The Executive Recruiting Playbook
Finding, Interviewing, and Closing C-Level Talent
Recruiting executive- and board-level talent to venture-backed startups is a competitive and ever-changing process.
That’s why having a solid (yet highly adaptable) system in place is critical for startups looking to land top leadership talent, says Greylock executive talent partner Holly Rose Faith.
“It’s key to put a process in place for any executive that you’re going to bring on to your team,” says Faith, who has helped place executives at companies such as Roblox, Nextdoor, Gem, PayJoy, and Snorkel.
This includes clarity on the company narrative and what context you’re willing to share with candidates, knowing what you really need in a hire at your current stage, and a clearly articulated strategy to get to know — and measure — the candidates you bring in.
As part of Greylock’s new “Brain Trust” series focusing on candid lessons and business advice from the most savvy experts in their spheres of specialization, Faith talks with Greylock’s Head of Content & Editorial Heather Mack about why finding the right high-level talent for your company is about much more than matching relevant industry experience.
In this conversation, Faith details search strategies, interview methods, effectively utilizing references, and how to best position your company to close on your top choice. Future episodes in the Brain Trust series will provide deeper dives into each part of the process.
Listen to the conversation here.
Holly Rose, thanks so much for being here today.
Holly Rose Faith:
Yeah, thank you so much for having me.
You’ve worked as a recruiter across a number of industries, and you’ve developed a playbook that obviously works well. Before we get into the nuts and bolts, why don’t you share a little bit of your background and some of the key learnings that you’ve found throughout your career?
Yeah. I’ve been in venture for about eight or so years now. And I’ve been fortunate to work at a couple of venture firms, NEA prior to Greylock, and Khosla prior to that.
One of the things I’ve been very conscious about observing and learning early on in my career is what works well and what doesn’t work well in recruiting executives into your companies. That comes from search partners, very senior executives, and spending time with leaders who have done this time and time again. What I have found is that it’s key to put a process in place for any executive that you’re going to bring on to your team.
The process can vary via company — and there are different things you can do to make it more authentic and true to your organization — but I think that’s one of the key learnings I have taken away. And making sure you really identify what you’re looking for when you’re trying to hire. Those are two of the first and foremost steps in any level of executive recruiting.
Let’s get a little deeper into that first step. When’s the right time for companies to reach out to candidates, especially if they’re particularly early in our journey?
Just to take a step back, the market right now is very competitive and is going to continue to be for top talent. The key is really mapping out what you want to share about your company when you are going to hire someone.
Your executive needs are going to vary as your company grows. Most of the time you start to bring on an executive at Series A and beyond. And sometimes at different points throughout your company’s journey, you may need to up-level an executive or bring someone in who’s more tenured. But if you are a seed-stage company, it doesn’t hurt to start networking with executives and building those early relationships.
I have the mindset that you can build a relationship now, that, five years down the road, three years down the road, is one of the individuals that you may then want to recruit onto your executive leadership team.
And to the question of what should the company be prepared to share and what should they be doing before the search: If we just start with the company piece, I’m a big fan of writing out or mapping out what context you’re going to want to share with any executive you engage with, whether it’s for networking or for an executive search.
And you can send this to them in advance of a conversation. You could also share this with them in the first dialogue. But what you really want to cover is: What is your company’s mission? in one or two sentences.
It often works well to then build into the story of: Why does your company exist, how did it start, and what are you trying to solve for? You’re going to want to touch upon the current growth of the business and what has been forecasted for it.
For the specific executive search that you’re hiring for, what does the team look like now? Save the candidate some time from having to do a ton of research, just lay it out there for them.
And then: What makes your company unique? What differentiates your business from others? Sometimes it can be an opportunity to share values. Other times it could be something that is unique in terms of diversity numbers, as another example.
And then, also, what do you want to cover in the conversation? That goes [back] to what should you be prepared to share about your company?
Companies that work with Greylock and other VC firms that have an in-house talent team have access to a lot of recruiting resources, but what about companies who are going at it alone? Should they try to find a search partner?
These are all very personalized questions you have to decide on your own.
If you do partner with an executive search firm, they take a lot off your plate in terms of helping with the scoping out of the role, building a market map of candidates, and doing the outreach to candidates. But I’ve also seen plenty of companies take that upon themselves.
Within the Greylock portfolio, I can tell you we have some companies that work with retained search firms, we have other companies that don’t, and then we have companies that do a hybrid of both. It really depends sometimes on the function you’re hiring for.
If you do have investors, many VC firms have a talent partner or a broader talent function. So you can leverage your resources, reach out to the talent team, and say, “Hey, I want to put together an interview guide for this upcoming position and the scorecard. Can you spend some time with me kind of walking through what you’ve seen? Do you have any samples that you can share?”
Then go through it in real time with them, get their feedback, and see if there is something you need to tweak or that you need to add.
If you do feel really crunched on time, which many companies do, working with a retained search partner is a great option because they do take a lot of that lift. They also have a fair amount of relationships with the executives that you’re going to be targeting.
The timeline of trying to recruit an executive could be much shorter when you partner with a retained search firm, versus doing it on your own, but it’s really a personal decision depending on the role and the function and what you’re optimizing for.
One example within the Greylock portfolio is an enterprise technology company of ours in the data space that wanted to find a very senior VP of engineering. They partnered with an executive search firm and gave them a very defined scope of, “Hey, here’s what we’re looking for,” and ended up finding the executive within about 45 days or so. In executive search timeframe, 45 days is actually relatively quickly. You tend to see more of an average of 90 days.
Now, on the flip side, there’s another Greylock portfolio company that, in the last year, wanted to bring on a VP of people. They had a very narrow scope in terms of what they were targeting. And instead of going to a retained search firm, they leveraged their network.
They touched base with the talent partners at their VC firms and myself and the other co-investors of ours. They also networked with executives who were currently in the space to share, [asking], “Hey, here’s the role that I’m looking for, do you have any ideas?”
And together, through various combinations, we probably put together a list of about 50 executives that could fit the profile. The CEO did take more work upon themselves in terms of helping with some outreach, doing a lot of the first interviews, etc., if it was someone that was new to the network.
Both searches ended up with great hires. The one that didn’t use a search firm did take a bit longer, but that company was also in a position where they didn’t need to hire someone within the next three months; they were comfortable if it was going to take six months or so.
If a company knows it needs a specific role filled, how do they go about figuring out exactly who might be a good fit?
The first step is to take a step back and think about the growth milestones you’re trying to achieve in your business. Do you have the right leaders in place to do this, or are there gaps that exist? I think that will help lead one to an answer with regards to: Do I need to hire this person? Do I not need to hire this person?
I’m personally a big fan of — before you go into the market and start interviewing any potential candidates — asking board members, advisors, etc. for intros to people who are high quality and who have done the role that you’re looking to hire for.
I often call this “calibration of candidates.” At Greylock, before our founders start meeting with an executive search firm or with candidates, we introduce both executives from within the Greylock network and from outside of the Greylock network to spend time with the founder/CEO, to allow the founder/CEO to ask any question that they want.
We also have various interview guides that we’ve put together around different functions, which they can use and leverage to find out more details. But [a “calibration of candidates” meeting] allows you to get a parameter with regards to: What should I be looking for? What’s the feedback that I’m hearing from other executives who have done this role before?
Other times people will reach out blindly on LinkedIn to executives. You can share what you’re trying to accomplish. I know that, depending on how busy people are, your response rate may be low. Sometimes it’s not.
There are so many impressive people in these fields. It’s easy to imagine that once founders know who the best are, they want them for their company. How should they balance their efforts to land those top, dream candidates — who might be extremely unlikely to even respond to them — with trying to gather a roster of more attainable candidates? What’s realistic?
When you kick off a search and you’ve done the calibration piece, you know what you’re going to hire for, based off of your score card. When you do go to market and you start meeting with candidates, you want your first four or five to have some similarities in the profile — but to also have some differences. Having a bit of a mix in those four or five allows you to narrow down what you are looking for, but it also gives you insights as to: How is this role resonating in the market?
If you’re working with a retained search partner, or if the intel comes from a talent partner at a VC firm, they should be able to give you feedback from the candidate: what did they think of the conversation, what did they think about the opportunity, etc.
What you’ll be able to gain across those four or five — I call it the first slate of candidates — is: are you going to be in a position to hire someone that maybe you didn’t think you could hire because they’ve done the role before or they’re very seasoned in their career, but are really interested in the space?
Or, based off of what needs to be done in the role, maybe it’s someone who’s more of an up-and-comer, where they meet eight of the 10 criteria that you’re looking for, but there are two areas in which they would be growing into that role. Those are some of the things you’ll start to decipher from those conversations.
When it comes specifically to stretch candidates, where I have seen some searches go a little bit off of the rails, is that if you only focus on stretch candidates, you just have to be really patient. It could take you a year. It could take you a year and a half.
Often, stretch candidates are relationships that you’re going to cultivate over time. You’re probably not going to enter them into a formal interview process right off the bat; you’re going to get to know them over coffee. You’re going to meet with them a month later for coffee again, and you’re going to more slowly try to pull them into your business. And that’s partly because, one, where they are in their career, and two, just reflective of the market right now, given how many opportunities there are for an executive.
If a company is not necessarily what they were looking for, it may take them time to start to see the bigger picture. But my advice is to not give up. If there’s someone you really want to hire, just kind of keep going for it, keep cultivating that relationship. And it could be that two years or so down the road, you get them.
Let’s talk more specifically about interviewing. Starting with: Who should be doing it?
Well, if we talk about the first interview: You as a CEO/founder want to be doing the first interview. If you’re working with a retained search partner, they’ll do the first interview in terms of getting someone’s full history, the talent partner at the VC firm will also have that too.
But in any executive role you’re hiring for on your team, whether it’s VP, C-level, or board, the CEO should be the first point of contact — unless the VP-level role is reporting into another C-level executive, but that’s more of a side tangent.
From there, as a CEO/founder, you want to spend as much time as you can with the candidate upfront — not only to evaluate for yourself, but also to build the trust and rapport should you determine that is the right executive for you.
And so when I think about that first interview, I break it down kind of into two buckets. There’s what to focus on, and then, secondly, how do you want to allocate your time together?
To the first part, you’ve got to get into the mindset of: What is the candidate’s mindset? What is the impression that I want to leave with this candidate? And then: What are the outcomes I want to take away from this conversation that are going to allow me to determine: Was this a good first interview? Was this not a good first interview?
And then, on the time allocation piece: In the beginning of the conversation, you want to set the stage. You want to set the stage for where your company is. You want to set the stage for how much time you want to spend sharing about the company versus how much time you want to be learning from them.
You also need to keep this thought in the back of your mind: