Founder's Guide

How To Find and Hire Your First Engineer: For Early-Stage Startups

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Hiring your first engineer at a startup is incredibly hard. As a founder, you’re already stretched dangerously thin on time. There are bugs to fix, customers to close and any number of urgent existential fires that demand your full attention. I’ve experienced this pain myself as the founder of two startups. I’ve also seen it as a partner at Y Combinator and through the hundreds of companies using Triplebyte for technical hiring.

The bad news is even once you find the time, much of it will feel like wasted effort. Hiring isn’t the kind of work that provides you constant dopamine hits like programming. It involves a lot of dead ends and frustration. This post is advice for early-stage startup founders who are hiring their first engineer. At this stage, traditional recruiting methods (e.g. hiring a recruiter) won’t work as well for you as they do for larger companies with brand recognition. I’ll talk through your options and discuss their pros and cons.

Before you start

Start by being clear on what exactly you’re looking for. In practice, hiring decisions invariably involve tradeoffs. You could trade quality for speed by rejecting solid candidates to wait for the dream one. Or you could trade money for time by paying a dream candidate above what you’d consider market rate to join now. Founders should be aware of all these tradeoffs and make the one that’s best for their particular circumstances.

I’d recommend starting by listing all the specific criteria your dream hire would have. This will be a combination of technical (are they a good engineer?) and non technical (would I work productively with them?). Then mark each candidate you interview against all these criteria and rigorously debate if you think they have enough strengths in some area to make up for weaknesses in others.

Where to find your first engineer

There are a number of ways to approach hiring your first engineer. I’ve broken it down by source/channel, in order of estimated effectiveness.

Note: As the founder of a hiring platform, I’m not neutral in discussing their effectiveness. I have articulated both their advantages and disadvantages.

Personal Networks

This is your most important source by far. As your startup scales it’ll become less important as you’ll have more budget to spend on recruiting tools and building a recruiting team. At the start though, it’s where you should exclusively focus your energy and only consider other sources when you’ve exhausted all possibilities here.

Hiring someone you’ve already worked with is your best option because you already know if you’ll like working with them. How much you enjoy working with any single person matters less as you grow larger; but for your first hire, it could be the difference between persevering to success and shutting down the company. (Caveat: startups are also uniquely stressful environments, and there’s still some probability you might not enjoy working with your friend under this kind of stress compared to when you were both at Google).

You’ll also have a better chance to convince someone you know to take a risk and join you. Asking someone to join as your first hire is requesting an order of magnitude greater commitment than asking an investor to invest. With personal connections, you’ll know what best motivates them — and you can lean on friends to convince them to make the leap.

Yet I’m surprised by how often founders don’t fully explore their personal networks for hiring. It’s easy to be quick in assuming that none of your friends are available before even asking them.

It’s understandable: asking your friends to leave their jobs and take a risk with you is scary. It’s also more awkward to be rejected by your friends than strangers. Still, if you’re optimizing for the success of your startup, you’ll have to put this aside.

Here’s a plan you could follow:

  1. Make a list of the best engineers you know, whether you think they’re available or not. Go through your Facebook and LinkedIn to jog your memory.
  2. Get lunch or dinner with them to talk about your startup.
  3. Make the ask – “would you consider joining us?”.
  4. Whatever they answer, ask a follow up question “if you did join us, which engineers would you most want to hire?”.
  5. Ask for an introduction to those people.
  6. Repeat 2 – 5 with them.
  7. Repeat 1 – 6 ad infinitum. I know public company founders who still do this.

Once you’ve exhausted this approach and you’re absolutely sure it won’t work, only then you should start considering other options.

Hiring Marketplaces

Newer recruiting startups like my company (Triplebyte) and Hired operate as marketplaces. There are candidates on one side and companies on the other. The value to candidates is increasing their number of options; and to companies, it’s reducing the time it takes to find the best talent.

These marketplaces are strictly inferior to using personal networks for your first hire. The good ones can attract high quality candidates, but most will want to work somewhere that already has an engineering team. They also charge a fee per hire that will usually be around $25,000 for an experienced engineer. Whether that’s good value for you depends on how much funding you’ve raised, and how much of your founder time you’d have to spend on making the hire.

Candidates on these marketplaces are also speaking with multiple companies, so you’ll face competition. You can get success though — we’ve had startups make their first hire on Triplebyte. Your results will depend heavily on how effective your pitch and closing process is.

At Triplebyte we’ve seen a lot of variance in how effective companies are at this. An engineer hired at Gusto through Triplebyte blogged about how much difference there is between companies in just being responsive. To get the most from a hiring marketplace you need a polished pitch for why your company is an exciting place to work and a speedy process for moving them from first call to interview and offer.

Despite the disadvantages, I still rank (good) hiring marketplaces as your second best option because they provide quick access to a pool of vetted, skilled engineers. The candidates on these marketplaces are mostly motivated to move jobs right now. You can quickly get on the phone to make your pitch and start interviewing the interested ones. This also helps you practice and improve both your pitch and calibration with your co-founder on what exactly you’re looking for. Getting better at pitching will increase your success at hiring in general.

Some of the marketplaces will also do a rigorous technical evaluation of the candidates before accepting them onto the marketplace. If that evaluation is done well, you can skip your own pre-onsite technical screening and expect a higher conversion rate of onsite interviews to offer which saves you time. (The average direct-to-onsite to offer rate for Triplebyte candidates is 40% vs the industry standard of 20%).

Generate Inbound

As an early stage startup you likely won’t get much inbound interest from good engineers, especially if you don’t have any press yet.

Post on job sites

The easiest way to generate this would be posting on job sites. With the exception of Hacker News, which is only available for YC companies, most job sites aren’t frequented by high-quality engineers. They’ll get you volume, not quality — and volume alone isn’t what you want. The majority of job applicants for any job posting are below the bar and it creates more work for you to filter them. The job postings I would recommend trying are on sites with a sizable engineering audience e.g. Stack Overflow Jobs, the monthly Hacker News “Who is hiring” thread (available to all companies) and Angel List.

Content marketing

You can also create content that appeals to engineers to generate inbound interest. This is especially easy if you’re working on a particularly exciting idea, e.g. self-driving cars. As soon as you publicly announce what you’re doing you’ll get a burst of inbound applications. As this type of startup, you’ll always have a hiring advantage by having an easier time getting press and building brand recognition.

Developer tool companies also have an advantage. Your product is already interesting to engineers and you should be investing in writing good quality blog posts about it – both to attract customers and hiring. Set a goal of writing an article that’s Hacker News front-page-worthy at least once a month.

If this doesn’t apply you can still blog about the technical choices you’ve made. Have you made any controversial or unusual choices in your stack? If so, write about them. You may alienate some engineers who disagree, but you may also capture the full attention of a few who agree strongly.

For example, Cognito has especially strong views on testing and wrote about how they use mutation testing. Not only does this get the attention of potential candidates, it creates content that you can also use include in cold outreach (more on that later).

Interactive content

A more time-intensive option is creating interactive content like coding challenges or puzzles, the Netflix algorithm contest being the most famous example. This can definitely work — Robby Walker, founder of Cue (acquired by Apple), wrote about how this worked well for them here.

It’s a high-risk strategy, though. If you can’t design something genuinely interesting, then spending time on this will be a boondoggle. If you’re confident in your ability to make something interesting, then go for it — but run the idea by some engineering friends first to confirm its worth spending time on.

Improve your job postings

Finally, your inbound conversion will increase with a higher-quality job posting. Invest time in making it stand out. Larger companies default to generic job postings that all look and sound the same (often because they’re literally using the same software to create them). As a startup, you can do better. You could make your job posting personal by writing about why you started this company and are excited to work on it. You could use an informal tone that doesn’t read like corporate boilerplate. Experiment with what feels right but move away from blandness.

Cold Outreach

Cold outreach involves messaging engineers online in some capacity. This could be on career/recruiting specific platforms like LinkedIn, or places online where engineers spend time like Hacker News and GitHub. (One advantage a technical founding team has here is they’ll already know the best places to look).

The challenge with cold outreach, especially on recruiting-specific platforms like LinkedIn, is the overwhelming number of messages good engineers receive on them. For your message to stand out from the crowd you need to put in work to make it personalized. Greg Brockman has some great advice on this.

You’ll also see a greater return if you can hunt down email addresses rather than sending messages. If you’re looking at profiles on LinkedIn, use the Connectifer (https://www.connectifier.com/) Chrome extension to make this easier. Otherwise, do what you can to find an email address (sometimes people include them in their forum profiles or google their full name to find a personal website that might have contact information). If you have any press articles or noteworthy mentions, I’d link to these too. You also need to follow up and expect it’ll take two or three emails before you get a reply.

This approach is how the majority of technical hiring, especially at larger companies, is done today. Teams of recruiters reach out to candidates and optimize their messaging over time to get more responses. There are tools to help you do this too e.g. Sourceress and ZenSourcer. If you send enough messages this approach will work and can result in great hires. You can find people just before they’ve started interviewing and if you move them through your process quickly, you’ll have a much higher chance of closing them.

The disadvantage: it’s very time consuming and will feel draining. The majority of your messages won’t get replied and you’ll be tempted to give up. This is part of what makes startups a grind – sometimes if other options aren’t working, you’ll have to commit to spending a certain amount of time per day sending emails and messages.

One time-saving trick you can consider is giving someone else access to your email (e.g. an admin) to send the messages on your behalf, and you just handle the replies. You have to gauge how comfortable you are with both the messaging and the person handling your email.

It’s hard to estimate how quickly you might be able to hire through cold outreach. If you’re lucky, you could get the right person in for an interview next week. More realistically, I’d expect this approach to take 3 – 6 months before it results in a hire.

Recruiters

Hiring a technical recruiter to make your first engineering hire is one of the tougher options for early-stage startups. What you need them to do is convince good engineers to meet you (sourcing). It’s very unlikely a recruiter could do this better than you as a founder. The best candidates are unlikely to reply to a recruiter message unless it comes from a company with a brand they recognize and respect.

What a recruiter does have is more time and focus than you are realistically able to allocate to recruiting. They can send more messages per day, and this could result in more engaged candidates than you if the gap between their effectiveness and yours is narrow enough. Larger companies have an advantage in making this strategy work because they can hire multiple recruiters and compensate for individual effectiveness with total volume.

If you go down this route, I recommend that you find recruiters who would work on a contract basis. You can agree on a rate per hour and a time period. Then, if they’re producing candidates, great! If not, you cancel the contract. Anecdotally, I’m noticing a trend where more of the best recruiters at companies are starting to move towards working as independent contractors.

Before working with a recruiter, make sure you’ve invested time in really training them on how to pitch your company well. I’d give them all the information they need, give them a day to prepare and then ask them to pitch it back to you. Only work with them if they do this well.

Meetups

Meetups are difficult to rank on this list because their effectiveness has high variance depending on both the type of event and who you are. Many meetups are primarily business conferences with corporate sponsors who send along some members of their IT department. These are almost certainly a complete waste of time. Smaller, informal meetups with a deeply technical agenda where people bring laptops and code can be great for meeting good engineers. Even these, though, will only be an effective strategy if you’re the right kind of person.

There are two types of people this is true for:

(1) Engineers who gain the respect of other engineers through technical conversation.
(2) Highly charismatic personalities

You need to honestly decide if you’re either of these. If you’re unsure whether you are (2), you probably aren’t. If you’re (1) and tend to avoid group meetups, you’ll have to get over this. If you’re the only technical founder, convincing engineers to join you is one sales job you can’t delegate entirely to your co-founder.

Even if you attend great technical meetups and you’re the right type of personality, it’s still unlikely you’ll make a good hire quickly through this channel. The better meetups have fewer people and they’re primarily not there to find a job. It’s a good way to build a network of smart people, which will become valuable as you scale, but they’re not a good bet to solve your problem right now.

Agencies

Traditional recruiting agencies tend to have bad adverse selection bias on the candidates they can engage. Most good engineers won’t work with them and the engineers that do are being sent out to as many companies as possible. I can’t think of a startup I know that made their first engineering hire through a recruiting agency. While I’m sure there are counterexamples, it’s more likely using an agency will suck up a lot of your time with little ROI.

Conclusion

As I said at the start, hiring your first engineer is incredibly hard unless you’re lucky enough to have a friend who you can convince to join. To make any other strategy work, you need to treat hiring like you did fundraising and start by refining your message and pitch. Candidates think differently than investors, and you’ll need to tweak the message that worked for your fundraise. Candidates will think less about your market size and more about your most interesting product challenges.

Once you understand what resonates most about your company with engineers, you can switch gears to working through channels to get that message out to potential candidates. Then be prepared for a lot of struggle and rejection until you find the right person. Good luck!

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Harj is co-founder and CEO of Triplebyte, a technical hiring marketplace used by companies like Apple and Dropbox to hire top software engineers. Previously he was the first new partner at Y Combinator since its founding and co-founded Auctomatic, acquired by Live Current Media.

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