Lessons Learned in Startup Recruiting

“The secret of my success is that we have gone to exceptional lengths to hire the best people in the world.” — Steve Jobs

How exactly do you “hire the best people”, and what is considered “exceptional lengths”? Over the past couple of years, I’ve been involved with recruiting at Spreemo Health, a startup based in New York City. Having experienced successes and failures in our quest to hire great managers, engineers, and data scientists, I’d like to share what I’ve learned. Some of my advice may be more tailored to startups in which there aren’t centrally-coordinated hiring processes / fully built-out HR functions, but the advice may also be generally helpful for first-time recruiters and hiring managers.


1. Figure out who you’re actually trying to hire

One of my biggest mistakes was not getting all stakeholders in the room at the beginning of a hiring process to develop an understanding of the ideal hire. You can read more about building candidate profiles at LinkedIn’s Talent Blog, but the main idea is that by thinking about your ideal candidate’s experience, goals, motivations, and concerns, you can better find the right employee since you now have keywords around their experience and hobbies, affiliated companies, or relevant schools with which you can search online. Plus, you can better screen candidates with every phone call and interview as you learn more about their goals, motivations, etc and compare it to your list of ideal traits.

2. Target candidates where they hang out

Another early mistake I made was paying to post our job description to every job board out there and hoping that the right candidates would magically find our posting and apply. Talk about naiveté!

These days, based on the candidate profile, I would try to find out where the ideal candidate is likely to spend their time and post accordingly. Are they regular attendees of specific meetups or conferences, are they likely a subscriber of Gary’s Guide or a regular reader of Hacker News, or are there any relevant industry / social organizations of which they will be members? If so, I would try to post a job ad or get a sponsored message directly into the community. If not, I would try to do targeted searches using LinkedIn and Google, an approach which you can read more about at RecruitLoop.

Lastly, you can leverage your existing employee base and the power of referrals to find your next employee. As a quick reminder, employees hired via referral are faster to hire, cheaper to hire, and stay longer than employees hired via alternatives methods (more info here). In this article from First Round Capital, Eric Feng (now a partner at KPCB) talks about the startup Flipboard’s policy of offering employees bonuses for referring hires. “At Flipboard, it’s part of our onboarding process. During that first week, new employees sit down with the recruiting team, and we talk about the referral program…while they’re together, new employees are even asked to do a quick pass of their LinkedIn and Facebook networks to jog their memory of any candidates they might know and recommend” Feng said. Another good practice is to highlight open positions at all-hands meetings.

3. Maximize the candidate experience by optimizing your process

According to the Google re:Work project (one of my favorite tech resources), the “candidate experience” includes every interaction a candidate has with a company, from getting an email that an application has been received all the way through to getting a phone call with a job offer. Given Google’s great guide on optimizing the overall candidate experience, I just want to focus on the number one thing you can do to make better hires: have the candidate do real work in their anticipated work environment.

While that isn’t always possible, some roles for which you may be hiring lend well to this exercise. If you’re hiring a developer, you can ask them to build a feature similar to what they would build on the job and give them a similar dev environment in which to do it. If you’re hiring a product manager, you can bring a user into the room and have the candidate gather requirements, create a spec, and communicate the feature to your dev team. If you’re hiring a data scientist, you can give them data and ask them to build a model and present it to the team. If you’re hiring an operations manager, you can have them spend a day learning a departmental workflow and then working with your team to implement an improvement.

4. Learn how to sell

The best candidates aren’t necessarily looking for a job, and even if they are they’re likely to be courted by multiple other companies at the same time. By leveraging social psychology and sales techniques, you can increase your chances of recruiting a specific candidate.

Starting from your initial reach out, beyond messaging the candidate via a personal email address (lots of services like Hiretual making finding an email address easy), you’ll want to leverage the in-group effect to get a higher likelihood of the candidate actually responding. You can do that by looking at a candidate’s LinkedIn and broader social media presence to get a feel for their hobbies, background, and skills, and then highlight a mutual connection in your reach out. For example, if a candidate also studied engineering, I would use the subject line “Hello from a fellow enginerd”, or if they also spoke French I would write “Salut d’un Fracophile à un autre” (Hello from one friend of the French culture to another). You can also have the hiring manager or a senior executive send the first email in order to demonstrate your affinity towards a particular candidate.

Following your initial reach out, you’ll likely have a screening phone call or introductory coffee. The call should be focused equally on understanding whether the candidate is a good fit for the position, as it should be on understanding their needs and desires. What are they looking for in their next position, what did they enjoy most and least in their previous position, why are they looking to leave, etc. These questions are important to answer in the initial call, because your competitive advantage as a recruiter will be in selling the company and the role with messaging that is specifically tailored to their interests and needs, a technique known as spin selling. For example, if you know they are highly motivated by an ability to make the world a better place, tell them stories about how you changed customers’ lives or are democratizing access to a product or service, and show them your CEO’s vision for future growth and even greater impact.

With respect to the on-site meeting, follow the re:Work hiring guides for best practices in structured interviewing and training your interviewers, continue learning more about the candidate’s wants and needs, and remember to prep your interview team as they will also need to engage in selling the candidate (e.g. they should not vent any of their frustrations around whatever current fires / life problems might be on their plate).

If and when you make an offer, have each person on your team reach out and congratulate the candidate, letting them know why specifically they would enjoy working with the candidate and what value they think the candidate can bring to the table. Lastly, loop in a senior executive or investor for breakfast or coffee to close the deal on an as-needed basis.

5. Be vulnerable

Whether you’re reaching out as a recruiter or as a hiring manager, it’s important to be vulnerable and share how you and the team are really feeling about the candidate. Otherwise, how can you expect the candidate to open up and share how they’re feeling about your company, role, and offer? I’ve learned to speak directly about things that might be truly awkward in order to better explore whether someone actually has weaknesses / traits that may be a deal breaker for the hire, or was simply a nervous interviewee. For example, “Hey man, you probably didn’t intend to, but a few people on the hiring team tell me you came off as a bit arrogant in that presentation. Have you ever been told that you come off as a bit dismissive before, is this something you’ve been working on, etc?” As another example, “I know you’re probably getting other compelling offers, can you walk me through how you’re feeling at this point?”