How to Sell AI to an Industry That Doesn't Trust It | David Gipson (Ocrolus)

Carter (00:01.274)
Hey David, give the people a quick intro. Who are you? What do you do now?

David Gipson (00:06.574)
Hi, David Gipson. am the director of sales engineering at Ocrolus. So Ocrolus is an AI infrastructure and automation platform for lenders. So we work with all sorts of lenders, small business, consumer, mortgage. I specifically work with

our mortgage team on our solutions to help make lives easier for mortgage professionals. But been with the company for about four and a half years. Prior to that, I was in mortgage for over a decade myself. Half of that in underwriting, some of that in as a loan officer and sales ops and kind of every role in between there. So it's been a long journey here. But yeah, I basically work with the folks I used to be in my previous life.

Carter (00:52.272)
Like you said, you were a mortgage banker and an underwriter before you ended up in sales engineering at Ocrolus. What do sellers get wrong when they pitch lenders on underwriting automation?

David Gipson (01:03.532)
Yeah, it's interesting because we're in this really new landscape where, when I started with Ocrolus four years ago, just coming off of the ice conference, which would be my fifth in a row, you know, AI was.

a bit of a scary term, a little bit of a new term, right? We're coming off of the good times of kind of post-COVID and everybody's really successful. And then quickly after that, it became different. And we're kind of back into maybe some middle ground. But I think what happens, what we've seen is just this rise of technology and rise of interest from mortgage lenders in utilizing some sort of tech to...

improve the efficiency for their team. That being said, we still have to understand who we're actually speaking to. that's something that positions me in a pretty advantageous space is I know the persona of the folks that we were speaking to, Feature, functions, all the latest and greatest and tech and things you can do, like those are awesome. But at the end of the day, these folks want to solve problems and you can have the best tech ever. But if you don't make it approachable for an end user to actually adopt and

feed into their day-to-day. It's a very, very difficult process, even if you have a very cool platform. So for me, what I have found is I like to take things that can be somewhat complicated and make them as simple as possible for the end user to understand, hey, here's why this matters. If you have a problem, here's how easy it is to solve that problem versus focusing on

all the technology going behind the scenes to be able to solve that problem. People in mortgage specifically often have been doing their roles for decades at this point and the fear of automation is a fear, but really I think what we try to do is instead of saying, hey, we're the big bad robot coming in to replace your jobs, it's we're here to help make your day better, right? I wanna be your co-pilot.

Carter (03:02.289)
Right.

David Gipson (03:04.302)
And I want to help take these menial parts of your day to day and let you focus on what we really like to do, which is using our brains and using our experience to solve problems within a mortgage origination cycle.

Carter (03:17.4)
Is there a lot of skepticism with these products or people now more open just because AI is more in the news and those types of technologies are more popular or more mainstream a little bit?

David Gipson (03:28.46)
I will say the skepticism is changing. And it probably depends on who you're talking to. think every president, CEO at IMBs, even banks and credit unions even, are having some sort of AI initiative. But what that means, they're not entirely always sure.

There's some skepticism then on the ground floor and maybe a little bit of disconnect between the expectations of senior leadership and the actual practicality of the floor and kind of meeting those in between. And that's why we make it, you're having, you have to understand who you're speaking to, right? And there's going to be multiple personas you talk to throughout the sales process. And I have to understand that while my

Ultimate messaging is the same. It's the things that are important to one person and can be important to a different person, right? So we see a fair amount of skepticism but ultimately we've done a really good job of kind of investing in Making things familiar

that are new, right? They're new, they're using new technology, but we don't want to completely reinvent the wheel. So the things that have been working in the past that we can utilize into our product, so they are familiar to somebody who's been underwriting loans for 30 years, that has been a big part of our growth and kind of understanding, what is important to an underwriter, right? Like, I can give you the best data in the world, but underwriters have been taught for...

decades at this point to trust but verify, right? Like, hey, I see data from a document or from a client, but I to, I can trust it, but I need to go verify it. So something we'll do is simple as if I give you an income calc and I show you a data point that we pulled off documentation to help accelerate the way you calculate income, well.

Carter (05:14.385)
Right.

David GIpson (05:23.438)
you can just click on that piece of data and see the document and where the data came from. Like that's the type of mindset of understanding who's on the ground for and how they're actually gonna use it day to day and how we're gonna adopt that technology that we've taken pretty seriously in building the product. And frankly, it makes it a lot more fun to have these conversations, because I can be pretty approachable with our end users about how we've thought about them when we were building out the product.

Carter (05:48.125)
So it's really just providing value and explaining it in a simple way and understanding what, you know, their day-to-day thing that makes it pretty easy to get around those objections.

David Gipson (06:00.78)
Yeah, mean, something we'll frequently do is ask, hey, you're looking at a bank statement. What sucks about that? There are parts of that review that are just tedious. Like, hey, need to find a.

mortgage underwriter and I'm doing it the way most people are today, which is manual. Our biggest competitor always is like Excel and just manual review. There are other companies out there. They are not usually what I'm changing from. Usually I'm changing from a very manual process. So I try to speak to them like, hey, you're looking at bank statements. What's important to you? Well, I got to look for large deposits. I got to see if there's undisclosed debt. I have to see more more.

Klarna and Affirm and Afterpay, these buy now pay later programs are like so prevalent and the GSEs are coming back and saying, hey, like we care if those are on bank statements, because those are liabilities that the borrower might have. We can help bubble those things up. So it's like I'm still making the decision as an underwriter, but I'm not.

looking for a needle in the haystack, that thing is brought to me. And then I can just focus on what we really want you to be doing, which is making a decision of what to do with that data versus going and finding that data before I can even make a decision on it in the first place. So long way to say, yeah, I mean, I think that's a big part of kind of winning over the hearts and minds of your end buyers and your end users. It's like, hey, talk to me about what isn't working today or what is frustrating to you and how do I help you solve that problem?

Carter (07:29.126)
When one of your SCs is prepping for a demo with a major lender, what do you tell them to do and not to do? Like, how do you coach them up? What things are you saying to those guys?

David GIpson (07:38.06)
You know, we have been on a big initiative ourselves to like utilize AI. So something that we used to do is spending lots of times going through like websites and LinkedIn and press releases and things like that to understand like what's going on at that bar or at that lender. You know, I had one today I met with and the client was, I found out through Gemini and deep research, like this client.

Started their business after being in the military for many years like they're really a VA focused lender. It's a big part of their business and kind of how they've embraced Embrace the market around them like that's some type of client that they want to serve and like I Normally in the day would have to go to the website and try to figure out what types of loan programs they have and what

you know, look on LinkedIn and try to get a background of the folks that we're meeting with. And like nowadays, the biggest thing that we can do as like an SE team, as we're getting ready to speak with a client is just understand them as much as possible. We're going to ask questions and we're going to prep with our AEs ahead of time, but there's so many tools out there to understand.

What makes this lender a little bit different, right? Mortgage lending is pretty similar. The outcomes are very similar. Like the structure is very similar. But everyone's got kind of their own way of doing things, their own niches. And it's really great. If I can go into a call and understand, okay, you do a lot of government loans or you do a lot of non QM or you're a big conventional shop, you're refi heavy, you're purchase heavy. This is data that we can understand. And while the product might be very similar, the messaging and what's important to them within that product is different. So once we know that,

Carter (09:01.083)
Right.

David GIpson (09:24.066)
We just need to hammer home, hey, being in this type of persona, this might be something that would be extremely beneficial to help solve this problem. And maybe something else we do isn't. And I don't want to spend time on a Fannie Mae direct approval to a client that's doing 90 % VA loans. It doesn't make any sense. So it's really understanding ahead of time so that we're

Carter (09:44.198)
Right.

David GIpson (09:47.486)
spending our hour that we have with that client trying to hit on things that actually impact their day to day and like their business.

Carter (09:55.607)
Once you get the deal closed, what's something that would kill a deal at let's say month six that looked like everything was good at month three?

David GIpson (10:07.084)
Yeah, so I mean, as far as like, what would cause fallout for a loan or for a deal, I guess I would say that has been, you know, getting two months six in general, like that's part of the problem. Time does kill all deals. And I think it's just a matter of, we have not done enough, we have not done our job of making client feel comfortable with the product. What kills that is paralysis by analysis and

Carter (10:13.692)
Yeah.

David GIpson (10:36.14)
Generally speaking, it's because we didn't answer their questions, right? They saw something that they weren't comfortable with or they didn't understand and ultimately like I put that back on myself on our team and if you're dragging out that long it's because you have

not been able to make a decision because you don't understand. Because either, you understand and you decide this is not the right product for you, which is a fine outcome for us, right? Not everybody's going to be our client. And I'd rather know that instead of spending a half a year testing and retesting and not to get to an outcome, we want to be in a spot where we are giving clear understanding of what we do, what we don't do, where we excel.

Carter (11:02.94)
Yeah.

David GIpson (11:19.286)
where you're still gonna have potential other holes in your process you might need to fill. There's things there. But really for us, it's how do I deliver an understanding of what we are, what we do, and how we can help efficiently. And if we're at month six, it's probably because we didn't do a good job in month two and three of really hammering that home and you really understanding what you're evaluating in the first place.

Carter (11:42.202)
Okay, yeah, that makes sense. So before you were an SC at Oculus during a brutal real estate cycle, how did the way you approach deals change and rates went up and lenders were cutting budgets?

David GIpson (11:50.338)
Yeah.

David GIpson (11:56.11)
That was a tough time. We actually launched our first version of our Encompass integration basically right before everything kind of went to hell. And it was a tough time in the market. People were scared. Rates were climbing. Volume was extremely low. And we really took that time to understand what was working and what wasn't working and iterate pretty aggressively on the product. And by the time the market did start to shift, we actually re-released a brand new version of the product. And we have been on an upward trajectory since. During that time though, I still was helping clients out. We tried to figure out, well, how can we still provide value to you? And honestly, while we have all these sweet things that we do, what we found was a lot of companies that we started talking to had gone through layoffs or...

shrinking of teams and we could provide some automation where maybe they over index on letting people go or maybe they're preparing for when the market comes back, like would you be able to handle a market surge with your current team? And like the delivery is a little bit different.

We are trying to set lenders up where we, hey, we understand that this time is bad, it is temporary, and if there's ever a good time to evaluate your tech stack, it's when things are slow, because I tell you right now, we're getting into purchase season, I just got out of ice. It's gonna be a conversation with folks, right? It's like, hey, how do we prioritize these things? Well, at that point in time,

That was kind of our messaging. And then it also gave us time to be very self-reflective on the ways that we can really be ready when that market does come back. when it came back, we were ready to attack at the right time. we went from doing a few mortgage clients a year and then a few clients a month to, in the last year, we've added like two or three mortgage lenders a week.

at Oculus and it's because we took that time to take advantage of it, be ready to go and kind of meet the market when it was ready for us.

Carter (14:24.13)
You sell into a very tight knit market. You had kind of said that with ICE, that's a big, know, it's more, it just is a very relationship heavy business. And you were saying that's a big pipeline driver. A lot of the people at the top lenders know each other. How much does your reputation carry from one deal to the next? Or does it not even matter really all that much?

David GIpson (14:33.326)
For sure.

David GIpson (14:45.23)
It's huge and I'll say like reputation compounds. When we started going to ICE five years ago roughly, we were a stand and people came up like, who are you guys, right? And this year we had 180 pre-book meetings, about 80 % of those showed up. Our booth was busy the entire day and we had clients come up to us and be like, wow.

Carter (15:00.197)
Yeah.

David GIpson (15:13.71)
I had someone come up to me and say, usually the booth with the most activity is doing something pretty interesting. Like, I want to chat. I've heard about you guys. And frequently I hear people say, hey, we hear a lot of good things about you, or you're coming up in the market, or we're in certain lending groups, and people are recommending to us to each other. Or often to your point, it's a small industry. Like, hey, we used to use you at our old lender. We don't have you.

we need you, we'd like to go ahead and talk. And like that has become this kind of snowball effect where what starts is like winning a couple of clients. You do a really good job. You take care of them. You solve a problem.

It just compounds and we see that every single year and ICE Conference being a really good example of that of these are our core ICPs. We have a direct compass integration. Every lender there is a potential client of ours and like over the years it's gone from small to bigger to bigger to bigger. And that has to do with taking care of your clients and we...

We put a great deal of effort into that. mean, our account management team, our support system, our team that helps clients actually ramp and use the product is significantly bigger than our sales team, right? And we understand that while we might have like, let's say we have 60 folks in revenue, maybe 10 of them are on the sales, direct sales team and the rest are.

on implementation and ramp and ongoing management and relationship building. And that is really proof of dividends to us to be able to grow our name within mortgage. It is difficult market to come in from the outside, right? We have mortgage professionals, but we were a company in small business lending and consumer lending. And to build a name within mortgage is difficult, but we were able to do it because we really took that kind of extra care on our clients.

Carter (17:02.99)
At this point, do most people that you talk to, have they already heard of you? Or it's usually they haven't? Like what is the breakdown percentage wise?

David GIpson (17:09.484)
I would say most people are somewhat familiar with us, if not very familiar to us. And that's been quite an interesting change over the last two years. Being here for a while, watching us in very early stages of mortgage to now, we're like, we heard about you. It's great. I you'll certainly run into folks that you do need to introduce yourself to, but it has been...

Pretty neat to watch a brand go from pretty small recognition to pretty widely known throughout the industry. And yeah, it's been a wild ride.

Carter (17:46.001)
Yeah, that's pretty nice. Walkme, can you think of a deal at Oculus that was falling apart that you came in maybe and saved it at the very end? What ended up saving it? Can you think of any?

David GIpson (17:59.468)
I can think of many, and I will say there's a common theme that we see that really helps us. I'm lucky enough to be able to work remotely. Oculus is centralized in Manhattan, but we have folks all over. But doing business over Zoom is super helpful, but sometimes you just need to get out and meet people face to face.

Carter (18:24.324)
Okay, yeah.

David GIpson (18:24.758)
What we have found is we are very, very open and I think there's a tremendous value, the ROI of getting on a plane, flying out to your clients and just walking through things together. Like I can explain how to use our product on a Zoom call and you can get a good understanding, but actually being able to sit down next to somebody evaluating things and make it more of a working session. Like we're just trying to be collaborative here. Like let's talk through things, let's walk through problems.

We have solved so many stalled deals by just level setting with people, getting in front of them and just showing them we care enough to go to the middle of South Dakota to...

Baton Rouge to California, wherever it might be. If we have a client, and these can be pretty big clients, can be fairly small clients too that we'll go out and meet. And we've just figured out that it's worth it. It's worth it to get in front of people. A lot of folks just are not willing to do that. And it kind of shows these guys care. They care enough that...

They want to come out, they want to meet us, they want to bring us to dinner, they want to actually work through and solve problems. People are way more candid about what they actually feel like if you are in front of them. It's pretty easy to be withholding of information or not be direct on a Zoom call. But when you're next to they're going to just tell you what they think and you're going to learn something. Whether you learn, hey, we're out of the deal, we don't have it. But more often than not, it's like, this is what's actually going on. Let's talk about how we can solve that.

Carter (19:44.284)
Yeah.

David GIpson (19:58.154)
That has saved most of those. Like most of the things I can think about has been because we've just, we've gotten on a plane, we've gone out, we meet people, and we've kind of made things happen.

Carter (20:08.444)
Do you always try to go out or is it if the deal is not moving very fast or there's issues, then you decide to go out?

David GIpson (20:14.902)
No, no, no, no, no. If the client is right, we'll go out often and try to preempt that. That doesn't need to be like a Hail Mary at the end of the, like that's.

Carter (20:29.532)
Yeah, yeah.

David GIpson (20:31.246)
Can be, but like really we want to get out early and often and whether I come or whether just our AE comes, I'll go meet with clients that have already closed too. Like I was just down in Houston with a client doing a training because they had some questions, they had a team that was kind of coming in and adopting. They just wanted to have some time together. Great, we'll do that as well. And we just have found that regardless of where you are, if you're a partner of ours, like we'll come out and spend some time with you. And usually that just shows like, hey, these guys care.

And whether that's caring that you understand how to use the product in an evaluation or caring because you're a client, you want us to get the most out of what we signed up to use. That has been a good decision every single time.

Carter (21:15.75)
Okay, yeah, that makes a lot of sense. Well, I think we got some good stuff here. I will end it here.

David GIpson (21:21.422)
Awesome.