Ep # 144: The Evolving Role of AI in Sales & Revenue ft. Ryan Milligan (VP, QuotaPath)

Adil Saleh 0:02 Hey, greetings, everybody. This is Adil from Hyperengage podcast. And, you know, it was long time coming. We are absolutely chasing GTM leaders like the one we have today and the companies that are making a huge impact in the SaaS world. I know that as a lot has changed since we last spoke to a GTM leader, like six months back, I'm talking about a lot has changed when it comes to AI, these language models, lot of new technologies coming in and making a very swift impact into the sales and success organizing. You know, support was pretty much done, and that's it ever since the conversational AI came in a year and a half back. So today we are talking to the chief, sorry, the VP of sales, marketing and revenue of QuotaPath. It's, it's a SaaS platform. Been there for about five years, more than five years now it's around seven years, helping sales organization with managing their quotas commission for the for the SDRs, you know, VDRs, account executives, even account managers, for the very long time. Thank you very much, Ryan, for taking the time a Ryan Milligan 1:07 Adil. Thank you for having me. I'm really excited, looking forward to this. Adil Saleh 1:11 Likewise. So Ryan, I was like, this was a big noise that was happening in the past. Like, first off, like, a lot of this, the sales organization, a lot of these, you know, lower tier roles. Talking about SDRs and BDRs has been a lot of people say, like, it's been replaced. A lot of them, a lot of these companies in, you know, doing serving the mid market, SMB in mid market, they're thinking that, hey, we can do more with less. We have, like, these AI tools. We can do like a lot of customers, research has been automated. A lot of agentic AI, like CO pilots, they're coming into play. How do you see it as a leader for your own team? Ryan Milligan 1:46 Yeah. So I think the mistake that a lot of people are making with their interpretation of AI is using it as a human replacement. I think about AI much more as a human augmentation than a replacement. And really the way that I think about it is at every stage in our go to market process, where are there places in which humans are doing work that humans are not uniquely talented at, and how can you use AI to fill those gaps and automate those processes so that humans can jump in The loop and spend more time doing except they're uniquely skilled to do so that for us is everywhere from outbound prospecting to managing deals and pipeline to navigating implementations. We're looking at the places in which we can inject AI into those processes to take the work that is less unique for a human to do, and that AI is really, really well suited to so on the outbound process, you know, using tools like clay and smart lead to build lists of warm audiences that we can reach out to through email to former admins, former reps, former users of our product, closed, lost ops, What have you. And like taking that SDR function and having SDRs focus much more on like high value creation work than sending a bunch of emails, for example, on the new business side of the house, it's a lot of stuff with crm management. You know, how can you use AI, a tool like momentum, which we use now to automatically fill out next steps and feel form fills and fields in CRM around bands and qualification, so that the human can spend more time demoing the product and multi threading and deriving value. So the way I tend to think about it is look at every place in the process where humans are doing work that they're not uniquely positioned to do, and leverage AI to do that work, so that the human can do stuff they're particularly good at. Adil Saleh 3:45 Absolutely. So it's, it's more about, like, high value tasks and prioritizing tasks, using AI to prioritize. And, you know, have the next section be like, customer research, be it like, you know, looping through different CRM context and updating CRMs. A lot of this, lot of tools that are building agents for this, and a lot of this is going to be transformed. So now, looking at COVID, I know that you've been, you've been there for more than three and a half years now, leading the sales organization. Like, how did all shape? And you know when? You bet, you know when you started, and did you replace some other VP of sales. It was the first VP of sale that they hired. Ryan Milligan 4:24 Yeah, so I have a funny story here. So I was, I've been a rev ops leader my entire career, marketing ops, rev ops and analytics for like, my past 15 years. And when I joined QuotaPath about three and a half years ago, I was hired in a director of Rev ops role, and I led the rev ops team, and kind of moved up and moved and joined our management team in more of an operations leader capacity. And then we had a leader of sales and service who decided to go more into full time consulting. And we had a gap in sales. Leadership, and I raised my hand to take on the role. And so I took on leading sales about a year and a half ago, and then marketing about six months ago. And my argument was, hey, I know this product really well. I know the customer and the pain points that customers facing quite well, because I calculate and pay commissions in QuotaPath, I can bring a lot of the operational rigor of a sales process and math of a sales process to pair with incredibly talented reps who have the more of the Art of the Deal skill set, and so I talk about this a lot on LinkedIn, but you know, I really do think that you're going to see more rev ops leaders wanting to step into these CRO positions because they're able to look at revenue across the entire organization versus just focusing on new business, and are looking for profitable, efficient, sustainable growth in orgs in a way that somebody who comes up through the sales org might be kind of biased towards being a CRO in The same way they've led their sales team before. Adil Saleh 6:02 Gotcha. And now, circling back to, you know, the vision of QuotaPath, I'm pretty much you guys are pretty vocal. By the way. I follow you guys on LinkedIn a lot, and you talk about a lot about the success metrics and the north star that you get to work with, with the customer starting off. And then you work around, around the product and make sure that gets served using QuotaPath. So could you tell us a little bit about, about a discovery part of of the initial sales process internally at QuotaPath, I know that it's pretty, you know, it's, it's more like, it's more like an art, not a science, like you, you're not like building it's not like one size fits all. So you gotta make sure that you, you know, you work through the success metrics and North Star, let's say a lot of companies, they most of the companies, they talk about Net Revenue retention and, you know, contract retention, or multi contract retentions. So tell us more about, like, how this all drives, especially on the deals that are most likely on the mid size to enterprise. Ryan Milligan 7:00 Yeah, it's really interesting. So, so I think historically, a compensation plan has often been this kind of after the fact byproduct thing that sits in the background, that after a rep finishes the quarter, they close all their deals, then Okay, now it's time to do the math to see how much they earned. And that's a fundamentally flawed order, because if the comp plan is not in front of the rep and driving their behavior, it's not working in real time, right? Reps are just throwing deals against the wall and seeing what sticks and trying to hit their quota. Our fundamental thesis is that your compensation plan is the best tool you have to drive your sellers, marketers, account managers, BDRs, what have you to deliver more of the right revenue for your business. And that is it's funny, like when you say it out loud, people are like, Yeah, that makes sense. But then when I talk to leaders about their actual comp plans. So many of them have these comp plans that, like, don't motivate the right behaviors. BDRs are motivated to demo more pipeline, but that pipeline is in high quality, so it churns at a really high rate. And like, the comp plans aren't working together to, like, drive the shit forward. And so in our discovery, I do a lot of free kind of compensation plan consulting in our sales process, the first question that I ask is, what one metric does this business really have to move this year? You mentioned net revenue retention? Others are, hey, we're moving into the enterprise. We have to double our average contract value, or we have this new product that we have to sell, and you figure out what that metric is, and then you say, Okay, how do all of these comp plans across marketing leader, BDR, rep, account manager, Solutions Engineer, how are they all motivating these individual team members to deliver more revenue that meets the needs of that metric. And so that's it's reshaping the comp plan from being this after the fact thing to being something that sits in front of a account executive and tells them, hey, you have these 10 deals. Go close these two because they're gonna earn you a higher commission rate more money because they're better for the business. And that's a win win for the org entirely. Adil Saleh 9:24 And basically it is the source of motivation for a lot of these folks, and to have, you know, clarity around, around the commissions upfront, and make sure, like they're absolutely motive, because in sales, I know it's not, it's not a primary reason a lot of these folks, they actually try to generate a lot of a lot of money, like income, you know, it's more like an income driven as well, especially for account executives and sdrb roles. So now, thinking about QuotaPath, I know that you integrate with a lot of workflows like this is something that you, you guys have done very early. So what kind of things that you think there's still maybe some. Um, CRM. A lot of these companies, New Age companies, in the first, like, four years, pre product market fit, they're trying to adopt some new technologies. A lot of CRMs, like Salesforce, lot of HubSpot customers. They're, like, actually getting rid of Salesforce. So how do you see this, the change in the tech stack and integration part within the sales organization for QuotaPath as a product. Ryan Milligan 10:23 Yeah. So in terms of how we integrate and what we're thinking a lot about, there are three kind of, like primary integration sources we think a lot about. One is, how do we pull data in on a deal level, or some sort of unit level to calculate commissions off of. That's a lot of standard CRMs, but you're also seeing a lot of orgs, especially in usage based pricing models, track that in data warehouses, or track that in billing systems. So there's a lot of different ways in which data enters QuotaPath to determine a record and calculate the commissions off of that record. Then a lot of orgs are starting to, especially in usage based models, operate with this concept of, like, payouts, eligibility. Hey, you closed it. You know, in the old SaaS model, you close a deal, it's 100k deal, you're gonna earn 10% about 100k deal, I'll pay you 10 grand. Right now, the problem is, with usage based models, you might think this isn't 100k customer, but they may end up being a 10k customer or a 300k customer, and you need to watch how that customer adopts the product over time to pay commission. So I spend a lot of time with orgs talking about usage based pricing and how to join in the invoicing system, like an invoicing tool, an ERP, what have you to actually unlock the commissions and tie the CRM, which is projected revenue, with the invoicing or billing system, which is actual revenue, and so we pull those both into QuotaPath. You know, you'll see org saying, I closed the deal in HubSpot, but invoices are paid through QuickBooks, and we have to kind of bring that data together to have the comp plan motivate ongoing adoption. And then the final one is actually pushing data from QuotaPath into payroll. Are what we're trying to evolve to be is a full end to end workflow, and we've coined it from pipeline to payroll, from the first time you're looking at a deal, what you could make all the way to being paid that deal. And so we just launched an integration with rippling where you can push the actual payouts from QuotaPath directly into rippling, and basically run from the demo is in, you know, demo appointment or demo occurred, all the way through actually paying the person. So we're trying to make sure that as a company, we're sitting in the middle of all these systems and become a really great systems integrator to pull data in from CRM, from ERP, calculate, join, do a lot of that messy work, and then push to payroll effectively. Adil Saleh 12:52 Interesting. I'm so glad that you already brought this up, because we have questions written around these users based pricing model, because that can become a challenge. Every other company is trying to go that way, like either seed based, using base pricing, because most of them are using some sort of a lambs or AI driven thing. So this is something built on top of it, so it's a lot of cost, so they would need to optimize the cost, especially in the mid market to enterprise, and that's where so you're trying to build a system from point, from a point of initial generation of the of the of the lead of the prospect towards and it's now reflecting towards the payroll on the on the inside. So it's basically reflecting on to the payroll. Ryan Milligan 13:36 Well, exactly. I mean, the way to think about it is, if you want, if you're holding true to the thought that your comp plan is a tool to drive performance, you need to have deals entering QuotaPath before they're closed. One and you want to rep to compare. Hey, I have these 10 deals in pipeline. If I close this deal, I'll earn five grand. If I close this deal, I'll earn eight grand, and you want them to look on a deal by deal basis, to understand the mechanics of how they'll earn, and have the comp plan be driving them to change their behavior. So you know a perfect example might be okay. I have 150, K deal and 510, K deals. The org wants you to close the 50k deal because cost of managing one customer is much lower than cost of managing five and a bigger you know, 50k deal might be a bigger customer you can put on the website, that sort of stuff. If you don't have something in your comp plan, motivating a rep to close bigger deals. They're going to close the 510 k deals all day, because it's always easier to close these smaller deals. So you want the rep looking at, what are the parameters of the 50k deal? What are the parameters of the 510 k deals? Here's how much more money I'll make. Maybe I have a big deal bonus, so I'll make a lot more money for closing the 50k deal, right? So that's the comp plan, like driving the behavior off of pipeline. And then for you. Usage based models. Cool, you've closed the 50k deal, but now we have to wait and see the commissions come through or the the usage come through, whether it's you price per outcome, you price per LLM hit, whatever, you have to see that invoicing come through to actually release the commissions to the rep. And that is what is changing? Sure, maybe in in standard SaaS, it's a 50k deal. So you're getting credit off a 50k deal in more outcomes based pricing, like you're seeing with a lot of agentic products, okay, it's actually going to be in 100k deal dripped out over this 12 months because of how they're using the product. Adil Saleh 15:39 Yeah, right, right. And now also thinking about, like, of course, the expansion a lot of these SaaS companies, they're like, of course, net revenue retention is all about like, how you're able to expand from the existing install base. So it goes the same way, like it follows the dollar value. It follows the the invoicing, whether it's usage based, seed based, whether it's standard, license based product, so it goes and beyond the same. Ryan Milligan 16:07 Yeah, and you're seeing a lot of orgs start to think about, how do I use my compensation plan to improve net revenue retention? That's like a classic conversation that I'm having. And the way that I think about it is you have to understand at the top of your funnel, what are the characteristics of a demo that you're running that convert to a customer who stays with you for a really long time. So in order to use your comp plan to drive high net revenue retention, first and foremost, you need to have a really clear ideal customer. Because if you don't know who the customers are, who will land and expand with you for a long time, you're going to tell your BDRs, hey, try to generate any demo you can. And so using your comp plan to drive an improvement in net revenue retention. Starts with the marketing team and the BDRs, targeting customers who are going to be a great fit then it's Mo and paying them more money for great fit customers and great fit demos. Then it's motivating the rep to close better Great fit customers. Then it's motivating the account manager to expand and renew those great fit customers. So it's got to be fully through the funnel. Everybody makes more money for working with, landing and expanding Great fit customers and then also signing them onto longer term contracts. Are like, the two big things I tend to talk about. Adil Saleh 17:30 Amazing also, like, I've got some more questions right here regarding, like, how do you see this? A lot of these companies at this stage, five years down, six years down. Now it's like lot of things that you can do then five years back, but product wise, like, how do you see it? You know, of course, you're sitting in with the leadership. How do you see it going? About Multi Product, multi license. You know, maybe a lot of these companies trying to have their CO pilots or multiple agents. I saw going like, long spent 10 plus agents last month. So how do you see about like, this could be one of the sales strategy, you know, more products, more Multi Product. You know phenomena? Ryan Milligan 18:15 Yeah, we're definitely seeing a lot of orgs we work with, releasing new products and using new product adoption as an nr expansion lever for sure. You know, it's something we always talk about here internally, as well as, like, what are the next things you could potentially what are the next kind of, like, problems you could eventually solve? Is commissions is a pretty meaty one, I will say. So there's a lot, there's a lot more work to do in commissions. But, you know, it's something you always have to think about. I think as we think about the evolution of our own product, and I can speak to what we're doing, we're spending a lot of time on how do you inject AI, kind of the same thing we talked about with your sales team. How do you inject AI into your product so that it replace like it does work that humans are uniquely great at and so earlier this year, we launched an AI powered Plan Builder. And the thought process was, you know, QuotaPath has a lot of clicks. In order to build a compensation plan, you have to build the quotas. Upload the quotas, build the rate structures, upload the rates. There's just a lot of clicking around. Great example of something that AI is incredible at right, upload a PDF of your comp plan. AI will read it and translate it into the components and plans so that it works in QuotaPath. It will build it in QuotaPath, or write a description of your comp plan and QuotaPath. The AI powered Plan Builder will do the same thing. So that's where we start with. AI is really interpreting and building compensation plans, but you could carry that logic all the way through. So can AI actually map automatically to your CRM? Can AI start to answer questions for a rep about what's their path to hitting their number and how should they. What deals should they close if they want to hit their number? There's, there's all these really fun things we can explore from an AI perspective. And it's really that augmenting human talent thing, and that's what we've been super focused on. Adil Saleh 20:12 Yeah. I mean, I think conversation AI, does it really, really good as well, like analyzing the data, analyzing the content, different data points and all. So now, thinking about a longer term view of QuotaPath, I know that you've been here for more than half of the time from the inception. So how do you see yourself moving like as a sea suit in the next few years? Like, are you planning about sitting here QuotaPath? What kind of do you think, like, impact that you're creating, what's what's learning had for you? Ryan Milligan 20:42 Yeah, I mean, I think a lot of our focus is going to be in a couple areas. We talked about some of the like, AI energetic work. I think that's a really, really big focus. I think the other one for us is continue to expand the types of comp plans we can natively support and easily support in the product. There's just a there's just an ever expanding world in which people build and design comp plans, and so we want to make sure the product remains super flexible to support those. And then there's always really interesting evolution on integrations, right? So being able to pull in data from more unique warehouses, more unique CRMs, pushing that data to more payroll providers. You know, there's always stuff that we can be doing to expand the like kind of aperture of world we can we can support, but I think for us, it's really about, how do we make it as easy as possible and as quick as possible to ingest load calculate compensation plans so that they are really interpretable for the rep and drive the right behavior. And that's and that's been a fundamental focus for us. Adil Saleh 21:48 Interesting and thinking about, like, tapping into different adjacent customer segments. How do you see it as a VP of sales? Like thinking about a lot of these industries, like even I've seen some just a few weeks back, we had, like a technology product. It was pretty much first doing climate simulation for cities, for buildings. So a lot of these, these, these industries, are basically going to go tech enable, and they're adopting to AI in some shape or form. So that gives them, gives platform like QuotaPath, an opportunity to tap into different other adjacent industries. So is there anything that you're thinking this this year? Ryan Milligan 22:25 I think for us, it's actually really interesting to spend time thinking about new potential customers. For us, you know, we like a lot of B to B software companies. Have a lot of tech companies using QuotaPath, because they have a structure that makes sense for commission tracking software. They track deals or opportunities in a CRM. They have a number of distinct roles, from SDRs to account executives to account managers who need variable Comp Help. So there's just a lot of like stuff there that fits our products very well. But you know, the truth is, from a tam for us, all sorts of teams sell something and variably, comp people, right? And so there's a lot of opportunity for us to think about, how do we evolve the product to be even more flexible, to serve the needs of a number of industries that are normally not high tech adopting early and that's what I've been putting my marketing hat on. That's where I've been spending a lot of my time. Is Where are the industries that we could provide a lot of value to and generate new customers from? Adil Saleh 23:30 That makes sense. That makes sense. And now you know, I found you one of the one of the advocates of sales rep, like one of the biggest advocate of sales reps all this time on LinkedIn. So what is it? Number one thing that you think like that has changed, whatever be the competent of change, like, whether it's an AI or whatever, that is different than when you started QuotaPath and you were doing sales back in the years. What has the core component that has not nothing to do with the technology, it's like at a human level, yeah. So I think, for example, it might be a sales rep adapting to tech stacks, or maybe using AI regularly, whatever you think. Ryan Milligan 24:10 I mean, I think with the rise and just like the explosion of AI and automated outbound, I think the reps who have evolved and started to do really well are the ones that are doing the kind of more human work incredibly well, which is funny to say, who are understanding the problem that me as the buyer, or that I as the buyer am facing with my business, and trying to tie their product to how they're going to help me solve that problem. The best sales reps I've talked to and the reps on our team spend a lot of time in discovery, understanding why this person is at the front door, taking a demo of QuotaPath one and two. What is the biggest problem that this person needs to solve this year? And they're really trying to map QuotaPath to be a solution for that problem. So an example might be, hey, you know, we really have to improve our net revenue retention of this business. That's the one thing that I'm talking to the board a lot about, and what I want a QuotaPath rep to do, and what they're doing a lot more now than they were ever before, is saying, Okay, let me help show you how QuotaPath can help you use your comp plan to drive higher quality revenue for the business in new customers, in renewals, and what have you that will then drive an improvement in your net revenue retention. And if you can make that tie so that I can think that QuotaPath is a tool that will improve my net revenue retention, my willingness to purchase something like that goes way, way up versus just buying a commission automation software. Adil Saleh 25:50 Yeah, that's evolving off of the customer pain, understanding the pain and walking in the customer shoes. So I mean, that's been fundamentally, fundamentally. It's been the same sales process even for the back years. But I think it's equally important now. It's just more about, like, hand wheeling the gun. It's not just a gun. Ryan Milligan 26:11 It's interesting because, you know, I think a lot of people think tailored outbound. They want to do tailored outbound towards like, the characteristics of the buyer. It's a great example. I get so much like, Oh, I saw you went to Dartmouth, or I saw you minored in French, or I saw you live in Philly, you know, whatever. And as, because I just get so much outbound, I just don't care about any of those things. But if someone said, Hey, Ryan, I saw that, you are really concerned with, you know, moving into the enterprise, for example. Let's say, as an example, here's how product z is gonna help you. You know, I don't know better. Multi thread to senior stakeholders to move into the enterprise like that. Okay, you're taking my fundamental work problem and showing me how you can solve it. I care about that way way more, especially in like, an AI spam canon outbound world, I care about that way more than I ever did before. Adil Saleh 27:12 Amazing. Yeah. I mean, it's more about like, you know, yeah, I can do that too, but you got to make sure that you are sitting on top of the AI and making sure you're doing the human as you mentioned before, the human work right and smartly. It's more about, like, intent based now personalized, not just like automated. That's pretty much dead. So now one last thing I wanted to explore with you. Like, you know, we are almost a quarter down 2025, how do you see this panning out for you? Like, what makes you excited? It could be like, your personal something like personal goals as well, anything that you think of. Ryan Milligan 27:46 I'm just really excited about the product that we're building. We have a lot of releases coming in the next three to six months that are incredibly AI first, that are going to solve a lot of problems that people have in administering comp, and by the end of this year, I'm really excited about how we make how we even further solve the like performance driving problem, and how reps are even more excited about using QuotaPath to actually change their behavior. And I think that's the big thing that we've been spending a lot of time on, because it's it's a win, win for the business, right? If a rep sell, let's say you you pay 10% commission rate for a one year deal and a 15% for a two year right? If a rep sells more two year deals, they make more money. And they make more money because they're selling deals that are better for the business, and that is one of the rare moments in which the rep wins, the sales leader wins, the finance leader wins like everyone's excited because they're shifting the shape of the revenue, and they're using their comp plan to do that. And so I'm excited for us to lean into that problem even further, and we're going to do that for sure this year, which I which will be really, really fun to see. And I'm excited to see how our customer play with it, for sure. Adil Saleh 29:01 Oh, absolutely. I was also looking at, you know, last week, my team sent the report that you shared, you know, that the ramp, ramp here, how you can, you know, actually fix the problem? Because this is a huge problem, like I've seen, you know, SDRs and BDRs knocking doors to their team, you know, their team leads. And you know, hey, I mean, I'm doing this, I'm doing this. What's going to be my commission? Could you tell me, like, it's so much of confusion around in the smaller organization I'm talking about, on the enterprise, that you know, they don't have anything you know to be motivated, and instead, they're wasting time on smaller deals that are not yielding enough revenue. And team members, you know, team leads, are pretty much content with that, because they're not even sure. A lot of times they're not even sure like, what, what they're like, what a BDR, SDR, needs to prioritize off of revenue or contract value, especially these, these products that are more usage based. So. So by the one last question, how do you see this notion, a lot of these, you know, post sales, you know, I'm talking about account managers and customer success managers, measuring things off of product usage, you know, the top features and the power features, with a lot of that drives the expansion. How do you see this, like integrating some of these metrics into QuotaPath, or maybe this can measure some sort of some level of projection on the commissions? Ryan Milligan 30:29 Yeah. So I'm definitely seeing org start to like layer in product adoption as a component of their variable comp. The reason that, like the standard account manager or comp plan is half of your variable is off of gross revenue retention, and then half of your variables off of expansion. And so the thought is, those together come into net revenue retention. The reason you split it is because you want somebody to feel the pain of churn. And if you just do net revenue retention, sometimes you can have a massive expansion that overshadows all of your churn and contraction and and it's just like it's not a great setup for the org, but for orgs that want comp plans that are a little more up funnel, I am seeing more teams use like implementation and adoption as components of the variable comp plan so that a a account manager cares about adoption well before renewal, basically. So, yeah, seeing that more and more for sure. Adil Saleh 31:26 Yeah, because adoption basically drives the retention a lot of times. Like, you know, I've spoken to more than 130 CS leaders like core VP of CS and head of CS, and what they say, like, 40% of your customers, they actually churn between onboarding and adoption. So that's a very critical stage. And I'm sure, like you guys are working through the composition plans around these customer success and we'll have more content share around this. And you know, having having your commentary on those blogs and newsletter in the next few weeks. Ryan Milligan 31:58 absolutely, yeah, for sure. Adil Saleh 32:00 Yeah, yeah, Ryan, it was really, really nice meeting you. It was quite a learning for me, like I was listening to you. And you know when I follow you on LinkedIn, seeing your posts and your readers quite frequently, and I learned a lot from you. And thank you very much for in this, these, these thoughts, and it was quite inspirational. Ryan Milligan 32:17 Yeah, Adil. Thank you so much for having me. I really enjoyed it, and we'll, we'll talk soon. Adil Saleh 32:21 Likewise. Have a good rest of the day, brother. Ryan Milligan 32:23 Thanks. See ya.