Are you just getting started in Insurance Content Creation? Do you secretly worry you may be doing it wrong and it might come back to bite you? Enlisting a Digital Mentor can go a long way in helping you learn the ropes — which is why I am posting 7 Interviews with “Insurance Leaders in the Digital Space” each Monday (Jun 16 – July 28).


We continue our series with a Insurance Thought Leader who has:

  • Has his own agency
  • Serves as a consultant to several other local agents
  • Has co-founded a Digital Marketing Academy for Insurance Professional
  • And has a wealth of experience with all things Digital Marketing


Insurance Thought Leader, Jason Cass



It’s always helpful to talk with individuals who not only have grown their own business through Digital Marketing, but who have also come alongside other local agents to do the same.. In this conversation with Jason Cass we will do just that. I had 7 Questions, we talked about learning from the old guys, persistence, and what our kids on iPads can reveal to us about what’s coming.


It was a lot of fun.


Insurance and the Emerging Digital Space


I have looked forward to picking the brain of Jason Cass for quite some time. When I saw his/her Agency was launching a new blog, I knew I’d found my opportunity.


Jason Cass’s recent writing further confirms what I have known for a long time….that Jason is an invaluable guide in the sometimes maddening digital landscape of Insurance marketing.


Jason Cass is a persisent practioner urging Insurance Agents everywhere to; keep trying new things, listen all the time, and don’t forget to learn from the old guys/gals.


In my interview with Jason, he mentions a mentor who built on the universal principals of insurance and his own unique journey into the digital insurance marketing space. Each story Jason shares is an example of iterative learning, creativity, and how the digital marketing works in the insurance space. I also took this opportunity to ask Jason some things I’ve really been wanting to ask. I hope you enjoy our conversation and that it gives you a solid start or a shot in the arm as you continue to maximize the digital space with your Insurance Agency.


Interview Highlights


We talk about:

  • How he was inspired to train local agents online through observing the Khan Academy (Free Online Education for Everyone)
  • Jason’s unorthodox 15-min work break routine
  • What he learns watching his kids digital behavior
  • His new initiative the DIMA (Digital Insurance Marketing Academy)


Memorable Quotes


  • “Be prepared to fail 250 out of 300 times.”
  • “I wrote a $120,000 commercial policy for a client who found me online.”
  • “If you wake up at a decent hour and do nothing but talk to people about insurance all day, you will be successful.”
  •  “I spend $3,400 annually on Facebook to generate $130,000 through contests and engagement.”
  • “I have a foot in two-worlds and that has served my business well”



The Interview

Duke Revard: Some of our readers aren’t as familiar with your background. So perhaps you could share some shaping experiences that have contributed to you unique perspective in the Insurance Space?


Jason Cass: I am product of the Big “I”. My father-in-Law told me to get into Insurance. I said no thanks. Then 9/11 happened and my home supplies business dried up. So I took his advice and started learning P&C Insurance. My first mentor, Mike Beard (Agency Owner) took me in and taught me everything I know. After my 3-4 month, he showed me the Big I young agents magazine. I got involved and learned a lot from other young agents. I was born in 1978 and therefore have the distinction of being right the middle of Gen-X and Gen-Y…I can related to the older guys and I can relate to the younger guys. I have learned the universal, unchanging laws of insurance from the older generation. I have learned what it means to be social and effective online from the younger generation. I have a foot in two worlds and that has served my business well.



Duke Revard: When and how did you find your stride in the digital insurance space? In other words, when did things start to click, where you realized “I think I can be really good at this.” 


Jason Cass: I realized that my agency owner wouldn’t let go of outbound strategies that were failing. He wouldn’t listen. So I went out on his own. I really just fell into the digital marketing space. I starting posting stuff in Facebook and created YouTube videos. The first year didn’t make any money, but I started to get more engagement. By year two (2011) I started picking up stream, and started converting traffic/engagement into dollars. I tried 300 things and 250 things failed. The reason you think I am a “Though Leader” is because I kept trying. There is no track for this thing you have to figure this out for your business and your unique style. I write a hockey player who found me on Facebook. I wrote a $120,000 commercial policy who found me online. I spend $3,400 annually on Facebook to generate $130,000 through contests and engagement. These online strategies generate real business with real people. But it took me time to learn how to do digital marketing well. But the first principal people need to know is…what works in the real world, works online. Agents in the world who are salespeople and those who are proactive are the most successful. Those who succeed online are also those who are the most proactive. Sell Proactively Online. Learn to move relationships from Online to Offline. I pick up the phone and call people who are showing interest. Too many agents are posting a few things on a blog and then sitting back saying “Digital Marketing doesn’t work because no one is calling.” Wrong. Digital Marketing doesn’t work like that.







Duke Revard:  Tell us a little bit about how you have persevered in Digital Marketing? How have you overcome the desire to quit when your efforts haven’t materialized like you had hoped?


Jason Cass: I have a drive to succeed and provide for my family. My kids need soccer cleats so I need to get out there and sell. I needed to build my agency. I like to help people and that internal drive has led me to do what I need to do. I talk a big game and need to walk a big game. I know that I can help people, I am vision-driven. I want to create the agency of the future. I am working towards helping other agencies stage for the future of insurance. I just keep trying, failing, learning and trying again. It’s that simple.



Duke Revard:  What disciplines do you have in place to ensure you are customer-centric; that you have the pulse on what your potential clients and clients really believe and care about?


Jason Cass: I ask people questions then I shut up and I listen. Seriously, this is so simple but I am able to differentiate myself from others with this simple practice. I am a learner. I cross-pollinate by listening to teenagers and listening to others in various businesses. I attempt to adapt and innovate for the future. But this begins and ends with listening. I tried 300 things that have failed, but then listening led me to the 50 things that worked.



Duke Revard: You have recently launched The Digital Insurance Marketing Academy (DIMA).


Jason Cass: DIMA is online Academy that exists to train Insurance agents in Digital Marketing. We allow you to learn whatever you want to learn at your own pace with a personal assistant to answer your questions along the way. It is personalized. Allowing you to personalize your instruction. Everything online is becoming personalized. Education is heading in this direction. It’s like the Khan Academy. Kids are learning various subjects online in the most democratic, personalized way imaginable. He started created videos to teach his nephew. And his nephew’s friends started benefiting from the videos. He has created 5,000 videos. You can back it up if you don’t get it the first time. The subject matter is specifically around Digital Insurance Marketing. I watch my kids on their iPads and they aren’t going to buy insurance in the future by calling up a local agent. I promise you that. We are working to get agents ready for what is coming. The learning curve is steep, but much more accessible through personalized training at my own pace. So far 275 agents have signed on and we are getting rave reviews. We are on the consulting side as well several agents are asking us to handle it for them. It is a growing community of practitioners.



Duke Revard: What are some other things you do to remain sane throughout the daily grind?


Jason Cass: I take PlayStation on breaks to clear my head. Call of Duty is my game of choice. Others have smoke breaks…I have “Call of Duty” breaks. Same thing. It works for me. I don’t play longer than 15 minutes but it’s enough to achieve mental rest so I can regroup for another run at the day’s business.




Duke Revard: What is your advice to young agents who are entering into digital insurance marketing?


Jason Cass: Learn from the Old Folks. It so, so important to listen and understand those who have come before us. The 50-60 yr. old Agents can tell you how to be successful. You just have to take that information and translate it into modern day mediums. I joined the Elks Club in my town and I learned a lot. Learn to adapt. Don’t be afraid to try something that others aren’t doing. Be prepared to fail 250 out of 300 times. Keeping iterating. Keep trying new things. If you wake up at a decent hour and do nothing but talk to people about insurance all day, you will be successful. Stay on message. Stay focused.



Duke Revard: Thanks for taking time out to participlate in the Insurance Thought Leader blog series. I appreciate that. 


Jason Cass: No problem. Thank you. 


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