98. Focus On What Matters With Winston Smith

In this episode, Jim interviews Winston Smith, CEO of Bridge, a customer communications management software designed for independent insurance agents. Winston discusses the importance of agency owners working on their business rather than in it, and how Bridge can help them achieve this. He highlights the bottleneck that agency owners often face and explains how Bridge streamlines operations and provides tools for sales, marketing, and customer communication. Winston shares success stories and feedback from Bridge users, emphasizing the increase in revenue per employee as a key metric. He also discusses the role of Bridge as a companion to agency management systems and the importance of customer satisfaction. The episode concludes with Winston's advice to be true to oneself and the opportunities available in the insurance industry.

Takeaways

• Bridge is a customer communications management software designed for independent insurance agents, helping them work on their business rather than in it.
• Agency owners often become bottlenecks in their own businesses, hindering growth and scalability.
• Bridge provides an all-in-one solution for sales, marketing, and customer communication, streamlining operations and improving efficiency.
• Bridge offers features such as video recording, marketing automation, and personalized communication to enhance customer relationships.
• Success stories from Bridge users include increased revenue per employee and improved customer satisfaction.
• Bridge serves as a companion to agency management systems, focusing on communication and customer relationship management.

Resources From Winston 

Website 
LinkedIn
Google Calendar
Think-Cell
How Will You Measure Your Life? by Clay Christensen

About Winston

Winston Smith is the CEO of Bridge, a customer communications management software designed just for independent agents.

Winston came to Bridge after a decade on the carrier side of P&C. Prior to Bridge, Winston ran his own micro-Private Equity fund, Hammersmith Capital.

While on the carrier side, Winston was a general manager responsible for P&Ls across multiple states for the Safeco and Liberty Mutual brands (but he takes no responsibility for the 'LiMu Emu') and spent a LOT of time in the field with Safeco-appointed agencies (and is lucky enough to count many of them as friends).

He started his insurance career at AIG on Water Street in Lower Manhattan as an underwriter of Executive Lines for Financial Intuitions during the Great Recession.

Winston holds the CPCU and API designations, has an MBA from NYU Stern and his undergrad degree from Princeton. He lives in Johns Creek, GA with his wife and two kids.

ePayPolicy 
The simplest solution for insurance agents to collect credit card and ACH payments

Transcript

Jim (00:00.945)
Welcome to Agents Growth Academy. I hope you're ready to grow big or go home. I've got a fantastic guest with me today. His name is Winston Smith. And besides what you're gonna hear in the bio, the only thing that's not in there is that he is literally my next door neighbor. We are, we're very exclusive in this neighborhood. We only let in insurance industry people, no, I'm kidding. But I'm very excited to have Winston on today. He's gonna talk to us about how,

as an agency owner, you can work more on your business rather than in it, which is a huge, huge thing, especially, you know, if you've been in the weeds trying to make things happen, you feel like you're not getting anywhere, this is the episode that's gonna change that for you. So Winston is the CEO of Bridge, which is a customer communications management software designed just for independent agents. Winston came to Bridge after a decade on the carrier side of PNC.

Prior to Bridge, Winston ran his own micro private equity fund, Hammersmith Capital. While on the carrier side, Winston was a general manager responsible for P &Ls across multiple states for the Safeco and Liberty Mutual brands, but he takes no responsibility for the Lemu Emu ad campaign. He spent a lot of time in the field with Safeco appointed agencies and is lucky enough to count many of them as friends. I love that.

He started his insurance career at AIG on Water Street in Lower Manhattan as an underwriter of executive lines for financial institutions during the Great Recession. Winston holds the CPCU and API designations, has an MBA from NYU Stern, and his undergrad degree from a little place you might have heard of called Princeton. He lives in Johns Creek, literally right next door to me, with his wife and two kids and a family.

neighbor, my son, no, I'm kidding. Winston, welcome to Agents Growth Academy, my friend. It is good to have you my neighbor.

Winston Smith (02:06.306)
Thank you, Jim. Good to be here, good to be with you. And yeah, glad I mow my lawn on a regular basis to make sure it's got the standards in the neighborhood.

Jim (02:13.093)
Me as well, my friend, me as well. Yeah, I'm super excited to just kind of jump right into it. I asked you beforehand if this were a master class, what would it be called? And you said to work on your agency, not in your agency. This will be practical lessons for owners to focus on what matters. So tell me, was there like an epiphany or a pivotal moment for you?

Winston Smith (02:16.238)
Hehehehe.

Jim (02:42.417)
where you realize agents need something that can help them work on their business, not in it.

Winston Smith (02:48.174)
Yeah, it probably goes back to my days. So I'm an insurance nerd, like a lot of us are, who joined the podcast and around the industry. I love the business. It's, you know, like Cass says, the best industry God ever created. And so I read the literature and one of the research that I'm a big fan of is the Agency Universe Study. And it comes out every other year.

Jim (03:05.553)
Absolutely.

Winston Smith (03:13.582)
and within the Agency Universe study, it tells you how many agencies there are out there in America. And the vast majority of approximately 40 ,000 agencies out there, give or take, are agencies with five or fewer people who work in them. I think it's something like 95, 98, some very high percentage of agencies are small. And if you think about the business model,

Jim (03:19.665)
40 ,000.

Winston Smith (03:39.278)
great margin business, you know, there's great macro trends behind it around growth, why are these agencies sort of getting limited to that sort of five -person threshold before breaking through to the next level? And I sort of came to the conclusion, I've spent a lot of time in the field speaking with agents in my Safeco and Liberty Mutual days, that it sort of became the fact that the agents themselves, the owners, were the bottlenecks in their business.

Why? Because they were working in their business and not on their business. So that was really the revelation for me is that you've got this great industry, so many macro trends behind it, so much opportunity, and yet very few agents are able to achieve that escape velocity that happens when you get to about five or 10 people.

Jim (04:28.209)
Yeah, and we've talked about this on the show before about like hitting that ceiling and it's so easy to do. And especially if you're a scratch agency and you're starting out trying to figure out all the things and do all the things yourself. And I know a lot of people out there that are doing that. It's, it is super hard to break through that, that ceiling. So what do you offer through Bridge that helps agents to do that?

Winston Smith (04:57.678)
Sure. So first off, let's sort of set the groundwork on how I view what an agency is, which is they're essentially sales and marketing organizations. And that's what independent agents are. They're salespeople. They're very gifted salespeople, and they're really good at selling insurance. The problem is when they get to a certain size, like we talked about, usually around five or so people, bottlenecks form. And that's because...

Jim (05:08.463)
Yeah.

Winston Smith (05:25.55)
suddenly operations become a big consideration for them. They realize they're no longer just in the selling and servicing of policies, but they have to build a business around it. They need to have sort of HR function, how to recruit the right people, how to retain the right people, not just the finance, the accounting, and some of the back office stuff that goes with it. IT becomes part of its systems. So your responsibilities grow. It was easy enough when you were just sort of on your own as a one person shop, slinging insurance.

But then when you decided to scale your business and you realized you had success in it, all these other considerations became a big pressure upon you. And because you had been focused on just growing to a certain size that you could achieve a livelihood, and I totally get that, that you got caught in the trap, sort of growth trap, where you cobbled together essentially what you could to support a certain size business. But the way that you went about that, which may have been a little bit more done out of necessity or.

haphazardly is what's holding you back from getting to the next level. So what Bridge is, is that it allows you to perform a lot of those functions, right? How you manage your agency from an operational standpoint to make you efficient and to be able to have all of the necessary tools to sell professional services in the 21st century, right? So the phone, texting, chat, e -sign, et cetera, all in one pane of glass. So we...

Jim (06:29.617)
you

Winston Smith (06:50.452)
streamlined our product just to an insurance agent's workflow and gave you all of those tools in one place that achieves 90 % of what you would achieve with the vast majority of horizontal solutions out there like a DocuSign or RingCentral or Twilio, etc.

Jim (07:05.873)
Okay, so it's like an all -in -one basically for sales, marketing, and helping agents basically get the message out. I mean, it sounds to me like what you're describing is a CRM of sorts.

Winston Smith (07:20.946)
It is. So we're Communications Management and CRM, but there are different use cases of the tool as well. So for example, one of our tools is video and video recording, and that's helpful if you want to send a video proposal. So you have a commercial insurance account, you have a life quote, right? You usually have to run it by several chains of command in order to get the sign off to sell that life policy or that middle market commercial policy. So it's helpful to have it recorded so you don't have to have the same meeting three times.

Jim (07:45.105)
Yep. Yeah.

Winston Smith (07:50.798)
What other people use it for is actually not just to send proposals to prospects and to customers, but also for HR reasons. Oh, so this is how you get into your management system. This is how you add a vehicle. And they can record these sessions so that every time they bring on somebody new, they don't have to have the same lesson again and again and again.

So yes, its nominal function is to help with sales and marketing potentially, but it could also be used to help you from an HR standpoint, which is again one of those operational constraints which you can find being a burden on your time.

Jim (08:12.241)
Okay.

Jim (08:24.305)
Yeah, that is brilliant. Actually, I've never even considered recording all of our workflows or procedures and putting them in sort of a library of sorts so that you're saying that agencies can access that from inside Bridge just the same, but they can also use video to send video proposals or whatnot to clients. So it's both external and internal for video. Wow.

Winston Smith (08:52.11)
Right. Exactly.

Jim (08:54.225)
Okay, that's cool. I don't know of a lot of other software suites that I've heard of that can do that. That's pretty unique. So what are some of the other use cases for what Bridge can offer agents?

Winston Smith (08:56.896)
you

Winston Smith (09:08.91)
Sure. So let's think about what an agent's superpower is relative to the other options out there for insurance, right? You could go to a dot com. You could call the 800 number. You can go direct or you can go to a captive. And what differentiates an agent from those different options out there really is the relationship that they have with their customers. That's why they like, you know, Southern States insurance. That's why they like other agencies because yes, they're doing business with Southern.

Jim (09:17.813)
Hmm.

Winston Smith (09:38.702)
but they're also doing business with Jim and that's why you buy. You can't, you don't have a relationship with the gecko. So, your superpower is really relationships and that hinges upon communication, right? And talking to your customers, but also the ability to have that personalized touch. What makes personalized difficult is that it's hard to scale.

Jim (09:44.861)
Amen.

Winston Smith (10:04.782)
Right? How can you have an individual relationship across, you know, let's say you have a normal book of business, 5 ,000 personal lines policies. That's a lot of relationships that you need to have. So with something like a tool we have, we use it for marketing automation, right? How to blast, you know, prospects out there, how to get them engaged with your agency, give them advice, why they might want to give you a call one day if they have insurance needs. But you can also do it on renewals as well. So let's say, you know, we've been in a hard market right now. It's not.

atypical to have 10, 20, 30 % rate increases. How to manage that is really important, but how to manage that at scale is difficult. So 90 days before renewal, put them into a sequence, right? Let them know, hey, it's gonna be a tough year this year, we're gonna get you through it. We're gonna get you the best deal possible just to manage expectations, just to get a renewal is a good deal, right? How to get that in front of all of your customers ahead of time so that what doesn't happen is three days before renewal,

because the carrier's late with their quote, you drop a 30 % increase on them, that kills relationships. So those are some of the different use cases there. Not just, hey, let me tell you about Southern states if you have insurance needs, but how to manage your book of 5 ,000 and set expectations in a way that seems personalized and that you're paying them individual attention.

Jim (11:17.489)
Yeah, and the key phrase that you just said there towards the end was set expectations. I think that's one thing that, especially in the market that we're in, if you're not out ahead of messaging to clients in 60, 90 days, hey, your renewal this year is gonna be the worst you've ever seen it. It's not gonna look pretty. I'm just letting you know now, but here's what we're doing to mitigate that internally.

Stick with us hang with us. And if you got any questions, let me know I you know, we just recently got a Actually was yesterday. We got a one -star review on Google, which I hate like, you know, we all our client service staff are trained to Reach out to get You know to request reviews and they're doing that manually by the way, which I want to ask you about in a second So when we get a you know, we typically get five star reviews

Winston Smith (11:58.41)
Thank you.

Jim (12:15.633)
But when you get a one star review, it's like, what happened? And it was because of the client's perception. Now it wasn't reality because I checked with the agent and the agent did what they needed to do. But it was the perception that they weren't being communicated with in the manner that they wanted to be communicated with in the timeframe that they wanted to be communicated with. So, my question to you is as far as getting out in front of...

Winston Smith (12:34.222)
Multiple touches.

Jim (12:45.361)
with that type of messaging, what are some best practices that agencies are using when it comes to Bridge to be able to do that? Okay. Okay. Yep.

Winston Smith (12:57.448)
Multiple media too. So it's not just an email You should also be hitting them with text messaging if that's their preferred method of communication, right? Depending on what sort of generations that they fall into and phone calls as well So it's just regular cadence and making them feel that they're part of a process the minute they feel like they're abandoned and that they have to figure it out on their own that's when they go to compare .com or give the gecko a call and see if they can get a better deal elsewhere and make that mistake of

Jim (13:12.529)
Yeah.

Winston Smith (13:23.36)
shopping on price and price alone, not realizing what the market dynamics are at a given time. So you have to hold their hand through it, which is again really tough to do at scale. But with the benefit of technology, you're able to do that, right, without even having to think about it. You set it one time, you know when the policy's expiration date is, you put them in a sequence that you know you're going to hit them at days 90, 60, 45, 30, whatever you need to hit them at, you know, depending on what line of business you're selling.

Jim (13:31.269)
Yep.

Jim (13:48.205)
Yeah, that makes sense. And when it comes to the review example I gave, I would presume that Bridge is gonna allow you to automate that in somewhat of a personalized way instead of having our client service staff manually emailing out. Is that accurate?

Winston Smith (13:53.134)
Yep, you would be able to have templating and, you know, notifications, right? That when you get those Google reviews, when you get those Facebook reviews, right? Like this is how you want to answer this type.

you know, complaint being related to the price increase, being related to the service, the communication, right? There's, there's typically a handful of reasons why people would, would give you a one star. And so you, this way you have like guided template of this is how you want to respond to this type of message. Sure. Sure. Um,

Jim (14:21.201)
Yeah.

Jim (14:32.401)
Sure, yeah, that makes sense. That's awesome. Success stories, any that come to mind or feedback that you've heard from clients about using Bridge, before Bridge and after Bridge?

Winston Smith (14:48.142)
So the metric we like the most, that's most important to us because it means that the customer has gotten value from our product and enjoyed those operational efficiencies, is revenue per employee. It's a very easy one. Everyone knows their revenue, give or take, right? And then everyone knows like the number of employees that they have. If you're able to increase revenue per employee,

Jim (15:03.665)
Oh, heck yeah. Yep. Yeah. Yeah.

Winston Smith (15:16.494)
that means that you have become more efficient operationally. So I'll start with one, which is a different kind of success story where it has to do more with the denominator than the numerator. So we had a customer who uses one of our tools, which is Activity Monitor. Activity Monitor helps agents, because now that we're in a sort of work from home, work from anywhere environment, particularly post -COVID,

Jim (15:33.361)
. . . .

Winston Smith (15:44.366)
to make sure that people are doing a shift, right, who are working on the front lines. And so what it does is that it will take screenshots of your employees' monitors. You have the option to set this up whether you want to or not. So if you have suspicions about someone, you can take a closer look. You can set the screenshots at whatever interval you want to. And so what turned out was that of the 15 employees, five weren't doing very much of anything, it turned out.

a lot of screenshots of ESPN and Facebook and stuff not related to, you know, working at an insurance agency. And so that agent was able to dismiss those five people and didn't lose a dollar of revenue in the process, didn't lose a single account. So that's one of those denominator issues. That's maybe not the happiest story, but it makes agents probably sleep better at night with the concept of not having everybody under the same roof, which I think is going to be less and less common as time goes by.

Jim (16:13.705)
Busted.

Winston Smith (16:37.206)
There are definitely other agencies too who have been able to grow their business without having to get rid of people, right? Just focused on the numerator just by using Bridge and it comes through prospecting, right? Like we said with marketing automation and the ability to have all of these tools that create micro efficiencies like e -sign, texting, document storage, whatever your needs might be. They're able to, just by limiting...

Jim (16:43.761)
Yeah.

Jim (16:51.569)
Yep.

Jim (16:58.905)
Mm.

Winston Smith (17:06.35)
like exporting to the management system. Let's say you have a phone call, you need to export it to the management system, the minute it's done, you click one button, it goes into the management system untouched by the employee. Rather than do it like the manual download, upload process, making sure it goes to the right folder, make sure it actually gets done, right? That's something that takes two seconds instead of 30 seconds, maybe 60 seconds, depending on what your management system is. Think about how many times that needs to happen over the course of a day, and that results in real gains.

from a time efficiency standpoint.

Jim (17:37.489)
awesome. My mind is still blown with the fact that you've got a little bit of Big Brother built into it for the screenshots. And I mean, 65 % of our agency's workforce is full time remote. We have we have people working in 10 different states now. And three years ago, we had two states, just Georgia and North Carolina. Now we're spread all the way out to Nevada, which is insane. Never would have thought that. That is a

Winston Smith (18:02.766)
Yeah, that's great.

Jim (18:06.673)
I've never heard of anybody being able to do that. That screenshot thing is quite intriguing. And the next part you talked about, you kept referencing agency management system and I was gonna ask you, does this replace your agency management system or is it a companion too?

Winston Smith (18:25.226)
It is a companion to the agency management system. We have no desire to be the agency management system. That's where all the transactions take place, right? Quoting, binding, all that kind of stuff. We sit on top of the management systems, all the major management systems by integration, and our job is to focus on the communications piece and the customer relationship piece and leave sort of the transactions and the policy management side to the agency management system.

Jim (18:42.289)
you

Jim (18:51.313)
Okay, that makes sense, that makes sense. Holy cow, man, this thing is like locked and loaded. You guys have really put a lot of hard work into this and I would imagine that this did not just happen overnight. I mean, like are y 'all actively adding different features like the screenshots thing? I mean, are these things actively being added through customer feedback or just like how's that working?

Winston Smith (19:16.846)
Yeah, exactly right. Through customer feedback, we continue to add features. So probably next on the list is to focus a little bit more on customer satisfaction. I think that's another metric that agents pay a lot of close attention to. It's not just revenue, number of employees, efficiency, how much you grew, but how satisfied your customers are. Because as we all know, as you focus on the growth side more,

Jim (19:30.171)
Yeah.

Winston Smith (19:39.448)
There's less pressure to grow when you retain more and you know that you'll retain more with more satisfied customers. So after interactions, after onboarding, after renewal, how did we do? What could we do better? Getting that automatic prompts and feedback there, particularly if you want to sort it by which of your CSRs or which of your producers handled it well. You're able to get that kind of granularity around how your business is performing so you don't have to worry about broker of records.

Jim (20:00.849)
Yep.

Winston Smith (20:06.744)
somewhere else in the middle of the night because you know that this customer's giving you positive feedback along the way.

Jim (20:12.849)
That is when we tend to think about broker of record letters, by the way, is middle of the night wakes me up in a cold sweat, especially if it's a larger account. Holy cow. All right, man. This is a lot of good information. I want to switch gears a little bit and kick you into the rapid fire round because I think we've got a lot of good information about bridge. So thank you. What's one piece of technology or software you can't live without? You're not allowed to say.

Winston Smith (20:15.246)
Hahaha

Winston Smith (20:38.05)
Yeah.

It's boring, but it's essential. Google Calendar for me. I use it specifically to plan my day and I have tasks in it related to it like rank order tasks and this is how I'm gonna do it in this order. And it's very difficult for me to go through my day without it, sort of to guide me through it and to help me stay sort of disciplined and focused in what I need to do on a daily basis. And then one other piece.

Jim (20:48.369)
Ha ha!

Winston Smith (21:09.838)
I know you only asked me for one, but I'm gonna give you one more. It's for people who are nerds about data, right? If you spend time in Excel and PowerPoint, there's a really, really good plugin for PowerPoint called ThinkCell, and that just makes the iterative process of telling stories with data much less laborious. So those are my two pieces.

Jim (21:12.899)
You're a rule breaker.

Jim (21:30.529)
Think cell interesting

Winston Smith (21:34.862)
Mm -hmm.

Jim (21:35.281)
Yeah, as far as the tasks go, that's something that I haven't gotten into on calendar on Google calendar. My, our, um, uh, head of, uh, finance and administration uses tasks a lot. And I've seen her do that, but I've never really understood the value. So I'm going to have to pick her brain and walk across a driveway to pick your brain sometime about that and figure out what am I missing with that? Um, what's one book that you are? I.

either currently reading or have read recently that you want to share with folks.

Winston Smith (22:09.294)
Sure. So I just finished this last month. It's Clay Christensen's How to Measure Your Life. So Clay Christensen is a highly accomplished entrepreneur and academic. He wrote a book, which is this book, How to Measure Your Life, which is the last lecture he usually gives to his students at Harvard Business School every semester. And it's about being very deliberate with your choices and cautioning.

Jim (22:17.753)
Whoa.

Winston Smith (22:39.034)
against getting caught in short -term thinking and the achievement trap that leads to unhappiness despite the traditional trappings of career success. So he has some good theories and maxims about that you can apply to your life and give you the best chance of success, which he defines as happiness instead of the normal measures of dollars in your bank account, your title, the number of people you manage, and other stuff that people get hung up on. So.

That was a very powerful book for me.

Jim (23:11.313)
I love that. And especially as a father of two young kids, I know like you realize now and it probably feels to you like, oh my gosh, I have like zero time for myself. And there's always something going on. By the way, it doesn't change when your kids get older like mine. Yeah, sorry, man. Sorry to break that to you. But yeah, that is measuring it in happiness versus dollars.

Winston Smith (23:28.59)
I was hoping you wouldn't say that.

Jim (23:40.401)
That is definitely a lesson that, that was a hard one for me to learn. I'm not gonna lie, you know, and I think a lot of people do. And even if you have good intentions and want it to be happiness, it can still be a struggle because we all need the money, right? And we all want to provide better opportunities for our family and our children. But at the end of the day, like at what cost, right? So yeah, that's a good one. I wrote that one down.

Winston Smith (23:49.166)
you

Jim (24:07.537)
Speaking of younger people, what advice would you give to your younger self?

Winston Smith (24:13.672)
So I'm still in my 30s, so I still consider myself sort of a young man. But I would say it's be more be true to yourself and live for yourself and be your authentic self in everything you do. You know, personal, especially professional and not how others think you should live your life or how you should act or, you know, who you should be. If there's a certain cast or mold that you think you should follow, I would encourage you to.

Jim (24:17.329)
I was gonna call you old man, but okay

Winston Smith (24:41.934)
to throw those notions out the window and just be you.

Jim (24:45.327)
Heck yeah, man. That's good advice. I actually saw a post on LinkedIn that Ryan Hanley made recently talking about that and how he's never had a problem with that, but he understands a lot of people do. And I definitely, I feel you on that. It's especially when you have a lot of people that you feel responsible for, whether it's your employees as a business owner or whether it's your family, your children, people are relying on you.

You know, you want to focus on them, but you also have to do it in your own way, right? Yeah, that's a good reminder. All right, what's one final piece of advice or actionable step that you would leave our audience with?

Winston Smith (25:20.174)
Mm -hmm.

Winston Smith (25:29.45)
Yeah, I guess it's less advice and more sort of pump up for all the owners and Producers and anyone who works in an agency out there Since times have been hard recently You know the market the way that it is It's just to remember that you're all in the best industry ever created and you have the opportunity to do amazing things not just for yourselves But for your communities too, and there will be real and lasting rewards for riding out this hard market

Jim (25:31.281)
you

Jim (25:56.433)
awesome man. Love it. Yes, very much understand that and feel it. As I mentioned before we got on here, I just got back from it's called Atlanta Insurance Ministries and to see 250 people in a room that showed up at 630 in the morning, it just shows you that yes there is more to

to what we're doing and the money that we're making and the opportunities we're providing allow us to have space outside of work to do things for your community. And that's a, yeah, love that, love that. Winston, besides coming and knocking on my door and asking which house is yours left or right, how can people find you if they wanna get more Winston Smith in their lives?

Winston Smith (26:45.87)
Sure, you can go to www .bridge .insure and you can find out a little bit more about the product as well as myself or you can friend me on LinkedIn, Winston Smith.

Jim (26:55.377)
Awesome, man. Thank you, my friend, for being with us. I appreciate it. You stick around for just a second. For everybody else, grow big or go home.