How to hire a start-up team

Denise Shepard

VP of Software Engineering and Data Analytics at Education Superhighway



In 2015, a friend of mine knew the CEO of Education Superhighway, Evan Marwell, and said to me that they had been looking for an Engineering Manager to develop a team for almost two years. I met with them, and felt that they had a good company culture. This was important to me, as I wasn't willing to hire a team in a toxic environment. They already had two engineers – one who was out of Dev Boot Camp, and another who had a lot more experience, but who was hesitant to grow a team as he liked working on his own.

When I started, I realized the business needed all sorts of software that we couldn't provide. In particular, there was an external pricing comparison website we needed to provide that drew on data from the federal government that was very hard to source, clean and turn into maps. Neither of my engineers knew how to do this, so I had to very quickly figure out how to hire people.

Actions taken

When hiring, the most important thing to focus on is assessing whether the candidate in front of you would make a good teammate. Ask yourself whether the candidate is someone you could have a fight with and disagree with in a constructive way.

I knew I needed a couple of senior people to act as anchors for the team, so I started working my network and rewrote the job description. I wrote the description so it catered towards senior engineers who wanted to make a switch into full stack web development, and through this, I found someone with a DevOps background who was really good. He had decided to teach himself Ruby, and he wanted to get out of DevOps, so this role suited him perfectly. My only concern was that he hadn't written code for a long time. So, I tasked him with convincing me that he really did want to sit and write code for 6-7 hours a day, which he was able to do.

In 2015, there were also a lot of boot camps going on, and I thought that there must be a way that I could use them for hiring. Because one of my engineers had gone through a boot camp, he was a coach, so he could tell me about who in the class met my requirements. This allowed me to meet with them long before any recruiters got access to them. I met with two women who met my requirements while they were still in the boot camp and offered them jobs.

With brand new engineers, who don't have computer science degrees, it's difficult to figure out if they are good at what they do. To work this out, I looked for a few things. Firstly, I look for backgrounds in music or in languages – specifically, I like when engineers have learned a language with a different alphabet to English.

In addition to language skills, I look for emotional intelligence – can they get along with other people, are they curious beyond belief, and do they have incredible perseverance? I check this by asking them a series of questions about how they tackle things and how they deal with life hassles. Do they stay with a hassle too long? Do they have a pragmatism about their curiosity? Is there a balance to how they approach things?

Finally, the last thing I look for is a candidates' ability to understand and master basics deeply. Because the boot camp engineers were in web development programs, I wanted to know how deeply they understood a browser works and how JavaScript works. I encouraged them to ensure that while they were in Dev boot camp to get to the bottom of things and to ensure that they really understood how a web stack really worked.

After building this basic team, I realized that I needed a developer who had experience with Rails. We were using Rails, but my senior Engineer and I hadn't used Rails for more than a year, and our lack of understanding of Rails was hurting our team. I hired a recruiter to find an engineer with 7-8 years' worth of Rails experience.

Lessons learned

When hiring a startup team, you face a paradox – you have to hire quickly, but you also have to hire carefully. The team said no to a lot of people who were almost a fit. When you have a lot of work piling up, and you know you can't get it all done, it's tempting to say yes too quickly, but the ability to wait for the perfect candidate is important.

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Denise Shepard

VP of Software Engineering and Data Analytics at Education Superhighway

Leadership DevelopmentCommunicationEngineering ManagementMentorship ProgramsTechnical SkillsSoftware DevelopmentCareer GrowthCareer ProgressionIndividual Contributor RolesTeam & Project Management

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