In some industries, trust is given freely. Insurance isn’t one of them. Many buyers approach it with skepticism, assuming their agent is holding something back, sharing details that work in their favor, or dodging the questions that matter most.
That doubt can be a serious hurdle, especially when what you’re selling is something as personal and important as protecting someone’s home, car, or business.
Berry Insurance knows this reality well. But instead of trying to sidestep the skepticism, they decided to meet it head-on. With the guidance of IMPACT Coach Brian Casey and the Endless Customers System™, they built a marketing approach rooted in trust, transparency, and consistent communication. Transforming the way their community sees them.
They didn’t shy away from the hard questions. They answered them openly, even when it meant publishing information their competitors avoided. They put their team on camera, showing the people behind the brand. They made their buyers feel informed, not sold to.
What we covered in this episode went far beyond theory.
Corin and Brian shared Berry Insurance’s full journey. From developing content that addresses real buyer questions and concerns, to embracing video as a way to show the human side of their team. Along the way, they navigated leadership buy-in, coaching, and the shift toward AI-driven search.
To understand why these strategies worked so well, you need to know where Berry Insurance started and how they transformed a century-old reputation into a modern marketing engine.
Berry Insurance is a family-owned, independent agency in Franklin, Massachusetts, that’s been around for more than 100 years. Generations of customers have relied on them to protect what matters most, and that kind of longevity comes with a well-earned reputation for stability and community trust.
But even the most established businesses can’t survive on legacy alone.
The way people buy, research, and choose services has changed dramatically, and Berry Insurance knew they had to evolve to keep up. That’s where Corin Cook came on board. She joined the team in 2019, bringing with her a background in journalism and public relations. That experience gave her a knack for storytelling and an instinct for asking the right questions, but digital marketing was a whole new ballgame.
“I had to learn digital marketing from the ground up,” Corin told me. And that’s exactly where coaching from Brian Casey made an immediate impact. He didn’t just hand her a checklist. He worked alongside her to build a deep understanding of SEO, the stages buyers go through before making a decision, and the strategies that would put Berry Insurance in front of the right people at the right time.
Keeping up with industry trends is a balancing act for any insurance agency. Some aspects of the business move at a glacial pace, with rules, regulations, and processes that have barely changed in decades. Other areas, like technology, online behavior, and marketing platforms, shift almost overnight. Brian’s guidance helped Corin navigate both realities, blending the company’s century-old commitment to service with modern tactics that meet today’s buyers where they are.
But learning the tactics was just the first step. The real challenge was staying sharp as the market shifted, which is where ongoing coaching became a catalyst for growth.
Even the most disciplined marketing teams can start to drift when they’re going it alone. Berry Insurance learned this firsthand when they took a short break from coaching. It wasn’t that they stopped caring about their marketing or content, but without that regular outside perspective, small gaps in strategy began to widen over time.
The turning point came when Corin attended IMPACT Live. Surrounded by peers, hearing from other companies implementing the Endless Customers System™, she started to see the shifts happening in real time. The biggest one? The rapid rise of AI in search and content creation. “The conference was a wake-up call,” she told me. “We were doing good work, but the landscape had changed, and we weren’t moving fast enough to keep up. We needed to get back into coaching to adapt and keep our momentum.”
Brian remembers that decision clearly. “Coaching isn’t just about tactics,” he said. “It’s about having an outside perspective to spot the opportunities you might miss and to challenge you to think differently about what you’re doing.”
That outside perspective became a catalyst. Coaching sessions brought fresh ideas they hadn’t considered, from small SEO adjustments to entirely new approaches for optimizing content so it would show up in AI-driven search results. It also gave the team a renewed sense of accountability. When you know someone will be reviewing your progress, it’s easier to keep priorities clear and momentum strong.
For Berry Insurance, returning to coaching wasn’t about fixing a broken system. It was about making sure a good system stayed sharp, responsive, and ready for whatever the next big change in marketing might be.
With a steady outside perspective keeping them focused, Berry doubled down on the single most important differentiator in their market: trust.
How can a distrusted industry go all in on trust?
Insurance has an image problem that’s been around for decades. Too often, people think of it as a world of fine print, hidden fees, and half-answers. Buyers expect to be sold to, not educated. That’s why Berry Insurance’s approach is so refreshing and so effective.
Instead of sidestepping the tough questions, they answered them head-on. They created articles and videos that tackled topics many insurance companies wouldn’t touch, from breaking down pricing to openly discussing common problems in the industry. When other agencies were busy polishing sales pitches, they were building a library of content designed to help buyers make informed decisions.
Corin summed it up perfectly: “Don’t let fear hold you back. If you put in the work, it will work.” That mindset is what allowed Berry Insurance to turn potential skepticism into genuine trust.
Strategies like this don’t survive without leadership that’s willing to embrace them. Berry Insurance’s owner, Kaitlyn Pintarich, didn’t just sign off on content marketing. She made it a company priority. She encouraged her team to be open, to share what they knew, and to take pride in educating customers. That meant everyone, from sales to service, understood why transparency mattered and how it could change the business.
Leadership buy-in is more than just a nice-to-have. It sets the tone for how the entire team approaches communication with customers. Without it, even the most promising marketing strategy can fizzle out. With it, like in Berry’s case, trust becomes a competitive advantage.
One of the most powerful ways they brought this transparency to life was through video. Putting real faces and voices in front of their audience.
Why did Berry Insurance add video to their strategy?
Berry Insurance’s marketing reached a new level when they brought a videographer on board. Up until then, most of their storytelling happened through written articles. The information was strong, but it lacked a certain human element. Video changed that completely.
Suddenly, prospective customers could see the faces behind the name. They could hear the tone of voice, notice the smiles, and feel the genuine care in the way the team spoke about their work. “It’s one thing to read about who we are,” Corin told me. “It’s another to watch us talk about what we do and why we care.”
Video also allowed them to show, not just tell. They could walk people through a coverage option, explain how a policy works, or share a quick tip for avoiding common mistakes, all in a way that felt personal and approachable.
Of course, adding video wasn’t without its challenges. It took time to integrate video into their existing content strategy. They had to decide when video should stand alone and when it should complement a written article. They also had to get comfortable with the fact that, like most content marketing, results wouldn’t be instant. It was a long game.
Over time, the payoff was clear. Video built a level of trust that text alone couldn’t achieve. It gave customers a sense of familiarity before they even picked up the phone. And in an industry where trust is often earned slowly, that kind of head start is powerful.
But transparency alone isn’t enough. You also have to deliver it in the formats and platforms your audience uses. That’s why Berry was quick to adapt when AI began reshaping the way people search for answers.
How is Berry Insurance adapting content for AI-driven search?
When artificial intelligence began reshaping the way people search for information, Berry Insurance saw another big shift coming. Instead of digging in their heels and clinging to old SEO habits, they decided to adapt.
“We’re moving from keyword-focused optimization to thinking about how to be recommended by AI,” Corin explained. In practical terms, that means rethinking how content is created and presented. It’s not just about ranking for a search term anymore. It’s about becoming the source an AI assistant chooses to cite or recommend when a user asks a question.
This required a different kind of strategy. Articles had to be clear, concise, and directly answer specific buyer questions. Information needed to be structured in a way that AI could easily parse and understand. And above all, the content had to demonstrate authority and trustworthiness, because that’s what both search engines and AI systems look for when choosing what to recommend.
With Brian’s guidance, Berry Insurance began experimenting. They tested new formats, refined how they answered common questions, and made sure each piece of content was more than just relevant; it was complete, accurate, and easy to use. Some changes were small, like reworking headlines or improving page structure. Others were bigger, like producing entirely new resources designed for AI-friendly search.
Embracing these shifts early, Berry positioned themselves to remain visible in an environment where AI is increasingly the gatekeeper between businesses and buyers. They leaned into the change, making it work for them instead of against them.
By combining their trust-first approach, human connection through video, and forward-thinking AI strategy, Berry began to see measurable results.
When all the right elements come together (strong written content, authentic video, leadership that truly leads, and consistent coaching) the results speak for themselves. For Berry Insurance, this combination didn’t just keep them steady in a competitive market. It pushed them ahead.
Their website traffic climbed. Leads became more qualified. Even during periods when the insurance industry as a whole saw declines, Berry continued to grow. That’s the advantage of building trust through transparency. People didn’t just find Berry Insurance online. They stuck around, engaged with their content, and felt confident enough to reach out.
This wasn’t about chasing quick wins. The results were the product of years of consistent effort and a willingness to go where competitors wouldn’t. While many agencies avoided talking about cost, limitations, or industry flaws, Berry put those topics front and center. In doing so, they became the source buyers could rely on for straight answers.
Brian captured it in one line: “Put yourself in the buyer’s shoes and have the courage to say what needs to be said.” When you operate from that mindset, you stop worrying about impressing search algorithms and start focusing on what will actually help people.
For Berry, these results were proof that the principles of trust, transparency, and adaptation work in any industry. And here’s how you can put them to work for yours.
If you’re a business owner or marketing leader, Berry Insurance’s journey offers a clear blueprint for building trust and standing out in your market.
Berry Insurance is committed to a long-term strategy that not only improves visibility but also makes them the kind of company people actively seek out. It’s a process built on consistency, trust, and the willingness to evolve.
As Corin put it, “Take risks and trust the process.” Over time, that approach creates more than just customers. It creates lasting relationships and a reputation that keeps people coming back.
Berry Insurance’s story is proof that even in industries with deep-seated trust challenges, a commitment to openness, consistency, and adaptation can completely reshape how buyers see you. By embracing the Endless Customers System™, they didn’t just update their marketing tactics. They built a culture of transparency that runs through every part of their business.
If there’s one thing to take away from their journey, it’s that success comes from showing up for your audience day after day with honesty, helpfulness, and the courage to answer the questions that matter most. That’s not a quick win, but it’s the kind of work that builds something far more valuable, a reputation that lasts.
How do you start building an AI-ready trust strategy for your business? Talk to our team about implementing the Endless Customers System™ and see how it can help you attract, engage, and earn loyalty from the buyers who matter most.
Corin brings clarity and confidence to insurance conversations. With a background in journalism and public relations, she joined Berry Insurance in 2019 as the company’s first official Content Manager and now leads the marketing team. She creates content designed to help clients feel informed and empowered.
Check out Berry Insurance
Connect with Corin on LinkedIn
How do I earn trust in a skeptical industry?
Be transparent about pricing, address common problems openly, and create content that educates rather than sells.
How can I make my content AI-friendly?
Answer specific buyer questions clearly, structure information with headings and lists, and demonstrate authority through sources and accuracy.
What role does leadership play in trust-building?
Leaders must model transparency and actively encourage open communication across the company.
Why is video important for trust?
It creates personal connection, shows authenticity, and helps buyers feel they know you before the first interaction.
How do I know if coaching will help my marketing?
If your strategy isn’t evolving with buyer behavior, coaching provides the perspective, accountability, and expertise to keep you competitive