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Philip Charles-Pierre of Semsee: “Flex your style”

“There is a big difference between being a great leader versus an individual contributor.” As a leader, I always keep this in mind that the ultimate goal isn’t my personal success and glory but making sure the company succeeds — and in turn each person that works at Semsee. Being a great leader at an organization is […]

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“There is a big difference between being a great leader versus an individual contributor.” As a leader, I always keep this in mind that the ultimate goal isn’t my personal success and glory but making sure the company succeeds — and in turn each person that works at Semsee. Being a great leader at an organization is about helping your team and colleagues grow and shine, which also requires you to know when to let go and when to stand your ground.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Philip Charles-Pierre, CEO of Semsee, an automated small commercial quoting solution for insurance agents.

Philip has a long history of building companies that create digital solutions to help small and mid-sized businesses. Before entering the insurance industry as CEO of Semsee, Philip worked in the real estate sector as SVP of Distribution for Smarter Agent, a mobile search and discovery tool used by leading real estate franchises such as CENTURY 21, Sotheby’s, Keller Williams, Berkshire Hathaway, and ERA. Earlier in his career, he helped build the multi-billion dollar Travelocity Partner Network, developing and managing travel sites for American Express.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

If someone told me 20 years ago that I would not only be working in insurance but building technology for that industry, I probably would have laughed and said you must be thinking of another Philip because early on, I had different plans. I majored in international studies and philosophy as an undergrad at University of North Carolina at Chapel Hill, thinking I was going to go to law school. However, I changed direction and instead obtained my Masters in Philosophy of Religion at Harvard. Following school, I started a career on Wall Street. And before moving to Semsee, I led technology startups in travel, publishing and the real estate sectors.

I’ve had a variety of experience but there is a general theme to all of the companies I’ve led. They all create products that enable people to do their jobs better and ultimately enjoy what they do. I like creating tools that help others serve their customers better. In fact, the b2b2c space is most inspiring to me — more than creating a product for the general masses that has millions and millions of users and being the cool kid at the dinner parties. I find it fascinating to take industries that are old school using legacy processes and create technology that moves them forward.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Disruptors usually eliminate the middlemen. But Semsee is turning that idea on its head, equipping insurance agents (in this case, the middlemen) with digital technology that enables them to deliver the same fast seamless experience to their small business customers that startups and disruptive solutions tout in direct-to-consumer models.

We are changing the way insurance agents have traditionally serviced their customers. This itself is a tremendous disruption because most agents have been using the same processes for decades. To get a commercial quote, most agents must go to one carrier portal, enter the client information and get one quote. Then they go to the next one, enter the same details and get the next quote. They do this several times until they have a few options to show their customer. Though tedious they were comfortable with this workflow.

But now we are entering the industry showing agents a different way. It requires them to learn a slightly new process, but it’s worth it for them because they become more efficient. We give them the ability to submit one form and return multiple quotes in a matter of minutes, a significant change from the hours it took them the old way.

We are also disrupting the relationship between carriers and agents by adding value to the services the agent provides. With Semsee, agents can compare prices and policy coverages. This helps them better advise their clients. For example, while Policy A might have the lowest monthly premium, Policy B may be only slightly more expensive but offer a lot more protection. This will ultimately force more transparency when it comes to policies. Agents will better communicate what coverage is the best value for their clients, which will require carriers to evolve with clearer explanations of what’s covered and what’s not. As we’re able to deliver more transparency in business insurance, it also helps the business owners understand what they’re buying and what it covers. This will help alleviate situations like many are facing today where many businesses are sadly realizing too late that their business interruption policies do not cover losses that result from a pandemic. And the carriers win too as they will have better insights on how their products perform in the marketplace by being on Semsee.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Early on at Semsee, I was too concerned about outsider input on our success. This was very early stage before we really started running full force. I remember working with a reporter at an industry media outlet who was quick to dismiss what we were trying to do, saying that it had been tried before and failed. At first we were quite concerned and thought “Oh no! This will be the first piece people will see when they google Semsee.”

But then we turned this into our rallying cry and it fueled us. I actually ended up meeting the reporter at an event, reminded them of the story and in a jokingly manner said, “I couldn’t wait to prove you wrong.”

Ultimately it didn’t get in our way or prevent agents from trying our solution and carriers from partnering with us.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Our investors, D.E. Shaw Group and Nephila Holdings, have definitely helped guide us and I am not just saying this to flatter our funders. We don’t have traditional investors. The structure they set up has been incredible at allowing us to learn and grow effectively and efficiently. They are also very data driven and logical which helped me become a better leader using more analytics versus intuition to make decisions.

Brad and Eric Blumberg, founders of Smarter Agent, a real estate product that was eventually sold to Keller Williams, were also great mentors to me. This was the first opportunity I had to really help run a growing and successful startup. They taught me to leave no stone unturned and to be persistent. But most importantly they taught me to build a value-based business; build a product that actually adds value rather than simply being something cool. Users should love the product to a point where they can’t live without it. They were true entrepreneurs always looking to build a business on their terms.

We also wouldn’t be here without the carriers that were with us from the very beginning, when Semsee was just an idea on a PowerPoint. They believed in what we were trying to do and they worked with us to build this. There were also a number of agencies who provided their assistance, including allowing me to shadow their workers for a day so I could truly learn about their workflows to answering my calls to bend their ears on a weekly basis. They understood how important our success would be for them and they worked with us because they knew we were ultimately trying to help their businesses.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I think disruption the way we are doing it is positive because we are not changing the essence of the relationship between the agent, the client and carrier. We are making those connections faster, easier, and more efficient which helps everyone have a better overall experience.

I think the disruptors which are less positive are those who try to change things just so they can capitalize on the digital transformation buzz. We see this a lot in the insurance industry. For example, an insurance disruptor will launch a product touting that customers can buy their insurance policies online without having to talk with an agent. People get excited and are eager to try it. But after they go to the site, answer all of the questions they find out that they actually do have to talk with an agent in the end in order for the policy to be finalized. This is bad disruption because the product really hasn’t done anything different. Often bad disruptors are trying to change the essence of the business–which often fails–instead of making the essence of the business better.

That is why Semsee is focused on making the small commercial quoting and buying process better rather than changing it completely.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

“There is a big difference between being a great leader versus an individual contributor.” As a leader, I always keep this in mind that the ultimate goal isn’t my personal success and glory but making sure the company succeeds — and in turn each person that works at Semsee. Being a great leader at an organization is about helping your team and colleagues grow and shine, which also requires you to know when to let go and when to stand your ground.

“You want people who are customers to be loyal beyond reason.” This piece of advice was given to me when I worked at Starwood Hotels from the CMO at the time. And it has been my North Star when leading companies that create products for people. We want our customers to be loyal beyond reason — in love with our solution and unable to live without it.

“Flex your style.” There are no cookie cutter people and there are no cookie cutter situations. You cannot treat everything the same. You have to adapt your style to respond to the situation, such as adjusting how you conduct a meeting because a potential investor doesn’t do PowerPoints. But just because you are changing your approach doesn’t mean you need to lose what makes you special and unique.

We are sure you aren’t done. How are you going to shake things up next?

All technology companies know the product is never perfect and we will continue to make our Semsee solution better by adding more insurance lines and carriers. We also think of our platform not only as a solution helping agencies quote but also as a connection point of sale between the agents and carriers. We think there are other ways we can help agents and carriers connect with each other and add value to the insurance transaction, such as sharing data. We want to leverage Semsee to enable agents and carriers to really interact with each other in new ways they have not done before.

We also want to continue to make the agent workflow simpler. We don’t just want to be another screen an agent has to go to in order to complete one client request. We want agents to use one screen to handle all their clients’ needs which requires partnering with other insurtechs, including agency management systems and customer relationship management tools. We are working toward building these relationships and enabling these integrations.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

How I Built This, NPR’s podcast where entrepreneurs and innovators share the stories behind the movements they built, is something that I have listened to and always find fascinating. I love to hear about how others have built their companies and the trials, tribulations — and most importantly–luck that it requires.

I know firsthand that part of the secret recipe for any startup’s success is luck. At Semsee, I know we work hard and we are smart but we also have had some very good luck. But I am also finding out, when things keep going your way while you might at first attribute it all to luck, consistent positive outcomes mean that you might really be onto something special.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

There are two quotes that I consistently live by. The first is, “Just because you can, doesn’t mean you should.” It is a lesson about restraint and having focus. I think about this a lot as I continue to strive to ensure that Semsee creates a product that provides value to agents.

The other quote is what I tell my daughter every day before she goes off to pre-kindergarten and that I think is a good motto for everyone, “Be your best self.”

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Insurance has a lot of power to do good — both within the industry itself and for society as a whole. As an industry, insurance has acknowledged that it needs to improve its diversity and inclusion efforts. And organizations of all sizes are taking this on, making their operations representative of the communities they serve.

The industry can play a larger part in improving society, driving social change for the positive just by choosing what they will require in terms of safety in order to provide insurance. For example, this could work with police departments. If a carrier takes into account the number of lawsuits a department has or practices they use that could result in lawsuits in determining whether or not to insure a town or city, this could require them to reevaluate their practices.

And insurance is beginning to take important steps. Insurance leaders are trying to develop processes to make sure the new technologies insurers are using don’t have unintentional racial biases in them so that everyone can get the fair coverage they deserve.

So this is an exciting time to be in insurance and I want to take part and help the industry achieve some good.

How can our readers follow you online?

They can follow me on LinkedIn.

This was very inspiring. Thank you so much for joining us!

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