How to Hire an Engineering Team at Each Stage of Your Startup


In the fast-paced startup world, there’s one thing you can always rely on: constant change. This makes work challenging and stimulating, but it also means recruiting can be a real challenge. How do you describe your company accurately to prospective candidates when the work environment is constantly evolving? And how do you attract people who will be the right fit for this precise moment in your growth, but who will also continue to be a good fit in the future?

These are questions we’ve spent a lot of time considering at Greenhouse, so we were thrilled when Entelo invited us to partner with them on the “How to Hire” webinar series.

In “How to Hire an Engineering Team from Angel to Series C,” Greenhouse’s VP of Engineering Mike Boufford shares anecdotes and advice from his experience overseeing the growing Greenhouse engineering team. As Greenhouse's first engineer, he has played (and continues to play) a critical role in the hiring of the team.

Read on to hear Mike’s insights into hiring engineers during each stage of the startup lifecycle—from the Angel Round, to Series A, to Series B, to Series C—and learn strategies you can put into practice as your company expands, too:

The Angel Round

One of the primary challenges of attracting candidates during the angel round is the fact that there’s not a whole lot to dazzle them with at this early point in the company. No big fancy office, no super sleek website. In Greenhouse’s case, all the co-founders had were some big ideas and a pile of index cards with a prototype scribbled on them. So, to win at recruiting during this round, you need to help candidates see the potential of the position and your company.

Insight #1: Show candidates how accepting your open position will tell the next chapter of their career story.

As Mike describes it, every candidate is trying to “write the next chapter in their career story.” They want to believe that each new job is going to help them grow and advance, but they also have a deep-seated fear that they’ll take the wrong job and wind up with a different and less desirable climax to their story. So it’s your job during Angel Round recruiting to paint a picture of how your company will help a candidate achieve some of their big, juicy career goals.

Insight #2: Candidates turn into hires when your open position brings them much value.

Compensation is rarely the primary concern for engineers; most of them want something bigger out of their role like the ability to take risks or oversee large projects. But what matters most to one engineer may not appeal to another, so it’s important to pinpoint the particular priorities of the person you’re speaking with. Saying something like, “We still haven’t ironed out all of our processes” might sound like opportunity to one engineer…but dysfunction to another. Learn as much as you can about the person you’re trying to recruit so that you can tailor your pitch to highlight what matters most to them.

Series A

In this next stage, your company’s growth will begin to accelerate. When you’re only looking to hire one or two people, you might be able to get by simply by tapping into your existing network, but that approach isn’t sustainable or scalable. As you gear up for big growth, it’s essential to implement structure and process.

Insight #1: Create and carry out a sourcing plan.

You’ll want to investigate a variety of sourcing approaches. Mike experimented with posting on job boards, hiring agencies, holding and attending meet-ups, reaching out to his existing contacts, and cold contacting people on LinkedIn to invite them to meet him in person. Decide which avenues you’ll pursue, and make it a priority to carry out your plan. And don’t forget to measure your success—otherwise you won’t know which efforts are working and which aren’t (and thus where to focus your future efforts). Even though he spent about 85% of his total efforts cold contacting people, it turned out that Mike only brought in one qualified candidate using this tactic. This was a pretty significant lesson learned!

Insight #2: Structure your interview process.

Getting people into your pipeline is an important first step, but how do you know when you’ve found someone who’s a good fit? Spending time to structure your interview process will ensure that you’re screening for the skills and qualities that matter most.

This stage is really crucial, so be sure to consider these points as you structure your own interview process:

Define the role

    • What will this person do?

    • Which skills and personality traits do they need to succeed?

Create structure

    • What do I need to know to advance or reject a candidate at each stage?

    • When and how will I sell the candidate?

Create questions

    • For each skill, how do I test whether the candidate possesses that skill?

    • How do I test for culture fit and communication?

Insight #3: Nail down the attributes that drive candidates to your company.

In the same way that you determined how your organization could help employees move along their career trajectory during the Angel Round, you’ll want to spend time outlining the values or attributes that make your company unique and appealing to candidates. For example, here are a few points that attracted engineers to Greenhouse during Series A:

• Easy access to company’s founders

• Everyone is full-stack—you get to build an entire feature end-to-end

• Many technical and process problems are still unsolved or evolving

• Building something people actually find useful and care about

• No bureaucracy; easy to get things done

Insight #4: Solution sell ’til the cows come home.

One of the biggest lessons Mike learned at this stage was the importance of solution selling candidates. Instead of simply telling a candidate why Greenhouse was so amazing in a very generic way, he began the process by really trying to understand the candidate. After listening to a candidate describe what they were looking for or what wasn’t working in their current situation, Mike was able to customize his pitch to focus on whatever mattered most to that person. As he went through his pitch, he’d confirm that he understood what the candidate had been saying, point out how working at Greenhouse would solve that pain point, and ask them to agree that this all made sense. Worked like a charm!

Series B

Now you’re really rockin’ and rollin’! You have a more robust product and team. But—you’ve also probably acquired some technical debt (a term engineers use to describe how certain aspects of quality may have been sacrificed in order to build a product more quickly). As a result, many of the hires you’ll be making at this stage will begin to address this issue.  

Insight #1: Evolve your company’s selling points as your company evolves.

What defined your team in its earlier, scrappier stages may no longer be 100% true as your company matures. For instance, when your company really starts to take off, your founders probably won’t be able to meet with individual employees as regularly as before, so you won’t be able to use a point like “we pride ourselves on easy access to our founders” to sell your company to prospective employees. But at this stage, you should have some pretty impressive growth or acceleration that you can get candidates excited about being a part of. Bottom line: always be on the lookout for new potential selling points.

Insight #2: Don’t wait too long to start leveraging talent marketing.

Mike admits that he wishes he had understood the importance of talent marketing in the earlier days of Greenhouse’s growth. He relied too heavily on an outbound strategy for sourcing candidates, but in retrospect, he would have dedicated more resources to setting up an inbound system. Learn from his mistakes! If you’re about to enter Series B, consider hiring an Employer Branding Specialist or a similar role to help build an inbound stream of candidates.

Series C

When you get to Series C, you’ve probably learned a few things about where your organization is and where you’re headed. And you’ll want to look to the future to try to anticipate what’s next. That’s why Mike’s final bit of insight is especially important:

Adapt, adapt, adapt!

Imagine how you will need to adapt, but make sure to pay attention! Reality will probably differ from your expectations. So as you prepare to enter recruiting in Series C and beyond, be ready to adapt and evolve. After all, that’s what startup life is all about, right?

Want to hear more anecdotes and advice from Mike on how to hire your engineering team? Watch the full webinar here!

Programming 101

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