Good People, Big Dreams

Growing the new generation of engineers in the Lemonade Makers program

Itamar Kestenbaum
Aug 3 · 7 min read

In 2019, Lemonade’s R&D demands started growing more rapidly than ever. As we entered this stage of hyper-growth, two things became abundantly clear. First, we needed more engineers. Second, highly experienced engineers are really hard to recruit.

So we decided to try something new. We’d hire developers early in their careers and provide them with the tools and mentorship to prepare them for Lemonade. This felt like a double win. By focusing resources to transform our engineering onboarding experience, we could coach and empower engineers who would grow into our in-house R&D team and help Lemonade become the most lovable insurance company in the world.

We called this experiment the Makers program, and it has since become an integral part of Lemonade’s company-wide hiring strategy and onboarding experience.

Good people with big dreams

We’re an ambitious company, so we try to hire the best. But what defines the best? We largely shun so-called “hero” and “10x engineer” culture. We don’t need keyboard-slinging misanthropes in our midst. We need good, empathetic, open-minded people with great coding skills.

In Lemonade’s first years we held ourselves to that standard by recruiting only highly experienced engineers. But as the business scaled and the demand for talent increased, we realized there is more than one kind of “best,” as counterintuitive as that might sound.

The most seasoned of engineers was once an ambitious kid out to take the world by storm. And so we started looking for like-minded developers. Maybe they wouldn’t have a ton of experience, but they’d have a passion to learn. Highly intelligent and ambitious people. Mission-driven, outside-the-box thinkers.

In short, good people with big dreams.

Lemonade’s insurance is especially attractive to young renters who can grow with the company. They go through many of life’s common milestones — buying a home, adopting a pet, thinking about their dependents — and they can get their new insurance needs covered with Lemonade products.

The same thinking works internally. We’re growing along with our Makers, and investing in their development. As with our customers, we’re in it for the long haul.

A graduation picnic for the Lemonade Makers program.

A mutually beneficial relationship

Some companies implement a sort of “baptism by fire” scenario for new engineers. They get thrown into the mix and are expected to churn out code. We’ve taken a different approach, creating an onboarding experience that allows our engineers to have the time and resources they need to join a squad with confidence.

It’s not about finding code monkeys; it’s about finding engineers who want to improve and learn with us. An employee who’s eager to take on new challenges is the perfect fit for a company that’s doing the same.

Creating a welcoming environment for new engineers isn’t easy when a company is already up and running. There are business goals and technical debts, plus any number of initiatives and task forces, not to mention tight deadlines. So a company can’t just stop everything it’s doing and help the newcomer get up to speed — can it? At Lemonade, we believe we can… and that doing so ultimately makes our business stronger.

A personalized path

New Makers are assigned a designated squad when they enter the company. This designation means Makers can get actionable assignments from their target squad. By the time they leave the Makers program, they already feel like they’re part of their squad.

They’re also assigned a Makers Lead whose job is to help them through their first weeks and months at Lemonade. The Lead’s main concern is ensuring that a Maker feels comfortable and confident in their work, abilities, and growth at Lemonade — from building a task pipeline that prepares them to join their designated squad, to helping them with their first dev workflows, from spec to deployment.

Aside from designated-squad work, Makers are also tasked with assignments that strengthen areas in which they’re less experienced. Let’s say a developer has a strong background in Ruby, but has no experience in Node or Typescript; we may give her a series of increasingly complex Node tasks, until she’s comfortable with the language.

At a daily Makers standup where several team members accidentally came to work matching.

Power in numbers

Cohorts began as a simple way of describing “people who started together, or around the same time,” but they took on a life of their own through the new lens of the Makers initiative.

The shared experiences of installing their local environment together, going through intro and onboarding sessions, and being there for each other while they deploy their first tickets, bond these groups and give them a sense of kinship that lasts long after they graduate from the Makers into their respective squads.

This also promotes a sense of community and mentorship between new hires and those who have been with Lemonade for years. In our #makers-help channel on Slack, for instance, current Makers pose technical questions and alumni Makers actively weigh in and share knowledge.

Another way the Makers community affects the overall Lemonade culture is by instilling high code quality standards from day one. Since Makers are, by definition, new to the company — and since they work directly with the squads around the company as they’re onboarding — all engineers and leads who interact with them are offering reminders on a regular basis of how high our standards are for code.

When doing a technical kickoff with one of the Makers, a Team Lead will never ask them to cut corners or skip writing tests for a feature. On the contrary — they’ll encourage the newcomer to test coverage and follow other best practices.

Good friction!

At Lemonade, we try to automate everything. Whenever we see a process that repeats itself and is predictable, our first instinct is to automate it.

For example, we wrote a CLI (Command Line Interface) that installs the entire Lemonade environment onto new developers’ machines. We could do away entirely with our multiple-day technical onboarding by automating several educational sessions and just being available “when needed,” but sometimes a lot gets lost when you pursue efficiency at all costs.

Shanee, a former Maker, was caught off guard at first. “I went through onboarding a few months ago. I was worried that I wouldn’t be able to understand what the environment looked like because everything was installed automatically,” she explains. “But over the first few days and weeks, the Makers Leads walked us through R&D training sessions and kickoffs, and made themselves available for questions. It was really great to get set up quickly, and understand the Lemonade codebase as a whole.”

We believe in “good friction”: leaving (or even creating) inefficiencies that force us to interact with our environment. It might technically be more efficient to record our educational sessions and have Makers watch them on their own, with headphones, but they’d be missing out on an opportunity to sit with a staff engineer, asking questions in person about how things work here.

We also have every new Maker do a kickoff for every single ticket they perform, no matter how small; that’s more good friction. A 15-minute kickoff is scheduled with the Product Manager who owns the ticket — even if they’re just fixing a typo. This affords both the engineer and the PM a chance to get to know each other.

This tradition was initially put in place to instill good work ethic in new engineers, but surprisingly, we started getting great feedback from the PMs and Tech Leads in the squads themselves. They were grateful for these brief but meaningful interactions with Makers. It became clear that even veterans in the company benefited from this opportunity for good friction, and appreciated getting to know the new Makers who would later become integral members of their squads.

Itamar and Mor (the Makers leads) discussing daily work activities.

A simple way to effect real change

The journey a Maker takes in their first days, weeks, and months at Lemonade grows their skills as engineers. By the time a Maker leaves the program, they’re virtually indistinguishable from other engineers in terms of their coding chops.

But this experience does something even more important than simply leveling up skills. It weaves the Maker into the fabric of the company. The community and connections new engineers build during their time in the Makers lives on, and these colleagues contribute energy and momentum that keeps Lemonade thriving as we grow with them.

A Maker who graduates from the program goes on to improve every piece of code they encounter. They know that Lemonade has taken the time to invest in them, allowing them the freedom and space to truly become part of this family. While the Makers paradigm was originally intended to guide our engineering hiring and onboarding process, we’ve since found that it’s not limited to tech-focused positions. Indeed, it can be replicated across all departments — from QA to Claims to Customer Experience — leading to a quality-obsessed culture throughout the company.

Itamar is a Team Lead at Lemonade. He leads the Makers chapter at Lemonade along with Mor Karol and Yuval Leshem.

Aleph

Aleph is a venture capital fund focused on partnering with…

Aleph

Aleph is a venture capital fund focused on partnering with great Israeli entrepreneurs to build large, meaningful companies and impactful global brands. It is a partnership of Michael Eisenberg, Eden Shochat, Yael Elad, Aaron Rosenson and Tomer Diari. Visit Jobs.aleph.vc

Itamar Kestenbaum

Written by

Team Lead @ Lemonade

Aleph

Aleph is a venture capital fund focused on partnering with great Israeli entrepreneurs to build large, meaningful companies and impactful global brands. It is a partnership of Michael Eisenberg, Eden Shochat, Yael Elad, Aaron Rosenson and Tomer Diari. Visit Jobs.aleph.vc