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Most of us operate within a hyper-competitive marketplace.  A compelling value proposition is a critical business asset and one of the most effective competitive differentiators. Companies that succeed in attracting and retaining customers are those that focus on delivering exceptional customer experiences and creating measurable customer value. In this episode of What’s Your Edge?, we explore how Rebecca Woan, founder of Chartwell Insurance Services, a boutique property and casualty insurance provider, built a thriving business by staying true to a customer-centric strategy, using her firm’s value proposition to stand out in a crowded field, and foster long-term loyalty and growth. Rebecca and her team recognize the importance of making customers feel valued and finding value.

Rebecca, congratulations on building a customer-centric organization.  I know our community is eager to hear what you and your team do better and differently to deliver value to your customers.

What we do is anything but radical.  We take care of people.  We had a retail brokerage that specialized in a very different end of the business, and I had a number of prospects in the high net worth or what is also referred to as the “successful individual” space.  I found markets and serviced them to effusive praise. I thought to myself, I’m just taking care of them.  Then I asked myself why their brokers weren’t taking care of the, and then I had the lightbulb moment that there was perhaps a business opportunity in being responsive and educating clients. This was the recipe for our growth, along with a team of people who care as much about clients as I do.  There is no substitute for hiring good people.

Attract Customers Who Want Value and a Good Reputation

Let’s jump right in.  I love this topic because we truly believe that a compelling, meaningful, and relevant value proposition is at the heart of finding, keeping, and growing the value of customers. It’s what enables companies to gain market share and charge a premium price.  You operate in an extremely competitive industry. I did a little research and learned that there are over 4,000 property and casualty insurance companies in the US and that the top 25 have nearly 79% of the market share.  And that the average churn rate for the industry is 16 out of every 100 policyholders.

Rebecca, what is your value proposition, and how has it enabled you to retain and create loyal customers?

Insurance is often sold on price, especially in the consumer sector.  We’ve all seen the name your price commercials and the you’ve been paying too much commercials.  We work with clients who recognize value over price and not as an unavoidable and unwanted expense, but as an important means to protect their real and personal possessions and help guard against assaults on their assets through liability lawsuits from aggressive third parties.  They also want to be placed with insurers who have a reputation for fair and generous claim settlement.  Not everyone is fortunate enough to make that choice, and that’s the market we operate in. 

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Empower Your Employees to Deliver the Promise of Your Value Proposition

I’ve heard you say that “the most recent interaction is the interaction the customer remembers.” We love Jan Carlzon of Scandinavian Airlines book, Moments of Truth.  He defined a “moment of truth“ as any interaction with a customer or any event in which a customer uses or experiences a company’s product.” A moment of truth has a huge impact on customer satisfaction, retention, and advocacy. Employees are the keepers of moments of truth.  What have you done differently to empower your employees to deliver exceptional interactions?

That’s so true, however, you can only empower employees once you know they are well-trained. It’s important to have mentorship and make employees part of the conversation so they learn by hearing and observing.  We also share experiences and how we solve problems, so we can be collaborative and offer a team approach to service.  It doesn’t serve a customer well if the one person who knows about their program is out sick or isn’t available.  Having well-documented files makes it easy for someone else to pick up. This requires constant reinforcement, and more than once, I have one of my team members reminding me when I need to do a better job.  No one is perfect, and the converse is also true, so we all have to own our mistakes.  I firmly believe customers cannot be fooled, and they appreciate an apology and a fix more than a cover-up, which only gets worse over time. 

The idea that customer experience is essential for long-term growth is not new. For a decade, Gartner has been saying, “companies will compete primarily on the customer experiences they deliver.” Even so, many companies still struggle to map the customer journey and eliminate the breakpoints.

Earlier, you said that the challenge is to consistently make customers feel valued and find value in the product.  Process is an integral part of creating customer value.  What kind of processes have you implemented to engage customers and deliver a superior customer experience?

I remind my team that we cannot assume our customers understand all the nuances and the insurance lingo, so we need to clarify in our communications.  We start with a welcome call to let clients know what to do in case of an emergency, to call us first, and that we have an emergency 24-hour emergency service.  We are very proud of our collateral materials, which are clean and easy to read for proposals and reviews.  We also follow up conversations with emails to memorialize, because you can never over-communicate, in my opinion.

Meet Customers at Their Comfort Level for Better Customer-Centricity 

People might not connect innovation with insurance.  Yet you talk about the need to think outside the box and to innovate as a critical factor for competing.  What kind of innovations have you developed, and how have they enabled you to outmaneuver the competition?

I’m not sure we have outmaneuvered the competition, but we have looked at how AI can improve our communication and education, and I believe this will be a critical differentiator going forward. I’m delighted to now be part of a larger organization. We sold to EPIC, which has a large national footprint, and they have the resources for the budget that this really needs.  I do feel that in the short term, there will be an advantage for the larger brokerages that have the resources to implement these AI strategies.

Two of the many things we have in common are our passion for customer-centricity and strategy. We believe that a good strategy that is customer-centric and well-executed has the ability to positively impact a market and a company’s competitive position. What kind of customer-centric strategies have you employed, which ones have been the most successful, and why?

We are in the service business, so I don’t think we could be anything but customer-centric.  We have people who communicate.  We make phone calls to deliver difficult news, and in this very hard insurance market, we have a lot of that.  We like to meet customers at their comfort level. Some want a lot of automation, and others want more interaction.  We’ll make file notes about issues that are specific to them, or how to best approach them, or if one spouse prefers to delegate to another, or if it’s important to include both spouses in interactions. 

Crafting a customer-centric strategy takes solid data about who your customers are and which ones are a good fit. I imagine in your industry, it is essential to be able to hone in on the right segments and personas. Rebecca, what data does your firm use, and how do you use it to find, keep, and grow the value of customers? And how do you use the data to distinguish an ideal customer from one that isn’t?

We have not been that granular with data.  We do track retention and success with prospects, and also data about how pricing has changed quarter to quarter. There is probably a metric out there, but instead we look at patterns and conversational responses in a prospect call to determine whether there is a good fit before we complete the labor-intensive proposal process.  The goal is to have a very high win percentage for proposals delivered.

To Successfully Compete and Grow, Focus on What You Do Best 

Win-rate. That’s a terrific metric. As we wrap up, I’d like to return to the start of our conversation about creating a customer-centric value proposition. Customer-centric companies build value props that offer a unique promise of value to their customers and articulate the benefits and solutions customers can expect. One of the key things we help our customers do is shift from value proposition construction to value proposition measurement. Measurement helps ensure a value prop remains strong, relevant, and capable of sustaining the vital connection between your business and its customers. We recommend selecting measures that measure the connection between your business and your customers, such as customer lifetime value, customer effort, customer retention rate, and others.  I’m curious to know what customer-centric measures you track and report, and why?

We look at the size of the account we need to be compensated for the cost of servicing. If the account is too small, we have made the difficult decision to politely decline the business. Also, once in a while, we have to tell a client that we cannot make them happy, which is our equivalent of the Dear John conversation.  Sometimes we recognize that our approach is not a good fit for someone who might not understand and appreciate our expertise and has an unrealistic expectation of what we should deliver. 

Rebecca, you’ve been at the helm of Chartwell for more than two decades. I imagine there have been both ups and downs. As we wrap up, what is some parting advice and lessons learned that might help our community outsmart their competitors.

You need to focus on what you can do best. I once heard a presentation about ideas which has stayed with me.  There are very few unique ideas, and chances are someone else is trying to do something very similar, and success comes from the one who executes best. Small businesses cannot afford to make a lot of mistakes, so they need to figure out where their profit margin is largest and which products or services are scalable.  If they can’t do this, or if the field is too crowded or the product is becoming obsolete, like the typewriter, for example, they need to pivot. 

This is an excellent reminder for all of us that to successfully complete and grow, we must focus and execute on what we do best, and that it’s important to know when to pivot. Thank you, Rebecca, for being our guest and revealing how you created and used a clear and compelling value proposition that served as a true competitive differentiator—even in a crowded and price-driven industry like insurance. Customer education and responsiveness and empowering employees, and leveraging processes for superior service delivery are critical to operationalizing customer-centricity. Your journey underscores that long-term success stems from consistent execution, deep customer understanding, and a relentless focus on delivering value.

Is your value proposition strong enough to attract and retain the right customers? Let’s talk about how we can help you assess and strengthen your value proposition to create a measurable edge in your market. Contact us to start your journey toward smarter growth.

FAQ:

(written by Penn of Sintra.ai)

Q1: What enabled Chartwell Insurance Services to stand out in a crowded, price-driven market?
A1: Chartwell’s differentiation was not built on gimmicks—it was built on a clear, customer-centric value proposition: responsiveness, education, and trusted guidance for clients who value protection and reputation over price. Rebecca identified a market gap: high-net-worth clients were not being “taken care of,” and the opportunity was to win loyalty by consistently delivering what most competitors under-deliver—clarity, follow-through, and human service. In a category where many firms compete on price, Chartwell competes on confidence, credibility, and the quality of the customer experience.

Q2: What is Chartwell’s value proposition—and who is it designed to attract?
A2: Chartwell serves clients who recognize insurance as a strategic asset—not an unwanted expense. These customers want:

• Coverage that protects real and personal assets and mitigates liability exposure
• Placement with insurers known for fair, generous claims settlement
• A broker who educates, communicates clearly, and responds quickly
  This value proposition intentionally attracts customers who prioritize value over price, and it filters out prospects who are likely to churn, dispute expertise, or demand service that cannot be delivered profitably.

Q3: How does Chartwell operationalize customer experience through “moments of truth”?
A3: Rebecca’s principle—“the most recent interaction is the interaction the customer remembers”—is operationally significant. Chartwell treats employees as the keepers of customer moments of truth by ensuring:

• Strong training and mentorship (employees learn by observing and hearing real problem-solving)
• Collaboration and shared knowledge (service continuity even when a primary contact is unavailable)
• Well-documented files so any team member can step in seamlessly
• A culture of accountability: own mistakes, apologize, fix quickly, and avoid cover-ups
  This approach protects trust, reduces service variability, and strengthens retention.

Q4: What customer-centric processes help Chartwell deliver a superior experience consistently?
A4: Chartwell builds experience through proactive communication and customer education:

• A welcome call that sets expectations and clarifies what to do in an emergency
• A clear directive: call us first, supported by 24-hour emergency service
• Clean, easy-to-read collateral for proposals and reviews
• Follow-up emails to memorialize conversations (“you can never over-communicate”)
• Plain-language communication that avoids assuming customers understand insurance lingo
  These processes reduce customer effort, prevent misunderstandings, and reinforce the firm’s promise of being responsive and reliable.

Q5: What role does innovation play in a service business like insurance?
A5: Innovation is less about flashy product change and more about improving communication, education, and service delivery. Rebecca sees AI as a near-term differentiator—particularly for larger brokerages with the budget to implement it well. Chartwell’s move into a larger organization (EPIC) reflects a strategic recognition: scale can accelerate investment in AI-enabled customer communication and education, strengthening competitive advantage.

Q6: What customer-centric strategies have been most successful—and why?
A6: The most successful strategies are practical and human:

• Deliver difficult news by phone (not email), especially in a hard insurance market
• Match service style to customer comfort level (automation for some, high-touch for others)
• Capture customer preferences in file notes (who to include, how to communicate, decision dynamics between spouses)
  This is customer-centricity as an operating model: meet customers where they are, reduce friction, and personalize service without overcomplicating the business.

Q7: What data does Chartwell use to qualify prospects and protect profitability?
A7: Chartwell is selective with formal metrics, but disciplined in qualification. They track retention, prospect success, and quarter-to-quarter pricing changes. More importantly, they use pattern recognition in prospect conversations to decide fit before investing in a labor-intensive proposal process. The operational goal is clear: a very high proposal win-rate—a metric that protects time, margin, and team capacity.

Q8: How does Chartwell decide when to decline or exit business—and why is that customer-centric?
A8: Chartwell evaluates whether an account is large enough to justify the cost of servicing. If not, they politely decline. They also occasionally have a “Dear John” conversation when expectations are unrealistic or the relationship is not a fit. This is customer-centric because it prevents broken promises: accepting misfit customers creates dissatisfaction on both sides, strains the team, and erodes service quality for ideal clients.

Q9: What is Rebecca’s most transferable advice for leaders competing in saturated markets?
A9: Focus on what you do best—and execute better than anyone else. Unique ideas are rare; advantage comes from execution quality, scalability, and margin discipline. Small businesses cannot afford repeated mistakes, so they must identify where profit is strongest and where delivery is repeatable. And if the market is too crowded or the offering becomes obsolete, leaders must be willing to pivot.

Q10: What is the core lesson about value propositions from this episode?
A10: A value proposition is not just positioning—it is a promise that must be operationalized through people, process, and communication. The strongest value propositions attract the right customers, repel the wrong ones, and are reinforced through measurable customer experience—responsiveness, clarity, reliability, and trust.