that we really want to zero in on. listening to them on what those types of projects would be. And then working closely with our VP in the same vein. Like just what are the things that we want to accomplish this year and what resources do we have to do it? our move into enterprise is a good example of that. So figuring out what does enterprise messaging look like? How do we bring the product into those sales cycles? you know, the the narrative that we need to kind of root the sales cycle in is a little bit different than it is in the lower mid-market. And so What does that sound like? How do we do it? What are the materials that we need to do it? How do we provide coaching in the right way so that sales reps are approaching these deals in a in a in a way that highlights business value, not just product capability? all that sort of stuff. So it's been it's nice to kind of have the freedom to be able to define some of those products, get or projects, get the the buy-in on it and then go and execute. Chris: Interesting. Yeah, it sounds really cross functional as well. I've experienced myself in that kind of role. You often get things that slightly fall between the gaps of product and product marketing and enablement. And Chapman Swaine: Big time. Chris: actually it takes a role like that that's a bit more fluid that can go in and and and and connect those dots and take on the work that maybe has

fallen through the gaps. Chapman Swaine: For sure. And I I think there's also like everyone has their day job. and you know that that can involve all kinds of different things that can reduce capacity or give less airtime for these types of types of projects that take a lot of focused thinking and focused work on. So it's been nice to be in a position where I'm trusted to do that and have the relationships across sales, product, marketing, product marketing to be able to kind of lean into it. so very fortunate and I think is definitely stemming from the the time I spent in seat doing this work and the success that I had in those seats. Chris: Yeah, interesting. So yeah, you mentioned that time and seat and trust and getting to know the business. I is there anything that you could share with the audience around how this role came about? It sounds like a role that was probably, you know, crafted and built around you and what you could add to the business, but like what what did that process look like and what were some of the prerequisites? Chapman Swaine: Yeah, for sure. So I I think like the career capital, for lack of a better phrase, like the the success that I had had and the the work that I had put in and the evidence of success, like like being able to point to things and say, hey, I've I've done this and it it's led to a positive impact. also like this kind of came about because of some personal changes with my family that I needed to make sure that I had capacity to deal with. And so kind of got to a point where the nature of the work I was doing wasn't fitting in with what I needed to have capacity for at home. And so we kind of sat down and thought, what can this role look like where I can still be having an impact at Ashby and lifting against important things, but also having the capacity to manage things with my family as well. And so again, very fortunate that there is willingness to do that. And I think the benefit is for myself, I've got really interesting projects to work on and interesting things to focus on. and for Ashby, not losing the like institutional knowledge and the the relationships and that sort of thing that I have. So it definitely is a unique position to be in and one that I'm I'm really grateful that I've been able to to take advantage of here. Cause I like I said at the start, I love the people and I love the product and I love the customers. So I'm I'm really grateful to be able to stay connected to that. Chris: Amazing. Yeah, and it's great that your work could be flexible around that schedule. It's one of the topics that's come up in other conversations, people that have really enjoyed the sales role or the pre sales role. But ultimately as, you know, changes come about in life, it can be quite difficult to fit around customer schedules. And so there are other roles within go Chapman Swaine: Yeah. Chris: to market or within the solutions engineering world that actually, you know, you can still stay involved within that, but you don't necessarily need to be beholden to customer schedules or or Chapman Swaine: Yeah. Chris: quite as much travel. Chapman Swaine: Well well, and I mentioned like how valuable earlier on, like I made a career decision to get the experience that I now have. And I think anyone who's sat in front of customers that has delivered the awkward demo and had to pivot midway through to figure out how to keep the audience engaged, that's been on the end of a tricky, like hard procurement call with someone who doesn't understand the product and is just pushing back on price. Like I said earlier, those are skills you Cannot fake, you only get them when you're in that seat. and there's a lot of people that have never been there. And that empathy and that understanding and the skills that you build from that is very transferable in these types of roles where you can bring that perspective and make sure that the projects are kind of that are being built for AEs or for the sales team are being shaped in a way that will resonate and actually lift. There was a joke at the company that I worked at before I went to Slack that the longer you've worked in home office, the easier it is to sell. And I think the more you can bring that perspective of what it's like to be in the hot seat to those projects, the better, which is kind of transitioning into the next role that I I'm probably gonna be moving into, which is more focused on go to market engineering and building things for the sales team. So Chris: amazing. Cool. B before we hop into that, I had one more question just around this rolecrafting side of things because you mentioned you needed to sort of earn the trust of the business, improve, you know, get some wins and success under your belt. I guess that makes it quite important the company that you choose, right? Because if you have a a a particular role like this in mind, then you're gonna need to join a company and be there for a little while before you can necessarily earn the right to craft it out. Did you have any thoughts on You know, as people are making that decision or maybe they're already at a company and they're trying to craft a role, you know, how they balance having the patience for building that process with knowing, you know, maybe that role crafting's not gonna happen, they have to step away. Chapman Swaine: Mm-hmm. So, just so I understand the question, like, what are you looking for when you're joining a company to see if this type of thing is possible? Yeah. Chris: Exactly, or e or even once you're within the company, it sounds like you you know, you need some patience, right, to get some Chapman Swaine: For sure. Chris: wins under your belt and earn that credibility before you're able to to craft that role. So for anyone sort of going through that process either choosing the company or if they're already in the company, is there any advice you would give to to them? Chapman Swaine: Yeah, I think Probably like being you

mentioned patience, and I think that that's something that's really important. I felt that when I was at Slack before the value consulting role came up, where I was kind of thinking, I could move into sales leadership, but that doesn't feel quite right. I could maybe be a pure S E, but that doesn't feel quite right at this juncture either. so kind of waiting for the right role to come up, but at the same time advocating for myself and having conversations with my direct manager and other leaders that I had build relationships with. around what I wanted to do and and what was important to me. there's a a mentor that I had when I worked at the company I was at before Slack MD, who basically said like don't if an opportunity opens up, be in a position to step through that door. so like gain the experience, gain the, you know, the the different yeah, gain the experience that you need to be able to take advantage of an opportunity when when one opens up. So that was Super important in the the Slack example. And I think for this one as well. And in this case, I was able to kind of make the opportunity because of the experiences that I had. So being patient, advocating for yourself. if you start to to feel like it's not going to be possible, then that's probably when it makes sense to start thinking about like what is it that I want out of my career? Can I find that at this company or can I, can I not? I also think the scale of the organization makes a big difference as well. Too small, and it's kind of like we need people who are doing the job or the jobs and and making things happen too big, and there just might not be kind of the willingness to have a generalist. Whereas if you're kind of in the right middle stage, which I think Ashby is at, is at now, where we're kind of still growing quite, quite quickly, but there's still that kind of flexibility to to be able to take a risk on this type of thing. And I I think that's what's really worked well for me. Chris: Yeah, interesting. Yeah, picking that company stage is is critical. I I had a another Chapman Swaine: Yeah. Chris: guest on the show, a lady called Saskia Van Daal. She's SE strategy and operations lead for Snowflake. And I always found that kind of role really interesting and Chapman Swaine: Yeah. Chris: and I sort of asked, like, well, how how does it come about? Like what kind of company has it? And she said, Yeah, the the company has to get to to a certain stage where, you know, the leader of the SE organization doesn't have the bandwidth to do the projects themselves. They could Chapman Swaine: Exactly. Chris: maybe farm it out to their reports, but they're stretch, particularly if it's a fast growth company, right? That's like so much of their work is going into hiring and building the team. And so this Chapman Swaine: Yeah. Chris: need emerges for a sort of chief of staff role or someone that can take on these projects or strategy work. Chapman Swaine: Yeah, totally. We're at the phase

now with our revenue operations team where we're hiding hiring strategy and ops folks in in the major functions and starting to build that out. And like that's probably a good signal that okay, we're starting to recognize that there's enough work for this type or or enough jobs for people to do for this type of work and starting to to prioritize it. but it's definitely like, yeah, too small and it's not recognized as a proper need, and and too big it's kind of established. So getting there at the right time, I think, is is important. Chris: Yeah. And you had mentioned a new role that you'll be moving into, some more of a sort of go to market engineering. I would love to hear anything about that that you're able to share. Chapman Swaine: Yeah, for sure. So I I think this is also kind of the culmination of a few different things. My experience having sold a product, having been in front of customers, having worked with AEs in all kinds of different capacities and kind of understanding what needs to happen there. my own kind of inclination towards leveraging AI when it comes to being as efficient as can as we can or or scaling things out. and so yeah, we're building out our go-to-market engineering team and starting to work more closely with that group to figure out. what that's gonna look like. How do we shape things? What should the architecture be? What are the different types of workflows we want to standardize versus allow for a lot of experimentation on? at what point do we call an experiment experimented upon and we're gonna formalize things? So we're kind of at the early days of of those conversations of figuring out how to make our our sales teams and our CS teams and our marketing teams as effective as possible. Tons of good experimentation has has gone on and we're kind of getting to the point where we want to start to formalize some of that. And so I think again, the nature of the work I'm doing now where I'm working three days a week and the nature of the type of work that needs to be done in that space kind of comes together really nicely for me and the skills and experiences that I've had. Chris: Interesting. I'm gonna need to pick your brain in about six months' time because I've had so many conversations with people on a similar topic and a lot of people, particularly SEs, they're interested in the go to market engineering role, but the job descriptions I see they're often biased more towards top of funnel and the marketing side of things and less about automation with the parts of the deal that an SE would be familiar with, which is where they're sort of excited. So I'm sure you'll bring a a really interesting perspective to those conversations given your background in in sales and pre sales and value. Chapman Swaine: Yeah, I mean one of the things, if I can go on a bit of a tangent here, but one of the things that we've really been working on is the the value framework that we use. And that is intended to connect like the high-level strategy of an organization down to the bundle of features that will actually support it. And so when you think of prospecting, you're probably focusing on identifying the strategy in an organization and what the hypothesis of how our product can actually help execute against that. But when you get into the middle of the deal, that's when you start thinking about how am I going to frame up this capability in the language of a VP and the language of an IC, and being able to translate between those different layers. And that's something that we've found a lot of success with with AI in in managing that translation between different stakeholders. I think every like value-minded SE has been on the discovery call that just zooms into what I call the vortex of despair, where we're just talking about feature after feature and click tracks and that sort of thing. and we wanna elevate it. And this can help you say, hey, I kind of have a sense of your your strategy as a business and there's these features you are interested in. What's the narrative that I would use with a VP or a CHRO to try to connect that strategy to the capabilities of our product? And I think that's something that's useful for SEs, for AEs, for value consultants, of course. Customer success managers as well as they're trying to make sure they're telling the right stories and and and crafting the right narratives if they're going into executive reviews and renewals and that type of thing. So that's one example of how I'm thinking about this, not just from prospecting at scale, but actual deal execution and how we're moving the needle on on the things that matter to our business with these types of tools. Chris: Yeah, it sounds super valuable. I know I I've lost count of the times I've seen a deck that starts out super high level and then immediately goes into very specific granular detail and there's that th that the connectivity or the sort of traceability between the two is is totally lost. So it sounds like it would be really valuable. Chapman Swaine: Yeah, for sure. And you want to get out of the like, do you think that button could change from, you know, yellow to red? And it's like, well, that but the color of that button doesn't matter. What matters is by clicking it, you're doing this thing that's allowing your team to be you know, capturing more market or launching products more quickly, that type of stuff. And I think, you know, whether I'm an account executive, an SE or a VC, like those are the stories I want to be telling. I don't want to be talking about how nice it is that you can be a little bit more efficient by using our tool. I wanna be talking about like the amazing things that are gonna happen for your business and the things that you're gonna be able to put in your resume as a user of our product as the adoption source. So yeah, anyway, bit of a soapbox there, but I that sort of stuff is what gets me excited day to day. Chris: Yeah, absolutely. It's very

interesting. So Chapman, I'd love to hear looking back over the the the entire arc of your career, and we've touched on a couple of things, the intentionality between the different moves, choosing the right sort of company in the right stage. But are there sort of two to three habits that you would attribute some of your success to? Chapman Swaine: I think for me, the coaching habit has been really helpful. So like working with a coach, whether that's on like broad existential career trajectory type of stuff, or I have a one-on-one tomorrow that I need to think about how I'm gonna approach it. And having somebody who can help me kind of keep that rooted in my own values and the things that are important to me has been really, really, really helpful. and I'm not just saying that because I also coach. I do think it's something that for me has been transformational. I also think like saying yes and figuring it out, especially in early stage companies, and I'm sure everyone that's been on your podcast has said this. There's so much wood to chop and being willing to say, Yep, I can figure that thing out, go and learn the thing, experiment, fail, figure out what's gonna work, and then share that with the rest of the team. that's the thing that that I like get out of bed for every day. Like I'm gonna approach this discovery call in a completely different way than I did yesterday, or we're gonna change the demo track completely for this particular customer and see what lands. that sort of experimentation I think is what what has allowed me to learn so much about what works with our customers or with customers in general. Chris: Yeah, interesting. I mean, you're right that a lot of people on the show have said saying yes to things. That is a very like common response. But the point around experimentation is quite interesting. I've not heard that one before. And is this this it sounds like these are sort of experiments that you are initiating yourself, not necessarily other parts of the business pushing on, but you're actually proactively thinking about how can I refine this pitch? How can I change the deal strategy on this one? Chapman Swaine: Yeah, and I I I there's a couple of very specific demos I can think of where we kind of got off after an hour and as an Ashby team, we're like, that didn't land. Like we missed the mark in a very big way on a high-stakes demo. What was it that caused that? And first off, being willing to admit that and be like, wow, that that was a stinker. What are we gonna do about it? But then spend the time of like analyzing it, thinking about how we could do things differently. I've had many afternoons with like our VP and a salesperson going through with a whiteboard and thinking about like how are we talking about this part of the product and connecting it to that product part of the product and then saying, Okay, great, we're gonna try this for the next three or four calls and we're gonna do a post mortem and see how it felt. and that type of iteration is what's led to a lot of the successful approaches that we've had. But also like never letting something be completely done and continually having those conversations to say, what could we do a little bit differently? How could we refine this? or another one, like as we enter a new market and we move up market, like things that resonated with a hundred person company aren't resonating with a five thousand person company. So what experiment should we run to figure out what does and and how do we frame that up? And that's what's kind of led us to the whole value selling approach again. yeah. Chris: I love it. It's it sounds very methodical. It's the sort of approach that you often see in product teams, but if I'm transparent, you don't often see it in in sales or go to market. You often get this is the collateral that's been given to you to product marketing and then this is a deck that I saved onto my laptop three years ago and I'm still presenting the same thing. So it's really refreshing to hear people that are sort of Chapman Swaine: Totally, yeah. Yeah. Chris: open to that idea of, yeah, continuously trying new things. Chapman Swaine: Yeah, totally. And the brand is three years old and it's the same deck of impresenting. I think, yeah, a willingness to experiment. It's funny. My dad, I did an MBA years ago and he my dad chided me for it and kind of said, The MB an MBA is just the scientific method for business. Like, have a hypothesis, figure out the experiment, test it and see what the results are. And I was You're not wrong, Dad. But anyway, it's been the MBA was helpful for me for another reason a number of reasons. But yeah, yeah, taking that scientific method and what is your hypothesis? How are we going to test it? What worked? And going from there. And I think the hypothesis thing is also important when you're working with customers as well. Like what's what do I think is going to work? And I'm going to validate it or get a different one from the customer and move on with that. Kind of shifting topics a little bit there, but I think it's a key, keep, key bit of experimentation and never being afraid to be told this doesn't work or you're wrong and this is a different approach to take. Chris: Yeah. Love it. And Chapman, people are gonna look at your career, they'll look at the roles you've had, they'll look at the companies that you've worked at, the growth that you've been through, and it all looks rosy. But I would love if you could share a challenge that maybe you've had in your career and what you learned from that. Chapman Swaine: Yeah, I think this is actually something that Ashby's been really intelligent about from the very start. But we actually have a core value or a operating principle around being frustratingly patient with hiring. And I think that that's really, really important. So spending time to get the right people. I was at one point the only solutions engineer supporting a goal global

team with, you know, probably a dozen different AEs. And there were times where It would have been very easy to just like hire anyone to come and help. And spending time to get the right people with good trajectory and the right skills and solid kind of alignment in in approach has been really, really powerful. even from something as simple as onboarding, taking, you know, two months instead of three with the right person, has a huge impact on. the success of the team. And so I think like taking the time to get hiring right is is definitely huge for me. I also think there's something around like the way that you internalize feedback and and how you're able to bounce back from it. So getting negative feedback can be devastating at times and letting it kind of wash over you, internalizing it, thinking about it, and then picking yourself up and continuing on. being really, really important. And I think like the story I just told around altering a whole demo structure because something didn't quite go right, it is really, really important. So I've definitely had times where I've gotten feedback and it's kind of crushed me. but being able to kind of work through it, take what's valid, ignore what's not. I've had another great mentor who used to say, sometimes you get feedback that you have green hair and you can look in the mirror and know you don't have green hair. And so really taking the time to I've doesn't work if you do have green hair, of course, but you know, taking the time to think about feedback and take what's valuable and let the rest of it kind of go has been really, really important for me to to figure out. And that's a skill that I'm still working on day to day. Chris: Yeah, yeah. I well I know they say feedback is a a gift. I really did not appreciate it until being self employed and starting my own business. And then suddenly you realise, wow, I used to have feedback on tap, right? Whether you liked it or not, you could quite easily get it. Chapman Swaine: Shoring. Chris: You would get it on a regular cadence, you could proactively ask for it. And there there's obviously still mechanisms to get it when you're on your own, but you do definitely Chapman Swaine: For sure. Chris: feel like, wow, I I I I didn't realise quite how lucky I was before being able to tap into that. Chapman Swaine: Yeah. I I also think like the the flip side of that feedback thing, like obviously getting feedback myself, but the other one is providing feedback, I think is is really important. So making sure that people you appreciate know that they're appreciated. so it's not left for them to guess about. also gives you more space for more challenging conversations, right? Like if you're kind of investing the time and building that relationship, that doesn't mean just like shower people with good feedback all the time so you can deliver them bad feedback, but Letting people know that they're appreciated. I think when you're in a leadership position, I talk to my

kids all the time about like casting magic spells on people by saying kind things to them. And it's the same thing with folks that are on your team. Like I know how great it feels to get good feedback. and that's something it's a a spell we can all cast day to day. and it goes a long way for making people feel good about the work they're doing. Chris: I love that. We definitely all need to be casting more spells. So the final final Chapman Swaine: Yeah, for sure. Chris: question I had, Chapman was you, as I said right right at the beginning, a lot of people in solutions engineering roles are considering a move into the sales side of things, but you've moved, you know, made that move either way a couple of times. Is there any advice that you would give to individuals who are maybe thinking about changing roles an SE that's thinking about moving into an AE role? and what your experience was like? Chapman Swaine: Yeah, for sure. I think Really spend time figuring out what you want from the change. So if it's, you know, God, I'm so stressed out carrying a quota and I just want to move into a role that doesn't have that aspect to it anymore, like that that's fine. But the stress is gonna come no matter what. And so if you haven't spent time understanding what it is you want out of your role, It it doesn't matter where you land, you you might still be kind of blindsided by the challenges that show up there. So being intentional about it. and also, you know, in the same way we're talking about, like have a hypothesis and and give it an experiment. pay attention to those things. Like, I'm making this role change because I want, you know, more autonomy, I want to spend more time with a product, and I I don't want to be involved in negotiation anymore. Or the flip side, right? I wanna be I want the stress of carrying a quota. I wanna be involved in negotiation, I want to build that muscle. Whatever intention you have behind that shift, keep keep checking in on that to make sure it's true when you actually make the change. So intention up front and then continuing to pay attention to it and see if those things are being satisfied by the new role that you're in. it's very easy, especially if you move into a sales role, to just like hit the ground running and kind of. deal with the ups and downs as they come and and not be thoughtful about it. But if you know what it is you want and how you're going approach it, checking in on that regularly will help you calibrate if it's the right choice or not. Chris: Yeah, I love that advice. And going back to the topic we talked about earlier on around AI and titles changing a lot. I mean a lot of people eye up a role that looks quite similar at say an AI native company, but actually the responsibilities are very different. They're just gravitating towards that 'cause it has the same title. And I Chapman Swaine: Yeah. Chris: definitely advise people to go like, Hey, just imagine the title wasn't there. You know, it's an interesting thought experiment of like just look through the job description and the responsibilities, Chapman Swaine: Totally. Chris: because ultimately that's the work that you're gonna be doing. Chapman Swaine: Yeah, for sure. Like solutions engineer anyway means four different five different things depending on the company you're talking to. Is it all pre-sale? Is it all post sale? are you writing SOWs? Are you not writing SOWs? Do you like writing SOWs? What's the RFP situation like? Like there's just so much actual work that happens day to day. And if you don't pay attention to what that work is, you might get a little surprised once you're you're feet on the ground doing the job. So again, being intentional about all that stuff, I think, is is really, really important. Chris: Yeah, amazing. Chapman, thank you so much for your time today. I've really enjoyed the conversation. Is there anything else you wanted to share with the audience before we we wrap? Chapman Swaine: No, I'm I'm super grateful for the opportunity to share my experience. Hopefully a person or two find it helpful and yeah, I'll look forward to checking in in six months to talk about how we're approaching the whole AI in the the middle of the sales cycle. Chris: Amazing. Sounds good. Thanks so much, Chapman. Bye bye. Chapman Swaine: Thank you, Chris. really appreciate it.