“Term Life Insurance: many people don’t have it because it’s too difficult to get” – Jamie Hale, Co-Founder, and CEO of Ladder

It’s a personal passion of us: Term Life Insurance policy is an important product that makes families and communities stronger in time of need. Regrettably, even with today’s digital era, there are weeks of medical exams along with mountains of paperwork that you need to check then sign. In addition some policies are super hard to understand – so having one for all of your family is still a hurdle up to now.

We share this passion for good term life insurance with Jamie Hale, Co-Founder and CEO Ladder. Therefore we are super proud and happy about this interview.

Inspired by his personal experience Jamie emerged from the kindness he received from his community, father’s old insurance policy, and now, passionately improving Life Insurance to be digitally fast and available.

How would you explain to a 10-year-old with your latest products and services?

Today, you depend on your parents to get you the things you need — to pay for clothes and food and the house you live in and even put aside savings for college. A term life insurance policy is a product they can buy to make sure that if something happens to them, you’d continue to be provided for in the years you need them the most. It’s a really good product that makes families and communities stronger in time of need.

Unfortunately, many people don’t have it because it’s too difficult to get. It takes approximately 8 weeks, medical exams, and a lot of paperwork. People are too busy with life to spend all this time figuring it out, so they just forget about it or put it off — and that’s a big problem. With Ladder, you can apply online in minutes and get an INSTANT decision because our smart algorithms underwrite you in real-time. Plus we have great prices, no hidden fees, and the flexibility to adjust your coverage with a few clicks so you never pay for more than you need. It’s a lot of work that we do in the background, but all of this makes getting life insurance super easy.

What kind of trends in the insurance and insurtech industry do you see currently in the US?

Large insurance companies are looking at digital insurance players like Ladder, Lemonade or Metromile and trying to close the gap by building (or partnering with) web front-end online application portals. While that’s a great improvement, it’s important to remember it’s just the first step in the process. Incumbents are struggling with the transition because they have an incredible amount of baggage under the surface — complex products, agent fees, paper administration, legacy technology, and analog underwriting. Until they are able to shift their entire mentality from paper and agents towards innovating for the customer, those efforts will amount to little more than online lead generation, not truly digital products.  

We’re also noticing that the insurance value chain is becoming more disaggregated. Many insurtechs have made the choice of focusing on specific functions along the value chain, such as lead generation or fraud analytics, and are collaborating with traditional insurance companies. We, however, strongly believe in taking an integrated full-stack approach. It’s only when data is able to flow back and forth along the entire value chain, and when you have control over the entire customer experience, that you can solve hard problems for real people.

What do decision-makers outside the US need to know about the life of the life insurance business there?

It’s tempting to think the US is a large and homogeneous market, however consumers are as diverse as regulations! The US insurance industry is regulated by 50+ different regulators at the state level, which makes a national rollout slow and difficult. There are also unique aspects of the market that drive key product features, processes and even business models. An example is the regulation defining a 2-year contestability period, whereafter insurance companies may not contest a claim.

As a startup especially for life insurance what was your biggest challenge and what are you the proudest on?

Committing to the decision of rebuilding everything from the ground up — not just the experience at the surface, but also the guts of the product like underwriting and policy administration— was hard. But today we’re so glad we did it. We feel like we hold all the cards to be able to rewrite the rules for the customer.

Ultimately I think that’s what I’m proudest of. We put customers at the center of everything and have aligned our incentives with them. We all believe we are solving an important problem for people and communities, and that has cemented our culture of authenticity, solidarity and passion. 

What drove and led you to your approach and how are consumers reacting to it?

I was 11 when my dad suddenly passed away. He had a basic life insurance policy that enabled me and my family to stay in our home, be supported by a community we loved and made college a possibility for me. Were it not for this simple act of love, my life could have turned out very differently.

Right now, there are 50M families without enough life insurance coverage in the US alone. I felt incredibly passionate about redeeming a great product that was sadly becoming less and less relevant to the digital consumer. And the most exciting part is that it’s been working. Our NPS (net promoter score) is almost 20 times the industry average (84 vs 4.5). Our customers are also significantly younger and more evenly split between man and female, which means we are making life insurance attractive to people who are being left out of the current system. And that’s also great for business. 

What kind of partners and customers are you looking for?

We want to make getting life insurance easier. Sometimes, that means making sure it’s available when and where people handle their finances. With this in mind, we launched the Ladder API — to enable banks and other financial platforms to seamlessly extend the Ladder’s offering in the context of their products.

In terms of customers, Ladder is built for today’s consumer — not yesterday’s agent. People largely understand the importance of life insurance but are deterred and disenchanted by the complexities and misaligned incentives associated with the traditional process. Our customers love that they can get fully-underwritten life insurance policies (up to $8M) in a matter of minutes, versus the 6-8 weeks. Because Ladder is flexible, they can adjust their coverage amount as their needs change over time, all from a simple web portal. 50% of customers access Ladder from a mobile device. 60% of engagement on Ladder happens outside business hours. All of that highlights that they need a life insurance solution that they can control on their own time.

How do you see your company in the next 3 to 5 years?

We have a big challenge and exciting opportunities ahead of us and we’re going to stay focused on solving fully underwritten term life insurance for the time being. I can imagine product and international expansion following.

Can you share 3 short do’s and don’ts for young startups who want to grow their companies?


  • Solve an actual customer problem.
  • Build a strong culture of cross-functional collaboration.
  • Have the courage to make hard bets today with the conviction they’ll pay off tomorrow.


  • Get tempted by temporary shortcuts.
  • Neglect your employees and the culture you’re building.
  • Be afraid to take risks. That where the reward is.

Can you share your top 3 books and 3 gadgets if you’re an insurtech CEO?

Sure,  I love to read and play with gadgets. 

For Books:

  • In the Distance by Hernan Diaz is a great and well-written pleasure to read. (Available in Germany, in the US, in the UK, in Italy, and in Spain)
  • Dare to Lead: Brave Work. Tough Conversations. Whole Hearts by Brené Brown has powerful insights into courageous leadership. I’d recommend it to all leaders. (Available in Germany, in the US, in the UK, in Italy, and in Spain)
  • The Lessons of History by Will & Ariel Durant is a sweeping overview of the themes and lessons observed from writing a 10 books series. The Story of Civilization covering 5,000 years of world history. (Available in Germany, in the US, in the UK, in Italy, and in Spain)

For Gadgets: 

  • The Bose Quietcomfort 35 are awesome noise-canceling headphones. (Available in Germany, in the US, in the UK, in Italy, and in Spain)
  • Kindle Oasis Paperwhite is the best device for portable linear reading. (Available in Germany, in the US, in the UK, in Italy, and in Spain)
  • Apple AirPods (GermanyUSUKItalySpain) paired with an Apple Watch (GermanyUSUKItalySpain) are the most underpraised Apple products and are a wonderful pairing.

Jamie is CEO and Co-Founder of Ladder, a startup in Silicon Valley that offers direct-to-consumer, fully underwritten term life insurance online, in an effort to close the coverage gap affecting 50M families in the US alone. 

Prior to co-founding Ladder, Jamie was Partner at Aldenwood Capital and at Oak Hill Investment Management. He also worked at NextCard, pioneering instant credit and the first ‘internet enabled’ Visa card. Jamie is a graduate of Bowdoin College and Harvard Business School.

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