PropertyCasualty360 is proud to recognize the winners of the 2025 Agency of the Year Award: The Zebra and Gannon Associates Insurance. In this feature, we spotlight The Zebra. Click here to explore the winner’s profile for Gannon Associates Insurance.
The Zebra strives to meet its customers where they are, which is increasingly online, and they want to make buying insurance as painless as possible.
Katie Gold, VP of Insurance Sales says, “Consumers just want to be able to do [everything] online and they want it to be quick. If we can’t meet that need, we are missing the mark, in my opinion.”
Offering consumers a quick online experience means investing in their tech stack, including implementing advanced AI tools, but The Zebra understands that nothing equals a personal connection with their customers. To create personal connections, they invest heavily in their people, which delivers great dividends for the company and its customers. The Zebra’s emphasis on people has earned them the 2025 Agency of the Year honor.
A people-centric insurance comparison platform
People want to operate in a digital space, but this doesn’t mean that they want an impersonal, automated experience when buying insurance. The Zebra ensures that each customer gets an efficient and satisfying experience and obtains the insurance that is best for their situation.
As with other insurance comparison platforms, people can input their information at their leisure and receive multiple quotes when they visit The Zebra’s website. However, after that, The Zebra takes it to the next level.
Gold says, “Even though we’re working in a tech space, we do give people white glove service.”
Advisers go through the coverages, explain what they mean and confirm what customers will and won’t receive prior to purchasing a policy, all over the phone. Or if they prefer, customers can purchase their policies via text chat or even go to a carrier’s website to buy directly from them.
Gold says that their goal is to create more ways to interact digitally and to do it faster, which includes deploying AI tools to automate interactions and pre-qualify leads, as well as supporting advisers with selecting carriers to offer and facilitating document collection.
Equally critical is getting the right people in place to help customers, starting with recruitment.
Gold describes the people they are looking for: “We can teach insurance, but do you have the desire to help people day in and day out, interaction after interaction? You can’t teach that ability to want to work with people.”
She explains, “We’ve found that teachers and coaches have made excellent insurance salespeople because they have the ability to educate. Are they willing to take the time to explain how insurance works and really walk alongside someone in that journey? That’s the talent we’re looking for.”
An ongoing commitment to inclusion
Gold jokes, “I have our values memorized, and I make sure even in our check-ins that our leaders and advisors are leaning into them. One of our values is ‘inclusion.’”
The company has numerous initiatives that support different communities within the organization. This includes employee resource groups (ERGs) that foster belonging and open dialogue across shared identities, including:
- Shebras (for women)
- Dazzle (for LGBTQ+ team members)
- Affinity (for people of color, immigrants and first-generation Americans)
- Starz + Stripez (for veterans and their allies)
Gold points out that since these ERGs are tied to their values, they take them very seriously. She says, “As you get your mid-year and end-of-year performance reviews, we speak to, ‘Did you live into these values of execution, accountability, inclusion?’ We’re making sure that our initiatives are tied to our values.”
Inclusivity also benefits The Zebra by making them more able to serve diverse markets, including offering bilingual advisers.
Investing in their people yields big dividends
“When we talk about meeting the consumers where they’re at,” Gold says, “we also try to do the same for our employees.”
This means giving talented people the training they need to succeed.
Advisers at The Zebra are all licensed, but they also go through eight to ten weeks of training before they ever interact with customers, supplying them with the tools they need to properly serve customers. The Zebra follows a stair-step approach to training, starting employees out with auto insurance, then allowing them to train on home insurance as well.
To help their people get ready to move into leadership positions, they pair experienced advisers with others in a mentorship relationship. Advisers get the opportunity to practice leadership skills in weekly meetings to help them build skills and grow comfortable with leadership challenges. This allows them to promote most managers from within.
The Zebra works hard to ensure that everyone feels that they have a voice that matters, and that they are supported by their managers and their people or HR team.
“Employees know that they can go to their manager or they can come to me,” Gold says. “I definitely have an open-door policy. Everybody matters, everybody has a voice — we’re names, we’re not employee numbers.”
Being connected is a challenge for The Zebra, which is a remote-first workplace. However, they are dedicated to maintaining connections through approaches like Zoom happy hours and Slack channels full of jokes and fun.
Gold also points to the extensive benefits offered to employees as an investment in their team. The Zebra offers 20 weeks of fully paid parental leave, as well as a $5000 “baby bonus” per child, whether through birth or adoption. Recognizing that families come in many forms, The Zebra also offers a $300 “pet perk” to celebrate new furry additions. The Zebra not only offers bereavement leave, but it also offers pet bereavement leave. Employees also receive a $100 monthly wellness stipend to support their physical, emotional and mental well-being. These forward-thinking benefits cement The Zebra’s people-first culture and create an environment where agents thrive.
These investments have paid off. In 2024, the turnover rate at The Zebra was just 2%. This helps them offer continuity of great service to their customers and controls the cost of recruitment and new employee training.
The Zebra shows that online interactions and remote work don’t have to make insurance impersonal. By putting people first, they remind us that the essence of insurance is people taking care of people, in good times and bad.
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