Olivia Borsje x The Future of Fandom

Ladder VP of Marketing Olivia Borsje on Ensuring Your Customers Are Set For Life

by The Future of Fandom

Listen now on your favorite podcast platforms!

Ensuring Your Customers Are Set For Life

Today on the Future of Fandom, get a life, or at least some insurance for it. On this week’s episode, we’re talking to Ladder’s VP of Marketing, Olivia Borsje.

 Ladder is a flexible insurance startup that combines the power of innovative technology and world-class financial expertise to make it easy for anyone to access life insurance. Olivia has been with Ladder for over three years and brings with her a wealth of marketing knowledge and expertise.

Connect with Olivia Borsje on LinkedIn: https://www.linkedin.com/in/olivia-borsje/ 

Read more about Ladder: https://www.ladderlife.com/

Full episode here:


Adam Conner (00:09):

Today on The Future of Fandom, get a life, or at least some insurance for it. My name’s Adam Conner, I’m your host, and on this episode we learn about some terms of digital engagement as a startup with Ladder and their VP of marketing, Olivia Borsje. Ladder lets you get a life insurance policy in as little as five minutes, which is obviously a great pull, but it got me thinking.

If you can get your customer to make a lifelong decision in such little time, how do you build community from minute six onwards? Olivia does a great job explaining that, as well as, how to set yourself apart as a startup via a little shock value, and all together, what a best in class digital insurance experience of the future looks like. So let’s stake a claim of our own and predict the future with Ladder and Olivia Borsje.

Adam Conner (01:06):

Hey Olivia, how are you?

Olivia Borsje (01:06):

I’m doing great. Sunny California today.

Adam Conner (01:10):

Oh, you know what? It’s been more frequent than not here to not be sunny. I’m on the East Coast, on the other side and we have just been back. I feel like every six hours it snows, so jealous already, but I’m hoping to get there quickly and I’m glad you’re here with us today to talk about, well, the sunny side of insurance, let’s say-

Olivia Borsje (01:28):


Adam Conner (01:28):

… and how you are building a community that sticks, and this will be a first for our podcast to talk about the insurance base specifically, and it carries with it maybe a few stereotypes that you can help me break apart.

Olivia Borsje (01:43):


Adam Conner (01:44):

But first, just for those who don’t know, obviously people know what insurance is and life insurance is, but why don’t you give us your spin on what Ladder is, and how it differentiates, and we’ll go from there.

Olivia Borsje (01:54):

Sounds good. So Ladder was created in response to a problem, which is the fact that over a hundred million underinsured and uninsured Americans know that they need to buy life insurance. 46% of them will tell you that they’ll suffer really harsh financial troubles within just six months of losing a primary breadwinner and yet those people still don’t have the coverage that they need. And that’s due to the fact that the barriers to buying life insurance have been so high.

You know, if you think about you and I in this day and age, we can pretty much buy anything we want directly on our phone, but when it comes to life insurance, it’s still very common for it to take weeks, six to eight weeks is what we typically see. It involves a ton of middlemen, it involves paperwork and involves medicals, so it’s just really fallen behind modern consumer expectations.

“You know, you’re talking about busting some myths, another common barrier is the cost of life insurance. Millennials in particular will overestimate the cost of life insurance by almost 10X. Whereas simple term life insurance for a young, healthy person, depending on level of coverage, can just be one to $2 a day.”

— Olivia Borsje (2:49)

Olivia Borsje (03:09):

And then the last point is almost this paralysis if you will, life insurance at its core is just this very simple promise for a company to step in if the worst happens, to take care of your family, but there’s been a proliferation of just very complex offerings, bundled with investment type of products, and so consumers don’t even really know where to start. They don’t know if they need term life, or whole life, or any kind of other life, they don’t know how much coverage they should get, they’re worried about being stuck with more coverage than they need, they’re worried about hidden fees.

Olivia Borsje (03:43):

And so there’s kind of this paralysis and all these three factors, right? The time it takes, how expensive people think it takes, how confusing it is, all of these three factors just contribute to this huge coverage gap that we see in the US today, that’s amounting to 16 trillion with a T. So what Ladder did, was invest in technology that would allow us to underwrite people in real time digitally. And this underwriting innovation is really what underpins everything else.

We still have upwards of 60% of employees today that are focused on underwriting in one way or the other, and it’s this ability to underwrite people in real time that powers our consumer experience. You know, the fact that you can get, if you’re approved with Ladder, you can get life insurance, it’s just five minutes on your phone from start to finish.

Olivia Borsje (04:36):

It’s also what underpins our ability to give you our best pricing adjusted for the risk. And it’s really… You know risk is really something that we need to be wise about if we want to make a lasting promise to our consumers. And so we have to remember that Insurtech is part tech, but part insurance, and insurance is about again, being smart on the risks. So that’s a little bit about Ladder. We’ve been growing very, very fast. We’ve been investing in a ton of fun stuff on the product and brand side, so we can keep talking about it if you want, but I’ll pause there.

Adam Conner (05:09):

Yeah. I really want to know, I mean the biggest thing that stuck out to me, which I want to jump on, is the real time aspect of the business which is highly valuable for the end consumer-

Olivia Borsje (05:21):


Adam Conner (05:22): …

but I hear five minutes. Is that right? So you’re telling me, somebody wants to get a life insurance policy, and I’m dumbing it down for, well, people like me. So if I want to get a life insurance policy and I’m like, well, I need to do it fast. I can get it done in five minutes with you guys. Huh?

Olivia Borsje (05:34):

That was, yeah. That five minutes was our fastest application ever from-

Adam Conner (05:38):


Olivia Borsje (05:39):

… you landing on our website, filling out our application, you getting an instant offer from us saying, yes, and walking away. We actually have consumer testimonials that tell us, I got my life insurance policy while waiting in line at the grocery store, or in the security line at the airport. Those-

Adam Conner (05:57):

How about that.

Olivia Borsje (05:57):

… are true customer stories that we hear every day.

Adam Conner (06:00):

Well, and you know, to me, I have seen this as a trend, but not in insurance-

Olivia Borsje (06:07):


Adam Conner (06:08):

… it’s been in other areas, the financial sector, where a big selling point has been, set this thing up quickly.

Olivia Borsje (06:16):


Adam Conner (06:16):

I’ve seen it in banking mostly. And-

Olivia Borsje (06:18):


Adam Conner (06:18):

… that speed has been the message with which others have built an entire brand identity, you know-

Olivia Borsje (06:25):


Adam Conner (06:25):

… get this done quickly and boom, how easy is that? Yeah, sure, you can get it in line at the grocery store. And it’s so popular, and I don’t mean to pander to the rest of the industry, but why doesn’t everybody do that?

Olivia Borsje (06:41):

Because it’s very difficult to do, and that’s what can be deceiving about life insurance, and that’s what’s been at times almost controversial for us as far as the strategy that we’ve taken to focus on underwriting first, is because it doesn’t bear fruit until you’ve invested in it for a little bit.

So it doesn’t look… It’s not obvious on the surface what you’re actually working on, but figuring out how to find alternate data sources, to accurately underwrite people to the standards of underwriting that have existed in the industry for a very long time today, so have machines replicates what humans and decades of data have done, is a very difficult problem and you get better at it over time, as you have more data, as you learn, as you do your post issue audits, and so we’ve been incredibly disciplined in investing in that.

Olivia Borsje (07:33):

And again, once you get that right, then you can confidently make an offer to a consumer, at a great price, in five minutes, and you can feel confident about your risk, but that is, it’s a lot of hard work. It’s not just about propping a pretty website and then throwing people back into an old school application, which has happened elsewhere.

Adam Conner (07:55):

Yeah, I was… I’m guessing that it takes a lot more than a polished front end to figure out-.

Olivia Borsje (08:00):


Adam Conner (08:00):

… how to do that well, and [in scale 00:08:02] there are a bunch of interesting business growth questions I could ask here, but I want to focus instead on, well, the word that we focus on for this show, which mostly starts with the Fandom, because-

Olivia Borsje (08:13):


Adam Conner (08:14):

… of course there are many ways in which organizations and insurance, or otherwise, seek to build passionate consumers and fans. If the process is so quick, I get it done in five minutes, or let’s say that I’m a slow guy and I get it done in 10, all right?

Adam Conner (08:30):

I go through that process and I wring my hands together and say, “Okay, great, it’s done check,” because this is a big life check mark, isn’t it? I mean, at least it’s what-

Olivia Borsje (08:37):


Adam Conner (08:38):

… I’ve been told. You got to have life insurance, okay. I come through Ladder, boom, I get it done in five, 10 minutes. How easy is that? But my biggest question here, is that assuming that you are building a community of people who are, well, fans of Ladder, how do you build community beyond that, when the-

Olivia Borsje (08:53):


Adam Conner (08:54):

… whole plug is to say, well, we’re going to get it done quick, and then you got it, what comes next?

‘Yeah. It’s such a great question. So yeah, life insurance traditionally has been kind of this one and done purchase, or this eight week and done purchase if you look at the traditional way of getting it, and indeed we really want to help you get through that painful part really fast, and actually make the painful part not painful. We have really high NPSs, it’s a pretty delightful experience, but when you think about it, then we’re entering into a relationship with the consumer that’s going to last 10, 20, 30 years.”

— Olivia Borsje (8:38)

Olivia Borsje (09:28):

So there’s an incredible opportunity for life insurance brands to expand on that relationship and add value to the consumer and vice versa. And it’s not just an opportunity, it’s also very legitimate if you think about our category, we just ensured your life, so we have a lot of credibility and a lot of aligned incentives in helping you live your longest, healthiest, best life.

Olivia Borsje (10:01):

So you can imagine how broad the types of innovations and cross sales opportunities might be in this category. So at Ladder, we thought about that two vectors, one being product, one being brand, of course the two are very intricately linked. On the product side, I think a quintessential example is our Laddering feature. So, we give users the ability to modify their coverage over time.

So if you imagine you’re sending off your kids to college, or you’re paying off your mortgage, well, you don’t need as much life insurance as you used to, and so we allow you to just decrease that coverage and decrease your premiums and save money in the same proportion. That’s particularly popular when we work with partners.

So for example, a [inaudible 00:10:50] which has Ladder pretty deeply integrated, not only will they be able to offer life insurance right from that platform, but as they continue to give you financial advice and help you manage your entire financial life, you can manage your life insurance dynamically right there, so decrease it or apply for more.

Olivia Borsje (11:06):

So that’s kind of one examples of product innovation that build on that one and done relationship. There are other things that I can’t quite talk about, but that you can imagine around health and general wellness and kind of the integrations that could add on to our product today.

“On the brand side, I really think of this category less as a financial category, but more as a lifestyle one, because of what I just said, the fact that we’re ensuring your life and that there’s so much heart and emotion in this category that we can engage with consumers beyond just talking about money and their finances.”

 — Olivia Borsje (11:28)


Olivia Borsje (11:51):

And so if you look at how we’ve developed the Ladder brand, the type of content that we put out there, our look and feel, it looks a lot closer to a lifestyle or almost fashion brand than it would your traditional kind of financial institution, which is also something that we’ve seen built trust with consumers and in some cases, especially younger generations, can be a little weary of the old established financial company and they’re really looking for brands that get them, that they can relate to, that look like all the other products that they consume.

And that’s really the direction we’re trying to take our brand than just a life insurance category in general.

Adam Conner (12:30):

It brings up a number of interesting dynamic levers to one’s life and some of which we can talk and some of which we won’t, but yes, it becomes easier to me when I think about, well, how should staying healthy reward you in other ways? And we’ve talked about this-

Olivia Borsje (12:44):


Adam Conner (12:44):

… on the podcast and in other measures, mostly within the world of credit and rewards with retail partners and things like that, obviously-

Olivia Borsje (12:51):


Adam Conner (12:52):

… life insurance have other implications, particularly in the B2B World. But again, we’re here mostly to talk about the Fandom and here’s another aspect of that, which I find to be prevalent in insurance more than anywhere else, and that is, there are a ton, a ton, and you mostly see it on a television of ad campaigns which seek to use humor, in some cases to use shock, to use gimmicks to hook a consumer, for example, well, I might not know everything that Progressive does, to throw a name out there, but God, don’t I know their characters from their TV commercials.

Adam Conner (13:33):

And in your case, you took the tact of using a bit of shock value. So I want to focus on this part next and listeners, you may be familiar with this, but we’ll describe it a little more. You had a campaign to market yourself that was called, The So Good Campaign, and So Good dot dot dot, I’ll let you finish the sentence, and created quite a bit of shock about you, I would say, in the marketing for a life insurance product, and I’d like to use that lens to get your perspective on how to use shock value in marketing to build awareness, no matter who you are, because that’s always the foundation of Fandom.

Olivia Borsje (14:09):

Yeah. Yeah. Thanks for bringing up this campaign. We’ve been very proud of it. It’s been working really nicely for us. So I’ll just take a big step back and talk about really the opportunity behind a campaign, which is the fact that there is no, beloved consumer, life insurance brand today. You know, if you go to a party today and you ask someone outside of the industry, what’s your favorite life insurance brand, they’ll look at you with a blank stare because the question doesn’t even make sense.

And again, we’ve talked about that this is a category that’s about the most selfless expression of love that you could possibly have. It’s about your family, it’s about your home, it’s about who you are as a person. So it’s crazy to me that in a world where we can love our shoes, or our thermostat, with a brand like Nest for example, we have at best, indifference for life insurance companies.

Olivia Borsje (15:00):

So we see an incredible opportunity as Ladder, to establish yourself as the beloved life insurance brand. On the other hand of that, we also recognize that building brand, is very expensive, and takes a lot of time. You mentioned Progressive, Progressive spends north of two billion dollars on ads every year. So as a startup, we know that if we want to pierce through, if we want to compete, we can’t compete with media dollars and sheer power of repetition, we have to compete with outstanding creative that’s really going to grab people’s attention.

So I’ll talk about the campaign a little more. So it is born out of a consumer insight, which is the fact that almost one in two couples that get life insurance will joke about taking each other out for the life insurance money. So we’ve designed those spots that is essentially about this dad that keeps coming home to his house that has been booby trapped by the entire family, including the dog, even the dog’s on it.

“You find out at the end that it’s because he has great life insurance with Ladder and the tagline is, Life insurance so good, they’re gonna want you dead. So, that’s kind of the shock value that you’re referring to, but what really works for me about this campaign is number one, just the memorability.

The memorability that comes through the humor, and the memorability that comes through having this inside joke that people make, be played out externally. You kind of… Good humor plays on that tension and that release, right, when that tagline kind of drops. The second thing is that it carries a true consumer promise, right? It’s not humor for the sake of humor, it’s telling you there’s something new there. It’s telling you this is not any kind of old life insurance, this is life insurance, so good, your family might come after you.”

— Olivia Borsje (16:05)

Olivia Borsje (16:54):

And then third, as I mentioned, it is grounded in a consumer insight. I think great ads resonate when there’s a real truth at their core and this is a truth, this is a joke that people actually make. So we loved the idea, I also love the fact that it had legs creatively. Right? You can imagine a whole series of these spots and we launched it at the beginning of last year.

As I mentioned before, brand advertising and awareness building is a different tactic than the traditional direct acquisition performance marketing, which we’re very used to at startups. And so it’s measured on a different time horizon with different metrics, but that said, I can already say that it’s been quite successful for us and it’s been resonating really well with our target market. So I’m looking forward to hopefully continue to build on it.

Adam Conner (17:46):

The first time I saw that ad, I was like, hang on, what, let me, what was that? And so I had to go back and rewind it again because I thought there’s no way that somebody would put out an ad like that, but that is the shock value, isn’t it? And I have found for the newest generation of consumers, no matter what they’re consuming, that this sort of, shall we say memeable message-

Olivia Borsje (18:06):


Adam Conner (18:06):

… is like jet fuel. I mean, it is some of the highest octane optics you could put out as a business and it sticks. I mean, who else does this really well outside of insurance? I mean, there are some tech players that do it, for sure. I think of like, well, somebody close to where I am just down the street, do a lingo, they use their mascot, an owl, to be just generally rambunctious on social media, completely separate from what the business actually does. And they have some of the highest social engagement out there. And so it-

Olivia Borsje (18:40):


Adam Conner (18:40):

… makes me wonder, as a startup, what are some things that startups need to be thinking about when doing brand building, when this sort of shock value marketing or nonsense meme messaging… Yeah, it sometimes makes for better messaging than anything relating to the offering. I’m curious because it’s not just that your startup will quickly grow, but you’re also within an industry, which is well, well grounded and has been for hundreds of years, you got to break through somehow, so I’m-

Olivia Borsje (19:14):


Adam Conner (19:14):

… just curious to get your thoughts on that.

Olivia Borsje (19:16):

Yeah, of course, it is a hard balance to strike. I think traditionally, if you look at the traditional life insurance or just general insurance industry, it’s very, very heavy brand, right? They’re really capitalized on that and they’ve started to catch up to performance marketing. And then if you look at startups, we’re very comfortable with performance marketing and we’re just kind of catching up on brand and figuring out how to invest there.

So we’re kind of coming at it from two opposite angles. You know, it’s in our DNA, as to companies, to just love clear cut metrics that we can measure really quickly. So usually that’s going to be all your direct response stuff. You’re creative is going to be very oriented towards your offering. You’re going to be able to calculate your return on ad spend by being kind of smart with all sorts of attributions, to just know, hey, I spent this kind of money, I got this much cash back, I’m right side up on my [inaudible 00:20:10] economics, feeling great.

Olivia Borsje (20:12):

And there’s a point where you need to, you realize that you’re not just building for short term growth and harvesting the current demand that you have, but you want to build, actually in our case with Ladder, a transformational lasting company. And in order to do that, your marketing is going to have to operate at two levels.

You’re going to have to continue to do the direct response stuff really well, but you’re going to have to start investing in brand, because brand will lift all boats. You know, when your direct response program starts to diminish in returns, brand is really what’s going to come to support your conversion rates, it’s going to come to support your organic growth, it’s going to come to help get more partners in the door and candidates in the door.

Olivia Borsje (20:58):

So it’s really a multiplying function and a differentiating moat, that I think startups need to figure out how to invest in, not too early, but as soon as they start thinking about the future and they have the financial backbone to do it at a level that’s going to pierce through. And that’s definitely not going to be a progressive level kind of investment, but if you’re smart about your creative, about your spend, you can really pack a punch with it.

The one thing I will say though, just to disambiguate is, I see brand advertising and just brand dots as two very different things, right? Brand is everything, brand is who you are, brand is your promise, brand is your product, brand it’s your look and feel. That is something that companies should invest in, in day one, really understanding clearly who they are, and who they’re for, and how to show up in the world. And I think once you’ve passed kind of that level, then brand advertising is just a different tactic that you layer onto your marketing mix.

Adam Conner (22:03):

Yeah. I really appreciate the deep dive there just because well, listening to this show right now is probably the next startup, not necessarily insurance but you know, in somewhere and I would be, and not that I’m a startup founder, but I would be really tempted by certain things and probably would misconstrue those, the nuances of brand as you’ve just said. So that was really nice, thanks for bringing that up and-

Olivia Borsje (22:30):


Adam Conner (22:30):

… given your expertise there, obviously, and as the person captaining the ship at Ladder, I’d like to know without diving into that which you cannot speak about, I want to peer into the future with you a little bit, because I predict that others in this industry will say, hey, we like what Ladder’s doing with regard to that speed to entry-

Olivia Borsje (22:52):


Adam Conner (22:53):

… and that digital experience Ladder leads in now, may become so popular that others might try to pick up the reins and take it themselves.

Adam Conner (23:03):

So it becomes then about an ideal overall experience. And maybe that relates to what the brand is overall, but peering into the future with you, I’d love to speculate a little bit and get your thoughts on what the ideal future insurance digital experience ecosystem looks like, because I’m still wondering, what really does come after that initial process to keep somebody engaged over time? Is it content? Is it layering of things?

And I think that’s a really great dynamic thing to lever, like I said at the beginning, but I’m curious what else you think in the digital landscape will keep folks in touch and conscious of their position with Ladder or any insurance player?

“I think there’s one thing to be said about insurance and the fact that there’s something about the, said it and forget it, that’s also nice. It’s something that you want to make sure you have, you do quickly, and then it’s just relief, such a huge burden from your shoulders, that you’re happy not to kind of think about it anymore, but we’ve had customers say, whenever I see my charge at the end of the month, fund my card, I know I’m covered, I feel good, I know my family’s protected if something happens to me.”

— Olivia Borsje (23:44)

Olivia Borsje (24:14):

And so sometimes just that is truly enough, honestly, to keep a consumer engaged and staying with you throughout the duration of their term. There’s also high switching costs, right, to leaving and to getting another type of life insurance company.

Olivia Borsje (24:31):

So there’s a natural high retention and kind of lock in for life insurance. So the question to us is more about, how do you add value on top of that, both to attract consumers to Ladder compared to other competitive offerings, and then to add more value to them and add more value to Ladder in exchange throughout this decade or 30 year long relationship?

So I do think some of that is going to come from all types of possible innovations and integrations in the world of physical wellness, in the world of emotional wellness, in the world of financial wellness. Right? So you can really imagine all the things that will help you live longer and healthier that we can add on to kind of our Ladder platform. You know, you could go as far as saying, hey, research has proven that having a dog helps you live longer.

Olivia Borsje (25:25):

It can go that far, right? We could do something with pets in the future. Right? Nothing we’re doing right now, I’m really being illustrative. And on top of kind of these wellness types of things, you’ve mentioned earlier, abilities to reward you over time for healthy or safe behavior.

So how many steps you’re taking every day, or are you driving safely, or are you paying your mortgage on time? Are you… So there’s a whole ecosystem of data as well that can be used just to give consumers some money back, which is always something that everybody appreciates.

Olivia Borsje (26:04):

So I can really see innovations in those two rounds and then the last [mode 00:26:09] around all of that, as we discussed, is just brand, right, is feeling like this is a great brand that gets me, that made me laugh, that engages with me. And then not only do I want to stay with that company, but I want to refer it to my friends.

You know, it’s a very word of mouth type of product. So really those three layers of a great product with built in with retention of value add around it, and a strong brand to cement it, is where we see our long term success.

Adam Conner (26:36):

I appreciate the outlook and I want to round out with one, fill in the blank, which brings us home with regard to the way that fans are made outside of the sports’ realm, which is this, and I’d just love to get your take. Finish this sentence and I’ll finish it with a blank. I know that my customer has turned into a genuine fan when they blank.

Olivia Borsje (26:59):

When they shout out from the rooftop that they love you and everybody else should get your product.

Adam Conner (27:06):

Well, can’t we all hope that happens with our businesses and I hope it does with yours as well, and maybe to get to the rooftop, they will use a ladder. But Olivia, thank you so much for joining us here, it was great to get your perspective, thanks for giving us all life.

Olivia Borsje (27:22):

Thank you so much for having me, it was a pleasure.

Adam Conner (27:28):

Thanks again to Olivia Borsje from Ladder for joining us. And hey, if you’ve been holding off on life insurance because it takes too long, I see you, you got no excuses anymore. And thanks to you, the listener, of course for exploring the Future of Fandom with us, I’d encourage you to stay connected beyond minute five.

So subscribe to the Future of Fandom, wherever you listen to podcasts, or you can also find all of our content at livelike.com/podcast and every episode has a sub page now. So you can go to the website and find that and across socials, we’re also on LinkedIn @LiveLike and Twitter @LiveLikeInc. I look forward to predicting the future again with you soon, until then, I’m Adam Conner saying, so long and thanks for being a fan.

Written By
Megan Glover
Content Manager
Written By
Megan Glover
Content Manager

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