When Dena Kaplan began her work for the Insurance Journal magazine in 1984, she was a 24-year-old Washington state native who had fled south to southern California to escape “freezing in Seattle.”
At the office headquarters in Pasadena, Calif., printing presses ran noisily in the large open space of a the company’s warehouse and offices sat along one wall.
Two offices to be exact. One office was for the head of the company, Mark Wells. The other office was for the 7 employees, including Dena, and it was sparse. Metal desk after metal desk served as their workspace, and paper was taped to the windows for shades as a single lightbulb lit the room.
The insurance industry was a totally new field to her, but she had experience in sales and was looking for something new.
At this point, the magazine was only in California, and Dena was the first non-family member to be hired on to sell anything with the company. Her job entailed selling ad space within the magazine, and in the late 80s she was given the title of Associate Publisher of the magazine — a title she still holds to this day.
“I’m sure [Wells] regrets that now,” she says. “I think we thought people would take me more seriously if I had this exalted title. So we thought it’d be good if I could introduce myself as the Associate publisher. And then you can’t really take that away,” Dena laughs now, sitting at her desk in the clean San Diego headquarters of the now-national publication.
She sits tall — and she is tall, taller than the rest of the women in the office by a good several inches —and her light brown hair is curled and swept away from her face. She holds herself with poise, clearly comfortable with herself, confident in who she is and what she’s there to do. She leans back in her chair at her desk comfortably as she remembers her early days with the company.
The insurance industry is like a large fraternity, where conferences feel like summer camp, and the relationships are much like summer camp friendships.
The language for the industry may as well be a foreign language only for the initiated — acronyms fly around as if they are a normally understood part of the English language. Terms like “inland marine coverage” may have nothing to do with the water, or the land, depending on the policy.
With help from Wells and others Dena started to learn and assimilate into the industry, and she dealt with an interesting mix of client experiences along the way.
She still remembers the client from her first sales meeting for the magazine: “He was this thin, overly tan, older guy,” she says, making a scrunched-up facial expression to show her displeasure.
“We sat down for lunch and he ordered a Jack Daniels neat. Twice!” she emphasizes with her eyes widening. “It was like the movies. I just remember thinking ‘ok…’” she drags out the last word, emphasizing her uncertainty from so many years ago.
As the company grew and Dena’s reputation grew, other publications began trying to woo her away. But she stayed. The company has been good to her, and she has been good for it.
Her tenacity is largely to credit when it comes to how Dena has operated in this sales business so well for so long.
“I wanted to show you this, too,” Dena says, swiveling her chair toward her computer as she pulls up a browser page with the Insurance Journal homepage open.
“EXCLUSIVE SNEAK PEAK: HANK HALDEMAN…” is spread in bold letters across the page.
H.R. Haldeman was the Secretary of State during the Nixon Watergate scandal, and served time in prison for involvement.
She turns back and begins to tell the story: “One of my friends in the industry is Hank Haldeman. And I met Hank in the early 90s. The first time I met him, I said, ’Haldeman, that’s not a very common name. Are you related to H.R.?’
“‘And he said, ‘That’s my dad,’” Dena continues.
Soon, though, Dena started to hear this edict in the industry: Never talk to Hank about his dad. It was mantra repeated for years.
In the fall of 2014, Haldeman was promoted to the President of NAPSLO — one of those many important national insurance associations that goes only by it’s acronym.
Spurred on by a couple of others in the industry, Dena got the idea then that perhaps the magazine could do a spread on Haldeman — not just focusing on his promotion in NAPSLO, but also talking about his dad, and how he had influenced Haldeman’s leadership role.
She pitched it to Wells, and his response was as if he was reading off the unwritten script: “No. We can’t do that. Never ask about Hank’s dad.”
“Why not? Why does everybody say that?” Dena challenged him.
“I don’t know. It’s just how it is. Don’t ask about his dad,” Wells said firmly, ending the discussion.
But Dena has a hard time letting something lie when it doesn’t add up.
She has an intuition for knowing when to chase something, when to question, when to push harder, and when, if she were in someone’s shoes, she’d want someone to tell her what people were saying about her.
Which is why, one day when she was talking with Hank Haldeman in the fall of 2014, she felt like she had an open door, and decided to ask him what she’d been told never to ask.
“I have a personal question. I just want to know, why does everyone say to not ask about your dad? Is that a really sensitive subject for you?”
“What?” Haldeman asked, confused.
“Well, everyone knows that your dad, as a topic for discussion, is off limits,” she said.
“I don’t know what you’re talking about,” he said surprised. “I’ve never heard that before. I don’t mind if people ask about my dad.”
So Dena jumped at the opportunity. She asked if he would be willing to do an interview with the Insurance Journal.
“I told him, I’m not talking about like, a little bit about your dad and the rest on NAPSLO. I want you to talk about your dad, growing up a Haldeman, Nixon, the whole deal.”
And he agreed.
In March of this year, the Insurance Journal ran an exclusive interview with Hank Haldeman, son of H.R. Haldeman, Secretary of State to Nixon during the Watergate scandal.
Not a little bit on H.R. and the rest about insurance, but a huge spread about Hank Haldeman’s personal story and his take on his dad’s role, and the relationship between his dad and President Nixon. It even included never-before-seen historic photos from the Haldeman family.
When Dena called the managing editor for the Insurance Journal to ask if he wanted to come do the interview with Haldeman, or whether Dena should do it herself, the editor jumped at the opportunity.
That’s who Dena is. She pushes the boundaries she’s told not to push. She chases the leads she has a feeling about. And when it’s time to hand it over to someone else, who she thinks may do the rest of the job better, she does so gracefully and willingly.
You won’t find her name anywhere on the several articles the Insurance Journal ran on Hank Haldeman, but they wouldn’t have happened without her asking the question everyone spent a decade telling her not to ask.
“I love my job,” Dena says, smiling a content smile.
Her bottom-line and her accomplishments are a testament to her balance between humility and tenacity.
She doesn’t need to be the one with her name on the front page. But she will be the one to chase down the long shot like she’s got nothing to lose.
And sometimes, in those gamble pursuits, she wins big.
If you’d like to support the Story Project (to cover travel expenses, costs of Stories for those who can’t afford it, etc.) you can do so below or contact me at firstname.lastname@example.org if you’d like to send a check. Thank you for your support!
To Donate to Stories By Jo: The Story Project click below