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If you’ve ever:
Well, you’re not alone.
We sat down with Zach Waterfield - an ex-YC Founder who’s led hiring across venture-backed startups and funds - and asked him about his approach.
Spoiler: He’s worked with 10-12 different search firms in his career and Artemis is the only one he’d work with again. And he means it: He’s brought us in to help him build teams at three different organizations… and referred us to countless others.
We covered:
👉 When does it make sense to work with an external search firm, and when should you go at it solo?
👉 What doesn’t work, and how can you avoid those common pitfalls?
👉 What to do when the role itself is unclear (and how that’s more common than you think!)
👉 Green and red flags in finding the right search firm… and the right candidates.
👉 What most companies get wrong with technical recruiting.
Whether you’re a founder or CEO hiring a technical team, a VC or PE operator hiring internally or for portfolio companies, or a C-suite or VP leader responsible for your organization’s next critical hire… buckle up. We have 3 organizations’ worth of learnings to share with you.
Zach worked with Artemis across three different hiring scenarios:
In all three scenarios, Zach and his team tried finding the right talent himself first. In doing that, he found:
Posting the job led to high applicant volume, but low relevance to his dream candidate: “You get a lot of people that just don’t fit what you’re looking for.”
But the catch: He didn’t realize this until he engaged with Artemis to run the search: “One of the things that Ashley [Sr. Executive Recruitment Consultant at Artemis] does well is almost everyone I've interviewed with is not actively looking. She's really good at finding people that are [currently working] in a job that is probably very relevant to what we're looking for, and she's able to convince them to come in and try to take a look. Sometimes, those people are not even looking at all.”
In the same way we tell sales leaders: Outbound sales is a skill. So is outbound recruitment. As Zach says, “It was very obvious that we couldn’t get the inbound talent we needed. So we needed someone to focus on outbound outreach.
But personally, I do not enjoy outbound. I prefer running the interview process once the candidates have come in and been pre-vetted.”
At Artemis, we often work with early-stage startups or companies at an inflection phase of their growth. In hiring terms, this means roles can be ambiguously defined.
Founders & hiring leaders know the outcomes they want, but may not have a concrete sense of the right role and scope to get them there.
Zach had a similar experience: “It happened every time we worked with Artemis… she [Ashley, Sr. Executive Recruitment Consultant] always came in and talked to all the stakeholders and understood [our needs] from different perspectives.
It helped shape the role.
I think one thing companies are really bad at is shaping their roles. They don’t actually know what they want until they see what they don’t want, and then they’re able to iterate through.”
With the help of a search partner, true requirements can emerge through (1) All stakeholders being asked the right questions as a forced reflection function, and (2) Candidate exposure.
Pioneer Fund was managing “hundreds of millions” under assets but didn’t have an engineering leader to build out their tech.
After spending months trying to find a Head of Platform Engineering on his own, Zach realized, “the fund was actually being limited by not having this person.”
You might be stuck in a chicken-or-egg situation.
You think you know what you’re looking for in an ideal candidate, but you need to actually meet with candidates to know for sure.
But what if your job postings aren’t attracting the right talent?
Unless you have a stellar employer brand (which you can learn about here!) you likely need to supplement with outbound, dedicated search efforts.
But of course: Ideally, you avoid the feedback & iteration loop in the first place.
Instead: By asking yourself and all stakeholders the right questions and getting timely market insights, you can save time by knowing exactly what you’re looking for.
Instead of starting with just a job description, Artemis:
When we asked Zach, he said: “Artemis took the time to understand our business. Ashley [Sr Executive Recruitment Consultant] talked to pretty much every stakeholder in the company, which was like 6 or 7 people to understand [the role] from all the different angles.”
Then, Artemis shared a “fruit basket” of candidates. In other words, they shared a variety of candidate profiles with Zach to get his feedback. By iterating on the ideal candidate profile up front, the search refined rapidly and Zach was already much closer to knowing his dream candidate profile before interviews even started.
“She [Ashley] sent me a link to your CRM where she had candidates shortlisted, and I went through and said yes or no. It helped her hone in on the types of people and backgrounds.”
We asked Zach: After Artemis helped you find your new hires, what changed for you personally?
He said: “It was nice to have the extra bandwidth on the team - that’s a big one.
The other thing that becomes obvious after you get the right candidate is that the fees are worth it.
During the process, it can seem like it’s a big cost because generally - especially at seed stage companies - you’re not spending that [money] on anything.
But ultimately, if you get the right person in the door, then it was worth it.”
We asked Zach what he sees other startups get wrong about recruiting. He says…
“It was very obvious that we couldn’t get the inbound talent we needed. We needed someone to focus on outbound outreach.”
“You’ll see companies in YC bring on 3 search firms and run them in parallel. They don’t get the value from them because they’re not working close enough with a single one and they’re comparing them…
It just runs into a lot of issues.”
“Make sure you get a good referral to a good search firm. I’ve worked with maybe 10 or 12 [search firms] and Artemis is the only one I’d work with again.”
“One of the things that companies are really bad at is shaping their roles. They don’t know what they want until they see what they don’t want.”
“So this is an interesting one. The best 3 engineers I’ve ever worked with had English degrees, not engineering degrees… I definitely don’t filter out people who are coming from a social sciences or psychology background because they think about things differently. They bring a lot of interesting perspectives.
“You can get more out of a candidate from an engineering perspective in situational discussions than deep technical interviews. Those deep technical interviews - especially with how AI is going - are becoming less and less important. It’s more about how they think about product and implementation rather than understanding the bits under the hood.”
Next time you feel like you’re spinning your recruitment wheels and not getting the needle-in-a-haystack talent you’re looking for, remember that you’re not alone.
Matchmaking is tough, especially when the stakes are so high. [The parallels between recruiting and dating never cease to amaze us].
And of course, we’re happy to chat to share our insights, advice, and explore if a potential partnership could help you land the dream candidate.
Until next time,
Read more insights from our team.
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Founded by Kristina McDougall in 2013, Artemis has grown to become Canada’s most trusted boutique executive search firm for startups.
We recognize that our work takes place on the traditional lands of the Attawandaron, Anishinaabeg, Haudenosaunee, and Mississaugas of the Credit. We honour Indigenous stewardship and commit to embedding reconciliation into our work, holding ourselves and our clients accountable.
