In celebration of Deland, Gibson Insurance’s 125th anniversary, Agency Checklists spoke with CEO Chip Gibson about the agency’s remarkable history, its current operations, and plans. During our conversation, Charlie Gibson, former President and CEO who led the agency for over 30 years joined briefly to provide a historical perspective on this fourth-generation family-owned business.
Can you give us a brief overview of Deland, Gibson’s history, and its founding principles?
Our founding principles have always been to do what’s best for the good of the client. More formally, our mission is to provide you peace of mind.
The agency was established in Boston in 1900 as The Deland Insurance Agency by Charles E. Deland. He started with a single office that he borrowed from an insurance company that eventually became Commercial Union and later One Beacon. They gave him office space downtown, and that’s how it all began as a one-person shop.
In 1935, George Gibson, Deland’s nephew, took over the agency and led it until 1986. During World War II, there was a significant disruption when my grandfather served as a colonel in the Pacific theater from 1941 to 1945. His wife Margaret and aunt Louisa stepped in to run the company during those four years he was serving abroad.
My father, Charlie Gibson, joined after graduating college in 1969, though he had to serve in the Navy first, returning to the agency in 1972. He became President in 1981 and served as President and CEO for over 30 years.
In 2015, the fourth generation officially joined the leadership. I became CEO, and my brother Ted Gibson became President while Charlie transitioned to Chairman.
When did you and Ted join the agency?
I joined in 2006, and Ted joined in 2009. Before that, I worked in finance at Brown Brothers Harriman as a fund accountant right out of college. I remember when I first seriously considered joining the agency – my bosses at the time were walking to lunch and asked what my dad did. When I told them he ran an insurance agency in Wellesley, they said, “What the heck are you doing here?”
Charlie never put any pressure on us to join the family business. But after that conversation, I went home and asked about the industry and how the agency worked. Charlie said he’d bring it up at a manager meeting – fully realizing after the fact that he could have just said yes, but he wanted to go through the right channels and tell everyone in the office they were considering bringing me in.
Could you discuss any pivotal moments or decisions that shaped the agency’s path to where it is today?
The pivotal moments were with the perpetuation of the agency to stay within the family. Especially in 2015 when Charlie decided to keep it in the family. We were just about $6 million in revenue at that time. That was pivotal because agency valuations were beginning to rise, and the pressures of scale, technology, and talent were showing that maintaining independence would be challenging for a long period. Charlie had the foresight to invest in the future and in his sons at a moment when others might have cashed out.
In 2013, we started talking about perpetuation, which was seven years after I had joined. Officially, in 2015, we initiated the perpetuation process. It was gradual – at first, there wasn’t any transfer of control, but over the four years during the buyout process, Charlie really started handing control over to Ted and me.
How has Deland, Gibson adapted its business practices over the decades to stay relevant in the evolving insurance market?
We are very diligent with annual strategic planning, using frameworks from SWOT to PESTLE (political, economic, social, technological, legal, and environmental) analysis.
When I joined, the demographics were quite different – there might have been just one other person within 20 years of my age. But Charlie was really good about listening to us, certainly pushing back in areas but being open to considering new things. He even said to me, “The worst answer I can give you is ‘because we’ve always done it that way.'”
From the start, Charlie realized we needed to reinvest in growth. We started to think differently about producer hiring, though we found that it was harder than anticipated because of all the infrastructure needed to develop a producer.
We were fortunate to have Tom Skelly join us. He was a great mentor to Ted and me, and he really bridged the gap between “the boys” – Ted and I – and Charlie. Strategically, it worked well with Tom, Charlie, Ted, and me, changing the culture to a more dynamic growth organization.
Tom implemented much of our planning approach. When we first started formal planning, our sales goal was $200,000 of new commission, and we didn’t hit it. Now, our new business sales goal is over $1.2 million in organic growth, and we are hitting it. It didn’t happen overnight – a lot went into it, but hard work pays off.
What role has Tom Skelly played in the agency’s growth?
Tom joined around 2010, bringing strategic planning and a growth mindset to the organization.
Tom ran his own agency before joining us. He had two locations and was probably generating $700,000-$800,000 in revenue. He was doing a lot himself and wasn’t really able to take vacations. When you’re a three to five-person shop, there’s a lot of day-to-day servicing pressure on the leader.
Getting back to how I mentioned getting people into their unique abilities and what they do best – Tom isn’t best utilized servicing accounts. He certainly can do it and do it well, but Tom is a big-picture strategic thinker. He likes coaching and teaching, and he was able to do much more of that at DG. He could also take vacations and spend more than three days out of the office because there was a full team to work with his clients.
How does Deland, Gibson maintain its competitive edge in today’s insurance landscape?
We work hard every day. We stay diligent with our strategic planning process and remain on the leading edge of knowledge, technology, and relationships within the industry. We make sure to map out time to work “on” the business versus always working “in” the business. Being part of larger groups like Assurex Global and Incite Performance Group has been tremendously beneficial.
Something that I sometimes overlook when thinking about our competitive edge is our internal operations. We have such a vision for seeing technology as a necessity. We have two main operational roles: a Director of Operations and Quality Assurance and a Director of Strategic Initiatives. One keeps us on course with what we’re planning and how we’re executing, while the other works toward the future.
The Director of Strategic Initiatives focuses on ensuring our data quality is high and helps us move forward technologically. Three years ago, we made a strong push into robotic process automation, so we’ve been working with bots and setting up our own processes internally for several years. We don’t have the resources of larger companies, but we refuse to bury our heads in the sand.
With the rapid advancement of AI, we’re constantly evaluating the “build versus buy” question. Three or four years ago, we were more inclined to build solutions ourselves, but now, with technology moving at such a fast pace, partnering with specialized companies might be a better option.
Could you tell us more about your involvement with Assurex Global?
We’ve been with Assurex Global for two years. We started working with Reagan Consulting in Atlanta, which helped us with the finance and strategy side. As we were growing, Ted and I wanted exposure to next-level resources, so Reagan suggested we consider joining CIAB or Assurex Global. When Fred C. Church sold to Assured Partners, it opened up the geographical area of Massachusetts for Assurex Global.
Reagan Consulting connected us with the Assurex leadership, and we learned about how the partnership works – over 100 agencies working together with capabilities comparable to a top-five broker. From benchmarking to data analytics to international capabilities, it’s really an advantage that allows us to compete with the biggest firms in the world.
Being the Massachusetts partner means we can help other Assurex members with Massachusetts-specific challenges like Mass Auto, which is a pain for everyone else in the country but something we know well. Recently, we had a logistics company opportunity and were able to tap one of our new Assurex partners with a speciality logistics expertise department. Their specialist came to Boston, and we met with them. We were able to win a large deal because of the collective expertise within the group.
There’s really nothing we can’t handle with the expertise of the Assurex Global network. We’re the only Assurex agency based in Massachusetts, though Starkweather Shepley in Rhode Island is also a member.
What are some of the most significant changes in the insurance industry that have impacted your agency during its 125-year history?
Over the past 125 years, we have weathered a lot of storms. If we thought the hiring environment was hard now, it couldn’t have been worse than during WWII when our grandfather had to leave the agency and have his wife and aunt step in to run the company while he was serving abroad.
The more things change, the more they stay the same – it has always come down to great service, enduring client relationships, and staying on the front end of technology and education.
How has the agency’s structure evolved over time?
When I started, we were really focused on property and casualty only – just commercial lines and personal lines. Fast forward to now, and we’ve segmented more. In the past five years, we’ve invested heavily in growing our employee benefits team with several dedicated people in that unit.
Within personal lines, we have a more formalized “1900 Club” – named for the year we were founded – as our VIP unit for high-net-worth personal insurance. This year, we finally established the 1900 Club in commercial insurance and employee benefits for VIP clients as well. Previously, employee benefits were more of a referral-based relationship, but now it’s a huge part of what we do.
We’ve also moved away from a model where producers owned their own book of business. With changes in laws regarding restrictive covenants and carrier compensation, that model wasn’t going to work with the amount of investment we wanted to make into the team. We wanted people to do what they did best, and in the old model, people had to do a bit of everything. Now, we can put together teams where people work within their unique abilities, doing what they do best as much as possible.
How is Deland, Gibson leveraging data analytics or AI in its operations, and what impact has this technology had on your business decisions?
We’ve been using Power BI, Applied Analytics, and AI to alleviate processing redundancies. Data analytics have allowed us to look at information on a daily or weekly basis that historically was processed monthly or annually. It allows us to make decisions faster.
How does Deland Gibson foster client relationships and ensure high levels of customer satisfaction?
From 1900 to 2025, this is still a relationship business. Developing trust and setting the right expectations is absolutely paramount to a good relationship.
About eight years ago, we established a client experience committee, and we quickly realized that before we could improve our external client experience, we had to master our internal client experience – how we communicate with each other and how well we know each other.
To define what a great client experience means, we took 60 days and asked everyone to come back with examples of good experiences they’d had in their daily lives. People talked about visiting Bass Pro Shops or getting their nails done, for example – random experiences. We put them all on a whiteboard and were able to categorize them into three areas: being educated about something, someone going the extra mile, and how a provider made things right when something went wrong.
We have core values internally, but we also have “client experience icons” displayed on our walls that emulate what we want to achieve with our clients. One icon represents education, another represents going the extra mile, and the third represents success through adversity. It’s not a matter of if but when something will go wrong. What we focus on is how we make it right – how we pivot and make lemonade when life hands us lemons.
Those three categories became our client experience icons. They’re in our HRIS system, and we recognize coworkers when they exemplify these principles. These are the things that make a company great.
What are the core values that guide Deland Gibson today, and how are they reflected in your daily operations?
We work with urgency, we are compassionate, we are life-long learners, we have grit, and we innovate.
We have an internal recognition program where people can be recognized by their peers. These values are part of our annual reviews, and we believe that if you embody these on a day-to-day basis, DG will achieve its goals.
Can you share insights into your agency’s approach to risk management and how it has evolved?
We have evolved from a “let me review your policies and see if I can save you some money” approach – what we jokingly call the “copy, quote, pray” sales process – to an enterprise risk management system called GRIP “Gibson Risk Improvement Plan” for identifying, assessing, and addressing areas of business, strategic, hazard, and workforce risk via a long-term risk management plan.
As Deland, Gibson looks forward, what goals or objectives are you setting for the next decade?
We don’t typically look more than 5 years out. We focus on a 3-5-year plan and attack it one year at a time. However, we strive to be the regional employer of choice and a top 100 broker. We’re looking to double in size within 3-5 years.
We want to be the top independently owned agency in Massachusetts. We want to be the employer of choice in the region. With so much consolidation in the industry, people often talk about “the good old days” in insurance – we want to BE the good old days in insurance. We want to avoid red tape and do what’s right for our clients, our coworkers, and our community.
If people are unhappy where they are, we want them to know we’re not as corporate as others. We’re still a family business. We’re not a faceless entity owned from somewhere else in the country. We’re making the decisions in Wellesley and focusing on our people, our clients, and the community.
How significant are acquisitions to your growth strategy?
We want balanced growth. We don’t want to grow just through M&A – we want to maintain a balance between organic growth from producers and growth through acquisitions.
A healthy organization has a 15% sales velocity, meaning they’re growing by 15% through organic growth. That sales velocity allows not just organizational growth but supports raises, bonuses, and new roles that develop from expansion.
Growth isn’t just about numbers – it’s about developing people, giving new opportunities, and exploring new industries within the insurance business. We won’t retain the best people if we don’t have growth, which is why it’s such a focus for us.
We completed six acquisitions in the past four years: three last year (Burr Insurance, Atchue Insurance, and Austin Chandler), and previously Gorman Insurance, Dickey Insurance Agency, and Keefe Insurance.
What strategies are in place at Deland, Gibson for nurturing talent and ensuring leadership succession?
As of 2025, we’ve launched an internal training department to complement Deland, Gibson University (DGU). Currently, DGU offers classes every two weeks, and we’re supercharging this effort.
We have a team of four people working on training: a Training Manager, a Commercial Insurance specialist, a Personal Lines specialist, and a Technology lead. We’re looking to add an Employee Benefits specialist.
We continue to hire people with no prior experience in the insurance industry. We want to find talented people and train them on how we do things. We currently have seven people who started from scratch, and we believe we can offer a career path that is exciting, engaging, and rewarding.
Andy Denton, whom we call “the Chancellor” of Deland Gibson University, is conducting weekly classes – some for people new to insurance covering the basics and others for experienced staff. Once a week, there’s an hour-long class dedicated to professional development.
What emerging markets or sectors does Deland Gibson see as opportunities for expansion and growth?
This isn’t emerging per se, but we are seeing a steady flow of clients exploring and joining captives. From employee benefits to P&C, there are significant advantages when the fit is right. We’re also exploring the expansion from group captives into 831(b) structures to fund parametric insurance.
The captive space, particularly in health insurance, is allowing smaller entities to take advantage of the scale that larger companies have enjoyed for years. It’s more work and more challenging, but the results can be substantial.
We want to be educated on all aspects of the captive market so we can properly advise our clients. We don’t want to simply push group captives – we want to educate our larger commercial clients on the entire captive landscape, from single-parent captives to rent-a-captives to group captives to 831(b) structures. We explain the appropriate applications for each based on a client’s specific situation.
Even if a captive solution isn’t the right fit, which is often the case, 100% of the time, the client wants to know about these options. We lead with education and let clients make informed decisions, but we never want someone else to educate our clients on the insurance marketplace.
Where does the agency have offices, and how is its growth?
We operate five office locations in Wellesley, Duxbury, Dennis Port, Franklin, and Worcester, with a team of 90 employees. We anticipate finishing this year with just over $19 million in revenue, up from $6 million when the perpetuation began in.2015. This growth has come from strategic planning, acquisitions, and a renewed focus on organic sales development.
What recognitions has Deland Gibson received recently?
Deland, Gibson has retained its Best Practices status for 2024, marking the agency’s sixth time achieving this award. We’ve been recognized as a Top Insurance Employer for five consecutive years (2020-2024) by Insurance Business America.
We earned the Bronze Regional Award for the East region in 2023 and the Silver Regional Award in 2024 in Insurance Journal’s annual Best Agencies to Work For.
Deland, Gibson was among the first agencies to earn the Five Star Designation in 2000 and has continued to demonstrate excellence, renewing this designation multiple times, including in 2024.
We’ve also been recognized as one of the Largest Insurance Brokers in Massachusetts by the Boston Business Journal for the fourth consecutive year in 2024.
Looking at the regulatory landscape, how is Deland Gibson preparing for upcoming changes in insurance law and policy?
We’re in a good position as my brother, Ted is on the legislative committee for the MAIA. He won an award for his help pushing the Commonwealth to increase PD and Liability limits. He is involved locally and nationally and has his finger on the pulse of regulatory changes.
Finally, what message would you like to share with your clients and partners as you celebrate this 125th-anniversary milestone?
The lessons we’ve learned over 125 years continue to shape our future strategy. While the tools and technology have changed dramatically, the fundamentals of building trust, providing excellent service, and putting clients first remain as relevant today as they were in 1900.
We’re grateful to our clients who have trusted us with their insurance needs, in some cases for generations. And we’re thankful for our team members whose dedication and expertise make our success possible. As we look to the future, we remain committed to our founding principles while embracing innovation that allows us to better serve our clients in an evolving risk landscape.
Editor’s Note: This interview has been edited for clarity and length. Deland, Gibson is celebrating its 125th anniversary in 2025, making it one of the oldest independent agencies in Massachusetts. During its long history, the agency has grown from a one-person operation in Boston to a regional leader with five locations and over 85 employees.
