Holly Rose Faith | Executive Recruiting Playbook

Hi everyone. Welcome to Grey Matter, the podcast from Greylock, where we share stories from company builders and business leaders. I'm Heather Mack, head of editorial at Greylock. My guest today is Holly Rose, Faith Greylock's executive talent partner. Holly Rose leads executive and board level recruiting for Greylock backed companies. Matching high level talent to startups isn't as simple as finding someone with relevant industry experience. It's critical for a company early in its journey to have the right leadership team in place in order to scale to the next level, which means having leaders who truly align with the founding team's mission, values and culture to make it more difficult. The best executives tend to already have jobs and often aren't looking for new positions. But Holly Rose has helped dozens of entrepreneurs land executives for roles at startups such as Roblox, Nextdoor Gym, pageoy and Snorkel. Prior to Greylock, Holly Rose helped place executive talent for NEA and Khosla Ventures, and she started her recruiting and talent career at Bain and Company. Holly Rose says that successful executive recruiting comes down to having a system in place that helps you identify what you are looking for, who has those qualities, and how to conduct the process. Today, Holly Rose is going to walk us through the most important parts of the process. Searching for a candidate, interviewing, checking references, and if all goes well, closing the deal. We will also be doing future episodes with Holly Rose and folks from our network talking in detail about each one of these parts of the process. This episode is 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. Holly Rose, thanks so much for being here today.

Thank you so much for having me.

So 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.

So 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, you know, NEA prior to Greylock and Khosla prior to that. And one of the things I've been very conscious about is observing and learning early on in my career around what works well and what doesn't work well from recruiting executives into your companies. And that comes both from search partners, very senior executives spending time with leaders who have done this time and time again and 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. And the process can vary via company and there's 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 then making sure you really identify what you're looking for when you're trying to hire. And I think 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 their journey, just to.

Take a step back. The market right now is just very competitive and is going to continue to be for top talent. So the key is really kind of mapping out when you are kind of going to hire someone. What do you want to share about your company? So 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 could build a relationship now that five years down the road, three years down the road, is one individual that you may then want to recruit onto your executive leadership team. And to the question you asked, what should a company be prepared to share and what should they be doing before the search? So if we just start with the company piece I'm a big fan of writing out, what is the context that 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 like one, what is your company's mission? And you know, one or two sentences. This often worked 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 what is the current growth of the business and what has been forecasted for it. What for the specific executive search that you're hiring for? What does the team look like now? You know, save the candidate some time from Having to do a ton of research just laid out there for them. And then what makes your company unique? You know, what differentiates your business from other? Sometimes it could be an opportunity to share values, other times it could be, you know, something that is unique in terms of, you know, diversity numbers as another example. And then also, what do you want to cover in the conversation? What should you be prepared to share about your company?

Right, 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?

So these are all very kind of 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, 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. You know, at this point many VC firms have a talent partner or a broader talent function. So you can also 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 a 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 and then go through it in real time with them and get their feedback and see, is there something you need to tweak? Is there something 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. So the timeline of trying to recruit an executive could be much shorter when you do partner with a retained search firm versus doing it on your own. But it's really a personal decision pending the role and the function and what you're optimizing. For one example, within the Greylock portfolio, you is an enterprise technology company of ours in the data space that wanted to find a very senior VP of engineering. And so they did partner with an executive search firm and gave a very defined scope of, hey, here's what we're looking for. And we ended up finding the executive probably within about 45 days or so. Which in the executive search time frame, 45 days is actually relatively quickly. You tend to seek more of an average of 90 days. Now on the flip side, there's another Greylock portfolio company in the last year that wanted to bring on a VP of people and 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. So myself and the other co investors of ours, they also networked with executives who were currently in the space to kind of share, 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. And then the CEO did take more work upon themselves in terms of helping with some outreach, doing a lot of the first interviews, et cetera. If it was someone that was new to the network and both searches ended up with great hires, the one search 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 market and start interviewing any potential candidates, ask board members, advisors, etc. For interest to people who are high quality who have done the role that you're looking to hire for. I often call this calibration candidate. So at Greylock, before our founders start meeting with an executive search firm or start meeting with candidates, we introduce both executives from within the Greylock network and from outside of the Greylock network to just spend time with the founder CEO. It allows the founder CEO to ask any question that they want. We also have various interview guides that we put together around different functions that they can use and leverage to kind of find out more details. But. But it allows you to kind of 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 depending kind of what's, you know, how busy people are, your, 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 is, they want them for their company. How should they balance their efforts in trying 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 scorecard. 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. And having a bit of a mix in those four or five allows you to narrow down on 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 intro comes from a talent partner at a VC firm, they should be able to give you feedback from the candidate on what did they think of the conversation, what do they think about the opportunity, etc. And what you'll be able to gain across kind of those four or five and 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, they're very seasoned in their career, but they're really interested about 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 then there's two areas in which they would be growing in on that role and that's some of the things you'll kind of start to decipher from those kinds of conversations. When it comes to specifically with stretch candidates. Where I have seen some searches go a little bit off of the rails is 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 just partly because of one where they are in their career. But to just reflective of the market right now. Just 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. Like if there's someone you really want to hire, just kind of keep going for it, keep cultivating that relationship and you know, could be two years down the road or so and 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 background 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 to into another C level executive. But that's kind of more of a side tangent. And from there, as a CEO founder, you want to spend as much time as you can with the candidate up front, not only to evaluate for yourself but but also to kind of 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 of what do you want to focus on? You got to kind of get into the mindset of like what is a candidate 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 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 in the back of your mind that in this first interview you are selling pending where a candidate is in their current mindset, they might be fully employed, not actively looking. You want them to be hearing all of the great things about your business that are going to want them to continue on in another conversation. My last piece is 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 and how do they make decisions, why did they do certain things that they did at their company. And then when you think of the broader interview piece, you want to think of who on your team should be interviewing and that's, you know, the other stakeholders. So once you, as the CEO founder have determined, you know, well, 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? And then towards the end of the process when you know someone's a finalist, I also find it helpful to set up a Q and A or a brown bag lunch type session with the executive and part of the team that would inherit said executive as their leader. My biggest piece of advice though is you want to structure that in a way where they're learning from the executive. What can the executive share about their background, that 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 is when the end of the day the CEO is not owning the decision, they're getting a lot of buy in from the team.

What kind of questions should people be asking during the interviews and especially at different parts of the interview?

My recommendation is to build an interview guide. So 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 an executive will be introduced to a company, they'll start meeting with the executive team and everyone on the executive team and asking them the same questions. And 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. So if you have the competencies and the accountabilities for how you're going to be mapping this executive potential hire to have each person focus 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. So one of the more direct ways of doing that is to build a scorecard. And a scorecard is what are the outcomes and accountabilities and competencies that are going to measure whether or not this person is successful in their role. So when you start with the 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. So another way of thinking about it, what will this person do? And then competencies are really what is required to drive results. So what does this person need to know or have experience in in order to get us from point A to point B? So when you're building this scorecard, you, whoever's leading the search, whether it's a 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. That's because the goals are to prevent misalignment during the process. And then it also allows each interviewer 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? So 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 are 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.

And at what point in the process is it appropriate to start checking a.

Candidate'S references, it's going to depend on the candidates. There's two types. You have candidates who are confidentially looking and then you have candidates who are actively looking. If someone's actively looking, then it's probably 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. One thing that kind of helps lead to just overall positive signal. If you are kicking off a search and you're asking for various ideas of executives, of, hey, you know, are there people you have worked with, are there people you would advise that I talk to, etc. You can kind of start to get a little bit of positive signal. I wouldn't call it a reference, but it is a good indicator of, you know, people's outlook on said person and their skill set. One of the things like I always stress in the searches that I'm involved with, with, with referencing is 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, hey, you know, 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 kind of touch base with them? And that gives the candidate opportunity to then say yes or no. Do they feel comfortable? Do they not feel comfortable? If you know 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.

What are some of the fundamental questions they should be asking references?

So 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 the success for 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 the knowledge you think that reference is going to provide you. So one reference call may differ than another reference call pending that interaction that 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 a360 essentially is 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 okay 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 in the beginning and explain the intention of why you're doing this reference to kind of ensure that the transition is successful and obviously you know better. Help 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 what is 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 a 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 did they interact with one another. And then while you're doing all of this, you also kind of 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 that you use. And then to the question on kind of, you know, 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. It's more of things like how would you describe, could you comment on? Could you give me examples? From there, you then want to kind of zero in on the most important areas. So 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 from there you can kind of drill down further and further of each one. And when I say drill down, ask for example, to support the comments that the person made, whether they are positive or negative. So an example may be this executive was an excellent manager of their team. They were very well liked by the other executives. So then, you know, it's pretty, that's a pretty vague answer. Don't just take it for surface value. Then say, oh, okay, well, would you mind giving me example? When you say, you know, they were a really great manager 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.

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

To summarize some of the things that we've just already touched about kind of earlier on in our conversation. Heather is not having a scorecard, not mapping out the interview process. All of those things candidates start to pick up on. They'll say, it's unclear to me what they're hiring for. They didn't really seem to ask me questions about my background. And so that signals they haven't really define the role. So that's one piece of it. I think the second piece is the lack of follow up. So even if you meet with an executive and you decide, you know, maybe I don't want to hire this person right now, or they're not a right fit, or you do, or 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. At the end of the day, you want to leave that executive with the best possible impression of your company, whether or not they did well in their first interview. And so that happens both in how you treat them during the interview process or a 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, examples in the past of it was a CMO search and been going on for a while and it started to kind of have a negative effect on the company. One, because the founder wasn't following up after he met with executives. But then two, you know, the, the CMO community is relatively small at times, depending kind of, you know, if it's consumer, if it's enterprise, if you're, you know, what's the scope of the role? And so different executives knew, okay, you know, this company talked to this person, this company talked to 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. And so that kind of goes back to the role not being right, not following up, not asking the right questions, reaching out to people that you don't know well, early on in the interview process, ask someone's perspective. That stuff very much travels back to executives. But then on the flip side, I've seen sometimes in instances where a founder's not picking up on yellow or orange flags during an interview process that maybe this isn't the right executive for them. Like, 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 both sides, both from the candidate 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 quick 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 regards to, you know, a candidate's timeline.

So the most important part, what can you advise on closing the deal?

It's a great question. So 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 doesn't close like your top choice, you have someone you're equally just as excited about, but maybe there's some, like, slight nuances as to why they're not your number one. So that's kind of 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 a search partner can test, a VC talent partner can test. But there's hypothetical ways if you are working with a retained search firm or if a talent partner where that person, because they're more of a neutral third party, could say, look, they're really excited about you. How are you thinking about the opportunity? Right. 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 on that and lead with your best offer. A mistake I often see is people leave a lot of room for negotiation. And what can happen there is you're not leading with your best offer, you're leading with an okay offer. How does that feel to 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 okay 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. Then the emotions and the sentiment that they have because you did that only contributes to the likelihood that they're, that they're going to accept. If you get a verbal acceptance for a candidate or if they even sign an offer letter, you need to walk through with them. Or the search partner can do this or a talent partner can do this. Scenario planning. 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 amount of money or equity they could offer the executive to have them retain? And the scenario planning specifically helps the executive get in the mindset of how are they 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 you may lose on the executive because the company that they're at gives them something that no one anticipated or the executive is using your offer to leverage. There's a lot of different dynamics that play into it. And so what does work well is if you can kind of coach them on what is their rock. And what I mean by the analogy of the rock is what can your company opportunity, etc. Offer this executive that their current one cannot? And if the executive hasn't thought about that yet, it's an opportunity to then plant that seed so that when they are getting pressured and they're getting guilt and they're getting the loyalty type comments, 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 kind of continually allows them to go back and focus on that. Other techniques, when you are closing a candidate, you'll have board members reach out to them, have the other executives that they've met with reach out to them and extend their congratulations and how excited they are to work with them. Another piece is, you know, you and the other executives and the board members, et cetera, have spent a lot of time getting to know this executive. What are their interests? Like, what are their hobbies? Is there, is there something special that you could give them when you extend the offer? That signals, hey, we, we really want you outside of the offer, but we also think we know you as a person. So here are tickets to a baseball game or tickets to a museum or something that a gift card to a sporting goods store because this executive likes to run. I mean, there's so many different things you can, you can do there, but it's showcasing, hey, we know you as a person and we want to recognize that. And then, you know, 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 interesting.

Great advice. Holly Rose, thank you so much for being here with us today. I've learned so much and this has all been really interesting.

Thank you. Thank you so much for having me.

That concludes this episode of Gray Matter. If you enjoyed this interview and want to hear more like it, please subscribe to gray matter on SoundCloud, Spotify, or wherever you get your podcasts. You can also find all of our podcasts, essays, news announcements, and other Greylock content on our website, greylock.com and you can follow us on Twitter reylockvc. Hi, I'm Heather Mack, and thanks for listening.