BTU #192 - 22 Years in the Marines to Military Programs @ Combined Insurance (Bob Wiedower)

My family had moved 17 times in 22 years after I got out, I let them decide where we were going to live. That’s what we did and we decided on San Antonio.
— Bob Wiedower

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Bob Wiedower is the Vice President, Sales Development and Military Programs at Combined Insurance, a Chubb Company. Combined Insurance is a leading provider of supplemental accident, health and life insurance products in North America, Europe and Asia Pacific. Combined Insurance Company of America is committed to helping people find the coverage they need at a price they can afford. Bob served as an Officer in the Marine Corps for over 22 years, and worked as an Executive Director at USAA for 15 years prior to joining Combined Insurance.

Why Listen: 
Bob made his transition to the civilian workforce after 22 years of military service with the US Marine Corps. His current employer, Combined Insurance, actively recruits military Veterans and actually guarantees military Veterans and their spouses an interview. We cover a lot of ground in this episode, including why Veterans should consider sales, larger companies, and companies that target military Veterans.

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Selected Resources: 

Transcript & Time Stamps:


Joining me today from Chicago is Bob Wiedower. Bob is the Vice President of Sales and Military Programs at Combined Insurance. Combined Insurance is a leading provider of accident and health insurance products in North America. Bob was in the Marine Corps for 22 years and worked as an executive at USAA for 15 years prior to joining Combined Insurance.


What does Combined Insurance do?

Combined Insurance provides supplemental insurance. Supplemental insurance is the coverage that takes over and above major medical policies. Let’s say you break your leg and can’t work, you have a major medical policy that is going to cover the hospital visit and medical treatments. What it doesn’t pay for though is the money that you’re losing because you can’t work and can’t earn a living. So supplemental insurance pays you for that time that you’re sick or injured.

Another example that happens frequently is if you have a child that gets hurt or injured. The medical insurance policy is going to cover medical interventions for the child but isn’t going to cover the time you have to take off to care for your child.


What do you do as Vice President of Sales and Military Programs?

I have several different responsibilities here. A large portion of them have to do with increasing our sales. Part of my responsibility is also running our military programs. We have a Military Program Manager that focuses 100% of his time on hiring more veterans at our company and supporting veterans that work at our company. We also do community giving programs that benefit military veterans.


That’s great. It sounds like Combined Insurance is extremely supportive of the military community.

In my role, I meet a lot of people from other organizations. There are a lot of other companies that claim to be veteran friendly organizations but when you dig below the surface they really don’t have the programming to support veterans. For us, it’s more than surface level and we really believe that veterans make our organization better.


What are some of the opportunities available at Combined Insurance?

We’re an insurance company so we have all the different careers that are typical to the insurance sector such as underwriters, actuaries, and analysts. But the largest bulk of our workforce is sales agents. I feel that veterans are particularly suited for this role. Our sales agents need to be very ethical and do what’s best for the customer. They need to have a service mentality and be able to overcome obstacles. And they need to be results and goal driven. That’s why we feel like veterans are a great fit in this position. Our sales process is structured but is also flexible. That coincides nicely with most veterans personalities as well because they are used to have guidance but also needing to figure out for themselves how to best get the job done.  


I agree with you. I think sometimes veterans are hesitant about the idea of a sales role but sales can actually be a great fit. 

Often people that think that they could not do sales are thinking about trying to convince someone to buy something that they don’t need or want. But it’s different here at Combined Insurance. We’re selling a product that people actually need and it’s a very solid and reliable product. You’re analyzing what someone actually needs and shaping an insurance package that can really benefit them.


What is your day-to-day like?

My job responsibilities are broad and that’s one of the things I really love about my job. Today is Monday so try to start the week of fast sales-wise. We get the staff together and talk about everything that’s going on. We also talk about upcoming events that will have an impact on the sales team. From time to time, we have veteran hiring events. We usually do one of those per week. That’s an all-day event either here in Chicago or somewhere else in the country. I also deal with our sales agents directly if there facing any issues. I also work with our managers to discuss various strategies. We have small offices across the country so I also am involved in figuring out what new offices we should open or what offices we should expand.


Do you see any common mistakes veterans make during the civilian job application process?

The most common mistakes that I see is a resume filled with military jargon. I would also like to say that Combined Insurance guarantees an interview for any military member or their spouse. We can’t guarantee a job but definitely an interview.


If someone is interested in applying to Combined Insurance, what can they expect from the application process?

On our website, we have an employment page where you can express your interest. You can also contact me and I can link you up with someone at the office nearest to you. There are really three steps to the application process. The first step is to meet up with the Sales Manager in your area so that you can start to get a sense for what the job entails. The next step is that we will send you out with an agent to do a full day of sales to make sure that it’s something that you can do and want to do. The final step is to meet up with the sales manager again and discuss the sales day. If both you and the sales manager think it’s a good fit, we fly you out to Chicago for a week of training and start integrating you into the company.


Where does Combined Insurance sell its products?

All across the continental United States. The other thing I wanted to mention is that our jobs are portable. So if you start out in Florida and your family moves to Pennsylvania, you can take the job with you. This is valuable for military spouses that are looking for flexibility and portability in a job position. Because of this we were recognized by the Department of Defense as a company that fits the needs of military spouses.


Can you describe a little bit more about the sales positions at Combined Insurance?

They are paid by commission only. But you are provided everything you need to become successful. We have many people who have been here for more than 20 years. On the sales side, we have two lines that you can go. We have a career sales agent path. You can progress up to very senior levels doing this. We also have a leadership track. After you prove yourself to be a successful sales agent, you progress up to leading sales agents and teams. So you can basically design your own career here.

Our company has been around for almost 100 years. Our sales process has evolved but it is basically the same as when the company was started. If you follow our sales process the way it was designed, you will succeed. If you have the drive and the desire to get ahead, there is real possibility here.


You were in the Marines for over 20 years. What was your first job search in the civilian sector like?

I went through a transition assistance program just like everyone does. I remember that the prevailing thought in that program was that you needed to network and find a job and go wherever that job was. But that wasn’t the way I wanted to do it. My family had moved 17 times in 22 years so I was going to let them decide where we were going to live. That’s what we did and we decided on San Antonio. So then I needed to find a job in San Antonio. USAA was the organization in that area that really stood out to me because of their military friendly brand.


Have there been any particular resources that have helped you in your civilian career?

One of the things that I wish I had when I transitioned was a personal 1-on-1 coach to help me through that transition. The transition assistance programs are so broad that they don’t always help you as an individual. But the organization, American Corporate Partners, is an amazing group that will match you up with a mentor that will help you as you work through the transition process.


Is there anything else you’d like to share with our listeners?

There’s one thing that we’ve kind of alluded to but didn’t come right out and say. When you’re transitioning and seeking a new career, you should really take a look at organizations that are known to be military friendly. Military Times comes out with a list each year of organizations that offer various support and programs for veterans. There are big and small companies that are known to be great places for veterans.


That’s great. One thing that I’ve heard from many veterans is that they miss the sense of community they had in the military. Organizations that make an effort to be great places for veterans are likely places with a very strong community in general.


That’s exactly right.


Thanks so much for being on the show today, Bob.