Engineering at Ladder

Everything we do is customer-centric.

As a young child, our CEO and co-founder, Jamie, experienced firsthand how important life insurance is when his father passed away unexpectedly. Thanks to his dad’s planning, his family was able to have financial stability during one of the hardest periods of their lives. At Ladder, we’re on a mission to make life insurance easy, accessible, and empowering with a digital solution. Given the importance of this real-world issue, it’s safe to say that our customers are at the heart of everything we do. In other words, we’re not building for building’s sake. Engineers are encouraged to ask questions, such as “what are we solving for and how does it impact users?” to understand what the higher level intent is behind every decision.

Our roadmap is directly informed by customer needs. For instance, we wanted to reward customers who have healthy lifestyles, and thus a lower mortality risk. This led us to create an iOS App where customers can sync their steps and get a discount for living an active lifestyle.

We also extensively use FullStory, a tool that provides videos of how our customers are interacting with our product. These are shared in our #fullstory Slack channel, where engineers can gain valuable insight into what’s working well, improve pain points, and catch bugs before they become bigger problems. In addition to assigning different engineers to various FullStory videos every day, we also do quarterly week-long on-call rotations so engineers are never far from our end users.

You can expect to ship code on your first day.

While we strive to write high-quality code, we recognize mistakes and edge cases that cause errors are inevitable. We have a bias for speed over perfection; the sooner we release a feature, the faster we can gain more data and iterate to provide our users with the best experience possible. We’re not afraid to break production (it happens!). In fact, it’s only by doing so that we can learn how to build better safeguards against future failures. Ultimately, this leads to a cluster immune system, which helps us deploy even faster and more securely (see Continuous Delivery below).

If something goes wrong, we never place the blame on any one person. Rather, we’re happy to jump in, help fix the problem at hand, and learn from it during blameless retros. For instance, we once misnamed an environment variable and accidentally ran a stub client in production. To avoid this class of mistake from happening in the future, we added a runtime check to prevent a server with this issue from ever serving real traffic. While this is a small example, by repeating the blameless retro process over 90+ times, we've built an environment where it's actually safe to make mistakes because there's a robust safety net.

We care about start-to-finish ownership for several reasons.

First, we believe developing our engineers to think at a high level is mutually beneficial. Companies exist to solve problems, and doing so effectively requires start-to-finish ownership. It is necessary to look at data that identifies a problem, build a solution, and again use data to determine if this solution solves the problem. If not, we’ll attempt another solution. At Ladder, we want engineers to be problem solvers, not just code writers. This means they’re involved and have the full context throughout the entire process.

Second, we've built our teams around stages of the user journey – and not technology – because we think it's more efficient for one person to build the frontend, backend, and data aspects of a feature instead of coordinating three teams to do this. We also find this diversity of technology and environment is good for a developer’s growth.

Third, we believe that a lot of incidental complexity and rigidity in software comes from establishing the wrong abstractions. We push engineers to think about the end customer result of their changes rather than the code-specific modules and interface changes. We've built a whole testing framework that makes writing these tests fast and deterministic.

In a great example of start-to-finish ownership, an engineer on the team noticed that a large percentage of people didn't accept their offers for coverage because they were too expensive for them to afford. The engineer built a predictive model to simulate the change in the offer acceptance rate if we made offers that were more affordable and quantify how many users solving this problem could impact. They worked with product and design to build several solutions to this problem and ran them in A/B tests. This engineer not only built and ran these A/B tests, but they also analyzed the resulting data to confirm the desired effect happened.

Championing our own talent is key, especially as we scale.

While many companies claim they want to foster growth internally, we have done so from day one. Six out of seven of our people managers were promoted from within. For example, Jack, our CTO, started as a tech lead. With one exception all our people managers were hired as individual contributors and later promoted into management. As we continue to scale, it’s important that our employees grow with us, too. That said, we recognize there are multiple paths to grow your career and not everyone wants to move into people management. If you prefer to level up as an IC, we fully support that option as well.

Whether you prefer a hybrid or remote work environment, we support both.

Our main office is located in Palo Alto, but we have team members who also work remotely across the United States. Upon joining, we provide a one-time $500 remote office stipend for all team members as well as a monthly $150 stipend to cover WFH costs such as internet and office supplies. Since the engineering team spans different time zones, we strive to overlap during core hours of 10am-2pm PST. However, we’re flexible and make sure to find meeting times that work for everyone. Outside of that, we trust you to manage your schedule and work in a way that suits you best. We also enjoy getting together for fun virtual and in-person events such as game nights and BBQs. Recently, we hosted our first semi-annual Ladder Meetup, where the team got together for a few days in Palo Alto.

We want everyone to take vacation and carve out time to enjoy their passions outside of the office. Many of us, including leadership, are parents. In fact, you’ll see Jack (our CTO) has time blocked off on his calendar for kid duty, which we greatly respect. If you’re looking to grow your family, we want you to have time to adjust without worrying about work, so we provide all parents (inclusive of adoption or fostering) 10 weeks of paid baby bonding leave.

Our average tenure for engineers is three years and all four founders have been here since the beginning.

We invest in our people and want to see them succeed. One main way we do this is with a career action plan, where team members can share what interests them, what skills they’d like to develop, and where they see themselves in five or 10 years. From there, managers help create daily, weekly, monthly, and quarterly goals to check in on. This dedication to professional growth speaks for itself – our retention rates exceed the industry average and our turnover rate was 11% in 2021 and 3% YTD.

Here’s what four of our software engineers have to say about why they love working at Ladder:

“Life insurance is a fundamentally good product, a net positive for the world. It’s awesome to know that everything we do translates into more families being protected.” – Guilherme

“Ladder has an open and supportive culture that fosters healthy discussion and promotes growth from our mistakes.” – Bobby

“Ladder does a great job taking care of its employees and making Ladder a fun place to work. Whether it’s a Ladder Olympics planned by the #fun-committee or making sure we have a ping pong table in the kitchen, it’s fun to come into the office!” – Chris

“As an engineer at Ladder, I work in an environment where I can grow professionally and contribute to the team while also enjoying work and having fun. The blameless culture set from the top-down makes this possible.” – Andrew

We’re completely transforming the insurance space.

Traditionally, applying for life insurance is a tedious task that involves too much in-person paperwork and time-consuming meetings with “salesy” agents. We knew there had to be a better way. Our digital user experience and real-time underwriting system is the first of its kind and reduces the months-long process of applying for life insurance to just minutes. What’s more, since life changes are fluid (think: you’ve paid down your mortgage, your kids are older than 18), we’re able to be flexible as well; our platform offers the ability to “ladder up or down” and add or remove coverage as needed. Additionally, we’re partnering with online-only banks like SoFi and Ally to serve a broader set of consumers and help close coverage gaps.

While we have quarterly goals, we eschew a strict deadline-driven culture. Outside of the day-to-day work we do during sprints, engineers have roughly 10-20% of their time to dedicate to other projects and ideas. We recently had our first hackathon (which we hope to continue 1-2 times per year) and look forward to having some of these ideas make it live into production!

We deploy 10 times a day – and sometimes even more.

Our approach to continuous delivery is a core part of our product development process. From the beginning, we’ve invested in multiple levels of automated testing, monitoring, and reporting. For example, we build on Blaze, which allows for fast, deterministic builds. We use Kubernetes to have parallel builds and we have a test leaderboard where we remove flaky tests. Engineers are responsible for owning their code’s quality throughout the software development process. Pull requests are approved by one reviewer and then automatically merged into the queue and deployed. We also actively use A/B tests and feature flags to get code safely into production quickly and often.

We raised a $100M Series D in October 2021 and are excited about modernizing the insurance industry. If working in a fast-paced, mission-driven environment speaks to you, we encourage you to check out our open roles!