Practical recruiting guide
I sent this email to a portfolio founder a couple years back, and wanted to finally share it publicly. It’s focused on recruiting non-executive hires. Hope you enjoy:
Welcome to WIll’s Recruiting Guide! As promised are some thoughts and learnings that might be relevant to you. I roughly break things down into a few different categories.
For key roles, it usually takes months to hire properly. Don’t feel like you’re doing it wrong. In general, I’d expect you to take a full month to source, have dozens (hundreds?) of quick intro chats where you pitch the company and test fit, and several later-stage discussions.
Ultimately, you just need to put in the hours. It’s not uncommon to block out a few weekends to crawl LinkedIn. Make it a “virtual hangout while sourcing” event.
Step 1: Ask everyone you know for recs
This is pretty self explanatory, but there is a trick to getting this right.
When you tell someone “we’re hiring a VP of Marketing”, they’ll run a query in their head that asks 1) who do I know that is a fit for what I *think* the role is, 2) who would be interested in this, and 3) who is actively looking for a job.
This quickly filters down to zero or one people. Numbers 1 and 3 especially kill you.
To get around this problem, ask extremely specific questions.
Instead of asking “I’m hiring an Associate, who should I meet”, ask “hey founder friend, who was the smartest Associate you talked to when recruiting last year? Ok I’ll go poach them.”
Don’t ask “I need an engineer. Know anyone?” Instead ask “what was the coolest side project you’ve worked on? Ok who’d you build it with? Can you connect me? I’d love to meet them.”
Make it known to relevant investors that this is how you will measure their value-add. Especially for your company, the VP of Marketing role will be critical.
If needed, you can pay someone to make a list of companies that have been backed by high quality venture funds, or “companies to watch” lists.
We’ve literally made a spreadsheet with relevant companies and checked off each row as we parse the search results for relevant employees.
Reach out to everyone you find using email or Twitter DM, *not* LinkedIn. You can use RocketReach to find people’s email addresses.
The cold email must come from the CEO. Response rates are significantly higher because people feel special when the CEO emails them with a personalized note.. Yes, you will be doing dozens (hundreds?) of quick chats, most of which will be poor fits. But you need to lead with your selling process and assume that each email address could be The One.
In addition to your brute force LinkedIn sourcing, here’s a trick for finding great people you can get warm intro’s to:
As mentioned above, very few people give you meaningful recs when you ask them for leads. To draw recs out of people, find a personal friend of yours who you really respect and may be connected to relevant people.
Founder friends are often good targets here.
Pull up your friend’s LinkedIn profile, and simply click on their list of connections. (Note: not everyone makes this viewable.)
Look through all of their connections. You may be able to do a search for keywords with the filter of being connected to the person you have in mind.
Take the list you generate, go to your friend, and say something like “hey do you know these 10 people? Which would be good? Any that aren’t good fits but might have recs? Ok which do you know well enough to connect me?”
You’d be *shocked* at how many great people are right under someone’s nose. Asking for recs just doesn’t work. You need to generate specific names and ask friends for intros.
I’ll keep this section very short. AngelList A-List is good, as is Triplebyte. As is (shameless plug) Contrary Talent.
One of the most high-leverage things you can do is to make a fun and engaging jobs page or JD.
For example, Google used to make billboards and ads saying things like “Love hard problems? Visit [largest prime number you can find in a substring of the first 10 million digits of Pi].com.”
People would see the billboard, and when they solve the problem out of curiosity, they’d type in a number like 34710394727.com and get redirected to Google’s hiring/culture page.
This is easy to construct for engineering, but trickier for other roles. I’d get creative here.
Repl.it also had a cool jobs page that emulated a terminal/file system, and each file in the Repl terminal was a different role they had. Super interactive.
In the early days, I’d avoid online job applications, and instead say something like “Email firstname.lastname@example.org with a link to your personal website and something you’ve previously built.”
This signals a pragmatic, low-friction process that focuses on substance over form. Great people like that.
That’s it! Hope these tactics were useful or at least framed in a way that helps you think through this. Let me know if you want to riff on any of the above.