November 9,2026

This week’s Monday Morning with Denise celebrates election wins by BIGiOK members before highlighting upcoming education, the Agency Compensation Study and the Young Agents’ Christmas party. Denise and Jerry then welcome Helen Kasper, COO of Dillingham Insurance and a BIGiOK board member, for a conversation about her 35-plus-year insurance career, transition from the carrier side to independent agency leadership, and the relationships that brought her to Oklahoma and Dillingham. Helen shares why she chose to serve on the BIGiOK board, the value of networking with fellow agents and competitors, and the challenges agencies face from rapid technology change, rising client expectations and the ongoing competition for talent. She also discusses developing future leaders, getting more involved in the association and the independent agent’s role as a trusted advisor. The episode wraps up with a fast-paced lightning round covering mentors, books, sports, coffee and more.


Happy Monday. Wow. It is.

I think it’s really fall. You know, yes. It’s raining and which again, I know we talked about this.

So it’s November 9th, 2026. I know we talked about this every time we come on here about plants and such, cause you know, that’s our secondary, everything’s blooming. I already put my lawnmower up and I got to get my lawnmower out for crying out loud people.

Come on. I guess that means go dormant. I guess that means my husband has to get his lawnmower out.

Our lily pads in our Koi pond are still blooming. Oh, those are beautiful. I know they’re so pretty.

Beautiful. What is that? Lake Liberty. Oh, if you ever get a chance to go to Lake Liberty during the summertime, go all the way down to the end.

There’s just like the whole end is lily pads and flowers and it’s just gorgeous. I’ve never been there. They’re in our pond.

I love them. They make me happy. You have go very far.

Yeah. How was your weekend? Uh, uneventful. Oh, mine too.

I loved it. That’s true. It was so great.

Curl up and honestly read a book and I didn’t go anywhere. It was so fantastic. I’m still digging on my 1960s sprinkler system that those two beautiful trees in my front yard have grown all over those pipes.

But anyway, that’s all about the story. We’ll skip that. Well, the good thing about living in a house built in 1899 is they didn’t put in sprinkler systems that they called it rain back then.

So but John put in sprinkler systems, didn’t he? Yes. I’m joking. I’m joking.

The only thing left on our house are the studs from 1899. We survived elections last week. Oh yes, we did.

I was so tired and, but all the good news, we had two BIGiOK members win insurance commissioner and a BIGiOK member is going to Congress. How cool is this?  so exciting. I said in all the years that I’ve done this or even served on the board, we’ve never had, I mean, we’ve had BIGiOK members that have served in the state legislature, but this is our first time to have one in Congress and an insurance commissioner.

So I felt like I was juggling BIGiOK members everywhere politically. And it’s been really fun because they’re excited. They understand independent agents.

And so many times that’s their, that’s their background. And so I am thrilled for Mark Tedford going to Congress for congressional district one in Tulsa, taking Kevin Hearn’s place and Kevin will move up to senator. So we have a new senator.

And I think I heard a word on the street that since Kevin Hearn gets to take the office of the senator that was appointed, there’s a chance that Mark will get to move up and take his office immediately after the elections are over. I heard that as well. Oh, you did? OK.

Yeah. Which I think is really cool. And then Bob Sullivan, BIGiOK member.

So he’s been a BIGiOK member for a long time, won his election for insurance commissioner. So our insurance department is getting ready to have a BIGiOK leader. So I will definitely be seeing his praises.

So we’re very excited about that. He’s been really excited and has a lot of really neat ideas coming up. So we’ll get to work with him a lot.

Yeah. So the only thing that I can say about politics is everything will be OK. It will.

It will. It will be OK. It’s called the ebb and flow.

We call it democracy. Yes, it is. You heard you’ve heard my little speech from being in Germany and hearing the difference of East and West Berlin.

So democracy is the ebb and flow. So I’m never I’m never quickly discouraged about it. I’m very excited.

So BIGiOK members that’s awesome for us. That’s right. And you know what? I will just say this.

How important is it that we have people stepping up at really the highlight of their careers to represent their people, which I love. So congratulations to both of them. So very exciting.

Agreed. Well, today, I know we have a couple of we have a couple of things coming up. We have some education.

I’m not going to go into a lot of depth. Free Friday ethics is on the 20th, November 23. We’ve started the agency compensation.

It’s not a report. What is it? Study.

Yeah. So we started back up. So if you did the first round, do the second round.

If you didn’t do the first round, jump in and start it because it’s important information. Get that information. Yeah.

Yeah. December 3rd. The young agents, the young agents are always having a party.

Do you really? This one looks really good, though. I know. I agree.

So they have to be a young agent for that day. Maybe we’ll do that. Yeah.

They’re having a Christmas party. Are they doing that here? No. Jones Assembly.

Jones Assembly. I wish they’d do it here. Well, but they’re having they’re having a costume dress up type party of your favorite Christmas movie.

Oh, my gosh. And what would I go as? You would go as Santa Claus. Simple.

I already sent you the picture of the St. Nicholas Catholic Church that you look just like. I don’t think I could curl them that much. Oh, man.

It looks so cool, though. I look pretty good. I agree.

Okay. Exciting today. We have a special guest.

Yes, we do. I’m very excited about this. So we have you probably have a big introduction written out for me, but can I just go a little off script? I just gave you notes.

That’s true. I know that. I know you, but I wanted to give you notes.

Yeah. Well, my good friend, Helen Casper, is actually going to be our guest today. She’s with Dillingham Insurance, who I, of course, just adore Jed and Chad and everything they’re doing up in Enid.

But one of the best and smartest things they did was hire Helen Casper for their agency. And she has an incredible background in the insurance industry. When she first moved down here, Sarah had gotten to know her.

And since then, I am lucky enough to call her not only friend, mentor. We have lunch together. She has an incredible amount of knowledge.

She is a woman of integrity. She’s a leader in her field. She has a background corporately in the insurance industry.

And so to get to work with Dillingham is an incredible opportunity for her. And we’ve been thrilled. The best part about it, not only does Dillingham get her, but she actually serves on our board of directors.

So we get her, too. So very excited. So please welcome on to our little stage, Helen Casper.

Yeah, let’s put her on there. Thank you. What an amazing welcome and intro.

Thank you, my friend. Delighted to be here. You know what I didn’t put on there because this is so impressive.

So I went completely off script, but she is a graduate of Notre Dame College and Harvard Business School. You’re so smart. She’s smart.

Thank you. Jerry, let’s just say she’s the smartest one in the room right now. She’s the smartest one in the building, I would say.

I would definitely say that. There are so many bright minds in our industry, please. I’m surrounded by them every day, every day.

You know what, to that point, which I love that you always say that, it really does take a team. We know we can’t do it all on our own. And so we’re surrounded by incredibly smart people.

And in an industry, I’m sure over your career, because I know for my career, we’ve seen so many changes that we have to figure out how to just move and change with it. Agreed. And think of all the change that we’ve navigated just within the past year.

I think the pace of change just within the past year is greater than I’ve seen. And I’ve been in the industry a long time. Tell us a little bit about your background in the industry.

You’re an Oklahoma transplant, but I still feel like you now are an Oklahoman. I’m an Okie. I love calling Oklahoma home.

And I do have a different background. My entire career has been on the carrier side, more than 35 years working for publicly traded insurance companies throughout the East Coast with most of that time spent in Chicago. And I did everything from starting as an underwriter.

I moved into sales and strategy and ran our national client group. And it just gave me just such a great perspective of the independent agency plan. I thought I knew the independent agency model because that’s what I lived the whole time.

I was on the carrier side. And boy, it’s so different when you’re actually on this side of the table, let me tell you. But what a gift it’s been.

So I moved down to Oklahoma nine years ago. I was still working for one of the large publicly traded insurance companies. So I felt like I lived here, but I wasn’t really connected to the business or the insurance community because I was traveling both coasts.

And I had the opportunity to join Dillingham four years ago. We are 100 years old, we’re four generations privately held. It has been an unbelievable high for me to step into the COO role.

And I touch everything from operations to sales to strategy to what I love most, which is developing the next generation of leaders and then obviously working so hard to delight our clients. So my boys still live up in Chicago. My daughter’s down here in Oklahoma.

And yes, despite all that time in Chicago, I am proud to call Oklahoma home. Well, you’re even getting a little of an Oklahoma accent kind of Chicago, right? So I slowed down, I slowed down when I when I met everybody at Dillingham, I said, you guys, truly, I probably run at 50 percent of the pace that I had in Chicago. And no one could believe that.

Oh, yeah, because you read that. So a question I get asked a lot.

So I want to ask you the same thing, because if you look at the let’s call it the little trail that you’ve led throughout your whole career, people, you know, a lot of times ask like, how did you make your plan to get from here to there? And I always like to say. I never had the plan to be sitting here, that was not the ultimate end game, but through a series of being at the right place at the right time, I ended up there. So tell us tell me a little bit about did you have this big plan? Because I don’t think you came here planning to work for an agency either.

When I when I moved to Oklahoma, I definitely didn’t have the plan to work for the agency. And, you know, again, I was still working for a national carrier and I had the opportunity. I was at a women’s networking event and I still remember it like it was yesterday in Oklahoma City.

And I heard someone in line talking about insurance. And I turned around and I said, who’s talking about insurance? I’m an insurance. And I just remember seeing this very confident, polished young woman and say, I’m an insurance.

And I said, who do you work for? And she said so proudly, Dillingham. And I said, why don’t I know them? And she said, I don’t know, but you should. Well, that moved into a series of email phone calls and then an introduction to Dillingham’s CEO.

And Denise, I’m going to tell you, like within the first 15 minutes of sitting down with Jason Wooliford, I just knew there was something there. Like it was the most authentic, honest conversation I think I’ve ever had with a business leader in our industry. And what was supposed to be a 45 minute coffee chat in Q4, which is the busiest season for benefits, ended up being three and a half hours.

And we ended with lunch. And what I didn’t realize is he was getting up and grabbing his phone and texting his admin to move his next appointment, move his next appointment. And we left lunch.

And I remember I got up to shake his hand and he just gave me a hug. And I just got in my car. And I remember thinking, what just happened? And that moved then into a conversation with Jed for a half a day where I learned the history that is uniquely Dillingham.

And I would leave you with this. I remember after a series of conversations, Jed said, what would be your dream job? Like if we brought you into Dillingham, where do you think you could have an impact? And remember, my whole background had been on the carrier side. And I said I would come in and I would help you create a different kind of experience and relationship with your carrier partners.

Let me come in and do that for you. And it’s just been a high from day one. So, yeah, that’s it was the most unlikeliest of places.

But, you know, isn’t that amazing that it started at this women’s networking event with a very polished woman who made that introduction? And here I am. So, you know, and I think to that point so many times, it’s not it’s not a purposeful, strategic plan to get where we get. Sometimes it’s just being at the right place at the right time, listening to the right people or the right people listening to us.

I never want to take that for granted. I agree. You know, and so because sometimes I think, oh, I have this goal.

But as you and I both know, God may lead us in a whole different direction and places where we need to be. So that was yeah, that was super exciting. So in the middle of Dillingham and we know that Dillingham’s a big supporter of Big I, which we love.

I served with Jed on the board of directors way back in the day. And so then whenever you and I met and of course, we just hit it off immediately. And so the problem I have is that whenever you and I go to lunch, I probably talk your ear off.

You’re like, oh, it works both ways. It’s so great. So tell me.

So when we first started talking about you serving on the board, tell me why you wanted to do that. Tell me why you thought that was important. Well, I’ll tell you, I saw the board as an opportunity for me to really get connected, not just in the business community in Oklahoma City, but the insurance community, because, again, even though I lived here, I had only been here a few years and I was still working on the corporate side.

So I was traveling the coast. I wasn’t really dialed in to the business and the insurance community. And I saw the Big I as an opportunity to really immerse myself in the industry in a whole different way here.

And I also felt that there was an opportunity for me to take everything that I had learned throughout my career and also bring some value to the board, the board and what we do at the Big I, OK, is so relevant to our industry. It’s relevant to our leaders at the Capitol. And I just saw an opportunity to give back to an industry that, for me, has given me so much.

And it has absolutely proven out to do that. And then some I have just it’s been a real high for me. So being engaged and being on the board that gives you an opportunity to probably see more than what even the normal member would be.

So as a board member, as you look through everything that we go through, what do you think is one of the most important things about a Big I membership? Oh, it’s hard for me to pick one. I really I mean, there are so many benefits. But I think of my very first event at the Big I. And I would tell you, I think the biggest benefit is the relationships and the connections.

I mean, you talk about an opportunity to expand your network and circle of influence across so many different events throughout the year. And I don’t care whether it’s on the carrier side, whether it is connecting with other independent agents and brokers and wholesalers that are that are navigating through the same challenges that we are. And it has been a tremendous opportunity for me to build deeper relationships, to learn more about how other leaders and industry professionals are navigating through the change that is this industry.

It would be the relationships, Denise. I think of the people that I met at my very first conference that first year I was here. Those are some relationships that are still my greatest today.

So the relationships. Don’t you think the misnomer of that is people say, why would I make friends with my competitors? You know, yes, I do. I do.

A board is a perfect example of that. I compete every day with those guys. And, you know, I will tell you to a person, I know I could pick up the phone right now and say, I have a business challenge.

Can I get 20 minutes? And every one of them would say absolutely like what’s going on. And I’ve connected with them. I’ve shared ideas.

They have shared ideas back. We’ve problem solved together on what we’re navigating through in our own agencies. And, you know, we may be competitors, but we’re all dealing with the same challenges.

And what a high to be able to, whether it’s our board members or whether it’s the members and relationships that we have in the association that allow us to work together and do what we are also passionate about in this industry. So, well, that’s part of our purpose of our board. We want to make our agents better.

So tell me what you think one of the challenges is today for independent agents. We’re a lot. We exactly like I would tell you, there are so many things coming at the independent agents today.

Think about it. There are market challenges. It we talk about soft market, hard market.

I think every market is a challenge. I think of what’s happening in the pace of technology. There is more advancement in technology happening right now than I have I have seen throughout my career.

And it’s not slowing down. I think of the challenge that our clients bring to us. The clients that we are serving, they have very high expectations.

And there’s also an element of this Amazon effect of like, I want it now. I want an answer now. And then let’s be honest, there is a war for talent, like attracting and developing and retaining top talent is something that we are that we’re all navigating through.

I think it presents, though, even with all of those challenges, the opportunity for our independent agents to be even more nimble and elevate what they’re doing as professionals and as a firm so that we can adapt and we can move forward and we continue to grow our firms with the talent that’s really going to be the future for our industry. So, yeah, so it’s a lot. Yeah.

And I love to tell younger people, get into the industry now because it’s an industry that doesn’t die because we always are going to need insurance. That’s what makes it successful. And so, you know, whenever I look at membership, I look at agency growth, hire young ones.

And then how do we keep them in there? Obviously, you know, we have a lot of programs that kind of engage them to keep them there. But holy cow, as we look back on our many years, I can’t imagine what we have combined our many years of being in this industry. It’s been so good to us.

And so I think it’s been like it’s a great experience. So when we have members that come in, like, what would you encourage? I mean, you talked a little bit about networking and conference, but what would you encourage someone to do to become more involved? Oh, step up like don’t wait to be asked. I think that is such a great question because those are the same things that I tell the leaders in our organization, like don’t wait to be asked to step in and do something.

You have bright mind, bright ideas. You see an opportunity to change something, make it better. You want to create a deeper connection.

Raise your hand, get involved. I love our website for the BIGiOK.

We’ve got all of our board members there is an opportunity if you want to get to know what we’re doing and get to know us and make broader connections, reach out to us. And I think every venue presents a chance to get to know someone and say, hey, listen, I’d love to be able to do more.

Denise, I remember when I met you at my very first conference and it was up in Branson and I remember telling you that Jed actually grabbed me and said, hey, there’s someone I want you to meet. And I introduced myself and I said, listen, I have just joined Dillingham. I’m new to the independent agency force, but I’m not a stranger to the industry.

I absolutely want to do more. And so that would be the advice that I would give any professional. And anyone that walks up to me and says that I say, OK, and here we go.

Yeah, right. Yes, exactly. Get ready.

Get ready. Get ready. We do not mess around.

Well, you know, I love being in the independent agent world because, you know, the benefit of that is that, you know, we’re not limited to one company, like we are getting to see the entire industry as a whole. So tell me what makes that community as independent agents special. Yeah.

You know, it is it’s the people, you know, we compete every day. And yet there is just so much value that we are able to bring to our customers. Yes, there is a choice.

But I think about the power of the insurance is still complicated. And, you know, the independent agents really elevating to that trusted advisor to help our clients like navigate through something that is so critical to their business, to their personal life. To break things down in a way that they can understand.

And, you know, that’s what clients want. They want someone that’s going to care enough to ask the questions that are really important to them. They want to make sure that, you know, that we as independent agents are not giving them more than they need.

So they’re overpaying for something, but not just short changing it and focusing on price and then leaving them exposed for something that they’ve worked so hard to build. And so by really understanding that story that is unique as every client we touch, I think that’s the power of the independent agent. We have choices, right? We can absolutely put the right program together that is unique and special as each one of our clients.

Yeah. Well, first of all, thank you for serving on our board, because as I say all the time, it’s a volunteer position. You do this out of the kindness of your heart.

I also like it because it’s a great way to give back to our industry. And to our association. So thank you for all you’ve done.

Thank you for being my friend. Thank you for the inspiration that you give to all of us. And so I think now Jerry is taking it from here.

And he has a lightning round. Oh, fantastic. All right.

Oh, thank you, Denise. Not only for our friendship, but for your leadership. And what you’ve done for the board and for the insurance industry.

If there’s any doubt in our mind about the relevance and the impact, just take a trip to the Capitol with you. And honestly, that’s where we see even greater value. So, my friend, thank you.

My pleasure. It’s it takes a team for sure. Yes.

OK, Jerry, you ready? Miss Timer, bring it on. I’m in charge of the timer. I always forget this part.

Oh, I don’t know what’s ahead. One minute. Pepper me with one minute.

You know, usually we do 30 seconds, but I got some really loaded. We’ve got good. Oh, my.

OK, I’m ready. I’m OK. Here we go.

Ready? Go. OK. What makes you smile? Oh, my kids and my granddaughter.

Can’t you see I’m already smiling? Yeah, I love it. Mentor or role model. You want me to name the mentor or role model? One.

Ray Sprague. He was the president of the Hartford. Big role model and mentor for me.

Very good. Dress shoes or sneakers? Oh, dress shoes. Wearing them now.

Book or movie? Book. Big reader. Favorite sports team.

Oh, the Thunder. There you go. And this from the Chicago Cubs, ladies.

Oh, and all the Chicago sports teams. That’s right. Dog or cat? Oh, dog.

Sweet or salty. Favorite season? Fall. Office or remote? Office.

Email or phone call? Phone call. Early bird or night owl? Oh, I’m an early bird, early bird. There’s your timer.

I have to throw this last one in. OK. Coffee or tea? Coffee all day long.

Thank you. Oh, you’re welcome. Nothing’s better than meeting than meeting Helen in a coffee shop.

That’s right. That’s right. It makes our heart.

That’s the only place to meet, isn’t it? That’s right. And there’s so many great ones in our town. That’s right.

Well, Helen, thank you for being here. Thank you for your service. Thank you for what you’ve done.

And I’m looking forward to the next step and what we’re all doing together. Thank you. Delighted to be here today.

Thank you guys. Thanks. Well, that was good.

That was so awesome. Isn’t she great? She’s just so great. We’re so lucky to have her on our board.

Yep. I know. OK, with that, have an awesome Monday and have an awesome week.

You as well. Happy fall. Happy fall.

All right. We’ll see you. Bye.