7 Things Everyone Should Know When Doubling Their Engineering Teams

By Ken Pickering, VP Engineering @ Hopper

Investing in growth is one of the most critical times as a company, especially when you’re looking for smart people to contribute within an advanced technical ecosystem. It’s one thing when the corporate goal to “double the engineering team” appears on the roadmap; it’s another to embrace the chaos, change and eventual rewards of that additional number of humans joining, growing and developing your team.

In the last year, Hopper has exploded from the fledgling headcount of a start-up to something double that, with the vast majority of the new team members starting after I joined as VP of Engineering only six months ago. Here are some of the things we did to make this occur as smoothly as something like this can actually occur.

1. Retention is Priority 0

Hopper already had an extremely solid engineering core group of very, very exceptional and talented people. The infrastructure itself is complex out of the gate. Flight and hotel systems are exceptionally complex, so our system needs to innately deal with their Byzantine design in order to provide some amount of simplicity to our customers. The worst thing I could have done would have been to just start throwing additional people into the mix without a full understanding of where the pain and growth points were. The first thing we did was get to know the cultural factors already at play, where the existing team wanted to go with their respective careers and what growth opportunities could be provided for them. It’s significantly easier to scale if you foster a good culture that isn’t just a revolving door.

2. Know who you need to hire

People aren’t resources. Seriously. Repeat after me: People aren’t resources. When you invite a human to join your company, of course, you’re taking a risk on them being able to do the job, but they’re also putting their career and a huge part of their weekly time in your hands. Understanding what skillsets you need to hire for and how to identify the right people is paramount to building out a successful practice. Hiring is costly (see my next point), so not going after the people you really need in a targeted fashion can hurt you in the long run. Understand what you need and when you need it, and construct your practice around that.

3. Keep your hiring process strategic

The next thing we did was evaluate our hiring practices and look at ways for us to be better and more efficient with our time so that we were honing in on the right candidates at the right time. How do we minimize the number of interviews people need to do to be hired? How do we maximize our time so we can cover a broad range of topics? How do we differentiate interviews based on levels of seniority? Does someone who is in site reliability/infrastructure engineering get the same interview as a product development engineer we’re looking at for one of our Air teams? Understanding everything about who you’re looking to hire and what you value as a team, even simply from a raw technical perspective can save you a lot of aggravation and poor hiring decisions.

4. Allocate the time you need to build the team you want

Hiring is time-consuming. And onboarding is even more time-consuming. One of the things we understand clearly at Hopper is that you need to invest in order to grow. If we need to put 10–20% of engineering time on hiring and onboarding activities, that’s not nights-and-weekends time — that’s middle of the day time. That’s time that could be spent working on product-related features that grow revenue or userbase. But, if you want to be more productive tomorrow, you absolutely need to invest in growing your team today, and then more importantly in onboarding those people so they are set up for success and will contribute something of value. If the ramp-up is ad hoc, you’ll churn people pretty quickly, and waste a whole lot of time and money bringing them in in the first place.

5. Invest in infrastructure and tooling

The first teams we aggressively hired for at Hopper had nothing to do with our air or hotels product. Instead, we focused on data engineering and infrastructure. Investing in tooling, clean data to make better decisions, and a framework for data-driven product engineering will magnify rewards in the long term. Don’t neglect your DevOps philosophies here. A lot of this work directly makes your team more effective and will reap rewards in both productivity and sheer quality of life for your engineering team well, well beyond anything else. Features can be hit or miss… building frameworks to rapidly deploy those features are far more permanent and impactful long term.

6. Don’t neglect the consumers

A lot of this discussion has been about slowing product engineering down to account for technical debt/infrastructure/hiring, but realistically, this is a business. We have a lot of customers who are downloading Hopper because we can help them book travel cheaper and more efficiently. We can’t neglect them or our peers across the company. Hiring and investing in growth is an exercise in give and take; it’s about long term effective planning and negotiating the best course of action for us to pursue as a business. Being honest and transparent about our challenges and letting other people across Hopper rise to help us with them has been our most effective development strategy. Always focus on finding a balanced portfolio of growing and scaling your team as well as making sure you can do the same for your product.

7. Apply Engineering skills to hiring Engineers

Pretty meta, but it’s true. We’re hiring for the longevity of Hopper and scaling is an incremental process, much like anything else we do in product development. We have throughput challenges, capacity constraints, and need to account for learning and development as time goes on. We retro every interview we do and communicate any changes broadly. We test new interview questions with our existing team to make sure they’re fair, and provide critical feedback… not uncommon from the same process we follow with pull requests.

One of the ways we find great engineers and engineering leaders is people that read articles like this on Medium. If you think Hopper could be a great fit for you, we’re hiring in our Montreal, Cambridge, Sofia and New York offices.