The do’s and don’ts of scaling from dozens to thousands of employees — McKenna Quint

[00:00:00] There are aspects of the Google experience that are just very Googly. Like I can't tell you the number of startups that I've talked to you. They're like, oh yeah, we have a five point rating system on our performance reviews. And I'm like, why, why is your talent that differentiated? Like you have 50 people in your company, how are you rating them on a scale of one to five?

And also how are you paying them that differently? Like where's that money coming from? So there are definitely aspects of it that I think a lot of people have copied and pasted that they should be very wary when they copy and paste. And they should think about the context under which Google build those things and not emulate it.

[00:00:45] Welcome to in depth, a new show that surfaces tactical advice, bounders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Berson, a partner at first. And we're a venture capital firm that helps startups, like notion, roadblocks, Uber, and square tackle company building firsts through over 400 interviews on the review.

We've shared standout company, building advice, the kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it with our new podcast. In-depth you can listen into these deeper conversations every single week. Learn more and subscribe today@firstround.com

today's episode of in-depth. I'm really excited to be joined by a mechanic. Quint McKenna was most recently the head of people at plaid and she previously built and led the people team at the self-driving car company, cruise automation. She's currently a talent consultant and seed stage in back. McKenna calls herself a glutton for punishment.

She's particularly attracted to startups that are in the messy, ambitious scaling phase of the company. So in today's conversation, we focus on the people, challenges that inevitably crop up when you're going from a couple dozen employees to a couple thousand as all here in this interview, McKenna has a really unique point of view on this problem.

Set. She's a former operator that approaches people problems with a slant towards analytics and frameworks. We start by discussing when startups should draw from established playbooks in the people space versus when they should start from first principles. She also dives into the details of bringing her data mindset to the people's space, including designing a sophisticated attribution.

Next, she tackles some of the questions she gets most often from startup founders, including whether the company should introduce levels, what to look for in your first people leadership and how to approach performance reviews. Totally. We dive into a larger conversation about the roles that companies play in today's employee experience from the company cultures that she most admires to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she's ready to leave behind.

During this conversation, she references a few different books and articles that were particularly impactful for her development as a people leader. And we've included the links to them in our show notes. Today's conversation is a must listen to for HR leaders, of course, but also for folks that startups across the org that want an inside look at what's top of mind for people leaders today, and the systems behind the scenes that powers startups to reach new Heights.

I really hope you enjoy this episode. And now my conversation with McKenna. Well, thank you so much for doing this with us. 

[00:03:57] here. I thought maybe we could start by broadly exploring the topic of company scaling and people scaling, and then we can kind of go, go down a bunch of different paths.

I'd be interested in starting by maybe talking about what are the things that you've seen happen over and over again. When you scale a company from dozens of people to a thousand or 2000. So 

[00:04:19] I have basically made every career choice based on whether or not a company is going through an ambitious scaling phase.

I don't know why these are the types of things I'm attracted to. I think I just must be a glutton for punishment, but from co to, to cruise to plod, I've been with companies that have grown really, really quickly. And so a lot of what I have worked on and is in my playbook is how to build things that can scale very quickly or being able to figure out when's the right time to knock something down and rebuild it.

And within the people function in particular, there are various different. Milestones where it makes sense to have certain things in place. Like when, you know, you hit 50 people, you're going to need some managers. So you're going to need to make sure you've identified the right ones. They know what they're doing, and you need to know how to train them.

When you get to the point where you need to have managers managing managers, you have to have a new set and level of expectations and supports and all that. So there are certainly some infrastructure, things that look the same from place to place, kind of similar, all are on recruiting. Like you need to be able to have a repeatable process for identifying the right talent, evaluate weighting them and getting them converted and working at your company.

So some of that stuff, some of that scaffolding tends to be the same, but. Even with the companies that I've worked at scale can look very different. And so really the devil is in the details with how you implement it. So for example, at cruise, it was in R and D mode. The entire time I was there, once fundraising was done, you didn't really have to worry about revenue too much growth was then able to be planned well in advance.

So we always knew three to six months into a 12 month period. I knew how many people I was going to need to hire and what the people programs are that I needed to have in place to be able to support that scale. But the unique part of that challenge was like the. Space that it was in and the insane competition that we had with other AAV companies for a really small pool of highly motivated and highly capable ML talent.

And so that was like one unique piece of how to identify and attract those people that we had to figure out. And the other challenge of that scale was we had to build out a really large contingent workforce that was co located like in our offices who needed to figure it out. How to make the experience that those folks had as consistent as the experience of a full-time employee.

So those were some of, I think the unique challenges at cruise and at plaid, we do have revenue and the focus is more on building out the maturity of its profile and then choosing what new products to build and how to get traction in them. And we had to navigate through COVID where growth couldn't be planted advanced, and you had to take it week by week, month by month, and build an, a ton of flexibility in particular to our recruiting team, to be able to.

Scale up and scale down, hiring as quickly as we needed to. So those are some examples of like, even within companies that kind of look pretty similar from the outside, just how different some of the people challenges could be. I feel like one of the most frequently cited examples of when not to stray from a playbook is, and when it comes to manage your training, like when, you know, you have managers, you need the manager training and all that.

Yeah. I think one of the things that I've always found very interesting is when companies overturn those assumptions. And I heard a story of over at Pinterest where they knew they were going to go through a very insane growth period within one of their product lines. And there was going to be a lot of growth and they were expecting, you know, average turnover.

And when you did the math on average, someone would have like maybe two to three managers in a single year. And instead of focusing on training up those new managers, like one would think you would do with that repeatable playbook, they thought, you know what, why don't we just focus on empowering? The individual contributor is to navigate that framework.

So they invested a lot in the other side of the training playbook. So, yeah, I think it's just a lot about the business context and just paying attention to the unique challenges there to make sure your playbook isn't getting rusty. 

[00:09:03] How do you think about the problems that need to be fixed now versus yeah, it's kind of fine.

It's not that big of a deal because there's always an unlimited amount of effectively broken things or things that you could work on. 

[00:09:18] Oh yeah. I think that is one of the harsh realities that anyone realizes when they join a company, that's either like going through that scaling period or has gone through it and never looks all that great.

Under the hood. They might have fancy websites that have beautifully articulated employee value propositions, but if there was a little bit more funky on the inside, the way that I have always. Try to approach this as one, making sure that you have the right ear pieces in place and you're listening and all the places that you should be listening, whether that's through pulse surveys or your HR VPs who are sitting in on various team meetings, you're just getting, as you know, a people leader, a lot, a lot of information and.

Then it's up to you to figure out, okay, now that I have the ability to do these really broad sweeps and get as much comprehensive information about what's happening in the company as possible. Now I have to make sense of it. Now I have to identify which of these things are problems to solve now, and which of these things are problems to solve later?

I think the way that I've differentiated. A lot of those things is having frameworks for identifying whether things are emerging trends, mature trends or past trends. And you can build out certainly these frameworks with your HRBP team who are some of the most frontline people out there. And you can say, okay, these types of things that are happening, maybe these would be easier.

These would be P one. These would be P two type things. And we'll take a look at all of those things that happen over the course of every month. We'll reflect on them and we'll say, okay, where are these things? Issues? Is our attrition risk pretty high with this team or not? I feel like if you have all of the right things set up, you're not going to make any dire mistakes.

If you're finding the problems after they've happened, you're really not doing your job. Your job is to make sure that the problems don't get past the point where they can't be addressed. So I feel like in figuring out what's just a cough, cause there's dust in your throat, or what's a cough because sickness, it's really just having the right listening pieces in place, gathering that information all the time and making decisions on it, on the fly.

And also making sure you understand, like, okay, what are the basic things that I, as a people leader need to be worried about? I need to make sure I have identified the roles that the company needs, that I can identify the people to fill those roles. I can build that talent, or I can buy that talent. And then I have to keep and develop that talent.

And if all of those things are going right, then coughs can be assumed to be things with Dustin the throat. But if one of those things is wrong, then you're in a bad place. 

[00:12:13] In terms of being somebody that's more analytical, I'm curious. What's the other data that you saw run your part of the business on?

Like, what are the top 2, 5, 10 pieces of data that you're constantly looking at and maybe what are you looking for? 

[00:12:29] So pretty early on at cruise, we built out a fairly robust predicted attrition model and our predicted attrition model had a bunch of things in it that companies probably only the size and sophistication of like Google were thinking about based on what you've typed in is your home address.

And our HRES, we're going to calculate your commute. And we're going to multiply that by the number of times you have to come in during the day. And we're going to correlate that to what we think is your tenure, because we think that basically your commute means you can only last at this company, like two years based on other data that we've gotten from other companies.

So that's. Has always been something that building out kind of a more robust attrition model is something that I have always done and always paid attention to because I think there's the shifts in that model can be very interesting to look at other pieces of data that I tend to look at. I think maybe the more interesting part is how I shift looking at different metrics based on like what the challenges are.

For example, earlier this year, you know, pod fundraised, and we were able to attract a ton of talent and our offer except rates, which is typically a metric that I look at, you know, was doing well. And I thought, okay, that's not the metric I need to be looking at. I need now to be looking at some of the information that we're getting from.

Feedback scores and evaluation and time to hire and making sure that all of the metrics that indicate the quality of our process, that those are the ones that I ended up looking at. So I don't know if there's like one or two that I always look at besides target to actual with recruiting and attrition, but there's a lot that'll gather and look at just below the surface and shift my focus based on what the evolving context of the businesses.

[00:14:26] Can you talk more about how you designed this attrition model or what are the inputs or how do you use it on an ongoing basis? 

[00:14:33] Yeah, there were a number of different things that we ended up looking at predominantly from information that we just had in our HR system. So it looked at people's commute. It looked at whether or not they had made an important life transition.

Did they get married? Did they have a kid? One of the things that I think. Companies like Google that have done extensive research into organizational science have taught us is that there are certain psychological moments in one's personal experience, as it relates to the company that impact whether or not they'll stay or they cause pause and reflection.

When was the last time that someone had gotten promoted, have they received multiple needs improvement, performance scores? There was so much data that we looked at. And it basically was just trying to figure out is there's something happening at work or is there something happening outside of work that we think is going to cause you to evaluate whether or not this is a fit.

So should we have a conversation with you about that to make sure we're aligned, right? Because if we're not aligned, then I want you to go find something that's better. We should have that conversation early. Or is there something that could potentially make you unhappy? And we predict the, you would a trip six to eight months from now or something like that.

First of all, it's, it's kind of creepy science, HR systems hold a lot of information about people. So you need to make sure if you're going to build something like this, that your employees know that this is something that you're putting together, who is actually going to see the data and how they're going to use it.

So if you're thinking about building anything like this, just make sure that it's something that you're very open. 

[00:16:24] And so did you tend to leverage this information more on an ongoing basis? Or you hire someone in the mental model would be like a customer health score or you're like, oh, this customer may churn.

Let's go focus on that. Or was it used in some other way? 

[00:16:38] I'm mostly focused on retaining people. So mostly focused on, okay. Is there something, again, happening in this person's experience that would warrant what we call a stay interview or a conversation that we have with you that basically asks all the questions that you would in an exit interview, but it's far more useful because you do it when you're there and you can ask them questions like, Hey, are you happy here?

What are some of the things about this experience that you would change? If you could, what are the ways in which we can support you better in your role? It was really designed to be able to figure out you're growing at a really high pace. And you have a lot of busy people. How can we figure out who to prioritize those conversations?

Yeah. Besides the folks that you might more typically go to, which would be like your top 10% talent or your senior leaders. This is a model that helps you figure out if there are other folks that should have those conversations. 

[00:17:35] Are there other tools or rituals, practices or frameworks a bit similar to what you designed with this attrition model that maybe are a little bit different or weird or not talked about for early stage companies that you've implemented or operationalized over the.

[00:17:52] One of the things that I don't think it's hard to overinvest in from a people function is that analytics mindset and the tools that can enable some of these things to happen. They're really, really helpful when you're growing really quickly because that data can help you figure out what to prioritize.

But I think that's certainly something that is a tool that is important to implement early. Another thing that I don't know if it's a tool to implement early, but maybe like a mental model to think about is, and I forget someone tweeted about this recently and I'm not going to properly credit them though.

I should, if I figured out who it is, we can credit them. But someone tweeted about how. It's an old school way of thinking about people as a percentage of your overall head count. So you shouldn't have like one HR person for every 75 or a hundred people. That's like what's on the Sherm website or whatever.

And that is something that I've absolutely tried to stay away from. I think there are some aspects of the people function that can be viewed in that way and is how many companies would evaluate them. But there are so many different types of teams underneath the people function that need a more dynamic operating model recruiting needs to be based on your head count growth.

Your learning team should be based on your specific model and strategy for what learning means to your company. Your HRBP team should have a different model based on the complexity of your organization. Right? It shouldn't be like one HRBP for every 250 to 300 people or whatever it should be. How complex is your operating structure?

Are you in one geography or 15? Are you functionally aligned or are you business unit aligned or are you a weird mix of both? If you're like a platform company. Right. So one of the things that I've also, I think brought is just a different way of thinking about how the companies I work in cannon should invest in the people function so that it's not viewed as this holistically back office operations function.

That should be a certain percentage of head, but. 

[00:20:05] That makes sense. It's the concept, that context is perhaps the most important thing. And many of these things are quite nuanced and are in service of some sort of outcome that you're trying to create. 

[00:20:15] Yes. Yeah, for sure. And they're just depending upon how you think about your people function, you could think of it as just a service function.

That's one way to think about it. I don't think that's the right way. That's not a company that I would join, but there are different teams under the people function that are not just operations focused. And so making sure that you have different operating models and ways of thinking about head count and using those teams is important, 

Isn't the right mental model. What in your worldview is. 

[00:20:46] The most common HR organizational structure now is the three-legged stool. So it's part service part center of excellence and part partnership. I think Deloitte is come out with a slightly different version of that, but I think it's kind of all hovering around the same thing, which is parts of the people organization should be service aligned.

If you have a question about what's in your paycheck and how much got deducted for what, there should be a service for you to understand that, but there's also an aspect of it that is partnership focused. And so that is a kind of talked a little bit about from the HRBP perspective that needs to be built out in a different way, based on the.

Type of partnership that needs to be done. And based on the complexity of what that partnership is, so kind of similar to how you might structure any team that works on different types of accounts that might have high complexity cross-sells or upsells, right? You would staff that differently than you would a more traditional.

Management team. And then, like I said, for learning or for what might be a center of excellence, companies can take really different strategies with learning and it can be based on a business need, like Intel and GE built out business leadership development programs. And it was based on the number of GMs that they needed.

And so the number of people to build what that training needed was what that learning team needed. Airbnb uses a model where their learning team focuses both on internal, as well as like external education for hosts that can't be viewed as a percentage of your head count that has to be looked at as what's happening in Airbnb's case with a host.

So I think it's just making sure you'd know what the function of each of those teams are and yeah, making sure that the operating models right size. 

[00:22:48] When we started chatting, you were mentioning that you orient and tend to be more operational and business oriented, as opposed to maybe some more the orientation of other people leaders.

Can you talk a little bit about that and maybe how it relates to the ideas that you were just sharing? 

[00:23:03] Yeah. I say this because one in talking to many other founders, just by virtue of the companies that I've worked at, I often. Founders and advisors and investors calling me and asking me questions. And a lot of them say, I want to hire a people person.

And I want you to tell me if I should hire someone with an HR background or someone who's been an operator and can move into HR. And I think what they want to hear from me is like, oh, you're an operator who moved into HR. Tell me what I suspect, which is this is a good profile to hire for. And I say it is certainly something, it being an operations focus experience in an analytic mindset, someone who understands what it's like to be in the business and understands common mental models and frameworks that are used, that stuff is important, but you have to have someone who understands what they don't know.

And certainly if I could rewind my own experience, I think I came into this work with. A lot of humility and networked and ask people who worked in HR, like who are the best people to learn from, how do I do this? Where are the tools who are the mentors that I need and was able to amass that very quickly.

But one of the things that I really don't do so well, and that certainly is a risk with hiring someone who is an operator, analytical is managing the organizational psychology of a company is really tough. And that is what people who have HR backgrounds are trained to do. So. Well, I think a lot of the leverage within the people function that has yet to be realized, can be found by hiring operations, focused people on analytics, focused people, especially as we move to remote work, which is something we can talk about too.

That is a background that you certainly need to hire for, but it can't be at the expense of like not hiring people who have been in this discipline and understand it really well. That's why I kind of still still like Lazlo box model of hiring a third, a third, a third. It was a third consultants, I think a third analytics focused research focused folks and a third HR practitioner.

[00:25:26] When you talk about organizational psychology, can you expand on that dimension of the role and the process? 

[00:25:33] Yeah. I think one of the things that a lot of the people who I have learned from in the people space is just how people work together in groups and in systems. And that is a discipline that people that people learn.

And it is a really important one for anyone who is in this field to understand, especially in growing companies where feelings of how to manage the company's approach to conflict is very important. You have a conflict avoidant culture, you have like a conflict, aggressive culture and people who understand that that's a basic concept and organizational psychology are going to be really fast to figure out what the company is and what it needs, and therefore, how to train people to operate effectively within that.

And I don't think that all folks who come from an operations background really understand that that's a huge part of this work and making sure that. A bunch of people can work really, really well together. It's just not something that I certainly learned. It was something that I, I had to learn. 

[00:26:40] And so what did you learn about that?

Or what are the most important, maybe high-level concepts that show up in the way that you run your sort of side of the business. I 

[00:26:50] think one of the ways in which it kind of shows up is in one of the qualities of people, leaders that I think is really undervalued, which is the question you asked me, especially for companies that are growing and that is in your people leader.

I would look for someone who is really good at storytelling, because I think one of the things that I've learned certainly about startups is that the one constant in startup is change and humans are not awesome with change. Like change makes us deeply uncomfortable. And so if you have someone who with an HR degree learned about change management, or has the innate ability to understand.

How people feel when they're confronted with change or uncertainty and how to tell them a story about how it's going to play out, how they can use that opportunity to their advantage. Someone who is telling this story from a place of having seen it before, or kind of knowing the ending is like a really comforting thing.

So some of them I have certainly learned in my experience is that the value of being able to tell those stories, which in another language is being able to manage change. They're kind of one in the same. That is a really important quality to making the scaling experience of a company. One that's not scary.

One in which growing pains aren't bad, but they're a thing that happens that we deal with that I think is incredibly, incredibly invaluable. Are 

[00:28:28] there things that you've done or. Ways that you've practiced to get better in this specific dimension, given how important it is. 

[00:28:36] Yeah. And for me, maybe this comes with like the ritual of annual planning to the extent that you can annually plan.

And if you can't, well, then that's another story you can tell. But one of the things that we definitely did a cruise is when we knew we were going to go in one year from 500 to a thousand, we're like, okay, Here's where we are now. Here's the end of our story next year and where we need to be. Now, let's figure out all of the changes that have to take place and how we want to go about making those changes and why those changes are important.

And in every change that we make as a team, let's invest very heavily in the communication around that. That is something that I definitely have been annoyingly, annoyingly, stubborn about with everyone that I've worked on. I'm like we have to have crisp communication campaigns that tell a story. And the reason I care so much about that is because part of the storytelling is bringing people along and making sure, like, they feel like they are not just a part of the journey, but they're able to co-create the journey with you.

So, you know, if you're going to be rolling out levels, making sure you understand. Why you're doing that, what the value of them are, what the drawbacks of them are, where the discomfort of them can be and inviting people into that conversation, but ultimately knowing really knowing your why, and knowing the story is, has been really, really helpful.

[00:30:09] Can you think back over the past few years of like an example of a crisp storytelling campaign or something that went well to better illustrate the idea? 

[00:30:18] So, one thing that we did applied when 2020 was happening and we were showing up to our desks and logging in, and maybe having Twitter on the one side and email on the other and watching the horrors of everything that was happening outside, and then having to deal with getting back to someone on email and okay.

In this episode with McKenna Quint, most recently Head of People at Plaid, she unpacks the unique people challenges when aggressively scaling, including decoding data, when to pull from existing playbooks, and looking for your first people leader. 