…and it’s pretty great.

A quick context:

Shepherd was started ~3 years ago with the goal of bringing the insurance industry to the modern age. We’ve built an all-star team to tackle this challenge; spanning engineering, underwriting, actuarial and more. As the business matured, and the hiring market has shifted, so did our process. This blog post outlines our refined approach after many iterations and learnings.

Getting organized

We’ve created an internal document that outlines our process, eng levels, questions bank and email snippets. This allows us to keep our message consistent, fair and scalable.

Communication with candidates

In all communication with candidates, we outline their progression within the process. For example, after the initial call, I send out this email:

The process

1. Initial call

All candidates have an initial call with the hiring manager. Today, this is me. I’ve experimented with 15 or 30 minute calls, and have found 15 minutes to be sufficient enough. No small talk, we jump right in.

The call:

• I ask where they are calling from. This gives me context and allows me to share that I am calling from the office and where it’s located

• I set the agenda on how we will spend the call

• We begin by talking about their experience, what teams/products they’ve worked on, if they are actively looking, what they're looking for in their next role, their timeline and whether in-person is desired. At this point, I can make a judgment call if there’s a potential fit.

  • Advice: we’re all busy, don’t be afraid to call out it’s not a fit and give time back. We’ve had candidates who aren’t seeking in person roles, and that’s fine. Best to let them know early. Everyone I’ve talked to appreciates getting time back

• The second half of the call is for sharing Shepherd’s vision, our products, the team, the role and next steps if it makes sense.

  • Advice: I look forward to the questions the candidate asks about Shepherd. I found the best candidates are thoughtful about the team, the mission, my leadership, how the team is organized, etc.

• We end the call by offering next steps

Interview: 15mins, over Zoom.

2. Tech screening

We take the stance that leetcode isn’t conducive to evaluating a candidate’s ability to do their job. Candidates tend to study leetcode when they are interviewing to maximize their success. Instead, we offer candidates 2 options: 1. A frontend challenge or 2. A backend challenge. These challenges are reflective of real work we have to do at Shepherd. Candidates are allowed to use whatever language and framework they are most comfortable with.

Interview: 60mins, over Zoom.

3. Eng experience

Previously, we had this interview as part of the on-site interview. On-sites ended up exhausting for candidates and for engineers at Shepherd. In addition, many times candidates were really good at tech screens but lacked deep engineering knowledge and experience. Instead, we now front-load this interview before the on-site. It also allows us to prepare our on-site interviews with some expectation (and shared knowledge) of what the candidate worked on and their ability. For our eng experience interviews, we asked candidates to describe a large project they worked on that they are proud of. We use the CAR framework:

• [C] context: ask about the problem, the team they worked on, stakeholders, and their role

• [A] actions: they’ve taken as part of this project

• [R] results: from completing this project. This could be from their direct work or from the project itself

The eng experience interview also allows us to understand the candidate’s ability to break down problems, explain them to someone who doesn’t have context and talk about their work.

Interview: 30mins, over Zoom.

4. On-site

Not too dissimilar to other companies’ on-sites, this interview spans a few hours where the candidates spend time with different team members. Our structure:

• Team lunch: this includes direct team members and others (insurance)

• Systems design

• Core values

• Cofounder/CTO interview

Interview: 3hrs, in office or Zoom if needed.

5. References

We always ask for references as part of the process. We typically ask for an eng and non-eng reference. While many consider references as low value (candidates will only suggest references who will speak highly of them), it gets us excited and tells us a lot about the candidates from peers they worked with. For example, we often like to ask about a candidate’s “superpowers” and “kryptonite”. We like to understand what makes them especially unique, and what areas we can help grow.

6. Offer

The fun part! We use market data to come up with an offer and follow the “First and Best” framework.

Closing thoughts

The process is made to be malleable – it will change as the business grows, the needs change, the market shifts, and the team’s bandwidth. Recruiting is a taxing process on both sides of the aisle. For now, this process is one that works and has been pleasant for both us and candidates (from what they tell us!). Our process is also made to be lightweight on candidates and fast – we’ve had some candidates go through within 8 days!

Finally, and most importantly, it respects a candidate’s time. This speaks to our culture. We care about people, and that should be reflected in everything we do.

Thanks for reading this far!

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