This February, we are excited to highlight Cyrus and Bobby Jaffery of Jaffery Insurance & Financial Services as our REInsurePro Agents of the Month! Based out of Omaha, Nebraska, this duo has built a flourishing agency that emphasizes the importance of fostering long-term client relationships while providing personalized insurance solutions. With a strong reputation in the Midwest real estate market, Jaffery Insurance continues to stand out for their expansive industry knowledge and unwavering commitment to their clients.
A Journey into Insurance
Cyrus entered the insurance world in 2013, introduced to the industry by his father-in-law. What started as a job soon turned into a passion as he realized the impact insurance can have on people’s lives. Over time, he evolved to focus on providing value to clients, emphasizing the importance of proper coverage over the lowest price. “Our vision has become how do we impact our clients in the most positive way possible and make sure they get the experience they deserve,” Cyrus says.
Bobby’s journey into the insurance industry began at a young age and was slightly unexpected. “I got dragged in here by Cyrus,” he jokes. At the time, Bobby was only 16 or 17, pushing carts at Walmart while envisioning a future centered on playing soccer in college. But an opportunity to help part-time with office tasks and cold calling sparked something in him.
“Over time, I realized I like building relationships and meeting new people,” he reflects. The insurance industry gave him a chance to grow not only professionally but also personally. “I was very shy, and I wouldn’t speak much. I’ve learned a lot of people skills and communication in this industry.”
A Trusted Insurance Partner
Specializing in real estate and mortgage referrals, Cyrus has spent the last 10 years building strong relationships with investors, realtors, and mortgage officers. Their ability to close deals efficiently has earned Jaffery Insurance a reputation as a reliable partner. “They love when you can close four or five deals out of 10 instead of just one or two,” Cyrus notes. “So, you build a lot of trust, which, in turn, translates into a better relationship, and they send you even more referrals.”
Maintaining strong relationships with realtors and mortgage officers isn’t their only concern. Most of all, their approach centers on doing what is best for the client, “Even if that means they would have to go to a different agency or captive channel,” Cyrus adds.
Meeting Market Challenges with Education
In a state prone to hailstorms, roof damage has become a significant concern for Nebraska property owners. For investors, understanding the full scope of insurance coverage has become even more critical as market dynamics evolve. Cyrus and Bobby have shifted the conversation from price-driven decisions to one focused on comprehensive coverage and long-term protection.
“The ball was in the investor’s court for a long time,” says Cyrus. “They would basically go get the cheapest [policy] possible.” And while that could have worked two or three years ago just to close a deal, the market doesn’t really allow for that anymore.
In Nebraska, where wind and hail are a common threat, cutting corners can have devastating consequences. Cyrus explains the risks of not insuring properly, especially in regions where severe weather events can cause substantial physical and financial damage. “If you go with the cheapest deal and a hailstorm comes through, you could potentially go bankrupt on that property,” he warns. “If you have to come up with $30,000 or $40,000 out of pocket, you’re not going to be very happy.”
“It’s educating [investors] so they can understand how insurance really works,” Bobby explains. “What are the coverages? What is Actual Cash Value? What would you have to pay out of pocket? Why should you go with a $10,000 deductible or a $5,000?” For Cyrus and Bobby, it’s not just about selling a policy. It’s about ensuring that their clients make informed decisions that protect their investments for years to come.
Connecting with Investors
Bobby recognizes the advantage given to agents who are quick to connect with current and potential clients. By staying active in an Omaha real estate Facebook group, he’s built a solid reputation and regularly receives referrals. When his name comes up, Bobby is sure to reach out within the hour, even if he can’t immediately start working on the quote. “I typically know what information I need to get things moving,” he explains.
Understanding that many investors dread a long, complicated insurance process, Bobby focuses on efficiency. “They think that it’s going to take so long, and they’ll have to be on the phone or come into an office and go through 100 pages of paper,” he says. By gathering as much information upfront as possible and using REInsurePro’s platform, Bobby is often able to send quotes within 24 hours.
His quick turnaround time has become a key selling point. While other agencies may take days or weeks to respond, Bobby’s clients appreciate how fast he works. “It’s just my process and how we do business, our communication is number one.”
Advice for Fellow Agents
“You don’t have to take every client,” Cyrus says. He recalls the excitement of receiving new leads as a young, independent agent but notes that sometimes there’s a reason a client is shopping around, whether their claims history isn’t ideal, or they just don’t fit within your company’s culture. “If someone has been denied by three or four other carriers, there’s often an issue that needs addressing,” he explains.
“If you’re confident in your product and your knowledge of insurance and the coverages for these investors, don’t be afraid to let your community know,” Bobby says. “The idea is to get your name out there. For us, we want to be the go-to insurance agency. Over time, others will spread the word. Just be a good person, always do the right thing, and success will follow.”
Congratulations again to Cyrus and Bobby Jaffery! We look forward to many more years of successful partnership.



