Inside the Strategic Shift Coming to Insurance in 2026 with Callan Harrington

Callan [0:00:00]: There's gonna be this window where people are going to be much more aggressive in their spend where carriers are gonna really start to spend a lot of money back and growth, so that can be on the marketing side that can be on the investment side that can be on sales side, their distribution models, all those different things, which lead to big opportunity for people and the entire eco ecosystem to help support that.

Callan [0:00:21]: Welcome to The Insurance Growth Lab.

Callan [0:00:25]: Where we go deep on the growth campaigns and strategies driving real results in the insurance industry.

Callan [0:00:31]: I’m Callan Harrington founder Flashgrowth and in each episode, I sit down with marketing and growth leaders from carriers and sure tech and top brokers to break down one specific initiative, whether it's how they marketed a product, scale a channel or solve a specific growth challenge.

Callan [0:00:48]: It's no fluff, just tactical insights you can apply in your own company.

Callan [0:00:53]: Welcome back everyone to The Insurance Growth Lab.

Callan [0:01:00]: I'm Callan Harrington, and today, it's just gonna be me.

Callan [0:01:04]: I wanna talk a little bit about something that I'm seeing because I think we're coming into a really interesting time, and talk a little bit about when I've experienced this time personally because I think there's gonna be a big opportunity here.

Callan [0:01:18]: So to get a little bit more specific.

Callan [0:01:20]: I think we're going into a period of growth again.

Callan [0:01:23]: I'm not gonna go on record yet to say that we're entering a soft market because we don't know.

Callan [0:01:31]: But I will say this, I think most of the stats out there saying that rates are stabilizing.

Callan [0:01:35]: And of course, this is very dependent on the different sectors and industries and lines of business, but We're seeing some rate stabilization.

Callan [0:01:45]: I saw this at It c, but I've heard this in a lot of our conversations.

Callan [0:01:49]: Carriers, agencies, insured text, it's starting to switch to going back on offense.

Callan [0:01:57]: And I'm not saying that this is a full blown growth at all cost, which call what it is in the carrier world really never gonna be a growth at all cost.

Callan [0:02:06]: But I do see some of that we're switching back, our appetite are loosening up a bit and we're starting invest in growth.

Callan [0:02:14]: And I think one of the best places that I've ever heard to look in, like, there's a great leading indicator on this is to look at what the lead providers are doing.

Callan [0:02:24]: And how are they performing in the market?

Callan [0:02:26]: In Coverage had an article the other day, and they talked about some of the bullets from ever quotes most recent earnings call, and this to me is very telling.

Callan [0:02:34]: Enterprise carrier spend was up twenty seven percent.

Callan [0:02:38]: Now if you followed this at all, over the past couple years, almost all the lead providers, the carrier spend in buying auto leads home leads was way down.

Callan [0:02:48]: And a lot of those lead providers were in a lot of trouble because the carrier spend the most money by far when it comes.

Callan [0:02:55]: And there are some digital agencies that can rival a carrier, but the big carriers are really the ones that spend the most money on media and paid media and leads and all those different things.

Callan [0:03:04]: So being up twenty seven percent, that's a pretty big deal.

Callan [0:03:06]: Separately, when it comes to investment in growth, nationwide announced that they're gonna be investing one point five billion in technology through twenty twenty eight with a hundred million per year dedicated to Ai over the next three years.

Callan [0:03:22]: Those are two pretty big indicators that we're going back on offense a bit in the insurance space.

Callan [0:03:30]: Again, I'm not gonna say we're going into a soft market.

Callan [0:03:32]: I think people are definitely still worried about what's going on.

Callan [0:03:37]: But at the same point, there's a lot of light at the end of the tunnel.

Callan [0:03:41]: And know, I saw a lot of this optimism at It c.

Callan [0:03:44]: And it felt like a lot of funding rounds were happening.

Callan [0:03:46]: That said, if you look at the objective stats, first three quarters were relatively flat, and it looked very similar to last year, but I'll be very interested to see q four twenty twenty five numbers and investment in Insure tech and then what the numbers look like in q one of twenty twenty six.

Callan [0:04:02]: So given it all this, I think we're going into a window where if people are going back on offense, the people that sees the moment can achieve significant long term gains.

Callan [0:04:17]: So what I mean by that is there's gonna be this window where people are going to be much more aggressive in their spend where carriers are gonna really start to spend a lot of money back in growth.

Callan [0:04:28]: So that could be on the marketing side that can be on the investment side that can be on the sales side, their distribution models, all of those different things, which leads to big opportunity for people and the entire ecosystem to help support that.

Callan [0:04:41]: And I think that agencies, they've had nothing but negative conversations for the most part.

Callan [0:04:46]: Now, negative events cannot often lead to really prime touch points to build a deeper relationship with your customers, but let's call what it is.

Callan [0:04:55]: A lot of the service people at agencies and had a rough couple years with the canceled policies, the rate hikes all the different things, and not not saying that those things weren't warranted, but they've had some tough conversations.

Callan [0:05:08]: And now coming out of this, it can focus a lot more on...

Callan [0:05:12]: I don't wanna say just growth because in a hard market, those premiums did go up.

Callan [0:05:17]: Those agencies oftentimes stayed stable or are still increased in the revenue, but now they can really grow.

Callan [0:05:22]: They can grow their policy count.

Callan [0:05:23]: They can get out there in market and sell again.

Callan [0:05:26]: And on the insure tech side, similar to what we said before, there's this big opportunity to support those agencies in carriers as they start to look more towards offense again.

Callan [0:05:37]: And so it's a really interesting time.

Callan [0:05:39]: And so with that, in the spirit of the show and actually diving into campaigns from my career, as a lot of people know I spent the past fifteen years in the tech space as sales, marketing and revenue leader, And so that's what inspired the shell.

Callan [0:05:54]: So I wanna talk about a story that maybe could serve as an interesting story for this time in particular.

Callan [0:06:01]: So this was back from my bowl penguin days, and we had this really big mark that we wanted to hit.

Callan [0:06:09]: We wanted to enroll two hundred agencies in thirty days into our commercial rating in market access program.

Callan [0:06:16]: Now, that number, it's a subjective number.

Callan [0:06:20]: Right?

Callan [0:06:20]: That could mean a lot somebody that could mean a little, so I'm gonna give you a little bit more color on that here in a minute on why that was a big deal and a very difficult number to hit.

Callan [0:06:28]: And if that number was hit, the people that were on that team, we're gonna get a significant bonus.

Callan [0:06:35]: Now this is oftentimes a double edged sword.

Callan [0:06:39]: Because what are the biggest mistakes that you can make, and I see this all the time.

Callan [0:06:46]: Know, I think many people would believe that salespeople people in particular are coin operated.

Callan [0:06:53]: And the reality is there's a lot of truth to that.

Callan [0:06:57]: And I would tell you early in my career, there was it.

Callan [0:07:00]: Ton of truth to that.

Callan [0:07:02]: I followed the money and almost every single thing I did within my sales career.

Callan [0:07:05]: It wasn't until later that other things became as important or more important.

Callan [0:07:10]: But that wasn't the absolute only thing.

Callan [0:07:13]: And often the times what'll happen is, and I would tell you, I've been As a revenue leader, I have personally been guilty of this, you'll put an astronomical payout tied to a goal, and then you'll put some ridiculous number that needs to be hit to hit that.

Callan [0:07:28]: So, yeah, you're gonna push really hard to hit that goal if you think that's reasonable.

Callan [0:07:34]: If you think that actually attainable.

Callan [0:07:37]: If you don't, it doesn't matter if the best salesperson in the world, that number is too high, it's gonna have the reverse effect.

Callan [0:07:43]: You're not even gonna care, you're not gonna work hard.

Callan [0:07:44]: You're not gonna even try to get that.

Callan [0:07:46]: And so it is kind of a tricky balance to pick that right number.

Callan [0:07:50]: To be really be a stretch.

Callan [0:07:51]: So if you're gonna put a big number, a big payout on that.

Callan [0:07:54]: Well, then that's gotta be a stretch goal, but it has to be something that you look at, you just don't feel like that's gonna be impossible.

Callan [0:08:00]: I think another good example of this, a parallel example of this is, if you're stepping up to the bench for press, and there's a thousand pounds on there.

Callan [0:08:06]: You're not gonna get that mode faith.

Callan [0:08:09]: It doesn't matter what somebody says in order for you to accomplish that.

Callan [0:08:12]: You know you're not going to accomplish that fee.

Callan [0:08:15]: Or maybe there's what one person in the world that possibly can and probably not.

Callan [0:08:19]: Right?

Callan [0:08:19]: That's a super high number and it's no different than setting a number that's way way way way way too high to hit.

Callan [0:08:25]: But that doesn't mean you can't put a stretch goal.

Callan [0:08:27]: Alright.

Callan [0:08:28]: So let's dive into the background of this a little bit.

Callan [0:08:30]: Let's talk about the product.

Callan [0:08:31]: This product at that time, and this was years ago.

Callan [0:08:35]: This was a really new product.

Callan [0:08:38]: And it was a new product within the market, not market access.

Callan [0:08:42]: You know, this was when a lot of people are adding market access to almost everything that they did, but the actual product itself, the commercial lines rating platform was pretty new.

Callan [0:08:51]: Now that being said, a number of players got into this at the exact same time.

Callan [0:08:55]: And it was critical for us as a company we had shown amazing traction, and we really did a really good job on the enterprise side.

Callan [0:09:04]: But on the Smb side, to those main street middle market agencies, we really needed to elevate what we were doing in that regard because there were a ton of other people that were getting into this.

Callan [0:09:15]: You know, And I would tell you internally, we were all thinking vi or applied gets into this, we could be in trouble.

Callan [0:09:22]: And so we needed to make a statement and it was really important to get those numbers.

Callan [0:09:26]: So to put this into context.

Callan [0:09:27]: So there's two hundred agencies that we wanted to enroll on this.

Callan [0:09:31]: That was our goal.

Callan [0:09:31]: At this point, we probably had sold ten to fifteen of these, so not a lie.

Callan [0:09:38]: Now I had been the leader of the agency sales.

Callan [0:09:42]: And so I knew this was going to be really difficult.

Callan [0:09:47]: But that said, I thought we had an outside chance at it.

Callan [0:09:51]: We'd have to do something really unique, really special in order to hit that, but I did think that we could do that.

Callan [0:09:58]: Oh, and then on top of that, that thirty days, that was December.

Callan [0:10:03]: And so last month of the year, we had to fight against time with the holidays That was daunting.

Callan [0:10:11]: Now here's a dirty little secret if you've worked with agency distribution for a very long time.

Callan [0:10:15]: If you support agencies, you know this, especially if you had any type of product that serves agencies.

Callan [0:10:21]: November in December.

Callan [0:10:23]: If you're coming from the outside in, you often think, man, we've got the holidays in November, get the holidays in December, fighting with all of the holiday parties and everything else.

Callan [0:10:32]: This is, like, we're gonna chalk these months up.

Callan [0:10:34]: But if you've done this for any amount of time, You know that those first couple weeks in November and those first couple weeks in December are by far the best weeks of the year that end up being the best months of the year.

Callan [0:10:48]: So if you're new to this do not rule out.

Callan [0:10:51]: November and December.

Callan [0:10:53]: Those are important.

Callan [0:10:54]: I would argue so important that ramping up in September on October to really knock to cover off the ball in November and December is really, really important.

Callan [0:11:05]: This why you see a lot of the conferences set up around that time.

Callan [0:11:08]: Alright.

Callan [0:11:09]: So still, nonetheless, we're kicking off this major initiative.

Callan [0:11:14]: We only sold ten fifteen a today, We gotta hit two hundred of these, and we all have to do this in December.

Callan [0:11:19]: Now, here's why December was interesting.

Callan [0:11:20]: We decided that it's gonna be an all hands on deck.

Callan [0:11:24]: The blitz was going to involve the sales reps on the Smb side that we're selling this, the sales reps on the enterprise side and anybody that was involved in leadership were all going to be totally focused on selling this Smb product.

Callan [0:11:38]: You're gonna d prioritize what we are doing on an enterprise perspective and focus on this Smb product.

Callan [0:11:45]: And you're hearing this, and if you've been in any type of sales leadership or have sold or whatever that might be for any amount of time.

Callan [0:11:53]: This went to start out about exactly how you would have thought it would.

Callan [0:11:58]: And I don't know that never really changed, but we're tripping all over each other.

Callan [0:12:02]: We're stepping on each other's toes and any process.

Callan [0:12:06]: So you'd had heard Nikola That was just on the podcast, which I'd highly recommend listening to his episode.

Callan [0:12:12]: If you wanna get a feel for how is Ai and Rev ops impacting what's going on in go to market right now, but we had worked together for years, and we were together at bold penguins.

Callan [0:12:20]: So any process that we put in place was just totally thrown out the window.

Callan [0:12:26]: I just remember, I was so...

Callan [0:12:29]: You know, I'm frustrated I've got a ton of anxiety because I'm like, this is gonna blow up in our faces because I'm not somebody.

Callan [0:12:36]: I am somebody that's very much...

Callan [0:12:38]: We're gonna put in scalable processes.

Callan [0:12:40]: We're gonna hit those processes.

Callan [0:12:41]: We're gonna measure that.

Callan [0:12:42]: We're gonna be very predictable about what we're doing.

Callan [0:12:43]: And what we decided to do here was the exact opposite.

Callan [0:12:47]: So I wasn't that happy about it.

Callan [0:12:50]: And then something changed.

Callan [0:12:52]: Because we had this big overall team goal and we started people started closing these deals.

Callan [0:13:03]: And man did the team rally around each other.

Callan [0:13:08]: Everybody was helping each other out.

Callan [0:13:10]: Everybody was getting each other's backs they're pushing each other, porting each other, and I just would have never guessed that we would had a push like that.

Callan [0:13:22]: You know, one are the interesting things about this too I found was sometimes, you often will have a decent sized Smb team, Let's just say ten twenty, thirty Smb reps, and it's so crystal clear who's really good who's not.

Callan [0:13:38]: And on the enterprise side, sometimes in a startup, it's hard to say who's really good.

Callan [0:13:45]: News who's not.

Callan [0:13:45]: Yes, you have the actual numbers.

Callan [0:13:47]: Right?

Callan [0:13:47]: But sometimes enterprise numbers can get skewed because one person can bring in a deal worth ten million where somebody else got five deals worth a million.

Callan [0:13:56]: I'm saying some random numbers here.

Callan [0:13:59]: And so you think, oh, man, the person that did ten million in production versus the person did five million in production way better.

Callan [0:14:05]: Well, maybe, and you never really know how that deal came across.

Callan [0:14:08]: Right?

Callan [0:14:09]: And anybody doesn't say that there's not some amount of luck for some of those mega deals?

Callan [0:14:13]: There is.

Callan [0:14:13]: It's just the reality.

Callan [0:14:14]: And so you don't know, you know, who does have kind of that either that natural skill set or really hone their craft or who's good Man.

Callan [0:14:22]: It opened my eyes when everybody was doing the same thing and seeing how they operated and I can't tell you how many people from that team.

Callan [0:14:30]: I just had the utmost respect for.

Callan [0:14:32]: So anybody that you know who I'm talking about on that bold penguin sales team during this time.

Callan [0:14:38]: Man, Just absolute killers, and I've got just a ton of respect for that team.

Callan [0:14:42]: And so we ended up hitting that goal.

Callan [0:14:46]: I knew the number was potentially attainable.

Callan [0:14:49]: But how that started out.

Callan [0:14:52]: With literally, the whole team, cold calling...

Callan [0:14:55]: This is largely cold card.

Callan [0:14:56]: I should also state that.

Callan [0:14:57]: There was marketing support, right, and we had air cover from that regard, but man, this was roll up your sleeves as cold calling, brute force, like true brute force in order to do all this.

Callan [0:15:11]: And when we hit the mark, you know, is getting pretty close to literally getting very close to the end of the year.

Callan [0:15:18]: We had a ridiculous pipe line.

Callan [0:15:20]: Pipeline means nothing.

Callan [0:15:21]: You gotta get the deals in the door in order to hit this.

Callan [0:15:24]: And so we did.

Callan [0:15:25]: We hit it with a couple of days to spare, but the interesting thing was, we ended up doing like another eighty ninety more before we wrapped up the year.

Callan [0:15:32]: So we were just shy of three hundred agencies.

Callan [0:15:34]: And we hit that bonus.

Callan [0:15:36]: And I gotta tell, I've never seen...

Callan [0:15:37]: I just changed my whole viewpoint on being...

Callan [0:15:44]: You know, I think I could get personally so overly caught up in Again, I talked about earlier that's scalability and making sure that we had, like, this exact process in place, and we could put fuel on this process and get the end result, but we can't do anything else on that.

Callan [0:16:04]: That was very much my mindset.

Callan [0:16:05]: That would I'm so I'm still probably eighty percent of the way there.

Callan [0:16:08]: But sometimes, in Paul gram, a y comb had said this best.

Callan [0:16:13]: Sometimes you just need to do things that don't scale.

Callan [0:16:17]: And I actually don't think that applies to just startups ups, and I'll talk about that here in a minute.

Callan [0:16:25]: But one of the things is I thought this was going to in the beginning, have this detrimental long term impact Say, we're never gonna be able to clean all this up, You know, it's people or we're gonna upset our entire agency force because we call it them pretty hard, but we did.

Callan [0:16:44]: We cleaned it up.

Callan [0:16:45]: Everybody came together as a team, and it was a pretty incredible time to go through that.

Callan [0:16:54]: And it brought us closer to a team and all the things that you can think of and I think there is an opportunity as we go into this window.

Callan [0:17:04]: Right?

Callan [0:17:05]: You know, if you think about some of the challenges that these past couple years have created, carriers are gonna need to repair the relationships with their agents.

Callan [0:17:15]: And look, I think everybody...

Callan [0:17:18]: I would say most people probably.

Callan [0:17:20]: Now I can't say that for every agency.

Callan [0:17:22]: I don't if every agency feels that carriers did exactly what they needed to do.

Callan [0:17:26]: But the reality is Cost of claims was going up.

Callan [0:17:28]: Inflation, you name it.

Callan [0:17:30]: It was just an absolute perfect storm.

Callan [0:17:32]: So...

Callan [0:17:32]: And then obviously, consumers are upset because every year you look your insurance bill the next year and it's set to renew, and it's just significantly bigger.

Callan [0:17:40]: That's tough.

Callan [0:17:41]: Right?

Callan [0:17:41]: And I talked about it earlier, agents, you know, they're in a state of constantly having to deliver bad news.

Callan [0:17:48]: So many great agents found silver lining in this and set them up for six Saas even more So as we come out of this, but I think for those carriers that can use this window to mend that relationship with those agencies build even deeper, support those agencies even more.

Callan [0:18:05]: That's a huge opportunity.

Callan [0:18:06]: Right?

Callan [0:18:07]: And If everybody's gonna be growing again, and I'm not saying that's necessarily gonna be the case, but I'm hearing.

Callan [0:18:13]: Anecdotally, I'm hearing a lot of people are trying to push back into this growth mode.

Callan [0:18:16]: And if that's the case, you're gonna have to do some things that are just outside of the norm.

Callan [0:18:23]: And I'll add sure text to this as well.

Callan [0:18:25]: Sure text, with nationwide comes out, as I'd mentioned and says we're gonna be investing one point five billion in technology over the next couple years, you better believe that everybody's gonna be fighting for that business.

Callan [0:18:38]: That's nationwide stated publicly.

Callan [0:18:40]: You can guarantee that all these other major carriers are gonna be thinking about.

Callan [0:18:44]: And let me take that back Doesn't need to be major carriers.

Callan [0:18:46]: You can pretty much guarantee all the All the majors, all the nationals, all the regions, all the super regional, all of them are gonna be out there thinking about Ai and how can they invest in that in technology in general.

Callan [0:18:57]: And so I think everybody within the space right now is in this window.

Callan [0:19:03]: And you're gonna have some opportunities to really capture market because these things just don't happen very often.

Callan [0:19:13]: And taking that short term risk and doing some things that don't scale can have that opportunity to have a very long term positive outlook.

Callan [0:19:25]: But I'm not gonna sit here and tell you that's not a risk.

Callan [0:19:27]: It is possible that you could do these sync that don't scale and it can hurt.

Callan [0:19:32]: But there's always a risk.

Callan [0:19:34]: Anybody is trying to get a massive reward.

Callan [0:19:36]: There's gonna be some sort of risk involved with that.

Callan [0:19:39]: And I truly believe that those that take advantage of that and those that pull some of these things that out that don't scale and create this experience and create these long term things, that's gonna really, really, really, really pay off.

Callan [0:19:55]: So as we're heading into wrap this up as we're heading this into twenty twenty six.

Callan [0:20:00]: And you're planning some of these things and you're thinking about your strategy going into twenty twenty six.

Callan [0:20:06]: I would just say you spend a little time thinking about those things that what can you do that it's just totally outside of the box.

Callan [0:20:14]: What can you do that if you had unlimited resources, this is what you do.

Callan [0:20:19]: And could you do that for a shorter period of time or whatever that may be?

Callan [0:20:22]: Just something to think about.

Callan [0:20:24]: Nothing else, it's worth the exercise to go through that even if you don't do it.

Callan [0:20:28]: You may go through that and say it's not worth it, We're growing.

Callan [0:20:30]: We feel confident about what we're doing, so be it.

Callan [0:20:33]: But some people we wanna swing for the fences and have a high risk tolerance I wanna give that a shot.

Callan [0:20:38]: Either way, great exercise to do.

Callan [0:20:41]: Alright.

Callan [0:20:42]: I'm bringing this thing to an actual close here and getting this thing wrapped up.

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Callan [0:21:00]: Every time you do, it very much appreciated.

Callan [0:21:03]: Thank you all for listening, and I'll see everybody next week.