Voiceover: What does it take to stay ahead in B2B SaaS? Welcome to The New Go-To-Market Playbook. I'm your host, James Kaikis, Chief Revenue and Experience Officer at Testbox. In our interview series, I sit down with go-to-market operators, leaders, and industry experts who are defining the next era of go-to-market by winning in the margins. These leaders are focused on incremental innovations and non-obvious advantages that drive big results. The goal of this interview series is for you to take action in your business. So sit back, grab a notepad and enjoy the episode.

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James Kaikis: Josh, great to see you, man. 

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Josh Aranoff: Oh, James, good to be here. 

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James Kaikis: Yeah, I've been looking forward to this. So for most people who don't know, we've known each other for quite some time through PreSales Collective. And I brought this up to you earlier this year. When I first started at TestBox I said,  hey, I'm going to do this. I want to have you on. And unfortunately, it's taken me a little bit longer than I planned on it, but I'm just glad this is happening. 

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Josh Aranoff: Same, and thanks for having me on. We talked about this at an event. And we were like, hey, what do you think? Can we just get together, just shoot back and forth, see what's going on? And I was like, yeah, it sounds great. And so I'm glad we could finally make it happen. 

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James Kaikis: Me too. I think some of the best things about this series right now is You and I have talked throughout the years about these topics, and now just talking about it on camera, right? And being able to record it, have an interview, and let folks listen to take actionable

takeaways to be like, oh, this is what I need to do in my business. 

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Josh Aranoff: Putting it down for everyone to see. Yeah. And see how it goes. 

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James Kaikis: I think before we get there, though, we have to comment on the attire man. So for those who don't know, you are the most fashionable-- I don't even want to just say, like, solutions executive, 'cause it probably goes beyond that. But I texted you before I was like, what shoes are you wearing? What watch are you wearing? How are we coordinating?

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Josh Aranoff: I guess fair, we did coordinate. We coordinated. 

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James Kaikis: We talked about shoes, we talked about watches. 

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Josh Aranoff: We got matching watches today. The watch, we both prefer plastic right now. I think it's just where everything's going. And we both went with Nikes. We went with the Girl Dads, which I can appreciate. Little Travis Scott's for me. But either way, our wardrobes, I think are a little matchy-matchy today actually. 

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James Kaikis: You've got a little more flavor in there than I do. 

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Josh Aranoff: A little flare underneath, but it was like, I was trying to be aware of color patterns and things like that. I read all my notes.

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James Kaikis: I love it, I love it. So Josh, why don't you give a little introduction to yourself, like who are you, what's your role, responsibilities, and really how did you get to your current job?

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Josh Aranoff: Yeah, so I run SE: Solution Engineering at Procore, as Global Vice President. And that includes what we would call our standard core as the organization. We have a couple of other groups as well in there. One is we have our acceleration group. And so that is a lot of your standard like business value, our proposals teams, what some people would call an overlay or a specialist. Those groups are in there as well, as well as our proposals teams. And so all the groups that you might imagine and some you might not.  And it's interesting to balance that. We have also a small but growing group that's around tools. So we call that sales productivity in the world that I came from, which was Salesforce before Procore, that would be considered Q-Branch. Not quite to the size that we were at. And so that obviously means that before Procore, I was at Salesforce. Yeah. I did an 18-year tour at Salesforce. 

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James Kaikis: 18 years, wow. 

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Josh Aranoff:  And I'm on year five now now at Procore, so serial monogamist when it comes to companies. 

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James Kaikis: That's pretty incredible. I mean, 18 years at Salesforce, you've seen a lot of iterations. I'm curious, let's actually talk about go-to-market and software generally. What did you see change over those 18 years at Salesforce? Or was there like a specific something that stands out to you?

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Josh Aranoff:  I mean, there was a lot of moments over 18 years. It's hard to recall, so sometimes that can be, I don't know, like an event that you went to, you're like, oh, I recall the best parts, or the parts that I wanted to remember, but one of them was actually when I was doing enablement. I was doing enablement for SEs, and it got to this moment where we had gotten so far on what was SalesCloud at that time, like that one product  that really got you to where you were, and all of a sudden we couldn't do that anymore, And everyone knew that, but comp plans and the way things were, it was just a lot easier to sell that, especially when you talk about CRM, because that's what salespeople use and do. So it was just so innate. Whereas selling something like service or a platform, not only was it new, it was hard. So go with what you know. And I see that cycle happen at a lot of places. I mean, it happened at Procore, it happens at so many different companies where the product that got you there, is not the one that's gonna get you to where you need to be. So it was those moments of how do we enable people to talk about a platform? And I think the way that shifted is, SEs had to become much wider, right? And so they had to go much wider on all their product sets and not quite as deep. And that involved things like bringing in specialists, people who were deep, and then who were those folks? Were they the most experienced? Were they the folks you hired from the outside and that kind of evolved and then how do you sell to that? Is it your existing sales team? Do you need new sales people? So it really broke into a bunch of things but the team itself, they continued to evolve. So you had this idea of folks that were really good at getting deep in discovery that was more of the generalists and then folks that really wanted to go super deep on a product and those were your specialists. 

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James Kaikis: Yeah. I mean there's so many things I want to dig into that, but I love that answer and I appreciate that. And it's got me thinking because we're talking with executives like yourselves about changes that are happening and go-to-market. And one of the things that has come up in a couple of conversations is just the general tech blow that has existed over the last decade, right? Like software has just exploded. There's so many companies out there, and there's so many companies that are just point solutions. And I feel like, you know, in this market where, you know, do more with less or David from Gartner called it “do less with less,” is, you know, companies need to figure out how do they become a platform? How do they become more than just a point solution? And I think that goes with an evolution in thinking, not just from product, but go to market motions, which brings us to today. Do you have any thoughts on, you know, how Salesforce navigated that shift, beyond just the specialists and building those other teams that allowed the acceleration. Is there something that stood out to you that you emulated at Procore and you think more companies need to emulate now? 

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Josh Aranoff: Yeah, so there's a bunch of stuff. I mean, early Salesforce days, it was around this idea of academies, right? It was enablement. You really needed to actually teach people, so you couldn't fault folks for not doing it 'cause they didn't know, they weren't just hot. And so in some cases, this idea of like moving to a broader approach, if it's not working, you gotta wonder like where's the fault at? Like have these folks been taught? Now a lot of cases, software's evolved, SaaS has been around for 20 years, right? And so I think a lot of people have understood that motion better, so you have reps that come that have done this in the past, SEs that have come that have done this in the past, so it's gotten better. I think when I like fast forward to Procore, it's this idea of, hey, we were originally doing a lot of point and click demonstrations because there weren't as many offerings out there, right? There was a couple of big competitors, but in a lot of cases, easy to use, right? It was still like, that was what was gonna hammer it home. And that becomes less and less competitors catch up. Everyone becomes easy to use. So then you get attacked by the top, big competitors and the bottom, to your point, of point solutions. So then you have to think about what are the types of demonstrations that you want to do, and we categorize those into three types of things. One is the dreaded RFP demo, uh, credit Todd Janzen with that one. But that is like the bullet points lists of things to go shut up and show, right? So shut up and show me the demo and every SE watching this right now knows that like that is the one that we like the least. But in some cases, that's what you get. So we have to be aware that is part of it. And there's actually a lot of solutions out there today helping take it away from us. Which I love, and you can probably speak to that more than anybody. The second is the process-based demo. So we've gotten up the stack a little bit. We've understood enough to take out an entire workflow or an entire set of what one person's job might look like. And we can show that. And the third is the persona -based demonstration, and that's where you've really unlocked almost that C-level or close to, you know what the economic buyer's real challenge is, and you can actually show them current state, (dystopian, gray), and then future state, (bright sunshine and rainbows) version of what it looks like with, in the best case, your solution, maybe partners, right? Or maybe some other set of technology that actually helps and make sure is even that much stronger. 

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James Kaikis: Yeah I think that's one thing that I learned at Salesforce the most was being able to tell that compelling story, right? And the approach that Salesforce takes and ingrains in you and then once you leave Salesforce you go and do that same motion and story at your own organization. 

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Josh Aranoff: And I think that's that's proliferating across a lot of other companies that I think like whether your Salesforce started or it happened in a lot of cases at the same time, I think a lot more people are starting to see the power of that and it's hard because it's experiential, right? If you've never done one, you're like, I don't know. It just like kind of seems like dark art over there. You know, part of my journey at Salesforce is we had an innovation function and what we learned early on was you really had to bring people into the process in order for everyone to understand like, Okay, I get it. Because otherwise it just feels like that just seems like something somebody else should do but like I'm going to go back to what's comfortable. 

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James Kaikis: Yeah, this is really interesting and you bring up the word comfortable, right? And I think when I reflect back on my solutions career, I feel like I've been told that there's just, you know, this is the way of doing things. And I think I have not enjoyed that so much, right? I think that the solutions professional is capable of so much more. And so, you know, you obviously spent 18 years at Salesforce. You've been at Procore for five years. You're well known in this profession. You're at the top of the game there. Is there something that has stood out to you in terms of the evolution of the solutions engineering role?

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Josh Aranoff: So it's interesting. I think Salesforce was so big by the time that I left. And big is relative, right? Still medium and small to like companies like Coke or something like that. But when I was able to go to Procore, there was just a smaller set of folks who were able to have more of an outsized impact, potentially, especially in process. And not just in like the land of Solutions, but in others as well. And so some of the things that we had started at Salesforce, I was able to actually think, meet the team first where they're at and figure out what it would look like there. So one example, and this is this kind of common thing that you'll get is you'll go to a sales leader be like, how do you understand what's going out the deal? And it would, oh, I just call the SE, right? Incredible, right? It makes you feel good, right? But that also does not scale. In any way, shape, or form. And so what we tried to do was operate under this idea of how can we at scale give back a correct answer, or at least what our answer was, how we're feeling about the deal, to the sales team, to the organization, to the CEO, to the CRO, to whoever it was. We had done something like the Salesforce, but credit to Kyle Pennington who's on our team now, he really wanted to drive this idea of a deal score in the way that Procore does it, in the way that our SEs would really be able to digest it. And we needed a little bit of encouragement along the way. But the simple answer was we created a stoplight of red, yellow, and green of how we felt about the deal and then we gave folks some parameters of like how you would actually think about that. This may surprise you, but not all the sales leaders were on board right away. So you may understand the reasoning, right? It may seem obvious, but they thought that we were trying to own the forecast. And the reality is, is we were a confidence lever. Choose to use it or not. But there was a great story and if he's still around I'd love to give him some hell for it but he was saying like hey why don't you own like the technical win and we'll take the rest. And I think I asked on the call I was like are you trying to tell me to stay in my lane? And we had a good banter so it was done in jest. I'm not puffing my chest in any way shape or form like, we were good friends and he's like no no but his perception was we were trying to take over. Reality was we were just trying to help, but there wasn't a way where he could just say, like pick up the phone and call the SE. Now they could do it at scale. And the way we were able to take that further was, we got our CRO at the time on that message of legal, technical, political, commercial, and what's the deal score, right? And so that was great. Now, the downside of that is like as SEs, we were worried in some cases about would that reflect poorly on an AE? Right, and the message has to be, it's not about the AE at all. Prosecute the deal and how you think about that and that alone and don't get caught up in the rest and let's just see where it goes. And so, the one thing you had to be careful of is yellow. Yellow is right in the middle, yellow is death valley. And that's what we found a lot. And so we just have a big push towards the end of a month or a quarter to move either on to red or on to green. With clear parameters on what that means. So they have a way to dig in their heels.

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James Kaikis: I love this topic, right? Like this is, I think you are the most well versed solutions professional when it comes to forecasting, right? And playing a role. And I really appreciate that you talked about how you got sales buy-in in that situation, but a lot of times where when I've talked about this topic I'm getting pushed back from the solutions team. So how did you handle that to be like, hey we're gonna play a role in forecasting and here's why it matters? 

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Josh Aranoff: Yeah, some of it was literally they hadn't been a part of it. So it was like, I don't know what I'm missing. In some cases this was a way for them to give their voice and the amount of times I've heard people say, like, we just need to seat at the table. And in some cases, people were pushing back against this. I was like, no, no, no, this is what, like everybody's trying to get to. Yeah, this is what everybody wants. So like, if other groups could hear you say that, they would switch places in an instant. But what it did is it not only gave like me a spot inside of the forecast, but all the managers. Because I can't own and and be responsible or memorize all those so now they came on and in a lot of cases they were able to articulate what was going on and then there all of a sudden a few managers started taking you a little bit further. Yeah, so we'd get to an end of a quarter  and let's say you want to start thinking about what else could we pull into the quarter? Now they're starting to look at deals that are outside of the quarter, but mark deal score green Yeah, because when the screen, you win, right? The other side of is that they're looking at in the quarter, marked as red. So I, 'cause we do win red deals, but like we lose a lot too. So now, if we can take a look at what are the deals that we're probably gonna lose or might lose or push, and which are the ones that we think we have a good shot of winning. It was just another way to actually work in partnership with sales, because everyone that says it's easy, like go spend a day in their shoes, like it is tough work being an AE and it's tough work being a leader too.

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James Kaikis: Yeah, yeah, I love that you just thought about partnership with sales, right? Because I think too many times, solutions professionals don't have enough empathy for the sales org. You just said this, right? And as someone who now owns a number, wow, the immense pressure that comes with owning a number, forecasting and trying to find predictability of the business is insane, right? And as solutions professionals, we're typically insulated from that. We don't have to see and feel that pain. We don't know what it's like to know that we might lose our job if we don't, you know, predict things accurately. And so I'm really glad that you've given that level of accountability to your team. But going back to that word partnership, how has that changed the partnership between solutions and sales?

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Josh Aranoff: I mean, for us, because we show up inside of the forecast, it puts more and more almost pressure on like, it can't just be a score. Like, we're going to check it and we think that if it's green, it will actually fuddle into things like our analytics, right? Our predictability models where, hey, I'm not going to ever compensate an SE on how accurate they are because if I ever do that, then if this idea of is it green because we're winning or winning because it's green, right? We'll wait. We'll wait to know until the very end. So we can't ever do that. So for those watching at home, like you can't ever compensate on this, on this metric, but it's important for SEs to understand that. Now, the byproduct of that was when our sales leader was out on deals, who was left running the forecast? 

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James Kaiksi: You were. 

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Josh Aranoff: I was running the forecast. 

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James Kaikis: I was so excited to talk about this. Like that's incredible. You were running forecast.

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Josh Aranoff:  Yeah, and it started to become a little more common but the first time I remember this happened we're all the call and we're like we're waiting for the sales leader to jump on and like oh, no I've got it this week and I remember there was just like this weird pause. And they were like really? I was like, yeah. They're like why you it's like why not? Yeah, I love no I love that and I took a lot of what I had learned and I was able to use some of that phraseology, that part, but I had my own spin on it too. And it's not to say that that sales leader wouldn't come back and ask their own questions. But it was really interesting and it got people into a different type of motion. So mine was different than sales and probably a little bit of that off and on give and take, have an egg, whatever you want to call it, was good for the team, right? Because they were focused on pieces of what, what I would ask or what sales either would ask each time. It was a ton of fun. And that was like a great learning in itself and like getting comfortable in doing that and being able to free flow a little bit. You find out, a sales either sometimes they don't, they may know, they think they know where they're going to go. And then all of a sudden they hear something and they're like, nope, I'm going to deviate here. Cause I feel like this may be the problem. 

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James Kaikis: Yeah. I love that you've got that experience and I wish that more solutions professionals could get that experience because you just feel a different weight. You start asking different questions and you bring that solutions curious mindset in a different approach to business predictability. What I'm curious about though, is as we continue to talk about building the relationship, one of the things that I have always felt like for myself is I've always been a more business savvy solutions engineer, solutions consultant, right? I can get technical where I need to, but I'm never gonna get hands on the keyboard. But that has allowed me to do well in my career in partnering with sales. And I think that it depends on the organization, depends on the product where you might need someone more technical or more biz savvy. But at the same time, what we've talked about at PreSales Collective is the sliding scale of technical. So do you feel like the team owning a portion of forecast has allowed them to become more biz savvy and to be more strategic partners to the sales executives, which at the end of the day, de-risks a deal? 

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Josh Aranoff: I think it is de-risking a deal. And I think, you know, I think part of where you're going to is, I'm actually seeing new hybrid roles in other companies. And I, I don't even know how to call what the Brangelina version of this is going to be, right? But there's this idea of like an overlay sales team, an overlay SE team. And I think what companies are starting to do now, in a lot of cases, they're like, it's one. Because it's a super expensive model.

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James Kaikis: It is. It's very expensive. 

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Josh Aranoff: So, like, is it the SE that starts to become more commercial, right? Like understand the commercials of the deal, or is it the traditional AE that becomes more technical. And I get a lot of cases, products are not getting easier to use, right? They're getting harder and they're getting more complex and things like AI brings a whole different level of complexity. So people that have a technical background tend to find an easier fit in some of these types of roles. The question is, are they ready to take on the bag?

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James Kaikis: Right, which is a big question that you gotta answer yourself, right? 

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Josh Aranoff: And then I think the other piece of that is how far down the line, like where does the roll and the line blend between like pre and post sale? And those are like two of the big things. If you allow me a little bit of the rant. 

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James Kaikis: I was gonna ask you to dig in a little bit. So let's go. 

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Josh Aranoff:  And I think we have some similar views on this. 

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James Kaikis: We do.

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Josh Aranoff:  Some of this probably will like, I'm like, did I say it here, did you say it? But like the idea of like SaaS of like SaaS, it's been around for 20 plus years, right? And I think when it first started, it was this new motion. And the people who were buying it, regardless of who it was, they needed a lot of help. They needed help with the relationship side, navigating. But now those same folks have implemented five, 10 sets of software, at least, right? SaaS is two decades old. And what they need from the types of people after a deal is sold, is more of a consultant. And I think this is where this kind of, what is the CSM and the SE? Those two roles, similar to this technical sales colliding, so is the SE and the CSM role colliding. And more and more, what I'm finding with customers and hearing is that they're like great, but like how do I do this inside of the product? Like yeah, I know I get it. 

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James Kaikis: Yeah, okay. light bulb rant time for both of us right because if you think about how expensive the model is right traditionally it doesn't make a lot of sense And if we think about how software has happened over the last you know decade two decades like we've talked about I tend to get rid of pre- and post-sales, right? I think sales exist forever right there in its pre and post signature is what we call it internally. But you have to deliver value constantly. Constantly, and you always have to deliver value. And my problem with traditional customer success orgs, and I don't mean this disrespectfully to any people because you talk about functions generally, is that they haven’t been enabled or equipped with all of the answers to handle things with the customers in that moment of time. And so when they become like information gatherers and go find the right person to solve, it comes extremely inefficient. And so when you think about, you know, whether it's a customer solution manager, if you keep the CSM or a solution consultant within those dedicated install base, you need to be able to deliver product value, you know, adoption/utilization value and meet the customer where they are in that moment. Unlike, you know, let me get back to you and it's one week, two weeks. It's just that lack of sense of urgency in the information passer, I just don't think it has a place in go-to-market moving forward. 

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Josh Aranoff: Yeah, it's tough because it's where we are right now. We had to be careful. We don't get on this bashing route of sales or CS because all the functions are needed. But I think what the customer needs right now is this level of we're in this time where technology is getting deeper and deeper and deeper and they need people to show them actually how to use the product. So I don't think that the folks are bad to your point. I think that the roles are changing now and like the expectations of the customer is what's causing that. 

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James Kaikis: Yeah, I was going to actually ask you what caused that. So expectation of the customer. So tell me about that a little bit more. Like what does that actually mean to you and why is that causing that shift? 

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Josh Aranoff: Yeah, well part of it is again, customers are more enabled than they've ever been before. They go to your website, they talk to other customers like they know your pricing equal or is better than you do in some cases and know exactly how to pressure point you. We used to joke at Salesforce that we've taught our customers how to buy in the worst ways. 

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James Kaikis: 100%, Salesforce did a lot of that.

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Josh Aranoff: Find the end of quarters and I think they've done a really good job of reversing a lot of that, so kudos. But at the same time, they have so many expectations and it doesn't stop, to your point. It continues through that so the expectation is you're going to be there not only right then when you're showing it, but that what you've shown is going to carry through and this puts a different level of pressure and emphasis on presales. Because I will say if you want to throw stones at ourselves we have been guilty of potentially just showing a few things to get things across the line and chucking it over the fence to our brothers and sisters. And that hasn't been fair either. So I think, you know, when we hold the mirror up in ourselves, those are some of the things that we have to take a good look at. How far do we push things? And this is, goes back to customer expectations and saying, Hey, look, we can show you what our product is now, or we can blast you to the moon. We want to be a partner, but we also need to understand, like, where are you in this kind of evolution or this journey? Cause If you're way over here, we have some ways to look at that. And if you're way back here, we have some things to look at. Either way is okay, but we want to make sure that we're giving you the right experience that you need. And so that's kind of how I frame it. 

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James Kaikis: Yeah, I really like the framing, and you're right. We've already talked about the AE/SCs, you know, converging, I know a number of solutions engineers that are moving to account executive roles within their business. They're going to have to learn a little bit different function, but they're going to be very dangerous with the product and value and telling customer stories. But when you talk about SC and CSM, very similar type journey, but I've seen some CSMs make them move to Solutions Consulting, and I've seen some orgs actually scale down and pare down their CSM model and invest in SC. Now my thought process, and you've used this word a couple times is it's all about the enablement. Again, it’s no fault of anyone in a function because you've been told this is your job, this is your description. These are the things that you do. These are things you don't do. But the reality is is like that's not always aligned to what the customer wants and what the customer needs. And I think organizations need to make more of an emphasis on enabling their current team because they've got domain knowledge. They've got industry knowledge. Let's turn some of those people (if they want to be part of that journey) and turn them into a more value-oriented resource for the customer. 

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Josh Aranoff: So what makes this even more tricky is that in a time where everyone's trying to be very smart about every single hire, enablement is looked at in an organization in a lot of cases that is not direct revenue impact. But I look at it as, I will literally give a headcount because I think for every one headcount that I give, 10 or so, SEs, I may feel that level of impact. Because they're getting trained specifically on a certain number of things. I'm focused on just a core set of elements, which is around like onboarding, soft skills, technical training. Like those three things, if we just do that on a rinse and repeat level, we'll be great. I also think that everything is one degree from compensation. So, and I think that that's a fair thing. People do what they're paid to do, right? We become forensic accountants with accountants when it comes to our compliance. It is just truth. And so, I think that to the point of how do you get these groups to align, the folks that are traditional presales, they need to have some adoption metrics. And I feel like the folks that are traditional post sales, they need to have some revenue metrics. And if you incent people to do that, who wins is the customer. And that's where we just need to make sure we don't get lost. That's all we're doing this for. 

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James Kaikis: Yeah, I love that. And you know, I've shared that I think both revenue and customer success are everybody's job, right? It's part of the company-wide mantra. I think the enablement conversation goes back to, anyone who's just passing information, I've worked with enablement teams that are just information passers, right? And they're not strategic partners because the sales leader or the ops leader in charge is not viewing them that way and deploying them that way. And more companies need to use that as a strategic resource that is helping gain efficiency within a company. I cannot see why that isn't a really prominent path for more solutions professionals. I know a couple of solutions leaders who actually have taken on enablement in the last six months and it's because they're product experts, they're customer story experts, they're value experts.

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Josh Aranoff: Yep, I don't really care where it lives, but I love for the folks to come out of my organization. I love that to be a path where either they're gonna go full time or they're gonna be a path where they go there and then come back for a bit as well. The other types of people that I think work really well in there are consultants. Whether you're in IT, whether you come from consulting, because they actually know how to dig through problems and they're used to being in unfamiliar territory. So they can be a little bit of a chameleon and almost act as if for a long enough period where the group accepts them and then they're kind of off to the races. But it gives them a path in.

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Josh Kaikis: I like that. I wanna come back to one thing that you highlighted and that is a very important topic is incentive striving behavior. Right? And so, you know, in terms of the traditional pre-sale, post-sale, right? I like what you mentioned on adoption. I actually talked to an organization who's copying their sales team on go live and launch and the commission's not paid until after go-live and launch. Do you have an opinion on that? 

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Josh Aranoff: That is putting your money where your mouth is right there.

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James Kaikis: It is, yeah. I was surprised. 

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Josh Aranoff: So if value and adoption is the new ROI, then I think that that's great. I think it's really tough to make a change like that in mid-stroke. I think if you start there, it's a great way to enter. I think it's really tough to try to make that shift unless you are making a ton of other shifts in your go-to-market motion at the same time. That said, I would love for there to be bigger kickers on like being able to get people adopting and actually measuring that adoption and then driving better incentive around cross-sell and needing high usage customers and that's where higher bonus incentives and structures come in. 

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James Kaikis: One of the things that I feel like I've had an evolving point of view on is how we comp solutions engineers and solutions consultants because, you know, I've talked to so many people, including myself, some of my own impetus of PSC is like my account executive or accounts like my team partnered with made four, five, six times the amount of money. And so, you know, I think about if there are ways for solutions to make more money, it's carrying a bag, it's carrying a quota, it's having more accountability in these other places that we wouldn't traditionally give them as part of their role, but that's where additional revenue comes from. And that's where I think the shift in roles and responsibilities ultimately plays out. 

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Josh Aranoff: I probably would have said, yeah, I'm going way down this path, right? Towards this like 50/50 type model, 'cause most reps are 50/50 model. Most SE organizations are still 70/30, some 60/40. Vertical SaaS has given me a whole new perspective. In a lot of cases, especially like we're talking about for Procore, we try to find folks that have been working in construction on the job site. So they are not used to incentive comp plan in a lot of cases. So a 70/30 plan all of a sudden is also just like a whoa big shift. Now you apply that to like anything in medical or in some financial cases where they're used to just a salary. And this idea of a split incentive program, much less 60/40, that's a tough one to swallow. But as I think people get more comfortable and more ingrained in this idea of what the rule is and how much impact they can have, I think that they will want to opt for that in a lot of cases. And I almost want, I love this idea of creating positions that generate more risk but generate more reward. 

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James Kaikis: Love it. Nailed it right there right. And this is what I'd love to see more in this next wave of SaaS is a little bit more risk-taking, you know. Creation of types of roles that are trying something because what I want to talk to you about is you kind of nailed it when it comes to change management within a big organization. I have been talking about things for the last couple years through PreSales Collective and now TestBox about shifts and go to market. And one of the reasons why I wanted to go back to tech is I wanted to put my money where my mouth was. I wanted to not pontificate at PSC about all these things. I wanted to go lead from the front and try to build these work structures. It's a lot easier for me to do this as we've built this company, rebuilt from the ground up. And if you look at series C or A or B, it's a lot easier to make these shifts. It's a lot harder for you to make those types of shifts. So how do you think about making that type of seismic shifts within a big organization because obviously you have to want to take on some risks at the same time you need to make sure it's going to work before you change the entire organization. 

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Josh Aranoff:  Yeah now are you talking about make the comp plan types of shifts? 

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James Kaikis: Any of these shifts, right? It's role mergers, it's comp plans it's any of these big shifts that we're talking about yeah that we're seeing across the micro like how are you gonna do that at a big company like yours? 

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Josh Aranoff: Yeah, so some ways are a little bit easier because when your company goes through a big shift, that's like a way that you can hop on board, right? So if you scale in smaller companies to larger companies, then you typically go from these big global models into a couple of different areas, right? You go into regional based models or vertical based structures or GM based structures. And if you're gonna make these big types of shifts, that's where you can actually do new role creation, new comp plan creation. The other thing is, and like sometimes this is not the greatest thing, but in role consolidation, right? So when you are consolidating, if you are a big company and you have gone through some tough times, some of these consolidations can also be potential great opportunities for folks where they have been doing a ton. Maybe they haven't been recognized in the way that they thought. You can create roles in that situation that actually encourage more risk and more reward. Sometimes you didn't realize how hard it was until you actually carried the bag. One of the things that we actually did in our last SE summit, we had a global summit, it was a global hybrid, so we had groups together in different countries and different parts of the world. But we had almost an internal career fair and it was this idea of people that had left the company, gone into sales and other elements, got into a product and we asked them to come back and be like, "Tell us how it was." 

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James Kaikis: Really? 

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Josh Aranoff: Yeah, and it was great. 

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James Kaikis: What were some of the learnings from that? 

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Josh Aranoff: Well, some folks that had left the company, they were like, "Hey."Pretty good. It's pretty good over there. There's some special elements that are going on and there's some cool things like when you leave the nest as well. There were some other ones that are going to sales and we've been really fortunate people that have left and gone to sales. Yeah, did really well. So they are great people to emulate. But they also gave us some things of, by the way, it is so much harder than you think. And the end of month, end of order pressures are real. And then going over to product and also just showing that is a career path. That's important. So many different elements that can that can help and so I thought that was a really cool way to show hey there are all types of ways that you can go in your career yeah not necessarily a bad choice and I just wanted everyone to know you can stay here. There’s a home and a path here as well. And so as we go into that like I said big growth opportunities, consolidation opportunities, those are the elements that create the opportunity to to create that type of change. The only other element that I would say is like, if you can, and if you're in a position to, depending on your budget and the way you allocate funds, try to create areas where you can experiments, where you've created opportunity to try new things. So we didn't have this idea of like a tools or a productivity team or demo engineering and kind of just created it one time and just used some of the headcount to do that. And the dream wasn’t realized for a little while. And now we're looking at what used to take us days to create environments, it can take us now minutes or hours. So like those things, you have to take a chance on too to kind of create those new opportunities. 

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James Kaikis: Yeah, so much goodness in that, right? I wanna talk about two different things. The first one is risk, right? A lot of times in solutions, folks are not always wanting to take on the risk, right? So what kind of advice can you give people watching and listening to this to think about risk in their business? Like how should they approach risk on if that's not their general DNA? 

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Josh Aranoff: It's tough. It's like, I almost think it was the risk factor in your life right now that typically translates to your work, right? And so when people are staring down the barrel of a couple of different opportunities, I think one of the big things to be real about yourself is like what is your level of risk that's acceptable right now, right? and How much do you think that you can go out and capture that and if you believe and you want to bet all on yourself and not to say that if you don't you're not saying that right right that's bad or you're bad. But but take that on because especially depending on where you are in your career a lot of people have the flexibility If you don't, just be real with yourself. And it's not to mean that you're gonna take a back seat or you're slowing down in your career, but just be honest about what the risk is like for you, what that means potentially you or your family, if you have kids, significant others, like everyone's in a different spot. Some people are caregivers. So like, I never judge anyone based on that because I don't know what's going on inside of their lives. But if they're capable and they want to, I encourage it. Because it's more of the-- I think it's you're listening for a couple different things. I'm not sure it's the right time in my life. I got that signal. But if I'm not sure I'm capable of doing it, that's just I'm a little scared and I need a little bit of shove. 

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James Kaikis: Yeah, totally. You need a little shove. And I would say-- I love that response in that when people ask me if I was crazy to leave Salesforce to start Slack channel. I think about what's the worst thing could have happened. I could have built my network. I could have made friends. I could have met people when, you know, maybe I didn't make as much money, but I would have, you know, potentially got a better job coming out of that, right? And that was a big personal risk, right? And if I think about company risk, you know, I've reshifted TestBox a couple of times and it's like, what is the downside that happens here? Evaluating evaluating that downside and that risk and knowing where you can turn the dials is an important part of actioning risk.

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Josh Aranoff: I think what you just said actually highlights a couple of things. One of which is people will in some way, shape, or form always emulate their leader. And if they see someone like you, who's leading go to market, taking risks, they're gonna feel like it's okay to take risks. Avery kind of silly story in my opinion, but it was one of just like personal risk taking of, I was doing an interview like this where I was sitting on that seat and I was doing an interview with an executive. And I remember at one point, nervous, and I was trying to make sure I asked the right questions and iPads in here. And I went like this 'cause I was nervous. And all of a sudden like the chat started lighting up and I was like, oh God, I don't know what I said, like, what did I do? It was the shoes that I was wearing. And it had nothing to do with what I said. And so, like, in my mind, I had taken this risk. But what people were commenting on were the shoes. And the funny byproduct was, is that they're like, I can't believe that you were sneakers interviewing an executive. And I was like, OK, if that allows you to do anything more with, like, bringing yourself, than like amazing. 

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James Kaikis: Yeah, I love that story, that's awesome. And you are so fashionable with the sneakers. I mean, it's a conversational starter, and nonetheless, right?

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Josh Aranoff: Yeah, I know, I'm all gonna get a little self-conscious and they get people like, if that is the only offer, the only thing that I bring to the table is could choose that I'm in trouble. - 

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James Kaikis: That's definitely not the truth. So I wanna close Josh talking about risk-taking and you in risk-taking, right? Again, I've really appreciated getting to know you the last couple of years and appreciate all that you've done for me and in my career and helping guide me in the right direction. One of the things that I'm very curious about is if you would ever move to a sales role or take on sales functionality because I've had a couple of guests on this interview series that were former solutions leaders that have now either owned a number or taken on sales or taken on other parts of the business And not to say that you're not just an incredible SE leader, but I could definitely see you in that role. So have you thought about that? Like how do you think about risk in taking that type of role? 

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Josh Aranoff: Yeah, it's funny. I'm probably more risk averse at home than I am at work. Asked me to choose from three things out of menu and we'd still be sitting here 45 minutes into the conversation, I wouldn't know. But at risk at work, I think that I have much more risk in me. And so I've always thought of myself as a business leader and not a solutions leader necessarily or anything. I'm just wanna do what is best for the business. I would take on that role. I would take on almost any role that the business really thought that they could see me leading well. So sales, yeah. Product, sure. Go to market, yeah. Like I just get excited about that idea of thinking through like, how do we make this group, like, even better than what it is now, or how do we change, or how do we shift, or how do we consolidate, whatever it might be. Like, I'm up for the challenge. That's what kind of gets my blood going. Like, you can like, just see, get excited talking about it. I'm ready, I'm up for it, but at the same time, God, do we have the greatest job in the world. So, I go in with like, sure, but at the same time, being an SE leader, I think is one of the best jobs. You get such a purview in this beautiful nexus between product and enablement and marketing and sales and sometimes you don't even realize all the impact and influence that you have. And so, like I said, depending on your risk level, I think people should go for it, but at the same time, you should always consider of having a happy home in solutions. 

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James Kaikis: I love it, yeah, happy home and solutions. It's the best job no one's ever heard of. I think more people know about it now, which is great. One thing I want to highlight though is, I think for you, having a mentality is the most important aspect, but as solutions professional and business professional, like you said, you've got exposures so many different places in the business that you could be like, you know what, I can go there and I'm gonna bring out a solutions, problem -solving mindset, a certain mentality of solving problems and getting things done. And I think that's why you'd be wildly successful wherever you ended up.

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Josh Aranoff: Well, I appreciate the vote of confidence. Hard to accept a compliment, but I'm going to just to say thank you and go on my way. 

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James Kaikis: Absolutely. Josh, it's been such a pleasure talking to you, man. And I really appreciate your time. Appreciate the way you conduct yourself and you're continuing to push the solutions profession for waird. It's inspiring. 

‍Josh Aranoff: No, I appreciate it. - Thank you for having me. If there’s anything else that I can be of service of, like a good SE, let me know.