A founder’s guide to making your first recruiting hire

Recently, a number of founder friends have asked me about how to approach their first recruiting hire, and I’ve found myself repeating the same stuff over and over again. Below are some of my most salient thoughts on the subject. Note that I’ll be talking a lot about engineering hiring because that’s what I know, but I expect a lot of this applies to other fields as well, especially ones where the demand for labor outstrips supply.

Don’t get caught up by flashy employment history; hustle trumps brands

At first glance, hiring someone who’s done recruiting for highly successful tech giants seems like a no-brainer. Google and Facebook are good at hiring great engineers, right? So why not bring in someone who’s had a hand in that success?

There are a couple of reasons why hiring straight out of the Googles and Facebooks of the world isn’t necessarily the best idea. First off, if you look at a typical recruiter’s employment history, you’re going to see a lot of short stints. Very likely this means that they were working as a contractor. While there’s nothing wrong with contract recruiting, per se, large companies often hire contract recruiters in batches, convert the best performers to full-time hires, and ditch the rest.1 That said, some of the best recruiters I know started out at Google. But I am inclined to believe they are exceptions.

The second and much more important reason not to blindly hire out of tech giants is the importance of scrappiness and hustle in this hire. If you work as a recruiter at Google, you’re basically plugged into the matrix. You have a readymade suite of tools that make it much easier to be successful. You have a database of candidates who have previously interviewed that spans a huge portion of the engineering population. Email discovery is easier. Reaching out to people is easier because you have templates that have been proven to work to rely on. And you can lean on the Google brand as a crutch. Who hasn’t been, at one point in their career, flattered by an email from a Google recruiter? As a result, if you’re sending these emails, you don’t have to go out of your way to write personal messages or to convince people that your company is cool and interesting and worth their time. You get that trust for free.

Contrast this setup with being the very first person in the recruiting org. You have no tools. You have no templates. You probably have no brand. You probably have, well, jack shit. You need someone who’s going to think critically about tooling and balance the need for tooling with a shoestring budget, especially in a space where most tooling has a price tag of at least $1K per month. You’re going to need someone whose methods are right for your particular situation rather than someone who does things because that’s just how they’ve always been done. You probably want someone who realizes that paying for a LinkedIn Recruiter seat is a huge fucking waste of money and that sourcing on LinkedIn, in general, is a black hole-level time suck. You want someone who is good at engaging with candidates independently of brand sparkle, which likely means someone who understands the value of personalization in their sourcing efforts. You want someone who compensates for your relatively unknown status with great candidate experience during your interview process. You want someone who won’t just blindly pay tens of thousands of dollars for career fair real estate because that’s just what you do, even though the only companies who get ROI on career fair attendance are ones with preexisting brands. And, apropos, you want someone who can start building a sparkly brand for you from day one because building a brand takes time. (More on brand-building in the last two sections on marketing chops and evangelism.)

Sales chops are hugely important, and you can test for those

People often ask me if having an engineering background is important for technical recruiters. My answer to that is always, “Yes, but.” Yes, it’s useful, but the main reason it’s useful is that it helps build credibility and rapport with candidates. A good salesperson can do that without all the trappings of engineering experience. To put it another way, at the end of the day, this is a sales job. Great engineers who are shitty salespeople will not do well at recruiting. Great salespeople with no engineering background will likely do well.

So, how can you test for sales aptitude? If the candidate is currently an in-house recruiter somewhere, I ask them to pitch me on the company’s product. If they’re an agency recruiter, I ask them to pitch me on one of their clients’ products. Most recruiters do a decent job of pitching the company as a good place to work, but unfortunately, many don’t have a very good understanding of what their company actually does. Given that they’re the first point of contact for candidates, it’s really important to be able to answer basic questions about product-market fit, challenges (both product and engineering), how the company makes money, how much traction there is, what the competition looks like, and so on. Moreover, a lack of interest in something this basic points to a lack of intellectual curiosity in general, and in a technical recruiter, this is a very poor sign because such a huge portion of the job is picking up new concepts and being able to talk about them intelligently to very smart people.

You want someone who can write

I was on the fence about whether to include this section because it sounds kind of obvious, but writing well is important in this role for two reasons. First off, your recruiter is likely going to be the first point of contact with candidates. And if you’re an early-ish company without much brand, correspondence with the recruiter will likely be the first time a candidate ever hears of you. So, you probably want that interaction to shine. And the other reason you want someone who cares about narrative, spelling, and grammar is that they will be the arbiter of these abilities in future recruiting hires. Enough said.

One exercise I like to have candidates for this role go through is writing mock sourcing emails to people at your company, as if they were still at their previous position. This portion of the interview process is probably the best lens into what it’s actually like to work with the candidate. In particular, because candidates are not likely to have a clear idea of what they’re pitching yet, I try to make this part of the process iterative and emphasize that I welcome any number of questions about anything, whether it’s the company’s offering, what companies my firm works with, what certain parts of the engineers’ profiles mean, or anything in between. What questions people ask, how they ask them, and how they deal with the ambiguity inherent in this assignment is part of the evaluation, as is the caliber of the research they did on each mock email recipient.

You want someone with marketing chops

I talked a bit earlier about how you probably have no brand to speak of at this point. I can’t stress enough how much easier having a brand makes hiring. Until you have one, especially in this climate, you’re going to be fighting so fucking hard for every one-off hire. If you can, you ought to put effort into branding such that you end up in the enviable position of smart people coming to you.

So why don’t early-ish companies do this across the board? Brand building is a pain in the ass, it takes time, and not all of your outbound efforts are going to be measurable, which can make it harder to get others in your org to buy in. If you can find someone who’s had even a little bit of marketing experience, they’ll be able to identify channels to get the word out, use their preexisting network to help with outsource-able tasks, and get the ball rolling on things like hosting events, which, if you’ve never done before, can be quite intimidating.

And because recruiting doesn’t live in a vacuum and needs help from other teams to send something high-signal and genuine into the world, someone with some marketing experience will likely have an easier time getting other teams to buy in and put time and resources into this endeavor, which brings me to my next point.

You want someone who can fearlessly evangelize the importance of recruiting… and get you to take an active role even when you don’t feel like it

The harsh reality is that the primary reason companies hire their first recruiter is so that hiring can be taken off the plate of the founders. It’s tempting to have the “set it and forget it” mentality in a founder’s shoes — recruiters aren’t cheap, so presumably if you pay them enough, they’ll just deal with this pesky hiring thing, and then you can get back to work. I get it. Hiring isn’t that fun, and as a founder, despite having been a recruiter myself, there are definitely days when I just want to pay someone to, for the love of god, take this bullshit off my hands so I can get back to talking to users and selling and figuring out what to build next and all sorts of other things.

But it doesn’t work that way. If you’re a founder, no one can sell your vision as well as you. And all that experience you’ve built up that makes you a subject matter expert probably also makes you pretty good at filtering candidates. You might take a lot of what’s in your head for granted, but transferring that over into someone else’s brain is going to take time and iteration. And you can never really dissociate from hiring entirely because the moment you do, the culture of “hiring is just the domain of recruiting” is going to trickle down into your culture, and over time, it will cost you the best people.

In my recruiting days, at a high level, I saw two types of hiring cultures. One had the hiring managers and teams taking an active role, participating in sourcing, tweaking interview questions to make them engaging and reflective of the work, and taking time to hang out with candidates, even if they weren’t interviewing yet. The other type had the recruiting org be largely disjoint from the teams it was hiring for. In this type of setup, team members would view recruiting as a hassle/necessary evil that took them away from their regular job, and most of the remaining trappings of the hiring process would be left in the hands of recruiters alone.

You can guess which type of company ends up with an enviable interview process, a sweet blog, cool, hiring-themed easter eggs in their code, and a wistful, pervading, nose-pressed-against-the-glass refrain of “I wish I could work there”. And you can, in turn, guess which company demands a CS degree and 10 years of [insert recent language name here] experience in their job descriptions.

Despite these realities, founders and hiring managers often forget how critical their role in hiring is because they have a ton of everyday tasks on their plates. This is why having your recruiter be a fearless evangelist is so important. This person needs to cheerfully yet insistently remind the team and especially founders (who are, after all, the ones who dictate culture) that time spent on hiring is part of their jobs. This person needs to be able to march into the CEO’s office and demand that they go and give a talk somewhere or consistently block off time on their calendar every week to send some sourcing emails. Or that they need to write some stuff somewhere on the internet such that people start to realize that their company is a thing. Marching into a CEO’s office and making demands is tough. You need a person who will do this without trepidation and who will be able to convince you, even when the sky is falling, that a few hours a week spent on hiring are a good use of your time.

In addition to these points, all the usual thought points about hiring someone who’s going to be growing a team apply here. Is this person already a strong leader? If not, can they grow into one? Are they going to be able to attract other talent to their team? Are they someone you want around, fighting alongside you in the dark, for a long time to come? And, though in an ideal world I’d choose someone with experience who also meets the criteria I’ve outlined in this guide, if ultimately faced with a choice between experience and someone green with hustle, charisma, writing ability, and smarts, I’ll choose the latter every time.

1As an aside, this process is an unfortunate side effect of employment law meant to protect contractors from being exploited. The thinking is that by capping the length of time that someone can work as a contractor, you can exert pressure on the company to turn them into full-time hires who have to be given benefits. But as with many well-intentioned, regulatory pieces of legislation, that’s not really what happens in practice. The practical takeaway, though, is that if someone is great at recruiting, they’re probably not going to have a bunch of short contracting stints.

9 Responses to “A founder’s guide to making your first recruiting hire”

  1. Cody Voellinger

    Good advice as always Aline. Although, from what I hear startups are holding off on hiring internal recruiters this year, they are so 2015 🙂
    With hiring goals less aggressive, seems founders are opting for more flexibility by spending that money on recruiting agencies and tools instead of an internal recruiter who they might need to let go later in the year… Just what I’m hearing.

  2. Robert Hatta

    This is all great stuff around sourcing. But your first recruiting hire must also a great interviewer and evaluator of talent. Further, ( in the same vein as evangelizing the importance of recruiting, they will need to build both a consistent and accurate process for interviewing and drive interview training across the business. As much as most people suck at sourcing, more suck at interviewing. Founders included. This is another reason why hiring recruiters from the big brands is risky – they are typically only sourcing candidates and handing them off to a different team, not actually interviewing or driving a process to close.

  3. Matt Massucci

    Great post. Plus the person most likely needs to do all of their own scheduling. And then plenty of companies expect them to spend time doing HR generalist work. A challenging profile indeed.

    • aline

      Thanks! Fwiw, I would strongly, strongly urge companies not to put HR and recruiting on the same person… or even under the same umbrella period.

      • tim

        interesting. could you elaborate on why you would advise against putting recruitment & hr on the same person?

        • aline

          They’re completely different functions. One is much more organizational/administrative. The other is a sales/marketing job.


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