How to scale a sales org to $50M ARR | Ian Grace (Ocrolus)

Carter (00:01.298)
Hey Ian, give the people a quick intro. Who are you? What do you do now?

Ian Grace (00:06.538)
Yeah, Ian, thanks for having me, Carter. My name is Ian Grace. I'm VP of sales at Ocrolus. We are an AI analytics and decision platform for lenders, primarily mortgage lenders, consumer lenders, small business lenders, merchant cash advance, property management, forensic accounting. If you're making a decision based upon financial documents, we'll help you, you know, with our AI and platform to make those decisions faster.

Carter (00:35.826)
You joined Ocrolus in 2023 at a brutal time in the mortgage industry. Somehow you tripled the sales team win rates that year. What were the biggest changes you made that moved the needle and got results?

Ian Grace (00:47.49)
Yeah, I mean, I think it was a combination of things. So I came to the company, my chief revenue officer, Andrew Rains. I've had the fortunate experience of working for him now for almost 10 years. We worked together previously at another technology company called Automotive Mastermind, but he brought me in. He got here about October of 22. He brought me in January. So, you know, I think for us, one of the big things was just establishing, you know, what we would define as like basic kind of nuts and bolts things, Carter, right?

putting in forecasting, forecasting calls, deal coaching, implemented med pick.

implemented, you know, we all as a team read gap selling. we sort of basically kind of blended, I would say our sales approach now or became, you know, a combination of MedPic gap selling and challenger sale, you know, kind of together. We restructured the team, you know, prior to then we had sort of a everyone sold all of our ICPs, like I was mentioning a minute ago.

know, middle of that year, we shifted to a model where it was we had a mortgage and enterprise team and then sort of a non mortgage team. So we give a little bit of specialization. We added additional frameworks. We added, you know, obviously better selling habits, better selling practices, better leadership practices. And all in all, we were able to, know, 2023 was our best year to date. 2024 beat 2023, 2025 beat 2024. So we were able to

in 2025, late 2025, be a 0.1 percenter in the tech space and hit 50 million in ARR. So it's been a nice run the last three years.

Carter (02:34.194)
That's awesome. Was it hard to come into a new industry and do all those things? Or all those systems and things you put into place? Those cross over pretty well anywhere you go.

Ian Grace (02:43.106)
Yeah, I would say that they're industrially agnostic, right? No matter where you go, mean, in the case of Andrew, right, Andrew has done this sort of thing five times. I've been with him for two of them and, you know, sort of more or less the same sort of stuff works, right? And it doesn't matter whether you're selling, you know, payment software or in our case, an AI kind of lending automation software, or if you're selling, you know, widgets.

You know, MedPic is MedPic and gap selling is gap selling. You gotta do deep disco. You gotta understand people's needs. You gotta tie pain and impact to dollars of impact. And if you can do that successfully and consistently, more times than not, you can certainly get people to say yes if they have a problem, they wanna solve it now, and they wanna solve it with you.

Carter (03:36.69)
Talking about the deep disco, you've said a lot of your coaching center is on depth of discovery. When you listen to AEs, what are the biggest signs their discovery was okay, but they're not getting deep enough to win the deal?

Ian Grace (03:48.578)
I would say, know, kind of what I alluded to a minute ago, you know, when, when you stop sort of what you call it sort of shallow, right? I guess would be the word, right? So when you stop at the problem, like getting to the pain or the problem is key, right? But taking it that step further and

you know, converting that pain or problem into dollars of impact to the business, whether it's money they could be making or money that they're wasting, what combination of both, right? Whatever it is, that's what drives the urgency. That's what converts this, you know, from a problem I have to a problem that I want to solve now. So I think, you know, when you hear your team, if you're listening to their gong calls or chorus or clary, whatever your, your,

You know, recording du jour is that you're using. If you hear them stop at the problem, but not go that two or three extra questions deep to get to the dollars of the problem. That's the fundamental difference. The best day is no matter what you're selling. If they stop there, they they're not going to be successful. They always push. They always get those dollars. If it's not on that first call, maybe it's in the demo. Maybe it's, you know, disco never really stops, right? But if they can get it early, the earlier you

get it obviously the stronger that you are. sort of I've used the analogy before where I think of discovery is sort of like you're the old man on the beach carter with a metal detector you know that we've all seen and you know boop you know you sort of like you answer yes to something well now I'm gonna put my metal detector down to pick up a shovel and I'm gonna start digging and every discovery question I ask is digging and I don't really want to stop digging if I'm that old man until I hit the treasure chest right so the treasure chest that you want to thud into

Carter (05:33.266)
Yeah.

Ian Grace (05:36.112)
That's when you convert that pain into the dollars.

Carter (05:40.454)
When an AE needs help on a deal that's not moving forward, what's the most common thing they're getting wrong? Does it come back to that shallow discovery or are there other things that are more common that tend to come up?

Ian Grace (05:50.446)
I think it could be that. think sometimes it's that sometimes it's they're not multi threaded. They're not you know, they are facing resistance or challenges to getting to power.

You know, they may be selling not to a true champion, right? I think a lot of people think, well, this is the person I started my conversation with. Therefore, they're a champion when that's the, that's not the case, right? Like a true champion, you know, meets the three criteria of, know, they have a, they, they have a vested interest in benefit from your technology or whatever it is you're selling. We be it financially or their quality of life gets better. They are selling for you when you're not around.

and most importantly they have influence in juice, you know, with the key decision makers or other stakeholders, right? So only if you're hitting those three kind of boxes to check do you really have a true champion and I think a lot of times a lot of AEs think they have a champion when they have sort of a shallow, you know, they might even have a coach or an influencer but they don't really have a true champion that they could sell with.

Carter (07:00.764)
That makes sense. You had a post where you said the Xanax that cures sales anxiety is a pipeline. When an AEs pipeline is thin, what are the first things you're telling them to do to build it up?

Ian Grace (07:12.462)
I mean it sounds crazy, but it's pretty straightforward.

how many hours this week are you going to be doing prospecting? you know, I, I often, you know, especially to newer AEs that are training and then I'm trying to work with and get them kind of transitioned from let's say SDR into sales. But I mean, it's, it's the same for a tenured sales rep as it is for a new sales rep. But really your, your calendar should be kind of focused on one of three areas. You can maybe say four, but it's trying to get somebody in front of me, right? Prospecting, preparing for somebody to be

in front of me, you know, getting ready for that meeting and I got somebody in front of me, right? Like, so the fourth you could say would be internal administrative things, deal coaching calls, your all hands, etc. But really, you know, the toggle on how much percentage of your week you're spending in each one of those three buckets is really predicated on how healthy your pipeline is, right? But it should never probably fall below, I would argue, you know, 10 hours a week, right? Probably between six to 10,

to 10 hours a week at the low end, but if you have an unhealthy pipeline, then obviously that should shift to 25 hours if need be, 30 hours that week to get yourself back to where you need to be. Yeah, yeah, from a prospecting perspective. if, you know, my first question is going to be, how much time have you been spending prospecting?

Carter (08:29.296)
You're saying for the prospecting part of it.

Ian Grace (08:39.102)
in be honest with me, right? Like, help me help you but like, if ultimately you're only spending, you know, two hours a week prospecting and your pipeline is unhealthy, clearly that's not enough, right? The other then kind of I think it always comes down to my my my conversation or thought process is sort of twofold. It's first to quantity, and then it's to quality Carter, right? So like, if your quantity of of prospecting is not there,

Carter (09:00.72)
Mmm, yeah.

Ian Grace (09:07.564)
Okay, well, then that's the first problem. If your quantity is there, you're doing 10, 15, 25, you know, hours a week of prospecting, but you're still coming up short. Now let's talk about the quality. What are you doing? You know, are you spending all that time calling? Are you spending all of that time doing outreach sequencing? Are you spending that time doing customized videos for LinkedIn messaging, right? Or what is it that you're doing? Are you spending it all in one? Are you spreading it around? You know, so but the first step is understanding like, what's the quantity level? And if the quantity is

they're great, but oftentimes it's not. That's usually the first sort of like rock you pick up and you see that there's bugs underneath.

Carter (09:47.717)
On a podcast, you said your job as a leader isn't to sell for the five people on your team or however many people are on your team. It's to create five of you. What does that look like in practice? Like how are you able to make that switch?

Ian Grace (09:59.19)
Yeah, I mean, I think one of the first pitfalls many knew

sales managers is definitely a difference between sales managers and leaders. But whether you're a manager or a leader, one of the first sort of pitfalls that an early manager falls into is trying to just do it by their own will. Carter, right? Like, so I'm working with Carter. Carter's a new guy. I'm a new sales, his new sales manager. And if Carter's struggling with something, my inclination might be Carter, let me just take care of it. Or I'll, you know, kind of almost, you know, proverbially push him.

out of the way, take over that call, take over the sales process, and I might get it done.

But is Carter any better for that? Is Carter going to be smarter and his samurai sword sharper for his next sales motion? Because I did that. Of course not. Right. So you really got to sort of stop and say, wait a minute, like resist that urge and really talk them through like, what is it that's going on? What is your process? What should this look like? Let's listen to, know, a big thing, you know, in those moments is certainly like, let's look at your gong calls together. Let's grab a couple of random

And I you know, it's like literally watching game film with a quarterback, right? Let's let's watch this together Let's listen this together and then there you know They're gonna ask a question or you're gonna ask a question and then I'm pause after they answer and say, okay This is what I would have said or this is a follow-up question You jumped out of the hole that hole that I was talking about earlier You jumped out of the hole and picked up your metal detector again, but there's still four more questions You could have asked. So what did you think about asking this this this and this so I think that real?

Ian Grace (11:41.764)
time sort of as real time as you can get you know kind of feedback of watching the game tape and giving them that actionable feedback in the moment is certainly one of the coaching methodologies that I've seen work nicely to try to you know in practice talk to people about what they could or should be doing as opposed to stopping where they did.

Carter (12:04.408)
What's one mistake you made early as a sales leader that forced you to change how you coach or manage people?

Ian Grace (12:09.902)
two things, the thing I said earlier, right? And I certainly was guilty of that and just sort of trying to lead by will. And I, know, what John Maxwell would call sort of a, you know, level one positional leader, right? Like, oh, I'm in charge, right? That's terrible, right? Terrible leadership style. So number one, leading by will. I would say number two was my career or my...

my sort of trajectory and I think my abilities as a sales leader changed for the better when I stopped thinking about myself.

Right? think as an early sales leader, you're worried about, it's my number and it's, need to do this and I need to do that. And this looks bad on me and those sorts of things, which is probably why many early sales go to that will kind of approach because like, they can control that. So they want to go that route. But, you know, for me, I think when I stopped thinking of it that way and saying, they give it more like, this is our number and how are we going to get there and how can I help you?

trying to really promote my people and recognize them for what they do and help them and think of it solely more as a lens focused on them and not on me. I think that was a sort phase two kind of sea change for me as a leader.

Carter (13:38.963)
That seems pretty tough though, because isn't your part of your pay is based on their performance. So that does seem that does, because we had one at rocket mortgage one time where our pay was based on our team hitting quota. And yeah, that was for me, that was tough. Cause you can all at least for me, I can only do so much to try and help the other people on my team. So that's teams tough to get out of that mindset.

Ian Grace (13:43.767)
Of course.

Ian Grace (14:02.764)
Yeah, it's definitely not easy, especially the earlier on you are in your career. I think with some time and perspective and some maturity, it becomes a little bit easier of a thing to understand. And what you really start to understand, at least for me, is...

The more I started to focus and try to help my team and that they felt that, they genuinely felt with sincerity that I was there to help them, support them. An early manager said to me once, and it stuck with me, she probably said it to me when I was like 23 or something, but it was the concept of the job of a good leader is not to point, I got you, Carter, I got you.

Ha ha, it's no, I got you. Right? And like, I'm here to support you, I got your back. Right? I'm not here to pick at your mistakes, I'm here to support you. And I think when I sort of got there, you know, I found the team, any sales team that I was working with responded to me better and more, and they wanna do the things, they wanna be more coachable, they know I care. And I think that that certainly helped, you know, grease those wheels.

Carter (14:52.668)
Yeah.

Carter (15:20.118)
You've taught, this seemed interesting to me, you've talked about using AI to make outreach, prospecting, enablement and training better. What are you actually doing with AI today and how are you using it across the sales work? Any specific tools that are really making an impact right now?

Ian Grace (15:34.646)
Yeah, a couple different ones, right? you've got, we've got, we, as I mentioned a couple of times, we use Gong. Gong's got a great AI embedded in it, you know, as sort of an ask me anything type of functionality, which is really awesome. We are our president and co-founder. We were

working last week on using Claude to actually build a sales kind of tool that would listen in aggregate to lots of different gong calls of, let's say, on Carter. And instead of me, which we all do, top down at the company, we all listen to lots of gong calls every week. listening instead of like, I can only listen to, let's say, three or four a day in bandwidth, but Claude can listen to all of Carter's calls this month.

So if you think about it then and then the way that we structured it and built it was built it through what I was mentioning like how is Carter doing with against med pick gap selling challenger sale, you know, we even sprinkled in a little never split the difference Chris Voss in there, right? So how how are you scoring against that? How are you call scoring on those against those sort of methodologies and and sales principles and that's converting and that's kind of created a new coaching

angle for us to take that we're in the very early processes, a process rather, of building out but it's showing early promise.

Carter (17:02.706)
That's pretty interesting. So it scores you and what it gives suggestions of how the salesperson can improve.

Ian Grace (17:08.352)
Yeah, gives several things. So to let you know like.

Are they a challenger? Are they a lone wolf? Are they a relationship builder? Right? So it'll, it'll categorize them according to challenger story, it'll score them and how they're doing against a med pic criteria. It'll score them, you know, in conjunction with how, you know, how well did they do in the principles of gap selling? How deep was their discovery? All of those things. And then it will give actionable feedback to me or to John, our other VP of sales or to Andrew or CRO, anybody that looks at it, it'll give us actionable feedback to talk to them about. So one of

things that we're working on fine tuning is like, what is it give? What am I hearing? Or what am I seeing? You know, in the AI's response? What do I feel should be the coaching feedback? And then what is the AI telling me? Right? So if I disagree with the AI, where, you know, we can tell like, well, this is we don't agree with this, this and this and this is why to fine tune it and take it, you know, you know, down from a shotgun blast into a laser. But, you know, that's sort of the concept behind

it is then now either they can look at it themselves, self-correct, without us talking about it, or it can obviously be a methodology and tool that we can use when it comes to individual coaching.

Carter (18:24.658)
That's pretty cool. Well, I think we got some good stuff here. I'll end it here.

Ian Grace (18:29.624)
Cool.