Ryan Milligan

James Geyer: [00:00:00] We are back everybody. Hello again for another episode of boardroom RevOps, where we are bringing you valuable tips from RevOps experts so you can make it to the C-suite. I’m James, co-founder of Accounting Next Gen BI solution for RevOps teams. I’m joined by Ryan Milligan today. Great to have you on Ryan.

Ryan Milligan: Thanks for having me, James. I’m, looking forward to this.

James Geyer: Ryan is the VP of sales, marketing and RevOps at Quota Path, a very, narrowly defined role. really pumped to have him on because Ryan has done what many RevOps folks aspire to do, but few actually accomplish, and that’s make the jump to senior leadership in a dedicated go-to-market function, being sales and marketing.

Ryan, before I say your thunder, do you wanna share your background in more detail?

Ryan Milligan: Yeah, absolutely. So, hi everyone. I’m Ryan. James mentioned I lead the sales, marketing and revenue operations teams. At Quota Path, we help teams automate their commissions process. So better motivating your reps to close the right types of deals by giving them access to, to understand how they’re gonna earn, and then save you a bunch of time calculating paying commissions.

I’ve been here for a little over three years now and so my background has been the classic jungle gym of go to market. so started [00:01:00] in data science out of undergrad, moved into performance marketing because wanted to take more of an operational leadership role and then naturally found marketing ops and then RevOps, at my last role at Homebase.

Really because I liked the systems and process to drive organizational change paired with being close to a GTM team is always really fun. So I joined Quarter Path to lead RevOps about three years ago, in a director of RevOps role. And through the classic things that happen with growth stage startups, a sales leader exiting to start their own consulting business, you know, moves in the org.

I was able to position myself to say, Hey, look like I’m ready to take on a revenue leadership role here. And felt like that was the right step for me. Vertically built our data practice here, built a lot of our operational rigor and process and said, Hey, we can bring a lot of that. technological and operational rigor into our sales and marketing processes.

It doesn’t hurt that I’m the person who calculates and pays commissions at Quota Path using Quota Path. So I, I’m the buyer and I know the product very, very well. But yeah, happy to talk [00:02:00] more about how I made that.

James Geyer: Yeah, that’s great. You started to allude to some of it. to start, maybe we can kind of double click even further.

you know, a lot of people talk about like getting a seat at the table with executives and RevOps. Based on what you just described, it sounds like you kind of already had that, in RevOps, which allowed you to make this transition to leading sales and marketing. How did you get to that point to actually have a trusted say with leadership?

Ryan Milligan: Yeah, so the one that I think a lot about, the one skill that I think every RevOps person should know is how to write sql. It’s like my, that’s my soapbox. I’ve been a data analytics guy for a long time, Data at growth stage startups is incredibly messy. it always will be, you know, there are ways you can make it a lot better with great BI tools and things like that, but there’s always gonna be some, some, object you want to pull data from.

And knowing how to write SQL is really great. And so I use that early on here to actually build our data analytics and BI practice. So standing up with data warehouse, standing up BI reporting. And then I eventually kind of started to take over all board reporting at the org. So my real way into that seat at the table was understanding our [00:03:00] data really well and understanding the drivers of why we were beating in some cases and missing in some others our plan.

And so that allows you to get a lot of credibility with the board in terms of, Hey, I know how these numbers work. I know what’s going on with our gross revenue retention. I can model what’s going on with average contract value and the changes we’re seeing. And I think RevOps is really, especially a growth stage startups.

Incredibly primed to be BizOps as well is the truth. Mm-hmm. Right? You know, RevOps is, knows how all the systems work, knows all the processes come together and should be able to know the data really well to tell the story of why you either beat or missed plan.

James Geyer: Yeah. I always say that RevOps should be the most strategic function in any business.

’cause the customer journey is really what matters when it comes down to things. That’s RevOps, right? I think that’s great advice in terms of knowing the data and the ins and outs, and that’s how you get a seat at the table, especially with board reporting is this very important kind of time of the quarter.

So many data experts stay siloed though I am thinking of data analysts and other folks like. Beyond just the technical know-how and the knowledge of the numbers, like any [00:04:00] tactics you have for actually maybe having the charisma or opinions that are needed to actually kind of build trust and leadership.

Ryan Milligan: Well, I think a lot of data analytics roles tend to talk about, understand the data really well, but then don’t know the systems and process of go to market to then make reasonable recommendations. So, you know, one for us, for example, when I started a couple years ago at Quota Path, about 75 to 80% of our revenue was in.

Single year, one year contracts. Hmm. And then another 20 to 25% of it was actually in month to month contracts with very little and longer term contracts. And so what we would do is, is I measured basically the gross revenue retention in the first year post sign up for a monthly, one year and two year contract.

And naturally saw that two year contracts were dramatically different than one year. That were dramatically different than month to month in terms of gross revenue retention based on the length of contract when they first got started. And we also realized that there was no real difference in our win [00:05:00] rate if we were offering, you know, a month to month or annual contract.

People were ready to either bi-annually from the start. And so I helped, like took that knowledge, went to our VP of sales at the time, and said, Hey look, I really think you can shift our revenue to be in multi-year first annual and then multi-year contracts. And so the first step for me was. Removing a month, month entirely from our go to market, which we did successfully using the comp plan and using the systems in place.

And then when I took over the sales team about a year and a half ago, we actually underwent that exact same exercise to move to two year contracts. So started with the comp plan, accelerated the rate that a rep earns on a two year deal versus a one year deal, a comical amount. They wouldn’t even consider selling a one year deal anymore,

So it was a fun exercise. Get them, get their muscle, you know, for selling to your contracts, and then flip the script on the actual go-to-market process and say, Hey, we only offer two year contracts. And so in a quarter we shifted from like 15% of our revenue into your contracts to like 85%, like quarter quarter.

Wow. [00:06:00] to answer your question. The challenge with a data analyst right now is they have the data, but then they don’t know what the recommendation should and really could be in terms of the go-to market motion. RevOps understands the go-to market motion, so if they can bring the data forward, they can then make the recommendation, Hey, you gotta make this change.

Here’s why. Here’s what we’re gonna measure.

James Geyer: really a phenomenal case study. Just to recap. know the data, uncover a problem, know enough about the business to have a hypothesis. First solution, make the case with data to executives. Put it to work. And that’s how you build trust and actually make an impact in RevOps.

Ryan Milligan: And that’s what CEOs wanna be doing more. Yeah. Right. But they, they don’t have the time. you think about things like ideal customer profile generation, you think about pricing and packaging. these are things that somebody theoretically owns at an organization, but no one actually does.

I think a lot of people are a little nervous to say, Hey, I want to take the lead on assessing and developing an ideal customer profile for this business. I wanna take this data, I wanna chunk it this way and make the recommendation. If you [00:07:00] went to A CEO, even if it wasn’t your job, with a really cleanly packaged ICP recommendation for how the team should measure an ideal customer in this business, they would be thrilled.

They’d be like, thank you so much. The data makes sense. Let’s get that in CRM as a marker so we can track our ICP pipeline over time, for example. It’s just, I think people are a little nervous to go, like overstep their role to do that sort of thing. and RevOps is a great place to be able to do that.

James Geyer: Yeah, totally agree. Okay, so we talked about how do you have the skill to grow in RevOps and have a seat at the table Now. Tell me about the pitch. You said you made a pitch to leadership to fill the void of departing go-to market leadership. I think it’s probably scary even if you proved yourself for a CEO to make that decision.

How, how did you frame this up? Not without having selling experience.

Ryan Milligan: Yeah, so a couple things. One that was nice was, cost savings, right? You can move me into a, Senior GTM leadership role without going to market and, and paying for that in the market, especially in today’s, interest rate and just total [00:08:00] tech market.

That was it. That was a nice component of the pitch. But the other was like, look, I really know the buyer of this product incredibly well. I am that buyer. I. I use Quarter Path all the time to calculate and pay commissions. I know the ins and outs of comp plant design. I advise the market and do free consulting on comp plant design.

Not to toot my own horn, but I do know the problem very well. what’s really interesting about having a sales team selling commission tracking software is the sales team rightfully thinks about the amazing impact that quota path has for a sales team. one of the big things is Quota Path makes the life of a seller incredible.

They can see how much they’re earning in commissions and it can drive them to close more of the type of revenue you want for your business. More longer term contracts. More contracts and multiple products, what have you. when we sold, we sold a lot from the lens of the seller. Because it’s kind of like a meta thing, like a seller loves quota paths.

They tend to light up about what they like about it. I could then bring the RevOps perspective and change how we talked about the product to say, yes, sellers love [00:09:00] it, but here’s why. RevOps leaders really love quota path because it drives the seller to close better revenue for the business, and that changes the shape of the revenue, which improves like gross revenue retention over time.

I had helped sellers with deals before from that RevOps perspective. Right. So I knew what questions people were asking. I had defined our ICPI had built with a member of our RevOps team, a lot of our outbound engines.

So I was very already closely tied to sales. And so it was a natural step to build like a more. Operationally rigorous process in our, in our sales motion.

James Geyer: Okay. I love it. What’s operational rigor makes a lot of sense to me.

Now, let’s say post getting this role, and you’re in the seat now, how did you make the transition to leading sellers? I hear you on the domain expertise, but there’s, I see hot takes on LinkedIn all the time of like ops people shouldn’t be CEO. They don’t have the personality for it, like the rah rah this rah rah that.

I imagine you probably didn’t have that much experience with sales methodology, although you can tell me if I’m wrong. Tell me how did you develop like skills technical. Skills and leadership skills to actually lead sellers?

Ryan Milligan: No, I mean, the imposter [00:10:00] syndrome was massive. I bet. Like I had never carried an individual quota.

I had never moved a deal to closed won in, in CRM, like I truly had no sales experience. And so I think the first thing is you just have to admit what you’re not good at. I talk a lot with Sam Manley, who’s a, who’s a great sales director in our org about like. How I, I’m not that like big rah rah person.

That’s not what I’m amazing at. I’m not, I’m not amazing at, and I step in to do it a lot like with the team, but I didn’t have a lot of natural experience with building sales culture before this role. And so I had really great, you know, leadership on my team who was able to like, help me there. But you have to be humble about what you’re not amazing at.

And basically what I said was, Hey, I can bring the science of the sell here. I can tell you if your opp has any path of closing, I Can be an operationally rigorous leader to drive systematic change to how we sell this product. We can redesign our demo, we can build the right materials and resources for you.

We can really like cut a [00:11:00] lot of the fluff from our process. But I am also gonna need my sellers to step up and lead in a lot of the cultural motivation side of the of the house, which has been really kind of amazing for them too. The truth is like you don’t want everybody in the team to be the same person and look the same.

a sales leader who’s been a seller before Your gap is that like more operationally rigorous thing. And so I think you just say what you’re really good at and you say what you’re not very good at and you’re very transparent about that from day one. That buys you a lot of credibility, because you’re not pretending to be somebody that you’re not.

The other piece is I’m a pretty outgoing, gregarious guy. Like I think you do have to have a little bit of that DNA and want to be with the team and motivate them I went down in person with them a lot and got to, spend a lot more time in person with the team, which was super helpful. But yeah, you gotta be very clear about what you’re good at and what you’re not, or else you have no credibility.

James Geyer: Yeah, people can spot a faker a mile away. So I think you have to embrace it and, and where the shortcomings are. That’s awesome. Okay, so now we’re on the job. Now I wanna talk a little bit about, you know, [00:12:00] running all three functions at once, but before I do, like, how do you define RevOps? Pretty nebulous term, depending on who you ask.

Ryan Milligan: Yeah, so my definition is that RevOps. Owns the entire process from prospect to closed one to your renewal. Like they are the systems glue and, and operational conductor of somebody having never heard of your product before, going all the way through being a great long-term established customer. And so that is marketing ops, sales ops, customer success ops, and a lot of product ops as well.

especially in a PLG motion like we are with a pretty heavily embedded free trial. That is my, my definition. They are the. Conductor and captain of a person’s journey from never having heard from you before, all the way through being a, a happy approach.

James Geyer: Love it. I think that covers so much of, like, people, process and systems too.

’cause it’s all wedded in there for sure. okay. I mentioned a few times, so you’re unique and that you’re running sales, marketing and RevOps. I think I’ve seen one other person with your background and, you know, my lifetimes of scouring on LinkedIn at this point. what are the pros and cons of [00:13:00] this approach of kind of, of pulling it all together?

Ryan Milligan: Pros, you’re constantly thinking about the customer journey. I spend a lot of time on the phone with prospects and customers, and then I spend a lot of time behind the scenes with the data. So you get, you get both worlds. You get the, you know, you get upfront view from a customer or a prospect about how they’re feeling about your sales process.

We survey prospects all the time about, you know, how are they feeling about the sales process so far. So we gather a lot of data and you’re upfront with customers and then you’re sitting in the back with your ops team understanding, okay, what is our validation rate of demos we’re, running and that sort of stuff.

So you get kind of both, both views of the system. You also get entirely rid of the whole, like marketing’s throwing leads over the fence to sales Bs that I really just can’t stand. So our team. Our demand Gen leader, Travis, comes to all of our sales team meetings. It’s one go to market team. It’s not like two teams that point fingers at each other for no reason, which has always just like been silly to me.

Cons are naturally, you can’t spend as much time with each [00:14:00] team as you want. It’s funny, when I read my reviews from my team, they’re like, I just wish I had more time one-on-one with Ryan, which I get, you know. But we’re a very lean growth stage startup, and so we try to keep things pretty operationally lean.

But yeah, the big, the big con is just you can’t spend as much time as you want, with all teams. The other piece that’s interesting from a pro, which I should have mentioned is, you know, I’ve been spending a lot more time on LinkedIn building a bit of a brand for the business. And so you can generate a bit of like a.

RevOps thought leadership, if you also are the person running the sales side. And it’s interesting, like I, all the things that I wanted sellers to do when I was in a RevOps seat, you can kind of get them to do now, but then also develop a ton of empathy as to why they weren’t doing them before.

Which is super, super helpful. So like for any RevOps person out there, if you have a side project, like shadow a rep for like a week and just say, Hey boss, like I just really wanna go shadow a rep for this entire week. And you’re gonna understand why they’re not filling in those like 38 fields. You’re trying [00:15:00] to push ’em to fill in in CRM, and you’re gonna learn a lot and you’re gonna bring that back into your RevOps process for sure.

James Geyer: Yeah. Now that you’ve seen the other side, you’re a bit more empathetic. Are you changing. Things on the red side as a result, or are you just a little bit more forgiving when things are slower or less populated than you would expect?

Ryan Milligan: Yeah, changing definitely as a result. So we’re leaning very heavily into AI in our sales process. using tools to automatically update pipeline next steps. like all the, you know, because we have a very technical sale and I think you, if you’re not in it, you forget that and you like lack that empathy from an ops leadership perspective.

And I used to say I had a lot of empathy. You develop a lot of empathy when you’re in a one-on-one with a rep and they pull up CRM and they’re like, I have to fill out these like 48 fields to move this op from, you know, demo appointment to demo curb or something seems kinda silly. And so leading the team has definitely allowed me to develop like a much deeper level of empathy.

it’s also pushed me to automate a lot of the manual processes. So, you know. We’re a big gong shop here. Gong AI is incredible in terms of like summarizing [00:16:00] calls and specifically like the meat of the call, right? Because when you’re selling quota path, I have to understand, ’cause everyone’s a special snowflake with their comp plan.

So everyone has a unique comp plan that they think is the best comp plan on the earth. We try to drive standardization, but there’s not a lot of standardization at the front door. You have to articulate the comp plan. You have to then articulate like where does all the data live within the CRM.

Then who are the sellers? and so there’s just a lot of questions in our sales process. and it’s not a one size fits all sale. And so using AI to automate a lot of that note taking and filling out makes it easier for us to successfully hand off customers, to our customer success team and get them up and running.

James Geyer: Yeah. I actually can’t even imagine that type of handoff, like pre ai. You know, I think even stepping into the sales, he, as a founder myself, not having call recorded notes. I don’t know how sellers did it even five years ago. I wanted to ask you about the flip side of what we just described too.

So what’s it like now being you’re, you’re the consumer of RevOps as a sales leader, like what’s your, let’s call it outsider perspective on RevOps now that you’ve been in the sales seat. [00:17:00]

Ryan Milligan: So I think that what I’ve been really starting to realize is how important it is for a RevOps partner. To justify what they’re trying to get RevOps to do with the expected impact on whatever metric they’re trying to drive.

Because, you know, a RevOps team, they’re not always variably compensated. Now I think they should be and I’ll

James Geyer: mm-hmm. Agreed

Ryan Milligan: partner to mind. but they’re not always variably compensated. And so, but if they are gonna be variably compensated, they’re gonna be variably compensated on like the core metric of the business.

You know, they’re gonna be variably comped on like net new a RR or gross revenue retention or something. Broader than just one of your silo teams. And so positioning, Hey, I really think, you know, we should bring in an external agent layer to summarize our calls and update, you know, next steps and all of these different fields on ops.

That’s a big undertaking for RevOps that only lands, if you can say, I think we should do [00:18:00] that because reps are spending such a comical amount of their time updating CRM. For nothing unique or value creating, let’s carve off more time for them to generate more pipeline and work more ops or something like that.

And so that’s kind of the, I think a lot of sales leaders just say, do this thing for me now. And they don’t get the why. And you do have to sell your work as a sales leader to a RevOps team. To get them to prioritize it. ’cause they’re as small as ever. And there’s a lot of cost pressure on that team.

So. Doing that is gonna be very fruitful for sales leaders.

James Geyer: Yeah, I totally agree. I think the people we’ve interviewed that have had the best fortune at keeping RevOps strategic and value add do exactly that and they kind of ruthlessly prioritize Any other tactics you have on that RevOps prioritization front?

Is it, is it really what you just described? Is there anything else there to keep the team focused?

Ryan Milligan: You know, I think that you have to leave the room for, well, one, you have to have a roadmap. So I’m a very big RevOps roadmap person. you have a product roadmap. Why don’t you have a RevOps roadmap? And then you have to empower your RevOps team to have the trade off conversations in the same way that you do with [00:19:00] product.

Hey, cool. I will add these fields to CRM for you, but that’s gonna bump this other thing that you told me was necessary. and RevOps has to be empowered to push back on the revenue, like a marketing leader to say, Hey, you wanted me to do this. This is what’s gonna fall off the roadmap.

And are people gonna make that sacrifice? I mean the truth is marketing thinks RevOps is just working on marketing ops stuff. Sales thinks RevOps is just working on sales ops stuff. CS is thinking that RevOps is just working on CS stuff or actually not enough on CS stuff usually.

So it’s important to make sure that you have that cus like that broader roadmaps that all these teams can see how much of their work is taking up your.

James Geyer: Do you have a mental model for how a RevOps team should build a roadmap if they were starting from scratch today?

Ryan Milligan: So I tend to think through what is the first place you have to start is what is the biggest metric this business has to move?

Like in order for this business to be successful this year, what do we have to do? And that’s pretty simply like, okay, do we have to move from SMB to the mid-market and like double our a [00:20:00] CV? Do we have to generate a ton more pipeline? Do we have to improve our net revenue retention through expansion?

Like, what is the thing that you have to do? And then ideate all the ways in which you think ops can help do that. And put those at the front of your roadmap and then gather, requirements or requests from the rest of the org and push them on, okay, how do you think that thing that you’re pushing for is gonna improve this core metric that we all really fundamentally care about?

And then, There’s other like Kanban and sprint style systems. You set it up and then it blows up pretty quickly. if you’re not in a room as a RevOps leader with your head of sales, marketing and cs, and you’re not all agreeing that the core metric that must move this business to be successful is X, then you’ve already lost the narrative even before you start to build the roadmap.

James Geyer: How about chronology? Like how are you, how far are you thinking ahead as a RevOps leader about what RevOps is gonna need to do a year from now, for example?

Ryan Milligan: I wish I would [00:21:00] say a year from now, you know, I’ll be honest, our business changes so much a year from now. who knows? You gotta have this quarter, you gotta have an idea of next quarter.

That’s honestly, as far as I tend to think, okay, we’re, 45 person company growth stage. So we we’re pretty nimble in terms of how we operate. And that’s kind of in line with our product roadmap where like, we’re this quarter and next quarter out, that’s as far as I typically go. We’ve done like, what do you want to get done by the end of the year kind of stuff before, and you have that broadly speaking, but things change so much.

I don’t really hold a lot of weight in what I’m telling you I’m gonna do in December.

James Geyer: Yeah, I think that’s fair. You look back at those docs, nine months later and they’re, they’re pretty stale and they haven’t been touched in a long time.

Ryan Milligan: Yeah, Exactly.

James Geyer: You mentioned something earlier about, I forget the exact words you used, but I’ll call it the mythical alignment between sales and marketing.

That like mo, for most companies, it never happens. The leads get thrown over the fence. Yeah. You’re in the unique position where you can find that mythical alignment because you control all functions. And you said that you guys kind of have tackled this at quota path, like what does it mean for sales and marketing to be aligned on this front And like any tactics [00:22:00] you have that really work well?

Ryan Milligan: Well, the tactic that I’m gonna bring up, which is very near dear to my heart, is that marketing comp plan. Right? So, you know, we variably motivate our marketing team based on close run revenue. Like you can generate as much pipeline at the top of the funnel as you want. It’s a, it can be a great vanity metric, especially if you go to some of these events and just like blow up, some huge amount of pipeline.

But if it’s not closable at the end of the day. You’re actually often like wasting time more than you’re creating value if you are just touting your MQL count if it doesn’t convert in the way you want it to. So we have our marketing team split 50 50 between pipe gen and pipe demoed actually, and close one revenue as a function of their comp plan.

So that gets them pretty myopically focused on the quality and the close rate. And then we have feedback sessions where sales will give feedback back to marketing. a lot of the pipeline we’re getting today is from teams that use like a non-core CRM to calculate commissions.

They use a tool that we don’t integrate really well with. It’d be pretty, we’d have [00:23:00] to go through an API to get their data into the product. And it’s just like not really winnable pipeline. And so that’s, that’s like some feedback you can give in kind of both directions. And then the third piece is just really having a super clearly defined ICP.

Right. So for us, you use Salesforce or HubSpot as a CRM to calculate commissions. You have anywhere between, 20 and, you know, a thousand or 2000 employees, which ends up being like five to five, 600 reps. you have a unique set of different roles like BDRs, AEs, ams, earning comp, like you’re gonna be a good fit for us.

And so. if we’re generating more of that pipeline and closing more of that revenue, we can track things like percentage of pipeline, that’s ICP percentage of close one revenue, that’s ICP, and you can start to just get everyone aligned on what great looks like. And that just, leads to a lot less finger pointing because if marketing’s generating a lot of ICP pipeline and our win rate declines, then it’s a sales methodology.

Like, what are we doing? But if we’re [00:24:00] not closing a lot of revenue, because we started. Generating a lot of, ops from people with one sales rep who tracked it in a Google sheet. Okay, well that’s not gonna be the right efficient path forward for our business and we have to change our marketing tactic

That aligned ICP makes things like really clean and really clear.

James Geyer: Yeah. my question to you was going to be what needs to be true for marketing to not freak out about this structure? And I think ICP probably is the answer there, right? We know exactly the target of the kind of pipe we need to generate.

is there anything else that needs to be true for marketing to kind of accept this plan? Or is that the main thing?

Ryan Milligan: It’s just knowing what great looks like, you know? And it’s using the comp plan to motivate the marketer to spend more of her energy on value creating activity.

Right. So we do a lot of events. You know, we’re big sponsors of Pavilion and RevOps co-op, and we’re starting to get into some more like CFO focused orgs and testing those waters a lot more this year because they tend to be involved In the sales commissions process for the, org of the size that we wanna talk to.

Right? And you have to learn how to say no. you [00:25:00] get some pipeline that shows up to your front door, Hey, you know, we have 5,000 sales reps and we use a combination of 15 different homegrown CRM systems. you worry ’cause your eyes light up. You know, 5,000 reps would be a very big sizable revenue deal for our business.

But the amount of work it would take to bring them down. Get them up and running the cost there and then the revenue retention headwind of like a non fit for us in that way. If you have a clear ICP, you can kind of say no more confidently. Yeah. And not risk repercussion in a way you might elsewhere.

James Geyer: Yeah. Really good advice. we’re almost at time here. We have a few minutes left. I wanted to touch on just data really quick because your background is in data. I know from a past conversation, quote, A path has a really robust kind of analytics and data stack and infrastructure.

maybe the first question, which might be obvious, but maybe not like. Talk to me just high level about the value of quality data infrastructure from a go-to-market perspective. Like so many companies, especially at the size of a company like Quota Path, it’s kind of a mess. So like, tell me why it’s worth investing in [00:26:00] and, what the roadmap looks like to get to good data.

Ryan Milligan: I mean, the truth is if you have bad data, you don’t have anything telling you what to do, and you’re like operating entirely off of conjecture. Right.

It feels to me like this thing isn’t a good fit and you can, you can take like a couple bad conversations with not great fit, like perceived not great fit customers, and all of a sudden totally wheel out and go this way and try to change the problem. You need a really strong data infrastructure to say no, actually like.

Yeah, you had a bad week with these three customers who are in real estate. But the truth is, like our win rate in real estate’s really strong. Our gross revenue retention’s strong, like they’re actually a really good fit. You just happen to be, not to any fault of your own, but we’re human. Right? You have three bad conversations in a week with VPs of ops at real estate firms who’re gonna all of a sudden be like, Ugh, real estate’s the worst.

James Geyer: It can’t be my fault. It’s definitely real estate’s fault.

Ryan Milligan: Exactly. Exactly right. So the data infrastructure is key to like. Understand what you’re doing and prioritize what to do next. We’ve done a couple big like pricing and packaging overhauls in our business that have been [00:27:00] massive. we doubled our average contract value last year through like a really smartly, well-built pricing and packaging layout.

So you can only do that if you have really good data. And then the other piece is like, it’s amazing for board credibility. If you look like you know what you’re doing, you are a. You don’t want to have a bad quarter, but you are allowed to have a bad quarter. If you can tell the board, here’s why and here’s what we’re doing about it, right?

James Geyer: Mm-hmm.

Ryan Milligan: But if you’re just like, we had a bad quarter and we feel like this might be the reason you lose all credibility and are probably not gonna get, be able to win that back. So

James Geyer: yeah,

Ryan Milligan: operational, operationally rigorous data, data-driven decision making is very core to how this business operates. It allows you to be leaner as a team from a headcount perspective, and it builds a lot of credibility with your board, which is massively.

James Geyer: That’s so well put. If someone is thinking about, you know, okay, we, I need to get at my company, the data in place. What does good data look like?

I’m curious to get your, your take.

Ryan Milligan: So I went through this whole exercise three years ago, you know, standing up, snowflake as data [00:28:00] warehouse. I train and portable to port that into BI tool. I went through that whole process. Which was great at the time. I imagine that if I did it today, it’d be a hundred times easier, right.

with AI playing a big role and a lot of great companies solving the problem. But I think the, what great looks like is all of the systems that have data that you’re tracking for, you have some way to join that data together. So you have, maybe you’re using HubSpot as a CRM and your billings in stripe.

You have some way on the account in HubSpot. To know what that customer ID is in Stripe. So you can join your billing and your revenue data together. So you have ways to join the data together. And then the first thing you have to have is just a really clean data-driven, like revenue growth plan for the business.

Hey, we’re gonna grow from 2 million in ARR to three and a half as a function of this pipeline and new business win rate growth. Paired with these dollars are up for renewal and the [00:29:00] gross revenue, like you have to know where your dollars stand and what your revenue growth plan is. That’s kind of your P zero problem.

And then from there you start to build better, like executive level dashboards on pacing towards revenue plans, win rates, you know, pipeline migration, pipeline growth, ICP, all the sort of stuff we talked.

James Geyer: That’s great. Really helpful. That’s about all we have time for. We do like to finish with a quick rapid fire finish.

So first sentence that comes to mind on a couple of these questions here, if you’ll indulge me. Sure. What do most RevOps folks get wrong about their go-to-market leaders?

Ryan Milligan: They, that’s a good question. What do most RevOps, they don’t understand what RevOps does.

James Geyer: If you could fix one challenge in RevOps, what would it be?

Ryan Milligan: Not understanding data well enough and being able to story tell with it.

James Geyer: And if you could describe a great RevOps leader in three words.

Ryan Milligan: Empathetic, data-driven, and forward thinker.

James Geyer: Love it. A data theme through the entire conversation. I love it.

Ryan, thanks so much for joining us. This is super insightful, a great refreshing take, kind of combining all of the functions together. And yeah, I [00:30:00] can’t thank you enough,

Ryan Milligan: James. I really appreciate it. Thanks for having me.

James Geyer: Thank you.