Interview with Jeremy Henrickson, VP Product and Engineering @ Rippling

Published on May 19, 2021

18 min read

image for Interview with Jeremy Henrickson, VP Product and Engineering @ Rippling

Vidal: [00:00] Good afternoon. I have with me today Jeremy Henrickson, VP of Product and Engineering at Rippling. Welcome to ManagersClub, Jeremy.

Jeremy: [00:07] Thank you so much. It’s good to be here.

Table of Contents


What’s your background and how did you get into management?

Vidal: [00:10] It’s great to have you. Could you share with us a little bit about your background and how you got into management?

Jeremy: [00:15] If we go back far enough, I grew up in Sioux Falls, South Dakota, and was a shy, introverted kid and therefore fell in love with computers pretty young partly because I think of my native inclination to that, partly because my dad got all these books on how computers work. And I was fooling around with my Apple II plus back in the day and really liked adventure games and taught myself how to code.

And that was the genesis of my interest in computer science which, over the years, as I got into college and then had my first job out of school, made me realize that what I really enjoyed about that was people. And how people act around computers and with computers.

And that kind of led to this sort of dual exploration of human-computer interaction as a part of that. And then, of course, as management itself. And so, when I was at a company called Reactivity, we were incubating companies and doing consultancy for people that were trying to figure out what this internet 1.0 thing was back then. The company started growing, and it made sense for me to start managing folks. And so I started figuring it out.

Vidal: [01:22] All right. Great. Yeah. And I noticed you had also were a manager. Guidewire, Coinbase, and now Rippling. So, you have a lot of years of experience in leadership, right?

Jeremy: [01:30] Yeah, I guess I do. I’ve been. I guess if I think back on it, I’ve been managing more or less for 25 years now. Yeah.

What are the biggest challenges you face as an engineering leader?

Vidal: [01:36] Oh, wow. That’s awesome. Could you share with us what are some of the biggest challenges you face as an engineering leader or have faced?

Jeremy: [01:45] Yeah, there are many I think strangely I think perhaps the most consistent challenging thing is recruiting. I’ve been lucky enough to be at a set of companies that we’re all growing incredibly rapidly and whose future depended on us hiring really amazing talent. And that really amazing talent, of course, is in really high demand. And getting really good at that has been one of the biggest challenges, and it’s different at every company. A lot of lessons are the same, but, in specific, it’s really something you have to work out, or at least I’ve had to work at it every company I’ve been at to really get good at it at that specific company.

The other challenge I would note is like finding the right people for the right job at the right time. And making sure that you can see around those corners of when an org is scaling beyond its capabilities or when people are accelerating quickly in their own careers and identifying them and making sure you give them the opportunities to accelerate and grow with the company.

And so I think those two parts, the recruiting side and the kind of the growth management, have been two things that have. But I’ve always been always been challenging, fun, but challenging.

What is your approach to hiring?

Vidal: [02:50] All right. Let’s set, let’s talk a little more to hire then because this is a key thing for all engineering leaders. People always say know; you should always be hiring. So what is your approach to hiring? What have you learned? What has worked well for you in hiring and recruiting?

Jeremy: [03:05] So perhaps the most important foundational thing is that I really believe in the places that I work and believe in the team around me. And so I am woefully unconvincing as a human being. If I don’t have deep conviction around those things. So that’s a, it’s a prerequisite. And then I think the approach is to really find people who. will also believe in the team and will also believe in the mission. Will also believe in the future of the company. And I think at a startup, in particular, that’s especially true when you’re sub-scale, and it’s not going to be a cushy, like nine to five job.

It’s going to be hard, and it’s going to be a grind. Sometimes you have to find people who can see through all that and really believe in the same vision that I do. And if you don’t have that alignment upfront, it’s unlikely they’re going to like their jobs, but it’s also unlikely that they’ll succeed with them.

So that’s really the first thing that I test for. And then right alongside that is, understanding if their values are consonant with the values of the company and the way that the company operates. Because again, you want to set people up for success on their way in and ensuring that they’re going to operate in a way that.

They bring their own experience to the table, of course, but also is going to work well with what the company is doing to start with is really important.

Vidal: [04:19] So it sounds like number one. And number two, you think if your values and align. If I could just ask more, where do things like technical ability and things like that going in your interviewing and hiring?

Jeremy: [04:31] Yeah, so that’s next. I think that assuming those two things are screened. I think you just raw horsepower is the next one, right? Because, particularly in a fast-moving startup environment, people that can take complexity and understand it and reduce it down to something simple as important.

And then specifically for engineers, the way in which they can do that in code. And so the ability for them to understand our problem space to understand their kind of own strengths and their own weaknesses. And then to really be able to demonstrate in a process that there are highly capable within their own craft is really the next sequence of things that I really look for.

And the thing that follows that or when I’m confident with that is, do I actually want to work with this human? So it’s one thing for them to be aligned with the mission and be aligned with the values and be like a really amazing engineer. But at the end of the day, if this isn’t someone that I’m gonna like working with, or that I feel is gonna make me better, or that’s smarter than me yet, what they’re going to do or something, then it’s probably not going to work.

Could you share with us a lesson you learned as an engineering leader?

Vidal: [05:26] Got it. Alright. So we talked earlier, you’ve been in management and leadership for. About 25 years or so, could you share with us a lesson or two you’ve learned along the way as an engineering leader?

Jeremy: [05:40] I think there’ve been maybe two really important lessons for me personally. The first of those is. Make decisions both sooner than you think you need to and more quickly than you think you need to. Velocity and, again, in the startup context, is hugely important. Like the velocity of decision-making is really important and being willing to make decisions with.

Partial information to the best of your ability is far more important in most cases than making decisions by accruing as much information possible. And then doing it or being racked by indecision because you can’t decide which of these two or three or four options that are in front of you are the right ones.

 That’s something I very much was not good at when I first started managing. I would let myself get paralyzed. I would like overthink kind of decisions or just think too long for the decisions. And I since learned to be much, much quicker.

And I think that’s been one of the elements of why I’ve generally been successful. So that’s the first lesson, and I think the second big lesson is it particularly as organizations scale larger and larger is it’s entirely about getting the right person in the right role at the right time.

So most of my decisions boil down to do I have the right person in that role because if I do, I can trust them in the role they’re going to do great at it. They’re going to know when they need help. We’re going to able to have a really candid relationship about it, and they’re in the right place in their growth trajectory to be like really successful in that role.

While being supported by me and the places where I’ve made mistakes have been, where like that’s misaligned for some reason where like the current state of the company or that team, or that role is misaligned with the kind of capabilities of a person. And that ends up. You can deal with that for a while.

And that’s always the case, too, to one degree or another. But over the long term, it can really kill a team. And so I’ve learned to try to identify those things as fast as I can and either kind of up-level the person, so they can do the job successfully or find a different role for them or hire somebody into the role or whatever you need to do to make that situation successful.

Vidal: [07:32] Do you manage other managers?

Jeremy: [07:35] Yeah. Yeah. Been managing other managers for a while. It’s an interesting job.

What’s your advice for managers who are just starting out?

Vidal: [07:41] What would be your advice for managers who are just starting out in the job?

Jeremy: [07:46] Number one is ask for help, ask for feedback from everybody from your manager, from the people you are now managing acknowledge that you. Haven’t done it before, acknowledge to yourself.

And most importantly, that you’re probably not going to be great at all of every element of the job. Like maybe the person you’re going to be ten years from now will be better at the job than you are now. And if you can like fully internalize that, you can develop a degree of humility or introspection about how you can be better.

And my experience there is that most people. Especially the people who are reporting to you react much better to that approach than to the attempting to be like the authoritative, always correct decision-maker. Because the reality is you’re not always correct. And authority is derivative of being correct.

And over and over again over time and earning the trust and earning the credibility for the people around you. And so really having that sort of humility is really important and earning your way to the point where people. Want you to be more directive, right.

And want you to be more forceful about your opinion because they trust that most of the time you are going to be right, but that’s earned, not given. And that’s a really hard thing to understand for many people. I think when they’re first starting out in a managerial role, and maybe they have this perception that.

By being a manager. Now you suddenly have power over the people that you’re working with at which couldn’t be further from the truth. In engineering, I think there’s other roles, which that is true. Still, I think in engineering in most great engineering organizations, that’s actually exactly the opposite of what the dynamic ought to be.


Vidal: [09:13] Yeah, it’s interesting. And engineering organizations. It’s if you’re talking about like the servant leader and these things where the engineering manager. Yeah. It doesn’t have the power you’d think.

Jeremy: [09:22] By the way, I’m making an assumption there, but I just interrupt. Sorry for on the side; that should be the assumption that you have a great team right now. If you’re a first-time manager and you have the misfortune of inheriting a really broken team, that’s a much harder deal because not only are you exercising managerial oversight the first time, but you’re also having to wrestle with these issues that are really hard, even for like super-experienced managers. I think my advice in that particular situation would vary a little bit.

What’s your workday like and how do you manage your time, emails, calendar, etc.?

Vidal: [09:46] Yeah, that would be rough.  A tough way to start. What is your workday like? How do you manage your time, emails, calendar, like all the things you have to do?

Jeremy: [09:59] Yeah, badly. I don’t know.  I have long since given up believing I can get everything that I ought to get done during the day. And so part of my role is understanding, like where do I need to delegate? Where, what are the most important things that I can do, and how can I make sure that I’m building up an organization around me so that the important things always get handled.

So what that means for me personally is, I wake up in the morning, I’m usually guilty of checking my phone. Very first thing, just to make sure like nothing broke overnight. I have an emergency email from somebody about something or a Slack message or whatever, then Go to, take a shower and stuff, go downstairs, say hi to the kids.

And then these days, my commute is about 15 seconds down to this room. And usually, I have some standing meeting at eight in the morning or something like that. So I have, I’m pretty sure. I jumped in and want to like unblock people as quickly as I possibly can. So I like looking through my emails, like in the gaps that I have in the morning, I’m like responding to people quickly.

If people are shooting me Slack messages and fielding those quickly. And I view the beginning of my day, largely about either having these standing meetings or ad hoc meetings or interviews important or unblocking people so that they can move as quickly as they can throughout the day.

And then usually, by around lunch, my schedule relaxes a little bit. And then I try to like make sure I’m building in time in the afternoon or evenings, depending on how the day is to get some focused work done. And that could be one of a variety of things. And then I just make sure I work down the list before I fall asleep at night.

And then I start over the next day. It’s a pretty busy time.

What’s a personal habit that contributes to your success?

Vidal: [11:22] What is a personal habit that you feel has contributed to your success?

Jeremy: [11:30] I’ve thought about this one a lot over the years. And I think that perhaps the most important attribute I’ve had, I think has made me successful, is just always thinking that I might be wrong. I always think I could be wrong no matter how confident I am in something, and matter conflict of stating something or appearing to be like always, there’s piece of, back of my head.

I was like, you know what, Jeremy, maybe you’re not seeing it completely. Or maybe you don’t understand that person’s perspective, or maybe you don’t really understand this domain as well as you do. And that. That attribute has kept me really honest. It has also been the reason that I’ve been too paralyzed with decision-making in the past.

So I’ve had to overcome that it’s been a weakness as well, that had overcome, but that’s the belief that I could be wrong means that at least more often than not, I’d like to think I’m a pretty good listener. And I hear people say what they’re really saying, not what I want to hear them saying.

And because I think I might be wrong. I, therefore, have a relatively high degree of confidence that, at the end, I’m usually right. Because I acknowledge the possibility that I might be wrong. It’s kind of one of these weird cycle things.

Vidal: [12:26] I think that’s really fantastic that you have that view, you’re trying to like you say, you’re trying to listen to what they really said, not what you hope they said, or you think they said and stuff. So that’s really great.

Share an internet resource, app, or tool that you can’t live without.

Could you share, is there an Internet resource app or tool that you really liked? You couldn’t live without to help you do your job?

Jeremy: [12:45] Google maps probably be lost, but I’ll go to the right place. I as a manager actually, I don’t really have one. I’ve never been a big user of like tools that operate on instinct a lot. And so, everything that I would name is really boring things like spreadsheets and email and communication tools that have been effective for me. But I actually don’t really have another resource out there that I tapped with any frequency.

If you could recommend one book to managers, what would it be and why?

Vidal: [13:07] If you could recommend one book to managers, what would it be and why?

Jeremy: [13:13] Okay, that’s a good question. I’m generally opposed to books on management. I think they are, I think there are good ones out there, but I think they’re mostly not very interesting. There’s one we use at Rippling that, while I don’t agree with all of it, I think particularly for new managers, Is really thought-provoking and has led to some really good conversations internally called Conscious Business.

And it’s less about management specifically, though. It’s written in a business context and more about understanding how people really work because so much of management is about that. And so it, as at Rippling, it’s been really nice to have this that all managers are reading this book at the company across engineering and every other function and having a common language with this, which this book introduces has been enormously useful to us to operate better.

And I’d recommend it to anyone who’s thinking about going into management because introspecting on those kinds of things is really important.

Vidal: [14:04] Oh, that’s a fantastic book. I’ve read that. And I actually saw the guy present. I think it’s like Fred Kaufman, and he actually worked at LinkedIn for quite a

Jeremy: [14:14] Yeah. Oh yeah, that’s

Vidal: [14:15] So yeah, that’s a really that’s a really interesting book.

What is your approach to developing, mentoring & coaching members of your team?

What is your approach to developing or coaching members of your team

Jeremy: [14:26] when things are working in an ideal fashion, and they’re rarely are ideal, but when working in an ideal fashion, the first thing I’d like to do is really just try to understand the person and understand what’s their aspiration. Where does this job that they’re coming into fit into that aspiration?

And I try to understand their context, right? Everyone has a different context. Some people like, married with kids and dogs and some people, like going hiking in the Appalachian. Some people like many concerts, like understanding all that context, I think is really important to being able to even start to like mentor and coach people.

Because until you understand the person, it’s really hard to get inside of it. Once I have that context. You don’t get all the context right away. It’s a lot of that, of course, is earned. But once I have enough context, I like to try to build enough kind of mutual trust.

So getting honest feedback but like lots of good feedback paired with kind of the other kind of constructive feedback because, unless they trust me unless I’ve earned that trust on them, it’s going to be really hard to give them. Like the really hard feedback when it inevitably comes.

And so, I try to provide as much immediate feedback as I can. I fall down on that sometimes. Just cause I, get myself a new mode or I think I’m too busy or I like to have flat organizations and too many people reporting to me. And therefore, I’m not able to give as much feedback as I should.

And so I think that falls apart sometimes. But really getting that immediate feedback support and because. Eventually, something will happen. The businesses scaling really fast, some bad thing will happen on the team where I’ll be like, okay, look, I really need you to like, to really stretch yourself here.

Here’s the thing where I know you’re trying to be like, it’s not working out, but I want to help you through it. And being able to have them like really trust me and really hear what I’m saying without it generating a negative reaction is really important. So I try to have as many of those moments as I can.

What does it take to be a great engineering leader?

Vidal: [16:03] What do you feel it takes to be a great engineering leader?

Jeremy: [16:06] I think that depends on context, right? I think there are leaders who are much better than I am in certain contexts. I think I’m better than other leaders or contexts. I think it depends on kind of time. I mean, in my personal experience, aside from kind of that ability to introspect and recognize he might be wrong.

I think it really is overall the ability to one act with urgency. And constantly be driving the tempo, particularly the larger the organization gets like you’re managing like three or four or five people. That’s one thing. But if you’re managing hundreds of people, like your job is to make sure that like you’re driving the tempo of the organization, both in terms of yeah.

Like the dedication to the job, but also in terms of making it efficient for them, making it possible for them to act with efficiency. So I think that’s number one, that kind of acting that acting with urgency and like making that sense, like pervade the organization, but second and very important to pair of that is the ability to see the future clearly that, so the ability to see if I take this action.

This is going to be the net effect of that action six months down from, or if I don’t take an action more, importantly, this’ll be the net effect of having not taken that action. Then I think all of the great engineering leaders that I’ve seen, particularly those who are like managing larger org, have that a little bit of an oracle inside them, where they can project in the future and understand the nature of those actions.

And, of course, it’s not a hundred percent. You don’t get it right. A hundred percent of the time, nobody does, but if you can get it right more often than not, like you’re better off than, Not having tried in the first place.

Vidal: [17:28] I think that’s a great answer. It’s interesting pushing the urgency and then having a vision of the future that you’re moving people towards.

Where can we go to learn more about you?

Jeremy, you’ve been really generous with your time. I really appreciate you coming on. And you shared some really great advice to people.

Where can people go to learn more about you if they want to connect with you afterwards?

Jeremy: [17:47] Yeah, if you want to connect with me, I think the easiest these places like LinkedIn or something like that I’m pretty quiet on the internet quite deliberately. But message me on LinkedIn, and I’ll happily return a note that you send there.

Vidal: [17:58] All right. I’ll put a link to your profile. So again, thank you so much. I really appreciate it.

Jeremy: [18:05] Yeah, I enjoyed it. Thanks for having me.

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