The Executive Recruiting Playbook

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.

Episode Transcript

Heather Mack:
Holly Rose, thanks so much for being here today.

Holly Rose Faith:
Yeah, thank you so much for having me.

HM:
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?

HRF:
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.

HM:
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?

HRF:
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?

HM:
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?

HRF:
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.

HM:
If a company knows it needs a specific role filled, how do they go about figuring out exactly who might be a good fit?

HRF:
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.

HM:
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?

HRF:
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.

HM:
Let’s talk more specifically about interviewing. Starting with: Who should be doing it?

HRF:
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:

My last piece is that you want to stay curious. You want your first interview to feel like a conversation. You don’t want to go in drilling them. You want to be able to pull out tidbits of their background: How do they make decisions, why did they do certain things that they did at their company?

Then, when you think of the broader interview piece, you want to think of who on your team should be interviewing — and that’s the other stakeholder. Once you, as a CEO/founder, have determined, “You know what? I like this person. I’m interested in them,” who are the other executives that are going to be a part of the interview process? Who are the board members that you’re going to want a part of the process? And then: Do you have any external advisors or experts that you would want to pull in?

Toward the end of the process, when you know someone’s a finalist, I also find it helpful to set up a Q&A or a brown-bag-lunch type session with the executive and part of the team that would inherit that executive as their leader. My biggest piece of advice, though, is you want to structure that in a way where they are learning from the executive.

What can an executive share about their background, their experience that may be helpful for the team to know, without putting the decision on the team? That’s where, in many executive recruiting processes, you start to kind of fall into pitfalls — when at the end of the day, the CEO is not owning the decision. They’re getting a lot of buy-in from the team, right?

HM:
Right. What kind of questions should people be asking during the interviews, especially at different parts of the interview?

HRF:
Before you even start meeting candidates, my recommendation is to build an interview guide. For each phase of the interview, which questions or which areas are your key stakeholders going to focus on?

One of the mistakes I see is that an executive will be introduced to a company, they’ll start meeting with the executive team, and everyone on the executive team is asking them the same questions.

What that signals to me, and what that also signals to the executive, is there’s not alignment on what they’re looking for, nor is there an actual process or structure in place in the background. If you have the competencies and the accountabilities for how you’re going to be mapping this executive potential hire, have each person focused on one of those. You can have one executive focus exclusively on culture and values that are important to your organization.

I’m a big believer in planning and scoping out and figuring out what you’re hiring for. You want to identify the key factors for the role and structure the questions around that.

One of the more direct ways of doing that is to build a scorecard: What are the outcomes, accountabilities, and competencies that are going to measure whether or not this person is successful in their role?

When you start with outcomes, that’s asking yourself the question: “Why is this executive being hired?” And then from there, it helps you establish the tangible and measurable accountabilities of how this hire will be successful.

Another way of thinking about it is: “What will this person do?” And then competencies are really: What is required to drive results? What does this person need to know, or have experience in, in order to get us from point A to point B?

When you’re building the scorecard, whoever’s leading the search — whether it’s the CEO or a retained search firm or a talent partner at a VC firm — that person needs to take it upon themselves to have buy-in from the stakeholders so there’s clear alignment before you even start the interview. The goal is to prevent misalignment during the process, and it also allows these interviewees to understand what they’re being assessed for and how a hiring decision may get made based off of their background or experience.

You want to keep the questions consistent across those candidates, not only in the first conversation, but with each interviewer. Each interviewer should be asking the candidates the same questions, so that you’re measuring everyone in the same way.

Now, when it comes down to the actual questions and interviewing, I’m a believer in asking open-ended questions, because a big part of what you’re doing in the time you’re spending with an executive is you’re trying to learn how did they decide, how did they make that decision?

When you lead with a question and an executive answers, it’s perfectly fine to then say, “Well, how did you decide on doing that?” Or, “What would you do differently? Who were the stakeholders that were involved in making those decisions?” And the more open-ended you can ask, the more insights you’ll be able to gain from that executive.

HM:
Right. And at what point in the process is it appropriate to start checking the candidate’s references?

HRF:
It’s going to depend on the candidate. There are two types. You have candidates who are confidentially looking and then you have candidates who are actively looking. If someone is actively looking, then it’s going to be a little bit easier to start checking references earlier on. If someone is confidentially looking, then you need to be hypersensitive, and likely build a reference process around what is going to be most comfortable for that candidate to not jeopardize where they are in their current role.

If you are kicking off a search and you’re asking for various ideas of executives, of, “Hey, are there people you have worked with? Are there people you would advise that I talk to?” etc., you can start to get a little bit of a positive signal. I wouldn’t call it a reference, but it is a good indicator of people’s outlook on that person and their skillset.

One of the things that I always stress in the searches that I’m involved with is that you don’t want to do any level of referencing if it’s going to jeopardize someone. I’ve seen countless times that people reach out to someone to get a data point not thinking about, one, how does that get back to the candidate, and two, does that put them in a compromising situation with regards to where they are?

If there’s an example in which you’re meeting with an executive and you’re very close to someone that they formerly worked with, I err on the side of transparency around saying, “Hey, we have a couple of overlaps in our network, of people you’ve worked with that we’ve worked with. Would you mind if I touch base with them?”

That gives the candidate the opportunity to then say yes or no, do they feel comfortable, do they not feel comfortable. If there’s a dynamic between someone you mentioned and an executive, it also allows them to be in a position to say, “Hey, feel free to talk to them, but here’s my perspective on that situation as well.”

HM:
Got it. What are some of the fundamental questions they should be asking references?

HRF:
First and foremost, when you do any reference checking, you want to plan in advance. And by that, I mean: You want to identify the key factors for success in the role you’re hiring for, and then orient your questions and the discussions around those topics. You also want to plan each reference call based off of knowledge you think that reference is going to provide you.

One reference call may differ from another reference call depending on the interaction that executive may have had with your candidate. The other piece you want to keep in mind is, when you are doing references, you want to do a 360, essentially. You want references from people who this executive has reported into, their peers, and people who have reported into them.

And so when you do ask an executive for their references, it’s more than OK to be upfront with that and say, “Hey, I’d love to talk to a couple of people in these three dimensions.”

Now, when you are doing a reference, you want to structure it in the beginning. Explain the intention of why you’re doing this reference: to ensure that the transition is successful, and, obviously, to better understand how to support this executive in their new role. Outside of introducing yourself, give some context on the company. Explain the role so that the person on the other end understands the situation that this executive could be walking into.

And then confirm the working relationship. I’ve been given references in the past where I’m so surprised the person actually hasn’t really overlapped or worked with that person that much. So then, to me, it signals maybe this isn’t a very good reference. Or maybe they’ve worked with this person for five years. You want to try and capture all that data in terms of how closely they worked with one another, how much they interacted with one another.

While you’re doing all of this, you also want to be capturing this in a Google Doc that you can go back to and reference — or Dropbox or Notion, whichever form of note capturing you use.

To the question on what are some of the fundamental questions, it varies. But my advice is to say, similar to an interview process, ask open-ended questions. Do not lead the reference or the question in a way that puts it in words where they can give you short answers, or they can say yes or no. Ask more things like: how would you describe, could you comment on, could you give me examples.

From there, you want to zero in on the most important areas. What are some of the behavioral competencies you’re trying to dig into? Are there specific technical skills and knowledge that you want to learn more about from this reference? What are some of the personal characteristics?

And then you kind of drill down further and further on each one. And when I say drill down: ask for examples to support the comments that the person made, whether they are positive or negative.

An example may be: ”This executive was an excellent manager of their team. They were very well-liked by the other executives.” So that’s a pretty vague answer. Don’t just take it for surface value. Say, “Oh, OK. Well, would you mind giving me an example? When you say they were really a great manager of their team, what are some ways in which you saw them manage their team that gave you that impression?” Because what you want to be able to do is walk away with tangible examples relative to that person’s prior work experience or current work experience.

HM:
What are some of the things you see founders or hiring managers overlook during the interview process?

HRF:
Probably, to summarize some of the things that we’ve already touched on earlier in our conversation, is: not having a scorecard, not mapping out the interview process. All of those things candidates start to pick up on. They all say, “It’s unclear to me what they’re hiring for. They didn’t really seem to ask me questions about my background” — and that signals they haven’t really defined the role.

So that’s one piece of it. I think the second piece is the lack of follow-up.

Even if you meet with an executive and you decide, “Maybe I don’t want to hire this person right now” or “They’re not a right fit” — or if you did have a great conversation and you want to continue on with them — you need to immediately follow up. You need to show appreciation for their time.

That happens in how you treat them during the interview process or your first conversation, but also in the follow up that you do. Do you just have a conversation and then never touch base with them? Those are things that candidates remember.

I’ve seen examples in the past. A search that was going on, it was a CMO search that had been going on for a while, and it started to have a negative effect on the company. One, because the founder wasn’t following up after he met with the executives, but then, two, the CMO community is relatively small at times, depending on whether it’s consumer or if it’s enterprise, or what’s the scope of the role.

And so different executives knew: “OK, this company talked to this person. This company talked with this person. What is going on in that company that they’re talking to all these different executives who I view as wonderful, but yet they’re not hiring anyone?” That goes back to the role not being right, not following up, not asking the right questions, reaching out to people you don’t know well early on in the interview process, asking someone’s perspective. That stuff very much travels back to executives.

But then on the flip side, I’ve seen instances where a founder is not picking up on yellow or orange flags during an interview process that maybe this isn’t the right executive for them. They have incredible experience, but they’re saying certain things about how they treat their team, and they’re taking it at surface level versus digging into it further.

So it kind of goes on on both sides: from the candidate’s experience, but then also for a founder picking up on certain cues that may signal this person may not be right.

I’ve also seen missed opportunities of not moving quickly enough on a candidate — where you do interact with someone who is excellent, but you decide, “I want to see five more people.” Which is fine, it’s 100% your choice, but that doesn’t mean that executive is going to wait around. So sometimes there’s a timing piece, too, that gets overlooked with regard to the candidate’s timeline.

HM:
The most important part: What can you advise on closing the deal?

HRF:
It’s a great question. You get a candidate towards the end of a process — and in an ideal scenario, you want to have two finalists, because if your first finalist, your top choice, doesn’t close, you have someone you’re equally just as excited about, but maybe there’s some slight nuance as to why they’re not your number one. But that’s just a process touch-point.

First and foremost, you should not extend an offer to a candidate if they haven’t given you the signal that they want the job.

This is something that you can test; it’s something the search partner can test, a VC talent partner can test. But there are hypothetical ways, if you are working with a retained search firm — because they’re more of a neutral third-party — to say, “Look, they’re really excited about you. How are you thinking about the opportunity?”

So you want to get into the mindset of, “Would this candidate accept the role?” If they do, you need to know their comp expectations and what’s important to them. Are they optimizing for higher cash? Are they optimizing for equity? Are there certain thresholds they have, maybe because of a family or a current life situation, that you have to be conscious of? I’m also a fan of the comp piece coming up earlier on in the interview process.

But when you do go to extend an offer, in an ideal scenario, extend that offer in-person. Meet with that executive one-on-one, tell them why you’re excited about them joining the team, how you think they’re going to contribute to the business, and hand them the offer in-person.

Right now it’s a little bit tricky, in our current world, but if there’s a safe way of doing that, I advise it.

And lead with your best offer. A mistake I often see is people leave a lot of room for negotiation. What can happen there is: You’re not leading with your best offer, you’re leading with an OK offer. How does that feel as the candidate on the receiving end? Does it signal you really want them, or does it signal: We want you, but we think you’re going to negotiate, so we’re going to give you an OK offer? Lead with your best offer.

Make it known it’s a really strong offer. If it is, the candidate on the other side of that will 100% feel it. And the emotions and the sentiment that they have – because you did that – only contribute to the likelihood that they’re going to accept. If you get a verbal acceptance for a candidate, or if they even sign an offer letter, you (or the search/talent partner) need to walk through scenario planning with them.

When they go to put in their notice, have they thought about the questions their company is going to ask them, what they may say or do to keep them? Is there an amount of money or equity they could offer the executive to have them retain? The scenario planning specifically helps the executive get in the mindset of how they are going to answer those questions. Are they prepared for that?

Unfortunately, there are some instances where an executive hasn’t done that, no one tests them on that, and then what ultimately ends up happening is that you may lose on the executive because the company they’re at gives them something that no one anticipated, or the executive is using your offer to leverage [them]. There are a lot of different dynamics that play into it.

So what does work well is if you can coach them on what is their “rock.” What I mean by the analogy of the rock is: What can your company, opportunity, etc. offer this executive that their current one cannot?

If the executive hasn’t thought about that yet, it’s an opportunity to plant that seed, so that when they are getting pressured and they’re getting guilted and they’re getting the loyalty-type comment, they’re able to say, “Look, this is really what I want for my career. Here’s what this opportunity is going to provide me. I’m very excited about X, Y, and Z.” And the rock just continually allows them to go back and focus on that.

Other techniques when you are closing a candidate: Have board members reach out to them, have the other executives that they’ve met reach out to them and extend their congratulations and how excited they are to work with them.

Another piece is you and the other executives and board members, etc. have spent a lot of time getting to know this executive.

What are their interests? What are their hobbies? Is there something special that you could give them when you extend the offer?

Offer tickets to a baseball game, or tickets to a museum, or something like that. A gift card to a sporting goods store because this executive likes to run. I mean, there are so many different things you can do there, but it’s showcasing, “Hey, we know you as a person and we want to recognize that.”

And then often, too, include some company swag. It could be a sweatshirt, it could be a bag, but it’s kind of all-together the entire package of, “Hey, we’re excited to have you. Let’s make this work.”

HM:
Interesting. That’s great advice.

Holly Rose, thank you so much for being here today. I’ve learned a lot, and it was all really interesting. Thank you so much.

HRF:
Thanks for having me.