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How Berry Insurance Doubled Their Business With Endless Customers [Endless Customers Podcast Ep. 134]
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This transcript has been generated by AI and not checked for accuracy.
00:00:00:00 - 00:00:02:12
Kaitlyn Pintarich
we're just incredibly busy that sometimes we
00:00:02:15 - 00:00:04:09
Kaitlyn Pintarich
actually have to turn people away because
00:00:04:11 - 00:00:08:17
Kaitlyn Pintarich
we are so overwhelmed with the amount of prospects coming in
00:00:08:17 - 00:00:18:15
Kaitlyn Pintarich
And that's kind of an interesting problem to have, which is great, but also why I know that we're going to be growing more quickly, you know, in the in the future.
00:00:18:17 - 00:00:36:02
Bob Ruffolo
You're listening to the Endless Customers podcast, brought to you by the team at Impact. Endless Customers is the proven system to become the most known and trusted brand in your market. You want to start to learn the principles of Endless Customers and how you can implement them in your business. Pick up a copy of Endless Customers, the national bestseller.
00:00:36:02 - 00:00:57:19
Bob Ruffolo
Wherever books are sold. Ready to start implementing Endless Customers in your business? Talk to impact about how our coaching program can help you implement Endless Customers to success. And if you want experience Endless Customers in person, do not miss our upcoming conference! Endless Customers Live in Chicago March 30th through April 1st, 2026. Registration is now open. And now onto the show.
00:00:57:19 - 00:00:59:15
Bob Ruffolo
Here's your host, Alex Winter.
00:00:59:17 - 00:01:07:11
Alex Winter
Today's episode shows what happens when a company stops chasing every lead and starts educating buyers. Long before the first sales conversation.
00:01:07:16 - 00:01:27:07
Alex Winter
I'm joined by Kaitlyn Pintarich. She's the president of Berry Insurance. Kaitlyn and her team have been on the endless customer's journey for years now, using content to answer real buyer questions, set clear expectations, and build trust early in the process by being open about cost, coverage, limitations and fit.
00:01:27:09 - 00:01:39:07
Alex Winter
Berry insurance has reshaped how prospects engage with their team and raise the quality of their sales conversations. The result has been better alignment, stronger relationships and long term growth.
00:01:39:09 - 00:01:50:00
Alex Winter
In this episode, we talk about how their approach evolved over time. What it takes to sustain the mindset as a company grows, and why. Committing to the endless customer's journey for the long haul really pays off.
00:01:50:02 - 00:01:52:00
Alex Winter
All right, Kaitlyn, welcome to the show.
00:01:52:06 - 00:01:53:16
Kaitlyn Pintarich
Thank you. Thank you for having me.
00:01:53:17 - 00:02:08:16
Alex Winter
Thank you for being here. And I'm so excited to talk with you. You have such a great story. Also unbiased. I'm a Massachusetts guy. You guys from Franklin, mass. But for our listeners, in our viewers out there, can you just set the stage, let people know who you are and a little bit about their insurance and what you guys do?
00:02:08:21 - 00:02:27:18
Kaitlyn Pintarich
So, my name is Kaitlyn Pintrarich. I am one of the owners of Berry Insurance. We're based in Franklin, Massachusetts, and we're a medium sized, independent insurance agency that helps consumers with, their property casualty and, life insurance, worker's compensation, types of insurance needs.
00:02:27:19 - 00:02:33:03
Alex Winter
Excellent, excellent. It's a it's a pretty old company. You guys have been around for a long time. Is that right?
00:02:33:05 - 00:02:38:13
Kaitlyn Pintarich
Yes. Yeah. We, we're just over 100 years, so we've been around for a while.
00:02:38:16 - 00:02:54:11
Alex Winter
Wow. That's incredible. So let's let's start a good starting point for me. Can you tell people what you were up to and what the business was like before you read the book? They ask you answer before you started implementing the endless customer system. So just paint the picture of like the before times.
00:02:54:13 - 00:03:22:10
Kaitlyn Pintarich
So, I, my, my husband and I bought the agency in 2017, and so at that point we were in this transition of going from employees to owners and leaders and trying to figure out what that meant for us internally, but then also what it meant for, guiding a vision for the agency. And so, you know, as as many small business owners know, they take on many hats.
00:03:22:11 - 00:03:44:03
Kaitlyn Pintarich
And my role was to do all the marketing amongst also running the agency. And I very quickly realized that that was not going to work. And I, you know, I was doing marketing and what they tell you to do in the sense of social media and put out a newsletter. But it wasn't very intentional. It wasn't very, focused.
00:03:44:03 - 00:03:54:00
Kaitlyn Pintarich
And we really just didn't have a good strategy for what that content would look like. And so I was feeling a little lost at that point.
00:03:54:02 - 00:04:13:02
Alex Winter
Yeah, that makes sense. And I think a lot of people can relate. When you own a business, you wear a lot of hats and it can be overwhelming at times, and there's only so many things that you can do before something slips, right? So what made you realize that doing, doing that and trying to do all the stuff and things wasn't working and like, what were you looking for to try to help fix that?
00:04:13:03 - 00:04:16:18
Alex Winter
Like, what did that look like for you guys as you were going through this?
00:04:16:20 - 00:04:41:20
Kaitlyn Pintarich
Yeah. Well, so I mean, I obviously knew that I didn't have a great, background in writing and, and content creation. And so I knew right away that I needed support in that realm. But also it became very clear to us that a lot of the conversations that we were having and a lot of the content that we were putting out was very much reactive, instead of proactive.
00:04:41:22 - 00:05:04:02
Kaitlyn Pintarich
And we were repeating ourselves, you know, every conversation that I would hear, you know, between our team and prospects were the same, answering the same questions over and over again. And we just didn't have a system in place for handling that. And so once that became real apparent to me, it was very clear that we needed to, you know, move forward with, you know, and less customers.
00:05:04:02 - 00:05:08:22
Kaitlyn Pintarich
And they ask you to answer and really commit to this type of a process.
00:05:09:00 - 00:05:32:14
Alex Winter
Excellent, excellent. So once you made the decision you're you're reading Endless Customers. It's it's obviously hooking up as you're getting like is connecting with you. You obviously are vibing with it. What what started like how did how did it start off. Did you go like, all right, I read the book. We're hiring a content manager or like, what was the next or the first couple of steps that you guys had in your journey within this customer's.
00:05:32:16 - 00:05:59:20
Kaitlyn Pintarich
Yeah, I literally went to the conference and then left and said, okay, we're hiring a content manager. Help me. And so that was step one. And our coach that we worked with was phenomenal. She helped me really figure out what it was that we were looking for, what we were hoping to accomplish, what our strategy was going to be, and by that process that allowed us to hire the right person for that role.
00:05:59:22 - 00:06:25:05
Kaitlyn Pintarich
And that was incredible. And then at that point, once we had, that person who's who is Corinne, who's now our senior marketing manager. In that position, we as a team read the entire book, and walked through what that meant for us as a team and what that shift in strategy, and really what the shift in conversations with our clients was going to look like and how we were going to implement it.
00:06:25:05 - 00:06:50:01
Kaitlyn Pintarich
So it was really important for me as a leader of the organization, to bring the whole team into that process. It wasn't something that I wanted to, you know, just dictate down to anybody. And so getting everybody on, you know, to have read the book and to have bought into the process was really integral. And that started, you know, really the momentum in, you know, our life cycle of this.
00:06:50:03 - 00:07:07:01
Alex Winter
Of this journey. Yeah, absolutely. You know, and I hear that time and time again with people that have success with Endless Customers and that really crush it. There's buy in from the top. So you and leadership, that's where it starts and it trickles down through the whole organization. You have everyone read the book, you get everyone swimming in the same direction.
00:07:07:01 - 00:07:22:03
Alex Winter
And when that happens, some really great things happening, Corinne. I mean, we got to give a shout out to her, and she's amazing. Yeah. And she's been on the show before. She's started out her journey as a content manager and now is running all the marketing for Berry and has just had an incredible journey in her own right.
00:07:22:05 - 00:07:22:20
Alex Winter
Yes.
00:07:22:22 - 00:07:26:10
Kaitlyn Pintarich
Yeah. She's wonderful. We're incredibly thankful for her.
00:07:26:12 - 00:07:43:15
Alex Winter
She's very, you know, she's very sharp. She's just a great, great, great value add to your team. But what I want to go back to my question. What made you go, like, I need to go to this conference. I need to go to the event, which is now endless. Customers live that we have twice a year. But like, what was what was the turning point for you to be like?
00:07:43:15 - 00:07:45:21
Alex Winter
I have to go check this out.
00:07:45:23 - 00:08:13:10
Kaitlyn Pintarich
You know, I think it was a number of things. Timing was was one of them. It was at, the conference when it happened was at that point where I started to feel significant overwhelm from just having taken over the agency and trying to do all of the things. And wear all of the hats. And I think it also came to the point where I realized, you know, I, I just don't know enough to be able to do this.
00:08:13:12 - 00:08:38:04
Kaitlyn Pintarich
Correctly. And I know that I'm not doing a good job of collecting the knowledge from my team, and I don't have the time to do this. And that was really the catalyst. So there's a number of things that, you know, triggered me to say, okay, this this conference sounds really interesting. I really like the vision of, you know, answering client's questions and being really mindful of the content that we're putting out.
00:08:38:04 - 00:08:44:08
Kaitlyn Pintarich
And I think that this is something that is going to benefit our agency so significantly in the future.
00:08:44:10 - 00:08:58:12
Alex Winter
And it sounds like you were right and it was the right decision. So bravo. Yeah. Bravo. That takes a lot. That takes a lot, though, to have the self-awareness as a leader to to say like, hey, these are some of the issues I'm facing and I need to fix them, or I need to do something about it and then actually take an action.
00:08:58:12 - 00:09:15:10
Alex Winter
So good on you. All right, so you hired your content manager, your you're implementing Endless Customers. You're on your journey. How did that start to shape the content for your business and how you're putting content out? Because I would assume not a lot of insurance companies are really doing what you guys are doing from a content standpoint.
00:09:15:10 - 00:09:18:01
Alex Winter
Is that fair? And saying that.
00:09:18:02 - 00:09:43:07
Kaitlyn Pintarich
You know, I think it has definitely increased over the years. But when we first started, for sure, there was not any other agencies that were doing the types of content and putting out the types of content that we were, and, and for us, what it started out as was, you know, in our, our normal department meetings, our normal team meetings, we started having the conversations of, okay, what what questions have your clients asked you this week?
00:09:43:07 - 00:10:16:23
Kaitlyn Pintarich
What questions have you been asked? And you know, what information do you have in in regards to that question that we can then, you know, pull into a concise article that would help other consumers with the same questions and doing that repeatedly is what really, you know, got us on the right track of creating consistent content. And in the beginning, we created, you know, a library of ideas of all of the questions that we were being asked and, you know, started to, you know, ask our team what how would you answer this if you were asked it?
00:10:17:00 - 00:10:33:20
Kaitlyn Pintarich
What information do you have? And that really created that cycle for us of, okay, you know, now it's a consistent thing. Every meeting we have. What questions are you being asked? What content are we not putting out there that clients need to know about before they, you know, make the phone call before they put in a quote request form?
00:10:33:22 - 00:10:45:11
Alex Winter
Yeah, absolutely. So it really seems like it's the content has shifted, into it, like the systems that your business run off of and how it drives sales and how it really drives everything for your success.
00:10:45:13 - 00:11:09:21
Kaitlyn Pintarich
Yeah. I mean, before we started, we didn't have a system. You know, and we didn't have any way to collectively capture the knowledge of our team. It was very, it was just a very much reactive process. And through working on Endless Customers and they ask you answer by creating this content and, and thereby creating a content library internally for us now it was a much more proactive approach.
00:11:09:21 - 00:11:33:15
Kaitlyn Pintarich
And, you know, I started to hear conversations where our team would say to clients, I'll send you, you know, this blog article that fully explains this more and you can make a decision after you've read it. Or let me send you this video that we created that really dives deep into this, you know, subject matter and that, you know, really started to make me aware that, okay, now we've really transitioned into our process, into a different type of process.
00:11:33:15 - 00:11:56:10
Alex Winter
Absolutely. That's that's the that's the goal. That's the dream scenario. When this when this comes together correctly, the results I mean it speaks for themselves. So like I just want to get into that a little bit with the results. How how did this like when you talk about cost and price and the content that you're creating and working with the sales team, how did this drive the content and then bring in business for for your company?
00:11:56:12 - 00:12:22:12
Kaitlyn Pintarich
Yeah. So it was really interesting because, you know, talking about prices is a scary thing for most businesses, especially in the insurance industry, because it's it's very subjective. And as an agency, I don't have control over the cost. So talking about cost really allowed us to be very open and honest and transparent with consumers, and that allowed them to really feel more empowered in the conversations before they called.
00:12:22:12 - 00:12:44:14
Kaitlyn Pintarich
And so what we were finding is, you know, when prospects started calling us, they were asking smarter questions. They were, you know, more educated about the process. And a lot of them were pre-qualifying themselves from even reaching out to begin with. If they found that the cost wasn't going to fit whatever their needs were. So we started seeing a better quality of prospects coming in to us.
00:12:44:14 - 00:12:54:08
Kaitlyn Pintarich
And, being able to not have to work on so many accounts that weren't going to end up being the right fit, because we had already put out that content ahead of time.
00:12:54:09 - 00:13:11:02
Alex Winter
Yeah, absolutely. Assignments, selling and working on building trust before you ever talk to a prospect is a game changer. If you do it correctly. It is a game changer. And we've heard Marcus say that we we preach that here at impact. It's a pillar in the book and in the system itself. You know, trust is it's a principle.
00:13:11:02 - 00:13:29:00
Alex Winter
You know, there's a lot of technology that changes and things that shift. But trust is something that's at our core. It's never going to change. So when people are coming in and they have this trust, starting to talk to your sales team, how did that how does that translate into like conversions in your business as far as like revenue and just like give it I'm looking for some metrics.
00:13:29:00 - 00:13:32:11
Alex Winter
I'm just curious how that changed and shifted your business.
00:13:32:13 - 00:13:53:08
Kaitlyn Pintarich
I mean, we are now probably turning away more accounts than we ever have before, because we're better able to pre-qualify accounts and be able to determine if they're going to be a good fit for us based on all of the content that we've been putting out and based on what we're publishing, in terms of who is the right fit for us.
00:13:53:10 - 00:14:17:18
Kaitlyn Pintarich
But also, you know, we're starting to hear conversations coming in of saying, I read your blog article, I already know base based on everything that I read this is what I need, and I'm ready to move forward. And so it really it's shorten the sales cycle. It became that we were able to, you know, close our, you know, business a lot quicker because prospects were already coming in much more educated into the process.
00:14:17:20 - 00:14:37:11
Kaitlyn Pintarich
And we even have prospects calling saying, you know, oh, I read this article by Robbie. Can I talk to Robbie? You know, and it was great because people were very engaged in the process. Or, you know, I saw your video and then they would go to our bio page and read all about our information on our bio page and feel like they had connected with us.
00:14:37:13 - 00:14:43:14
Kaitlyn Pintarich
So really that just the whole process started creating trust and it made things much quicker in the sales process for us.
00:14:43:19 - 00:14:53:16
Alex Winter
Yeah. That's incredible. So from from hearing that, how did that change, like your revenue, how did that help with your growth trajectory for the business?
00:14:53:18 - 00:15:16:08
Kaitlyn Pintarich
It's really been incredible. You know, we have grown significantly every year since we've started doing and less customers. And, you know, it's always something that when we get visited by the carriers that we work with, they always ask, you know, how are things going? How are you guys continuing to grow? And, and and it's it's mind boggling to them that everything that we're doing is organic.
00:15:16:10 - 00:15:39:06
Kaitlyn Pintarich
You know, we don't pay for any advertising. We don't do any direct mail or any type of, traditional advertising at all. Or any digital advertising. Everything comes in through our website, through our content or word of mouth referrals. And we've been able to grow significantly. I mean, we've hired so many employees since we first started to maintain that growth.
00:15:39:08 - 00:15:53:21
Kaitlyn Pintarich
Whereas other agencies right now are being bought out. They just they haven't been able to figure out the system to, continue to grow on their own. So it's been really phenomenal for us. And we're, incredibly thankful to be on this journey.
00:15:53:23 - 00:16:16:13
Alex Winter
That's wonderful to hear. And you guys have grown substantially and it's well-deserved. And I love hearing, too, that you're not doing the traditional tactics of like, paying for ads and trying to do all these these tricks and throwing money at it. That doesn't really work. It's mostly all organic. It's content that you're creating and putting out there. That's that's I'm sure some of your competition is scratching their head, going like, what are we doing wrong?
00:16:16:15 - 00:16:42:08
Alex Winter
That's amazing. Yeah. So you've been doing Endless Customers for a long time. I mean, you've been part of our ecosystem for for years and years now. What would you say to people out there as far as being a leader and being in that leadership seat? How do you maintain that? And, and over time, stay consistent and continue to push, endless customer system through the company and make sure that it's still working as you as you said, you keep growing and growing and growing.
00:16:42:08 - 00:16:51:19
Alex Winter
How do you how do you do that? Because that that takes that takes, some serious accountability. And just like, passion to, to make sure that something doesn't fall off. Right?
00:16:51:21 - 00:17:13:14
Kaitlyn Pintarich
Yeah. I mean, it's it's exactly what you said. It's it's accountability. It's consistency. It's always making sure that you are reminding people why we're doing this and reminding, you know, the team. So I see a lot of conversations or I'll hear a lot of conversations where, you know, we'll find out something new in the industry, a new coverage or a new topic.
00:17:13:16 - 00:17:40:17
Kaitlyn Pintarich
And immediately I'll say, well, have you reached out to Robby and Corinne and then sent that over to our marketing team to create content on, and we still in our meetings will ask everybody, what have you been asked? And that hasn't stopped because we always want to continue to add deeper content onto our site. So for people that are just starting out, it's a it's a it's a commitment and it's not something that you can do on a quarterly basis on a monthly basis.
00:17:40:17 - 00:18:13:12
Kaitlyn Pintarich
It's something that you have to live and breathe and make a cultural shift. And then also if if it's going to be something that you're going to commit to, it's got to be a buy in from your entire team and having the right team in place to help maintain that process throughout your journey. And if you are willing to put in the work and you know, do that, do the hard things like role playing and, you know, making the hard, you know, decisions to stay consistent and to stay at it, you will reap the rewards significantly.
00:18:13:14 - 00:18:31:04
Alex Winter
Preach. Amen. I can't I can't say anything other than heck yeah, that's so true. Also, you've been working with impact for a long time. Why do you find value in the coaching program and in the services that we offer? And how does that play into the accountability piece for you and for your team?
00:18:31:05 - 00:18:54:08
Kaitlyn Pintarich
So, I mean, I just love working with all of the coaches that impact. And number one, they really hold me accountable and hold my team accountable. To make sure that we're staying aligned with what our goals are, what our strategy is, they push us and ask us the tough questions, which really make me think a lot harder into my business and what I'm doing and why I'm doing it.
00:18:54:09 - 00:19:17:12
Kaitlyn Pintarich
And to me, that's incredibly valuable. You know, it's very easy to be in an industry and to attend industry conferences where you're amongst your peers and, you know, start to get that groupthink going. But when you work with an impact coach, they aren't in your industry. And so they are able to challenge you and ask questions to you that you probably wouldn't have thought of otherwise.
00:19:17:13 - 00:19:33:00
Kaitlyn Pintarich
And that in and of itself is just been incredibly valuable. And I mean, we've worked with, you know, video coaches, content coaches, business coaches. You know, I don't even know sales coaches that, in fact, and all of them have been wonderful and have helped us grow our business.
00:19:33:01 - 00:19:59:21
Alex Winter
I'm happy to hear that. That's that's great to hear. And I have to say, I really love and respect your perspective on having outside, like having people that aren't in your industry necessarily to like, come in and give you that outside perspective because you may not be seeing things and they can bring this extra value to the table and experiences that they have that can really help you disrupt and change and shift things that maybe you wouldn't normally do if you stayed in your lane, as they say, right?
00:19:59:23 - 00:20:00:19
Kaitlyn Pintarich
Yeah, exactly.
00:20:00:20 - 00:20:23:11
Alex Winter
Yeah, that's really cool. So I'm curious, you had mentioned earlier the conferences too, right. So I see you or I see Corinne or your team or at almost every conference, whether it's in Chicago, whether we're here in Hartford. Why do you keep coming back to those? And what's the value for you there as far as attending those those meetups and hearing the coaches and markets and people speak and just and all that that goes with it.
00:20:23:13 - 00:20:46:12
Kaitlyn Pintarich
So education is is super huge for me. And continuous education is really important. And it's something that I really push my entire team to participate in. So going to the conferences, is it really important because things change, you know, and the marketing changes the way that Google tracks, things change. And I can't stay on top of that 100%.
00:20:46:16 - 00:21:08:05
Kaitlyn Pintarich
My team can't stay on top of that 100%. So by attending the conferences, they're able to get the updates, get the knowledge, find out what's new, you know, find out the trends and I and be able to bring that back to our entire organization and start to strategize on, you know, what we might want to do to bring that into our process, to help grow our business.
00:21:08:07 - 00:21:25:07
Alex Winter
Absolutely. That's really cool to hear. So another question for you. I'm just I'm having so much fun talking with you. This is just exciting. And, I have another one where I wanted to ask, where do you see Berry in going to the future? You know, we're just getting into 2026. What's the next five years look like for Berry Insurance?
00:21:25:07 - 00:21:29:05
Alex Winter
And where do you hope and envision it going?
00:21:29:07 - 00:22:02:13
Kaitlyn Pintarich
You know, I, I love this question because, I think a lot about it every day. You know, I want to continue to keep growing our organization and doing what we're doing best, which is educating our consumers and making them feel really empowered in the insurance buying decision. I envision that we're going to continue to add a few more team members on as our growth continues, and maybe even another marketing person on to our team, because, you know, our four person team is going to need that support as we continue to put out content and video.
00:22:02:15 - 00:22:31:15
Kaitlyn Pintarich
So my goal is to keep growing, maintaining our independent insurance agency status and hopefully empower other insurance agencies to see what they can also do. And, you know, maybe encourage them to take on this, this opportunity to, you know, do marketing on their own to to create that content on their own and to maintain their independent status and, you know, hopefully not get bought out and not lose, you know, their business that way.
00:22:31:17 - 00:22:47:07
Alex Winter
Absolutely. Yeah. I love that vision. So, you said something in there too that just got me thinking. You have four people on the marketing team now. What was that like, building out that team? Did you ever think you were going to have a marketing team as as an insurance company? That's. I mean, that's not usually typical.
00:22:47:11 - 00:22:58:23
Alex Winter
The big the big box ones. Do you know, if you go to travelers here in Hartford or some of the. Yeah, anthem and the big ones, of course they have marketing teams or they hire big agencies. But did you ever think that you'd have your own marketing squad?
00:22:59:01 - 00:23:23:22
Kaitlyn Pintarich
No. Absolutely not. It became real, real clear to me once we hired, you know, once we hired Karen and started writing content that, it was very apparent I was going to need to expand our marketing team rather quickly. And for us, for our organization, it's very important that all of our content came from us.
00:23:23:23 - 00:23:43:15
Kaitlyn Pintarich
You know, there's a lot of organizations out there that will offer to write blogs for our insurance agencies, our produce content for your business. And that's that's, you know, there's a place for that. But if you want it to be authentic, if you want it to really be accurate to your industry, to your state, it's got to be owned by you.
00:23:43:15 - 00:24:02:18
Kaitlyn Pintarich
And that became very apparent. And so it was a real quick decision that once we had, you know, somebody to write content, we also needed somebody to produce video content. And then when that started to take off, now we need somebody to maintain our, you know, community presence and our social media presence. And now we need somebody to run all of that.
00:24:02:18 - 00:24:22:06
Kaitlyn Pintarich
So we need another content. And and I envision that's just going to keep going. You know, I see that, the amount of content that we're putting out is going to get to a point where we need to bring on more people to support that, whether that's somebody that just does video editing so that Jason can produce, you know, or what that looks like.
00:24:22:06 - 00:24:51:10
Kaitlyn Pintarich
I don't know yet, but I look to my team to tell me, you know, where they are in their in their process, in their planning, so that they can say to me, you know, hey, look, we we need this, this person to fill this role. You know, we're that's where we're getting to. I let them have that, you know, authority to be able to come to me and say, you know, now our next person that we need is going to be this, because I don't know, you know, I'm not producing the videos.
00:24:51:10 - 00:25:03:01
Kaitlyn Pintarich
I'm not, you know, editing. I'm not writing. I don't know, you know, per se, what exactly they've got and how much workload they've got. But I envision that we're going to keep growing in that department.
00:25:03:03 - 00:25:26:16
Alex Winter
Yeah. That's wonderful. And I love what you're saying. The growth really leans back into authenticity. And you guys are so authentic with your content. And it just really speaks volumes about who you are and how you are as a business. And that's the best way to disrupt is to keep it real. I think people today are more savvy than ever when it comes to like, oh, they just hired an agency or oh, this is AI, and they just put this article on GPT.
00:25:26:18 - 00:25:43:22
Alex Winter
Like people can tell now so that keep it real. To have that authenticity is a differentiator. And I think you guys do exceptionally well with that. So I yeah, I hope it's okay if I ask this. Can can we just very bluntly paint the picture of like when we started Endless Customers, we were this size doing X amount of revenue.
00:25:43:22 - 00:25:51:03
Alex Winter
And today we're here just so that people can really get a sense because of the growth that you've experienced is is pretty unbelievable.
00:25:51:05 - 00:26:07:21
Kaitlyn Pintarich
when we started Endless Customers, we were probably half the size of our team. And we've probably. I would say, without, you know, knowing all the numbers and looking at the reports at this point, I'm going to guess that we've almost doubled our revenue.
00:26:07:23 - 00:26:16:06
Alex Winter
Wow. So you've doubled the team and doubled the revenue since you're your embark manager, since your start with Endless Customers. That's incredible.
00:26:16:07 - 00:26:31:17
Kaitlyn Pintarich
Yeah. Wow. Yeah. So and we've turned away more, more prospects than ever before. You know, it's a it's a totally different dynamic because not only are we writing more but we're also turning away, you know, way more than we ever did before.
00:26:31:19 - 00:26:40:22
Alex Winter
Talk to me about that a little bit. What does that mean when you say you're turning people away? Is that not right fit? Is that not a good geographic thing? Or like, what does that translate to?
00:26:41:00 - 00:27:01:22
Kaitlyn Pintarich
You know, it's it runs the gamut. So a lot of it is not the right fit. You know, based on all of the content that we're putting out, we can easily tell people, you know, unfortunately, we're not the right fit for you or this, you know, this isn't going to work, which in the past, it wasn't that way we would, you know, as many small businesses, you want to write business, you want to grow, right?
00:27:02:00 - 00:27:21:21
Kaitlyn Pintarich
So, you know, there's some of that a lot, a lot of our content because it's out there, we'll get this. We'll get quote requests from people that don't live anywhere in our geographic area or that we're licensed to sell insurance with. So in those, situations, we do turn away because of, you know, geographic location or things like that.
00:27:21:23 - 00:27:22:18
Kaitlyn Pintarich
But then also,
00:27:23:00 - 00:27:46:09
Kaitlyn Pintarich
we're just incredibly busy that sometimes we actually have to turn people away because we just can't. We we are so overwhelmed with the amount of prospects coming in looking for insurance support that we can't help everybody. And that's kind of an interesting problem to have, which is great, but also why I know that we're going to be growing more quickly, you know, in the in the future.
00:27:46:11 - 00:28:09:13
Alex Winter
Totally. No, it sounds like a good problem to have, but also the opportunity for growth into the future to help something that that's that's really cool to hear. All right. Last question for everybody out there that's listening and watching, right now, maybe they just started reading the book. Maybe they haven't heard anything about Endless Customers. What would you say to to them as a business leader as to as to why they should do this or why they should check this out?
00:28:09:15 - 00:28:35:03
Kaitlyn Pintarich
I would tell anybody that's, you know, just starting out in this process or learning about this process that, if they really want to grow their business and have control of that growth and have consumers and clients that they bring on that are going to have a longer lifespan with them because they know and trust and like them and know how authentic they are, that they've got to commit to this process.
00:28:35:05 - 00:28:44:02
Kaitlyn Pintarich
Read the book, start somewhere, start with content, put it out and get going. You absolutely have to do this.
00:28:44:04 - 00:28:51:16
Alex Winter
Well said. And such a great conversation. I love chatting with you Kaitlyn. Thank you so much for your time and for being on the show and for sharing your your journey with us.
00:28:51:18 - 00:28:54:04
Kaitlyn Pintarich
You know, thank you for having me. I'm always happy to help.
00:28:54:07 - 00:29:04:06
Alex Winter
Awesome. Well, I think we're going to have to have you back because I want to hear how things progress as you move into 2026 and beyond. And am I am I going to see you in Chicago and in the spring?
00:29:04:08 - 00:29:08:05
Kaitlyn Pintarich
I don't know if you're going to see me, but you're definitely going to see somebody on the team.
00:29:08:07 - 00:29:17:01
Alex Winter
Excellent, excellent. Well, I can't wait for that. Thank you again for your time and for everybody out there watching and listening. This is Endless Customers. I'm your host, Alex Winter. We'll catch you on the next episode.
If you sell something that buyers think they can get anywhere, it can feel like you are competing in a "sea of sameness". Same promises. Same buzzwords. Same claims that you are different.
When that happens, it is easy to get stuck in one of two modes. You either chase more leads, or you spend your days explaining the same things to the same kinds of prospects.
Berry Insurance chose a different path. They focused on educating buyers so well that the right people show up already informed, already clear on fit, and ready to have a real conversation.
In this episode of the Endless Customers podcast, I sat down with Kaitlyn Pintarich, President and Co-Owner of Berry Insurance in Franklin, Massachusetts. Kaitlyn shared how Berry turned overwhelm into a clear system, using content to answer real buyer questions, talk openly about cost, and set expectations before the first call.
In this article, I will walk you through the conversation and what I took away from it. You will learn how Berry Insurance built a simple system for capturing team knowledge, how that content changed the quality of inbound leads, and why they now sometimes have to turn prospects away because demand is so high.
Note: IMPACT has worked with Berry Insurance for years, and we believe strongly in this approach. This write-up is here to be useful whether you ever work with us or not.
The opening line that sets the tone
Kaitlyn started with a statement that made me smile and cringe at the same time, βWe're just so incredibly busy that sometimes we actually have to turn people away because we are overwhelmed with the amount of prospects coming inβ.
If you are a business owner, you know that feeling. You want demand. Then demand shows up, and you realize demand also comes with calendars, people, processes, and countless decisions.
When she said it was βan interesting problem to have,β I laughed because it's true. It's also not the kind of problem you solve with another inspirational quote on a poster.
What this episode is really about
At the top of the episode, I said, βToday's episode shows what happens when a company stops chasing every lead and starts educating buyers. Long before the first sales conversation.β
That is the heart of it. Berry Insurance didn't win because they found a magical marketing trick. They won because they took the questions buyers already ask and answered them in public, with clarity, over and over again.
They built trust before the first call.
As someone who has worked with hundreds of companies implementing the Endless Customers System, I've seen this pattern a lot. Even so, I still felt excited hearing Kaitlyn talk, because she was not selling a fantasy. She was explaining what they actually did, how messy it was at first, and why it worked so well.
The before times felt like many businesses
Kaitlyn and her husband bought the agency in 2017. They were going from employees to owners and leaders. That shift was exciting and also heavy.
She described wearing too many hats, as most owners do. She said marketing was on her plate while she was also running the agency. Then she hit a wall.
Kaitlyn put it plainly, βI quickly realized that approach was not going to work.β
I felt a lot of respect when she said that. Not because she was admitting a weakness, but because she did what many leaders avoid doing, she was brutally honest with herself.
Then she explained what they were doing for marketing. Social media and newsletters, mostly. It was not focused, it was not planned, and she felt lost.
That's a hard place to be, because you're busy, you're trying, and you still don't feel like you are moving forward.
The moment she realized they needed a system
One of the biggest shifts for Berry Insurance was moving from reactive to proactive. Kaitlyn said they were repeating themselves in sales conversations. Same questions. Same explanations. Same back and forth.
She told us, βWe were repeating ourselves, you know, every conversation was the same, answering the same questions over and over again.β
When she said that, I was nodding right along because I've heard this statement countless times. It's one of the clearest signs you need content that supports sales.
Kaitlyn also said they didn't have a way to capture the knowledge of the team. It was all stuck in peopleβs heads. That's risky. It is also exhausting.
So once it became clear they needed a real process, the next step came fast.
She went to Endless Customers Live and made a bold decision
Kaitlyn said, βI literally went to the conference and then left and said, okay, we're hiring a content manager. Help me!β
I love the honesty. It's not dressed up. It is not overly polished. It is a leader saying, I need support, and I'm going to make a decision.
At IMPACT, we can teach frameworks and principles all day, but none of it matters unless a leader takes action and backs it up with resources.
Hiring a content manager was not just a marketing decision. It was a leadership decision.
She also gave a lot of credit to their IMPACT coaches and said the coaching program helped her figure out what they were looking for, what they wanted to accomplish, and how to hire the right person.
Then she mentioned Corin, who is now their Senior Marketing Manager. This is another detail I loved hearing about. It shows they didn't just hire a person. They invested in a role, a path, and a long-term commitment.
Buy-in from the whole team was not optional
After hiring, they did not keep the strategy tucked away in leadership meetings. Kaitlyn brought the whole team in.
She said they read the entire book as a team and walked through what the shift meant for them. She also said something I wish more leaders would copy, βIt wasn't something that I wanted to, you know, just dictate down to anybody.β
That's culture building. It is slower at first, but it creates real momentum in the long run.
I have seen companies try to βdo contentβ by handing marketing a list of topics and hoping it works. Berry did something different. They made it a shared way of thinking.
How their content system actually worked
Kaitlyn described a simple habit that became powerful. In meetings, they started asking the sales team, "What questions did clients ask you this week?"
Then they turned those questions into articles and videos. She explained it like this, βWe started having the conversations of, okay, what questions have your clients asked you this week? And doing that repeatedly is what really, you know, got us on the right track of creating consistent content.β
This isn't complicated, it's consistent.
They built a library of ideas from real conversations. They asked team members how they would answer each question. Then they used that knowledge to educate future buyers.
This is what it looks like when content is not a side project. It becomes part of how the business runs.
When sales started using the content, things changed
There is a moment I look for with every company on this journey. It's when sales stops seeing content as βmarketing stuffβ and starts using it to help buyers.
Kaitlyn said she began hearing team members tell clients they would send an article or a video that explains the topic. She described prospects reading it and then making a decision with more confidence.
She said, βI'll send you, you know, this blog article that fully explains this more. Or let me send you this video that we created.β
When I heard that, I thought, yes. This is the point where content becomes a sales tool, not a vanity project.
The pricing and cost conversation that most businesses avoid
Kaitlyn told us something a lot of insurance agencies struggle with. Talking about price can feel scary, especially when you don't fully control the cost.
She said, βTalking about prices is a scary thing for most businesses, especially in the insurance industry, because it's very subjective.β
Then she explained why they did it anyway. They wanted to be open, honest, and transparent. That made consumers feel more empowered before they even called.
What happened next is one of the most useful takeaways in the whole episode.
Prospects started asking smarter questions. They were more educated. And some people screened themselves out before contacting Berry because they realized it was not a fit.
Kaitlyn said, βA lot of them were prequalifying themselves before even reaching out to begin with. So we started seeing a better quality of prospects coming in to us.β
That is the goal for most businesses, even if they don't say it out loud. Better fit leads. Better conversations. Less time wasted.
Shorter sales cycles and more confident buyers
Kaitlyn shared a few examples that made the change feel real.
She said prospects would call and say they read a blog article and were ready to move forward. She said it shortened the sales cycle because people came in educated.
She also shared a story I loved, because it shows trust on a personal level. A potential lead reached out and asked, "I read this article by Robbie... Can I talk to Robbie?β
That's not just a lead. That's a buyer who feels like they already know your team.
She also described people watching a video, then going to the bio page, reading about the team, and feeling connected.
That's what trust looks like online. It is not mysterious. It's built through useful content and real humans showing up consistently.
Organic growth and a business that keeps hiring
One of the biggest results was growth without paid advertising. Kaitlyn explained that their growth was organic, driven by the website, content, and word-of-mouth referrals.
She said, βWe don't pay for any advertising. Everything comes in through our website, through our content, or through word-of-mouth referrals.β
As she said that, I felt two things at once.
First, I felt excited because this is what so many owners want. They want a demand that doesn't depend on constantly feeding an ad budget.
Second, I felt a little jealous, in the best of ways, because who wouldn't want to build a machine like that?
She also said they've hired many employees to maintain the growth. That's a real outcome. It is not a marketing metric. It's jobs and capacity.
How leaders keep the momentum year after year
This was one of my favorite parts of the conversation because it addresses the hard reality.
Starting is one thing. Sticking with it is another thing entirely.
Kaitlyn said the keys were accountability and consistency. She talked about constantly reminding the team why they do this. She talked about keeping the question habit alive in meetings. What are you being asked?
She also said something worth repeating, βIt's a commitment, and it's not something that you can do on a quarterly basis. It's something that you have to live and breathe and make a cultural shift.β
That is the truth. If you treat content like a campaign, you will get campaign results. If you treat it like a culture shift, you get a company that compounds over time.
Why they keep investing in IMPACT coaching and Endless Customers Live
Kaitlyn said coaches held her and her team accountable and pushed them with tough questions.
She made a point I really respect. When you only learn from people in your space, it's easy to adopt the same tactics without thinking. Outside perspectives help you spot blind spots faster.
Kaitlyn liked working with IMPACT coaches who were not in her industry because they challenged her in ways peers might not.
Then she shared why they keep coming back to Endless Customers Live. Continuous education. Trends change. Search changes. Marketing changes. They want updates and new ideas they can bring back to the team.
That is a smart posture. No panic. No chasing shiny objects. Just steady learning and steady improvement.
Building a marketing team inside an insurance agency
Kaitlyn said she never expected to have a marketing team in an insurance agency.
Once they hired Corin and started publishing content, it became obvious they needed more people. She also shared a belief that many businesses wrestle with, they wanted content to come from them. They wanted it to be authentic and accurate to their industry and state.
She said, βIf you want it to be authentic, if you want it to really be accurate to your industry, to your state, it's got to be owned by you.β
So they added video support. They added social media and community presence. They built a real team, and they expect it to keep growing as output grows.
She also said she lets the team tell her when they need help because she is not writing, filming, or editing herself. That's healthy leadership based upon trust. Trust the specialists, then support them.
The blunt growth story people want to hear
Near the end of our conversation, I asked Kaitlyn if we could paint the picture more bluntly. I wanted listeners to feel the scale of the change.
She said, βWhen we started our Endless Customers journey, we were probably half the size of our team. I'm going to estimate that we've almost doubled our revenue, too.β
That is a huge win for the Berry Insurance team. Honestly, that's the dream scenario. Double your revenue. Double the size of your team. Most importantly, attract better-fit prospects.
Turning people away and why it is part of growth
Kaitlyn explained that turning people away can mean a lot of things. Sometimes it's fit. Sometimes it's geography. Sometimes they are too busy to take on more.
She said, βWe actually have to turn people away because we just can't. We are so overwhelmed with the amount of prospects coming in, looking for insurance support, that we can't help everybody.β
If you're reading this and thinking, must be nice, I understand. However, it's important to note that this is not luck. This is years of building trust, publishing consistently, and setting expectations publicly.
Also, turning people away forces a business to grow up. It forces process. It forces hiring. It forces focus.
In a strange way, it is a compliment from the market. It's also a challenge.
Kaitlynβs advice to business leaders who are just starting their Endless Customers journey
At the end, I asked what she would say to leaders just starting out.
Her answer was direct, βRead the book, start somewhere, start with content, put it out, and get going.β
That is the right mindset. Don't overplan. Don't wait for the perfect moment. Start with the questions you already hear every week.
If you want a practical next step, here's one that matches what Berry did, without adding a bunch of new meetings to your calendar.
-
Ask your sales team one question this week: What are the top five questions you answered in the last five sales conversations?
-
Pick one question that keeps coming up.
-
Write a simple answer in plain language.
-
Put it on your website as a short article.
-
Next time the question comes up, send the article before the next call.
That's it. That's how a content library begins. It starts small, then it stacks.
Closing thoughts from me
I walked away from this conversation feeling energized.
Kaitlynβs story is not about being flashy. It's about taking action. It is about building trust early. It is about leadership doing the unglamorous work of making content part of the culture.
Also, I'm obligated to say this, if your business is over 100 years old and still growing, you are doing something right. You've clearly earned the right to keep writing the next chapter.
And if you're a business owner reading this, feeling overwhelmed, and thinking you don't have time for content, I want you to remember what Kaitlyn said when she started.
She was overwhelmed, too. She wore too many hats, too. That's why she implemented the Endless Customers System.
You don't need to do everything. You just need to start answering the questions that matter, one by one, and keep going.
Want to learn how to implement Endless Customers the right way, with an Alignment Day? Talk to us at IMPACT. Weβve helped hundreds of companies do it right.
Connect with Kaitlyn
Kaitlyn Pintarich is the President and Co-owner of Berry Insurance, specializing in business insurance. Her real passion is teaching and coaching. Whether itβs helping her clients better understand their insurance policies, writing blogs on various insurance topics, or teaching small businesses within their community about social media and digital marketing, youβll find Kaitlyn at her best.
- Connect with Kaitlyn on LinkedIn
Check out Too Cool T-shirt QuiltKeep Learning
- Watch: They Ask, You Answer vs. Endless Customers
- Learn: What is the Right Way to Get Started with Endless Customers?
- Learn: What Roles are Needed for Endless Customers Success?
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Endless Customers is a podcast for business owners/leaders, marketers, creatives, and sales teams who want to build trust, attract the right buyers, and drive sustainable revenue growth.
Produced by IMPACT, a sales and marketing training organization, we help companies implement The Endless Customers System by focusing on the right strategies and actions that build trust, educate buyers, and generate more leads.
Interested in sponsorship opportunities or joining us as a guest? Email awinter@impactplus.com.
Facing a challenge in your sales and marketing? Schedule a free coaching session with one of our experts and take the step toward business growth.
Posted On:
Feb 3, 2026
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