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This week on Power House, Diego chats with Windsor Mortgage CEO Chris Vinson. After his company, Journey Mortgage, was acquired by the South Dakota-based Plains Commerce Bank, Chris joined the Plains Commerce team to head their growing mortgage division.



He and Diego talk about how Windsor is differentiating itself from other wholesale competition by personalized and localized coaching and tech services. They also talk about Windsor’s daily accountability strategy for account executives, their focus on community banks, and how they maintain growth amid a high-rate environment.



Here’s what you’ll learn:

Windsor focuses on the wholesale channel, primarily conforming agency and jumbo loans.
They pride themselves on personal customer service with a small team of account executives.
Chris emphasizes the importance of coaching and support for originators.
The company leverages personalized technology to enhance the closing experience.
Chris believes in accountability and metrics for account executives to drive success.
Windsor Mortgage aims to be the best fit for brokers and originators, not the biggest.

Category

🤖
Tech
Transcript
00:00We're never going to be the biggest. I don't want to be. I just want to be the best for the right
00:04fit brokers and originators that fit our model. And it's amazing when you find that fit, how loyal
00:10we are to them and they are to us. And that's in a sense, that's Windsor's business plan.
00:23Welcome to Powerhouse, where we interview the biggest names in housing and ask them about
00:28their strategy for growth. I'm Diego Sanchez, president of HousingWire. My guest today is
00:34Chris Vinson, CEO of Windsor Mortgage, a division of Plains Commerce Bank. Chris,
00:40it's so great to have you on the show. Yeah, thanks for having me. I'm honored.
00:45Yeah, it's really exciting to have you on the show. For those in my audience who don't know
00:50you or Windsor Mortgage, could you briefly introduce yourself? Yeah, I mean, I started
00:57off as a mortgage broker in the year 2000. Weird enough, I actually sold to a bank in 08
01:06and really just had one big goal was to figure out how to get number one in market share.
01:11Got that market share in 12. And then in 16, really started to work community banks throughout
01:19the Midwest. And that was like, in a sense, the birth of Windsor. Windsor was never going to be
01:25Windsor. In fact, our demographic was a 45 to 55-year-old male that wore a suit every day.
01:33And so the Windsor originally was the tie knot of connecting us with community banks. However,
01:41as things change and you start one thing and you think you're going one direction,
01:45and then you're like, wait, we're going to go another, I get a call. And I get a call from
01:50Fannie and Fannie's like, we know this wholesale group. They're actually making a shift and change.
01:56Would you be interested in adding that to your arsenal of Windsor? And what really happened with
02:01Windsor was, is that a lot of community banks in my market used us and they would say, we use
02:08Plains Commerce Bank. Well, the consumer was like, well, we're paying two people. We shouldn't pay
02:13two people for this product. And they weren't, but in their minds, they were. And we're like,
02:17we're going to have to rebrand this channel differently. So in a sense, Windsor is really
02:22a product name. Our licensing and everything houses underneath our federally charted bank,
02:30which is Plains Commerce Bank. So in a sense, that's like how that whole thing transcribed of
02:37day one in 08, which I didn't have a crystal ball. I'm not super smart, but in 08, they purchased us
02:46because I didn't have enough. And maybe this is a challenge to maybe some that's listening,
02:52but I didn't have enough warehouse lines as a small broker and warehouse lines in 08 were harder
02:58than they are today. And I was looking for additional partners and I ended up with a
03:03company that wanted to purchase and partner at the same time. And so off we went, been here ever since.
03:10And then in 2000, we really got serious in wholesale, COVID hit, and here we are,
03:17the beginning of 2025. So what is being under that Plains Commerce Bank umbrella
03:26done for you and your mortgage team? Well, I mean, just like everything,
03:34I think there's positives and negatives. The positives are we're a nationally chartered
03:39license in all states. We have a different set of regulators, so they maybe view things
03:49differently, good and bad, or I should say harder in some areas and easier than others,
03:54if that even would make sense. But I don't know if it really truly matters. I would say
04:01the negative is, is that we're capped on the total dollar of servicing tied to our capital.
04:07So it's a negative as a community bank. It's something that we're passionate about figuring
04:11out why to change. I get that they didn't want to use depositor money to build a servicing portfolio.
04:19So I totally get that philosophy, but what if and how could we set this structure up differently?
04:26That would be a big challenge that a smaller community bank like us would have over,
04:33say, another mortgage company or some that are my biggest competitors, which wouldn't have that
04:38as a requirement. Your primary focus at Windsor is on the wholesale channel. What is the size
04:47of your account executive team and do you have a geographic focus with your business?
04:54Yeah, I would say, that's a great question. Of course, we're in all of the states, Florida,
05:03Texas, the Midwest. We're really strong into those states. We're a small company. We're a
05:11boutique mortgage company. We pride ourselves in when you call into us, you're going to actually
05:18talk to somebody. So we run about 21 AEs. We don't have 100 AEs. We work hard every day and
05:30we're not the perfect fit for everyone because we don't do non-QM. We do primarily your conforming
05:37agency, jumbo, and then state bond programs are our real focus. It's because we feel like a loan
05:45officer needs a full toolbox. And our way of doing business doesn't obviously fit some of the
05:52non-QM products. So we've just never really got into that game. So our customer is a conforming
05:59agency, government type products is most of their fit. That's our perfect customer.
06:07I mean, we have the big guys, we have the small guys. So we don't really concentrate on the size
06:13of the mortgage company, but we see that we do really well when we get a really good originator
06:20that's out there proactively generating leads. So we work really well with a loan officer that's
06:26generating self-leads and we work really well with an originator that has a team as well,
06:33so that we can integrate with that team to be able to help that originator do more loans.
06:38Now, the Wholesale Channel is dominated by United Wholesale Mortgage and Rocket.
06:45What is your strategy for competing against these two juggernauts and kind of carving out
06:52your own slice of the market?
06:55If I only knew how big they were when I started, but I think there's a... I tell everybody we're
07:03a perfect fit and there's a room for both. If you think about how you shop,
07:13would you choose this place over this place? And there might be saying,
07:16well, I would choose both. I mean, in this situation, I would go here and in this situation,
07:20I would go here. I think that's true for the originator. My main focus is helping originators
07:26be better. So we do a lot of coaching. We offer a lot of tactical things that they can go out
07:33and generate more business. So our philosophy is that, look, if you want to learn how to get
07:38better and to generate more, we'll help you. And in lieu, you help us. That's really been our
07:46philosophy. Am I going to win in this particular area or this particular area? Maybe not, but I
07:53feel like we do win helping an originator generate more leads, more closings, figure out how to hire,
08:01how to do metrics, like all of these topics, run a P&L, all of these major topics that originators
08:08are working on today. They're like, where do I go? Do I hire a coach? That's why I started
08:12Battle of the Coaches because I wanted the originator to understand that not one coach
08:18is the same. And there's times in life where you need this coach or you need this coach.
08:24And to understand, because it was a coach that kind of changed my life, but understanding that.
08:30So our originators and our AEs, we always tell everybody, look, our AEs aren't telemarketers.
08:35They're not calling you unless they have a purpose. And our purpose is to grow in the relationship
08:42and to be able to help them succeed. It's tough out there right now. And so being able to run
08:48scenarios, have our live Zoom rooms, being able to talk to our underwriter are all unique things
08:53that I think Windsor offers to the broker community that maybe some of our competition doesn't.
08:59Yeah. I mean, if you think about the variables that people are competing on in wholesale,
09:04you know, it's tech, it's speed to close, it's rate, obviously, but there's also the
09:08service and education component. It sounds like that's where you're really trying to win mindshare.
09:14I mean, yeah, everybody wants to be competitive and you got to be in the game.
09:18And we always tell everybody, hey, look, if I'm within a quarter, would you choose me?
09:22And I feel like that's like, that's like that spot. If I'm 100 basis points out,
09:27I wouldn't expect them to choose me because how am I going to offset that value? Maybe I've put
09:32that into my head, but I think that's probably more reality. And at the same thing is how do
09:39I stay in front? So my last word for the last year was stickiness and how do we become sticky?
09:46And so creating warehouse lines, because we're a bank, that's definitely a benefit. So we have
09:50a warehouse division that we've created and we have some unique advantages for that warehouse
09:56line. It was not having a warehouse line that got me to Plains Commerce Bank, which then got
10:01me purchased. And so I understand for a mortgage company to have the proper warehouse lines,
10:07have the proper mix, not just have one and understanding that is super important.
10:12But then also we've created an executive banking suite for mortgage companies to bank. So a bank
10:20that understands mortgage companies and understands what costs them the most in their
10:24bank statement. Most mortgage companies don't dive into the statement enough to understand the fees.
10:32So an average company, if I save them four or $5,000 a month in just fee stuff,
10:38mainly incoming and outgoing wires, then I'm putting money right to the bottom line.
10:43So we're always looking for it. I think we get asked all the time, what makes Windsor unique?
10:48We're like, we're looking for your problems and we're figuring out a solution.
10:52And if we did that, we feel like then we've earned the right to ask for the business.
10:57Yeah. Yeah. That makes a lot of sense. I was going through your LinkedIn feed prior to this
11:02conversation and you actually had some frequent posts about your tech stack. And so maybe talk
11:09a little bit about what your tech stack consists of right now and how you're maybe trying to
11:15differentiate yourself a little bit on the tech side. Well, yeah, I think the big challenge on
11:20the tech side is, is that what LOS is the originator or broker using. And it's really
11:26gotten to a smaller pool, which is nice. Arrive, LendingPad, these two great companies and us
11:34partnering and being able to figure out how do you make it easier for us to connect in.
11:39So I guess you could call us old school or stubborn to change. We're still with Encompass
11:45because the back inside of Encompass is so good in connecting through all of our back channels
11:51and bank side. It's how do we make the front side better? So our utilization through third
11:57party in Salesforce, our utilization and new partnership with Arrive, even Arrive now has
12:03got it set up to where not only could they start the application, lock the loan, and now send us
12:09the initial steps up front without ever having to leave Arrive. So the technologies, I would say,
12:17has really become even a more of a level playing field. But we're working on all of our new
12:25technologies with the ICD so the broker can originate that. That'll be next month. So the
12:29broker can have that ICD done at approval. They can have everything set up. And then, boom,
12:34soon as we're ready to go, it's already done. So each at SnapDocs, SnapDocs and integrating
12:41that piece to where we can eliminate 30 to 40 minutes from a closing because all the preliminary
12:46forms are getting signed up front. We're coming in, we're signing six or seven forms, and then
12:51we're out. So problem is an originator that wants to go to closings and it starts to get busy.
12:58They can only go to so many a day and then stay on the front side of helping all of those other
13:02customers. That becomes a challenge to a top originator. To an originator doing one to two
13:07loans is not that big of a challenge, but to an originator doing 30 loans becomes a big challenge.
13:12And so SnapDocs is someone that we've really partnered with. We believe in what they're doing
13:18and they're just really changing that whole closing experience for the borrower. So we spent
13:23two hours today, actually, working through our tech set. What's next? What's next? What next?
13:28How fast can we get the file index? How fast can we get an underwriter? How do we reduce
13:32underwriting error? How do we be able to give a good condition list? Because we don't want to send
13:37and do an LPDU underwrite, which means you read DU, you LP, you send it out, you say your loan's
13:44approved. Because most originators don't dive into the DU or the LP report. So I'm going to give you
13:5140, 50 conditions. Or what if I did all the work and got you 12 and then got you organized so that
14:01you could stay on the front or your processor could handle the majority of those conditions?
14:06That's like, in a sense, our thought process. If I don't need to condition for something,
14:10I'm just not going to send it out just so I can catch everything. I just want the conditions that
14:14I need. And I think a broker appreciates that. And that's where we go, we're probably worth a
14:18quarter because I saved you maybe an hour or two hours up front. Yeah, someone could beat me into
14:24an approval. But is that a DULP approval or is it a full underwrite approval? And that's like
14:30one of the differences that we feel like the originator brings to the broker.
14:35So we started 2025, kind of in the same place we ended 2024. Not much movement on rates,
14:42still above 7%. And I think looking into the crystal ball a little bit, probably rates stay
14:50higher for longer than anyone would really like. How are you keeping your team of account executives
14:59focused on that growth mindset while these rates stay stubbornly high?
15:04Yeah, I'm probably not a fit for every AE. I hold our AEs accountable. We run their metrics,
15:12we figure out what it takes an AE to win every day. Our AE is going to have a count pyramid to
15:17know who are the most important originators in their life. How many talk to's are you getting?
15:24How many apps and locks are you getting every single day? And then we have a casino report.
15:29So you remember Ocean's 11, right? And he sits down with Julia and they bring him the report
15:37and he looks at the casino report right before they eat dinner every single night at the same
15:42time. And I'm going to go, that's what we need. I want my originators and AEs to know what does
15:48it look like to win each and every day, not for the month or quarter and then they get lost.
15:52Because there's a lot of account executives lost. And it's just simply because they don't know what
15:58it looks like to win every day. So if I see apps and no locks, well, I know they're not converting.
16:04If I see all locks and no apps, I knew they're not getting new business,
16:08they're just locking the existing business. So I can go to them instantly and go, hey,
16:12we need to make a tweak. We need to make a change. Let me hear what you say.
16:15How are you connecting to your most important people? This is what I think it takes to make
16:21an account executive successful. But here's the truth, Diego. There's business out there.
16:26If I'm not going to get it, someone else is. Is there a lot of business out there? No,
16:31but there's business. People are buying houses. People are looking.
16:34Even I sit in South Dakota today, there's no snow. People are looking at houses.
16:40It's my opportunity to be able to go out and get it. And so the way we teach our originators in
16:45South Dakota, I only have originators in South Dakota. Last month we had 25% market share of
16:52the city and we have 23% market share of the state with 17 LOs. It's that same accountability
16:59that we teach our LOs, that we teach our AEs. We're like, we're never going to be the biggest.
17:03I don't want to be. I just want to be the best for the right fit brokers and originators that
17:09fit our model. And it's amazing when you find that fit, how loyal we are to them and they are to us.
17:16And that's in a sense, that's Windsor's business plan.
17:20I really like that sort of daily dashboard approach. I think that makes a lot of sense.
17:25And do you distribute your account executives geographically or by product? How are they
17:33organized? Yeah, I would say maybe I'm weird on that. I'm a little bit geographically for new
17:41opportunities or leads to come in, but if they get a referral and a connection and they've done
17:46a really good job, it's hard to fight that. And so if they get a referral, I'm not going to
17:52geographically lock them in. I want them to have that opportunity, but I also don't want
17:58them to have too many accounts where they can't take care of. So it's a careful balance that we're
18:02always looking at. We're always looking at it. It was like looking at each LO and seeing who
18:09sends us business each and every month was probably the biggest lesson I ever learned.
18:14And I learned it, A1, I went home frustrated and my wife said it was my fault.
18:22She's like, you're not analyzing the data soon enough. You're not knowing the data soon enough.
18:28And you can't catch it. Surveying, understanding, connecting, and an originator takes their phone
18:37and they scroll with their finger and they're like, oh, let's call Diego. Oh, he's safe. He's
18:42easy. Oh, let's call this. And so technology for an AE on the front side through Salesforce is
18:48just as critical and giving great customer experience as is the LOS and the front side
18:55of them to import their documents in and get to closing.
19:00Well, Chris, it has been really interesting to learn about the Windsor mortgage business and
19:07your history in mortgage. Thank you so much for joining me on Powerhouse today.
19:12I appreciate it. Thanks for having me.
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