Recruiting, the Hard Way

Alan Gilbert
6 min readAug 23, 2020
Photo by jesse orrico on Unsplash

I am writing a series of blog posts about lessons learned in my career, including my time at CoverMyMeds as the company grew from 30 people to 800 and was eventually acquired by McKesson in 2017. This post covers what I learned about recruiting beyond the standard things that all companies do. I call it “Recruiting, the Hard Way” (lovingly ripped off from Zed Shaw).

Like all of us, I am also living a different life with COVID-19 this year, but throughout my posts I am assuming we’ll return to face-to-face interaction and social gatherings before too long.

The opinions expressed here are, of course, solely my own and do not represent any employers, past or present.

Recruiting is hard. There’s just no way around it. Sure, you have to be organized, methodical, and efficient. You have to attend career fairs and conduct on-campus interviews. You have to scour LinkedIn and Google. But those are just table stakes. The hard part is the work you do in building an employment brand and finding and engaging exceptional candidates. In many ways, it is just like sales. In fact, it is sales.

In my time at CoverMyMeds I ran both Engineering and Talent Management. Recruiting and hiring was a major part of my job in both organizations. Which brings me to my first point — we were very successful in recruiting great people because we made it a priority.

As VP of Engineering, 75% of my time, literally three to four days a week, was dedicated to finding and adding the best possible software developers to our team. The approach was very personalized and hands on. We didn’t use external recruiters because we felt being able to say “you should come join our team,” describing the business and culture from first-hand experience, gave us a competitive advantage. With all due respect to external recruiters, and I know some really good ones, we felt like using them was akin to using a third-party to do your sales. It’s just not the same.

I learned to code in Python, Ruby, and JavaScript — not so that I could write production code — but rather so that I could attend meetups (remember those?) and conferences and have topical conversations with people we wanted to hire.

When we did hire a technical recruiter, the first thing we did was to put her through an internal 30-day mini coding boot camp. That’s right… we hired a recruiter with a masters degree in HR, and taught her how to code so that she could better relate to software developers. I’ll never forget when a candidate approached her at CodeMash and asked her, “Can I talk to someone about your tech stack?” I waited to see how she would respond and was delighted when, with zero hesitation, she walked him through our stack from the database all the way up through our CSC framework and then explained our tooling and process. I also quite enjoyed the “boy do I feel dumb” expression on the candidate’s face. This approach, recruiters becoming experts on the work of our teams, eventually spread to other areas of the company.

Photo by Marília Castelli on Unsplash

We also committed ourselves to creating a strong employment brand. First and foremost, we had to have a great culture to attract great people. I’ll cover that in another post. We invested our employees’ time and the company’s money in all manner of local events and causes where our target audience lived. We sponsored numerous events such as Stir Trek, the aforementioned CodeMash, Startup Weekend, Independents’ Day, and the Pride Parade.

Our developers participated in tech meetups and hackathons as organizers, speakers, and mentors. This also provided them with great professional growth opportunities, which helped feed a virtuous cycle of employee growth and company success that I’ll also cover in a future post. I was surprised and bemused when more than one of my peers from other companies in town told me that we were “distracting” our employees and risked losing them by exposing them to these outside activities.

I recall working with one of our developers to mentor a team at a Startup Weekend and noticing that a technical manager from another, more corporate company was trying to recruit him. Finally he responded, “That sounds great, but you have to talk to my boss first,” pointing to me with a wry smile. The manager looked at me and said, “You let your developers go to Startup Weekends?” Ummmm…. What?

We also worked hard to make sure that every candidate who interacted with our company, hired or not, had a very positive experience. That meant timely followup and saying “no” with compassion, often with a phone call, especially after going deep into the interview process. Columbus is a small community and, considering that we interviewed 10 people for every one we hired, we always wanted to ensure that they all had great things to say about us. With one such candidate, I heard through the grapevine that she was badmouthing our interview process. I invited her back for lunch, discussed her concerns, and we made changes to the process based on her feedback. She went on to run a women’s coding advocacy group and we ended up hiring a couple of their members.

We also were very deliberate in achieving high rankings in the various “best workplaces” awards. We did this by first and foremost ensuring that we had a truly great work place but also by understanding and responding to how these rankings worked. We kept a close eye on Glassdoor and made sure to respond respectfully when we received a rare negative review. In fact, we took these responses as a free marketing opportunity to promote key elements of our employment brand.

Also, believe it or not, we chose our tech stack (open source, Linux, Python/Ruby, JavaScript), not primarily for technical reasons but rather to attract the kinds of developers we wanted in our company. Specifically, we found that the people who worked in these tech stacks had a sense of community, inclusiveness, and purpose with their work that transcended their “day job” and was consistent with the culture we were building.

Finally, it didn’t hurt to have a big sign on our building right on a major downtown interstate route. We also created a “Better Cup of Coffee” campaign to recruit and train (or “detox,” as we liked to say) Java developers and teach them Ruby on Rails with a giant wallscape on the Orange Barrel Media building on another high-traffic commuting route.

Next time I’ll talk about the other side of the recruiting coin, Interviewing and Hiring, the Easy Way.

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