Agency Acceleration Lab


Episode 14 – How Will Winter Builds Agency Cultures That Actually Win

What if the secret to growing your agency isn't a better sales script… but a better environment?
In this episode of the Agency Acceleration Lab, Alex Branning sits down with Will Winter — former COO of Agent CRM and founder of the Greatness Incubator — to unpack what it really takes to build a thriving culture inside your agency.
Will shares why most agency owners skip the most important step in leadership, how your hiring funnel communicates your culture before you ever speak to a candidate, and the seven practical tools every agency owner can use to shape the world their team lives in every day.

From defining your core values to crafting the language your team uses on every call, this conversation is a masterclass in intentional leadership — the kind that turns a group of agents into a team that's genuinely bought in.
Most agency owners are so focused on recruiting and production that they never stop to ask: what kind of world am I building for my team? Will breaks down exactly how to answer that question — and then do something about it.
In this episode, you'll learn:
 If you want to stop losing good agents to bad environments and start building a team that actually stays, grows, and wins together, this episode is your starting point. 

What is Agency Acceleration Lab?

Agency Acceleration Lab is the podcast for insurance agents and agency owners who want to scale smarter, not harder.

Hosted by Alex Branning, each episode breaks down real growth strategies, marketing systems, and client retention frameworks that help you attract better clients, increase lifetime value, and build a more predictable agency.

If you're serious about building a high-performance insurance business, you're in the right place.

Alex Branning
Hey, what's up guys. I'm here with Will Winter. Many of you who have been following me know him as the COO of Agent CRM. He has since jumped out, he has flown the coop, and he is flying on his own with the Greatness Incubator, where he is helping leaders just like you create world-class leaders. We're going to talk about how to walk alongside your agents today with encouragement to help them maximize their potential and create a really healthy culture, which is what we have and still have at Agent CRM, thanks to a lot of the values that Will instilled. Will, thank you for joining me on the podcast, man. Let's dive right into culture. I guess my first question is, how do you define culture? Like, the way that it feels, like your energy, like, how would you define that?

Will Winter
Yeah, I think the first thought here is that often the word culture can feel so squishy or intangible, but really culture is the combination of habits and beliefs and behaviors and attitudes, all of these things fit together to create a way of life. Think of a country's culture. What is your work culture? And there's an energy behind that. There's a momentum where often we have a plan or a strategy, but our culture, people have beliefs and attitudes that go against it, so we need to look at the way of life, all of the pieces that go into what our team experiences. It's a way of life.

Alex Branning
You did a really good job at Agent CRM. You actually said, you know what, I'm gonna write out what our culture's core values are, and we would go over that on a pretty regular basis. Don't forget, this is our core values. This is who we are as a company, and it really dug these seeds deep in the soil. Like, at first it was like, okay, we're going to go with these core values. These are really cool, they sound fun, but then you got to put it to practical use. When you walk with an agency owner or any business owner, what steps do you take to help them build a culture of winning?

Will Winter
Culture of winning. Part of it is being clear about who you're attracting in the first place, and I love being a part of this process with Agent CRM. The hiring funnel itself is the first stage where we need to understand what are we communicating about what it's like to be on our team, and part of that is even knowing who we are and what kind of team environment we're creating. If you go on our hiring funnel, there'll be a video, it's probably still me, and it talks about we're looking for A players, we're looking for people who love putting in a hard day's work and who love to grow and push themselves, so we have this language that right out the gate talks to those kinds of people, and then you scroll down and there's our values. Here's the kind of people we are. We made a few bad hires early on, and part of that was because we didn't know what we needed or what we valued. We didn't have those core values. We want to filter out the wrong people. There's a type of person who likes to color outside of the lines, who likes to work outside of the box. And for us at Agent CRM, we would onboard so many agents every single day that we need people who understand processes and systems. If you are an outside of the box, can't be controlled kind of person, there's a place for you, but not on our team. So we needed to understand who are the kinds of people that represent the skills or the mindsets or the values, and we put that on the hiring funnel, so that the attitudes — are you someone who loves to give it your all, and are you someone who values these things and thinks in this way? So even right out the gate, we would start to hire people with a little bit more alignment with what we needed and the work environment that we're looking to create.

Alex Branning
Yeah, we did it. At the end, man, I just feel like we got it dialed down to almost a science of being able to attract people, and a lot of that was us again just putting our core values out there and creating a reputation. Let's talk directly to the business owner right now. You do a great job of encouragement, so let's encourage the agency owner who doesn't feel like they can even define what their culture is right now. How would you encourage them to get started in setting that foundation for their agency, for their team?

Will Winter
Part of it is just drawing a map. What do you want? I think even for how you imagine your home life, how you imagine your friendship circles, how you imagine work — what do you want to see? And then we can work backwards and unpack it. But I would encourage you to take some time. There's some beautiful ideas and values inside of you. Has it been committed to pen and paper yet? So there's a mini homework here. Take some time and actually write out — what are some of the things? Do I want people to feel connected? Do I want people to feel inspired? What is the day in the life? What would the dream scenario look like? Take some time to just soak in that vision, that picture in your mind. And then we can start to unpack and reverse engineer what does it take to get to that point.

Alex Branning
That's so good. You've studied under some of the greatest leaders that we've both been able to meet, and you've actually been able to sit under them. What are some of the things that you learned from those leaders, and how do you take their concepts and bring them into the marketplace, into the business world?

Will Winter
Yeah, I think the biggest lesson is that leadership is influence. You don't have to have a title, you don't have to have a position, but you can shape the environment around you. The leaders I've sat under have taught me that the most powerful thing you can do is create an environment where people feel seen, valued, and challenged. And when you do that, people rise to the occasion. They bring their best. And the way you do that is through intentionality — being deliberate about the culture you're creating, the language you're using, the stories you're telling, and the people you're surrounding yourself with.

Alex Branning
Talk about the seven tools that you bring when you talk to a leader who's working to create this culture. One of the biggest things that I learned from working with you is that creating culture and building up people is not something that happens on accident. You have to be really intentional. You have to create a vision of what you want to build — how do you want the culture to feel, how do you want the people to feel, how do you want them to treat each other and treat the clients. Talk to us about the tools that you build into these organizations.

Will Winter
Yeah, I've got seven core tools for building culture, and it's like the world that your team and your agents live in. The first thought before I share the tools is that many people start as agency owners by selling policies — you were the one in the weeds on the front line. Then maybe you started recruiting and you've got a team. Maybe you're training your team. Hopefully you graduate to the next level where you're training leaders to train your team. But there's still a higher step — it's world building, it's culture shaping. You're shaping the environment itself, and the environment starts to shape people.

So the seven tools for building culture. The first one is celebration. When we make a rhythm of celebration, we start to reinforce the right behaviors. People want to get encouraged, they want to get affirmed, they want to get recognized. We use this tool strategically. Second is values — we need a phrase or a word or an idea that becomes a filter for our decisions and our team decisions, and we need to actually express those values in tangible ways. They can't just be cute sayings on our wall. Third is language. What phrases or words do we use to describe our clients? What words do we use to describe challenges? Think of Chick-fil-A — everyone knows "my pleasure." That's language that reinforces key values. Fourth is modeling. What are the vital behaviors that each of your leaders must buy into? We want to demonstrate them and show them so that they catch on. Fifth is team — who is on your team? Are you bringing the right fit or the wrong fit? Because each person, even on the front lines, is shaping the environment. Sixth is stories. What are the stories? You shared in one team huddle why we do insurance, why this platform, why this niche — and all of a sudden people are brought into a mission, something bigger, and they're swept along. And then finally, time commitments. What do you actually plug into your week? If you value development and growth, you need to put time in the calendar where your team learns and studies. Those are the seven tools: celebration, values, language, modeling, team, stories, and time commitments.

Alex Branning
I love it. So we're going to end the podcast here. I know the people listening right now are like, please tell me more. You can follow Will and grab the playbook on his website — there's going to be a link to his masterclass so you can watch that, and reach out to him to schedule a one-on-one call. But here's some homework for you as the agency owner. As soon as you're done with this podcast, go to each person on your team and encourage them with something that is going to be meaningful to them. Don't just say you're doing a good job — tell them what you see in them doing that job, and call out, as Steve Backlund would say, call out the gold in their life. For those of you that are like, I've got to do this, I need to take action and I need someone to walk alongside me — highly recommend reaching out to Will. He can work alongside you. Will, thank you for joining the podcast, man. Appreciate you. We'll have to have you back for a follow-up in a couple of months.

Will Winter
It's my privilege, and thank you for letting me go down memory lane with you today.

Alex Branning
All right, thanks guys. Thank you for watching. Please take notes, please take action, and subscribe. You will not get any value from the lesson you just got unless you implement it in your business. Please share this episode if you got value from it, and I'll see you online.