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The Rabbit Hole Podcast

Welcome to The Rabbit Hole, the definitive developers podcast. If you are a software developer or technology leader looking to stay on top of the latest news in the software development world, or just want to learn actionable tactics to improve your day-to-day job performance, this podcast is for you.

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69. Becoming a Manager with Kyle Rush from Casper

On today’s episode of The Rabbit Hole we welcome our friend Kyle Rush, VP of Engineering at Casper to help us discuss becoming a manager. Kyle is a great example of a developer who made the change to a successful managerial role, a transition that oftentimes has its challenges. We discuss the different paths one might take to this position and the essential components and skills that it requires. Kyle gives us some insight into the importance of feedback and learning curves and how indispensable these concepts are to adapting to a manager’s role. We also look at a few pieces of helpful reading to ease your growing pains before considering salaries and the potential switch back to a developer position. For all this and more be sure to tune in!

Key Points From This Episode:

  • An introduction to Kyle’s role as a manager at Casper.
  • The paths to becoming a manager and the skills needed.
  • The importance of giving and receiving feedback.
  • Kyle’s vital points for developing better feedback skills.
  • The correct attitude to mistakes and their value.
  • Some of the team’s helpful literature of leveling up to managing.
  • The transition period from dev leader to manager.
  • Kyle’s own path and transition to position of manager.
  • The questions to ask yourself when considering the step up.
  • The positive and negative effect that managers can have on their team’s lives.
  • Salary considerations for managers and developers.
  • Switching back to a dev position after managing.
  • And much more!

Transcript for Episode 69. Becoming a Manager with Kyle Rush from Casper

[0:00:01.9] MN: Hello and welcome to The Rabbit Hole, the definitive developer’s podcast in fantabulous Chelsey Manhattan. I’m your host, Michael Nunez. Our co-host today.

[0:00:09.8] DA: Dave Anderson.

[0:00:10.8] MN: Our producer.

[0:00:12.0] WJ: William Jeffries.

[0:00:12.1] MN: Today, we’ll be talking about what it takes to be and become a manager.

[0:00:17.6] DA: Do you have what it takes?

[0:00:19.1] MN: Do you have what it takes? We’ll find out in just a second. But before we begin, we have a special guest today. We have Kyle Rush, who is the VP of Engineering at Casper. How’s it going Kyle?

[0:00:30.5] KR: Great, how are you?

[0:00:31.5] MN: I’m doing all right, again, ready to talk about this topic. This whole becoming a manager. Could you shed some light on some of your responsibilities at Casper?

[0:00:40.2] KR: Yeah, sure. In my role as VP of Engineering, I manage a team of about 50 people that’s spread across IT, security and engineering, there’s another component to tech a product team that’s led by the VP of Product so I work really closely with the product team and you know, we write a lot of software, manage a lot of devices at Casper.

The software that we write ranges the public website that people see most of our business is e-commerce, the order management system where we receive orders and they get placed all the way to getting an order to your door which is surprisingly complicated.

[0:01:13.6] DA: Yeah, traveling salesman all that logistics.

[0:01:17.3] KR: Just getting a package to somebody’s door is a lot harder than I ever thought. 

Then there’s you know, we have retail operations so we built our own POS, we have an international operation out in Berlin so it all culminates in a lot of software.

[0:01:30.2] DA: Yeah, love it.

[0:01:32.1] MN: I guess you were not always a manager, at some point you did break?

[0:01:37.5] KR: Yeah, I wrote code solidly for probably six or seven years before becoming a manager, there’s a transition period of course where you’re like kind of doing both, you don’t really know what you’re doing but –

[0:01:47.6] DA: The [inaudible].

[0:01:50.5] KR: Back in my day, I wasn’t u sing either. What was I using? I got it started on Notepad ++.

[0:01:56.0] MN: Classic.

[0:01:57.2] DA: Java, classic. The good stuff, the best.

[0:02:02.7] KR: I love it. Then I switched to a Mac for  a while so I was using, I had like a port somehow of running Notepad ++ on the Mac.

[0:02:09.6] DA: Yeah.

[0:02:10.7] KR: Because I wouldn’t let it go for a while, then I switched to some hipster thing, you know, at the time I don’t remember what it was.

[0:02:16.0] DA: Right, yeah, flavor of the week.

[0:02:19.2] KR: Vim person.

[0:02:19.5] DA: Yeah, a bam. I had a flashback when you said Notepad ++, it was like college, so good. That’s good stuff. I guess Mike and William, you guys both became managers recently as well.

[0:02:36.6] WJ: Yeah, a couple of years ago, I started managing people. I’m definitely not as long as the VP over here, but yeah.

[0:02:45.4] MN: But it’s still a thing?

[0:02:47.7] WJ: IT’s still a thing, although,  you know, I’m not really purely a manager, I still code every day, you know, I would say like my primary responsibilities are delivering functionality even though management is eating up more and more of my life.

[0:03:02.9] DA: As it goes. I’m not a manager so I’m curious like what the paths are to be a manager, right now, my path to being a team lead is having the current team lead go on vacation.

[0:03:13.2] MN: Yeah. It’s the way to do it.

[0:03:16.3] DA: I’m going to all the meetings and I have written 10 lines of code in the past two days. I’m feeling shades of this. Yeah, we could start off like talking about like what are some of the paths that one can take to become manager.

[0:03:30.6] KR: Yeah, I’m sure there’s like infinity paths to become a manager.

[0:03:34.2] DA: It’s like logistics.

[0:03:36.0] KR: Yeah. The way that I talk about it with my team is, there’s a lot of like sort of basic skills as a manager that you need to use and so I always try and encourage people to develop those and start thinking about it that way.

These are like, really kind of basic things that we don’t think of as engineers. I think when you’re an engineer and you walk into the office, you think, my job is to write code but you know, in reality, that’s like such a small, I mean, like such a small, I mean, like micro but it’s a small part of the overall picture, there’s like communication, there’s feedback, there’s collaboration, how do you collaborate with people, a lot of those things get forgotten because we all just like lover to dig into the code.

Those are skills that people need to really have perfected by the time they become a manager.

[0:04:17.6] DA: For some reason, it does feel like you know, become a manager, to feel like it would be like a binary thing. It’s like, “Now you’re Mr. Manager. You have the responsibility now and you didn’t yesterday,” or what have you but I guess like when you put it like that, there can be kind of a gradient.

[0:04:36.6] KR: The phrase that are the analogy that I always use when I’m talking about it is, I never want to throw anybody into a cold pool where there’s like shock, right? Imagine if like jump into a pool of cold water, you can’t breathe for a second and you’re like, disorients you.

If you have not been coached and you have not practiced like communication and leadership and collaboration, all those important sort of qualities that are not writing code, it can feel like you’re jumping into cold water and it can be a bit of a shock but if you practice those things and you get feedback and you're genuinely interested on improving those things then it’s more like you know, walking slowly into a pool with this thing, rather than doing a cannonball in the deep end.

[0:05:17.7] DA: Right. To the cold waters of management. They can be cold.

[0:05:25.2] WJ: Full of sharks.

[0:05:28.2] DA: Man, is this what I’m in for next week? Sharks?

[0:05:31.0] MN: I don’t want it to sound scary, let’s make it be fun. It can also be scary. Some people like cold water.

[0:05:37.4] KR: That’s true.

[0:05:38.1] DA: It’s a trend, cold showers are big.

[0:05:40.7] WJ: A lot of times, the water actually feels pretty warm once you’re in it.

[0:05:43.5] DA: Yeah, that’s true. I think you mentioned two things that I thought was interesting there, you were trying to like, practicing skills, intentionally practicing skills and also like getting feedback and having a coach, maybe you could talk a little bit more about those two things?

[0:05:58.5] KR: Yeah, for sure. Feedback I think sometimes we forget that there’s like a tow way street, right? You can give and receive and it’s in my experience, nearly impossible to be a good manager if you can’t give and you can’t receive feedback and so you have to look at it from both angles.

In my experience, most people are afraid to give feedback more than they are to receive it, especially negative feedback but –

[0:06:21.7] DA: That’s true, yeah.

[0:06:22.4] KR: It’s so important for everybody’s professional development that they get the negative feedback because they need to know what to improve.

Actually, we had – we hired a company to come do a sort of like a communication, like internal communication training at Casper and one of the presenters that was showing the slide were some HBR researcher or the article ended up in HBR but they did a survey of thousands of companies, own feedback and one off the questions was like, do you want to receive negative feedback and the overwhelming majority of the respondent said yes.

[0:06:54.9] DA: I think when we have negative feedback for somebody, we don’t want to give it because we’re afraid they don’t want to hear it but overwhelmingly, everybody wants to hear they want to know what it is, that’s just something you have to do as a manager.

[0:07:05.4] MN: That’s true, I guess like if you do ask for a feedback and you only get like positive feedback or lukewarm feedback. Yeah, it feels like, no, wait, I am my worst critic right here, I can certainly come up with some negative feedback. Please help me out.

[0:07:22.8] KR: Nobody’s a 100% consistent or 100% perfect, right? The feedback could never be 100% positive so if you’re only getting positive feedback then something’s definitely wrong.

[0:07:33.3] DA: Or you’re amazing.

[0:07:35.2] KR: Nobody can be perfect.

[0:07:37.2] MN: Before you become a manager and you have to practice this two way street of feedback, is this something that you would just do amongst your development team like to your peers and like just practice that way so that when it comes time where you become a manager, you have those skills readily available?

[0:07:55.0] KR: Yeah, what I like to do is give people a little bit of training, there are certain ways to structure your feedback so it can resonate with the person, a lot of that is like, make it factual, provide evidence of what the issue was, put a timeframe on it. You know, if I go to William and I’m just like, you make me feel stupid when I’m talking to you, is it’s like, is that actionable?

I don’t even know really what that means but if I came to you and I said, “Hey, yesterday, in that meeting, we were with Michelle and she said, what do you guys think about barbecue and I was like, I love it and you’re like, barbecue’s disgusting, that didn’t make me have a good experience,” right? that’s actionable and it’s specific.

Then you can finish that up with I would have rather you said, I personally don’t like barbecue rather than barbecue’s disgusting as like declarative statement. There’s a structure to that but I think you know, how I like to prepare people is, you know, all my director ports what I’ll do is I’ll say, you know, in my first one on one I’ll say okay, next week I’m going to give you negative feedback, I’m going to give you positive feedback and we’re going to do that for two weeks and then we’re going to switch.

In two weeks you’re going to give me negative feedback and positive feedback and you’re going to have one piece of each in each one on one and my theory is, if you can give negative feedback to your boss, which is really hard. You can give negative feedback to your peers.

[0:09:12.7] MN: I agree because like, there is that power dynamic that people may look at and feel somewhat like afraid to give feedback to your boss, right? Bobby could fire me if I say something wrong.

When that avenue is open to kind of practice that, because it’s god for you too and I think, when you mentioned that to your peers then they will also use that as like a practice tool to get better at giving and receiving feedback.

[0:09:38.1] KR: To me, it’s kind of like a safe zone. I know when I’m asking a direct report, they give me negative feedback, they don’t feel like it’s a safe zone but to me, I know that if they miss-deliver the feedback or you know, they mess it up somehow or t hey say something they didn’t mean, I can get over that because I’ve had a lot of experiences like that. My fear is that they don’t practice it in that sort of safe zone than when they go to deliver it to a peer.

You know, it can bob but nobody should be afraid that it’s going to bot me, just have to get over your nerves at some point and deliver the feedback, right?

[0:10:08.0] DA: That’s part of being on a team, it’s just having trust.

[0:10:10.0] KR: Exactly.

[0:10:10.7] DA: Yeah, cool. It sounds like I can’t just read a book? My god, I wish. I mean, there’s so many books out there of any topic like, I’m actually, dieting also has also a lot of topics, a lot of books out there, it feels like I don’t know if I can really trust these things but there’s a lot of like really good thought out there like I picked up a copy of First, Break All The Rules recently at William’s suggesting. It’s pretty good.

Yeah, there’s a lot of information in there, I think that kind of makes sense that you would – you’d have to practice that. You know, practice breaking all the rules or what have you.

[0:10:50.8] KR: You have to like make mistakes I think. Like maybe that’s another way to put it instead of breaking the rules. I just think that you know, everything is so contextual and there’s really like no check list, I mean, there’s like you know, at Casper for my managers I have a performance scorecards so they know like the broad areas that they need to be focusing on but like it’s okay to make mistakes.

The nice about making a mistake is you know what not to do next time which if I ever wrote a book, it would be like, ‘My Career is a Pile of Mistakes’.

[0:11:22.3] MN: I would just list the millions of mistakes that I’ve made, you know? In my entire career but then the nice thing is you learn. You know, some people have the advantage of having a mentor that they learn from and maybe you can –

[0:11:32.9] DA: Right, from their mistakes?

[0:11:34.1] KR: Exactly. Sometimes it works that way, sometimes you have to learn from your own mistakes.

[0:11:37.9] DA: Yeah, that’s true.

[0:11:39.1] MN: Do you have any books that you’ve enjoyed reading or on management or –

[0:11:42.4] KR: On management? I don’t think so actually. Just my own pile of mistakes.

[0:11:47.7] MN: Okay, nice, yeah.

[0:11:49.1] KR: I don’t think I read a management book, no.

[0:11:50.9] MN: Interesting, cool.

[0:11:52.4] KR: I read HBR a lot. They’re not books but they’re like articles.

[0:11:56.6] MN: I guess it’s like more digestible

[0:11:57.1] KR: Bit sized, yeah, exactly.

[0:11:59.5] MN: I think one of the books that I’ve read when I became a manager, the name of the book is called Team Geek by Brian W. Fitzpatrick and Ben Collins-Sussman.

[0:12:10.0] DA: Do you want to start from the beginning of the thought?

[0:12:12.1] MN: Yeah, just don’t remember.

[0:12:14.4] DA: When you make a manager.

[0:12:15.3] MN: When I became a manager and I almost felt like I was ready to take that responsibility and not at the same time. I read a book called Team Geek by Brian W. Fitzpatrick and Ben Collins-Sussman and this book is very interesting, it’s because it uses the example of developers who magically became managers.

Their job called for them to be a manager of a particular team when they themselves weren’t really like, they were just trying to level up to be like – they were trying to level up to be more like architectural centric or like just dealing with code but often times in a place of work, they may ask you to become a manager and that could be really difficult for someone who has been coding for as long as they have been coding and management’s fairly new.

This book was very interesting in introducing that tot individuals who magically became managers on what to do.

[0:13:08.9] DA: When you say magically, do you mean like their title changed or like the over time the responsibilities grew and they became more responsible for like mentorship of the team and you know, kind of managing the direction of things?

[0:13:21.5] MN: I think it was the latter where the title changed, the title was changed to become a manager, you can be a dev lead at a particular team and then the next step is okay, well if you’re going to be promoted, you’re going to become a manager. Some of the things like.

Oftentimes, one of the things that I hear a lot of managers speak about is the fact that they don’t write a lot of code and they feel bad about that because you know, you come from a job or responsibility where your job is to deliver features and to write code and stuff like that but as a manager you may be in more meetings and you know, doing more personal things.

When you look at your week and see that you only have four commits in the past five days, people tend to feel bad but that’s not your work anymore, you have to ensure that your team is improving and moving forward and making sure you’re delivering feedback to individual and stuff like that.

They go over a lot of those different concepts of what it takes to be a manager and what are some of the changes that will happen because you now become a manager.

[0:14:21.0] DA: Yeah, that’s interest, I guess like, that kind of feeling like – especially when you’re in stand up and you like, with a bunch of people who are like, yeah, crushed this feature, I did that. It’s like, well, I was in meetings all day. Didn’t plan for that to happen but it happened.

[0:14:39.0] KR: I think it’s an important psychological change to make for you personally because when you go from – I mean, I’m like fully transitioned out of this now so I used to love delivering features. Now I’m just like “Hey, I didn’t deliver a thing this week.”

That feels normal to me but when you’re a new manager and you’re not delivering features, it can kind of feel like there’s less value in the work that you’re doing. I feel like even –

[0:15:01.7] DA: Prove yourself.

[0:15:02.8] KR: I could tell when you said, “I was in meetings,” like, it was the negative thing or had no value, right? It’s an important transition for managers to make psychologically, to see value in that work or else you just, you won’t be satisfied, which is fine you know? You don’t have to be, you can go back to writing code if you want to be but you have to be able to see the value in the work that you’re doing, or you’re not going to do good at the job.

[0:15:22.8] DA: Right, and not feel like you have to prove yourself to your colleagues.

[0:15:26.4] KR: Yeah. And you have to be excited about other people delivering features, right? That’s a big part of your job is to increase the rate at which you know, and the quality at which people deliver those features.

[0:15:35.5] DA: Yeah, do you feel like ownership of the features that your team delivers to a degree?

[0:15:41.0] KR: I think I’m a little bit too removed to feel ownership of the features but what I get a lot of pride out of is where, I have like a twinkle in my eye idea. When I first came to Casper, we didn’t have a contact management system, any change on the website an engineer would be involved in.

[0:15:56.1] DA: Yeah, sure.

[0:15:57.9] KR: Make this a capital T or like, add a period here, that would be a ticket into somebody would solve which is you know, just debilitating for productivity.

[0:16:07.0] DA: Right, change those legal terms. Literally happened the other day.

[0:16:11.3] MN: Yup, I’ve been there.

[0:16:14.2] KR: You know, we’re on the process now to implementing a CMS and I cannot claim any credit for the quality of it but the idea of that launching and how much it’s going to change our engineer’s lives, that’s where I get a lot of value out of it. You know,

The actual shipping of the features and how it performs and everything, the engineers, you know, should take credit for.

[0:16:34.8] DA: Cool, yeah.

[0:16:35.8] WJ: What was your personal path to management?

[0:16:39.2] KR: I wanted to bring this up because of the book title which is something like you know, you magically became a manager.

[0:16:44.0] MN: Team Geek, yeah.

[0:16:46.5] DA: Team Geek but you magically become one, that’s what it is.

[0:16:49.9] KR: Looking back on it, I think it was bizarre but maybe it’s not so bizarre. I was just writing code and agencies just pumping out websites for a bunch of clients and I had the opportunity to go work on the Obama campaign. I like, had wanted to do it so bad and then my friend who was at the agency that I was at went to go work for the Obama campaign.

Just straight up asked me, “Hey, do you want to come here, we don’t have any developers, like it’s all outsourced right now.” I was like, “Yes, I got to do it.” You know, the leadership at the campaign was like, “Okay, can you be here in two weeks?” And I had to relocate from DC to Chicago and I was like, “Quit my job in two weeks and then relocate my life? I’m going to do it.”

I went out there and I was the first engineer and nobody was like, “Kyle, you’re a manager, you’re going to manage all these engineers,” they were basically just like okay, we need more engineers and I was like, guess I got to figure this out. I just started posting roles on the website, started doing interviews. I had really never done interviews, you know, at that point. Participated in a few but I never structured an interview process.

I never used a system to enter feedback, I had no idea how to evaluate candidates and so, I just, you know, made a ton of mistakes and figured it out eventually and then when the people came, “I don’t know whose manager. I guess I’ll just be the manager without the title,” and then I don’t know, six months later I was like, “Okay I am not officially the manager.” So it was very bizarre.

[0:18:15.8] DA: And that is a high pressure environment.

[0:18:18.9] KR: Very.

[0:18:19.9] DA: Like you’re in the crucible.

[0:18:21.1] KR: Yeah because you are working seven days a week, 12 hour days. I think luckily in that situation, people don’t go to an opportunity like that unless you are very passionate about the purpose of it and so in my experience, when you are on a political campaign like that, your passion for the work overshadows any sort of issues in your job like at a normal company you’d be like, “This is terrible structure and terrible management.”

But there you’re just like, “I just want to win and let’s just write some code.” so I think it was a little bit easier on that respect.

[0:18:51.4] DA: Yeah, cool. I think it is pretty open just failing fast, you know?

[0:18:56.2] KR: Yeah, everybody just wanted to win and write some code and get it out there. It was a bit easier but it was strange and that I was managing people without the title and it wasn’t clear that I was their manager and I wasn’t prepared for it. No training, no nothing.

[0:19:09.5] DA: Yeah, it is really interesting how things formed in that all these bonds like the data team from Obama’s, I forget the company they formed but they formed this great company and I met some people who are working for it. It’s very fascinating.

[0:19:23.6] KR: Yeah, there is definitely deep bonds there. When you go through that kind of experience, it’s like a new family.

[0:19:30.6] DA: Okay, thanks. That is super interesting. So I guess the question is now, should I become a manager? You guys, you have to tell me if I should become a manager.

[0:19:40.7] KR: I wish someone would tell me.

[0:19:43.4] DA: I guess someone did.

[0:19:47.4] KR: Yeah like I said, they told me without telling me. It’s a great question. I think you have to really appreciate I think and be okay with not writing code and really picking up a whole different skillset. That is not necessarily unique to tech, right or software.

I am of the opinion that good management is good management across the board and leadership is good leadership across the board. I think that if you could lead a software project, you could lead it whether it is written in Ruby or Python or if it’s data engineering versus – or data infrastructure versus just like a regular web application. I think you can do a good job.

So I think if you are ready to first of all not to write as much code and you’re ready to deal with people problems and people opportunities and hiring and interviewing and building teams, if you think you’d get a lot of value out of that, that is definitely a good sign that you should be a manager and I think if you see yourself as a problem solver not just on the technical side. If you are a bit of a people person, I think that is also a good sign.

[0:20:50.7] DA: Yeah, I guess I also have an engineering background. Even if you are not working in the same domain or same technology that you have expertise in the past, you have the empathy for the struggles that the people underneath you are going through. So you can identify with that.

[0:21:06.7] KR: Yeah and I think to be a good manager you don’t necessarily have to be an expert in whatever the discipline is of the person that you are managing. You know I personally manage a lot of people that I have never done their job before but I can identify what success looks like and what failure looks like and I can try to lead people through a normal sort of scientific process of picking a hypothesis, testing it out, measuring it, did it work, did it not, okay let’s try something else. Those are the leadership skills that you just need there.

[0:21:35.3] WJ: I think that as a manager, you have an incredible responsibility on your shoulders because the number one reason that people leave is because of their managers. You have a massive impact on the lives of the individuals who you manage and that’s a weighty thing that you have to be ready to take really seriously. It is a much bigger deal if there is a bug in your management than if there is a bug in your code.

And so I think if you want to be a manager, then there should be an ethical component to it. Like for you, you have to be excited about the challenge of having a really incredible impact on someone’s life for the better and be willing to take it seriously. Understanding that the inverse is also true, you can have a big impact on people’s lives for the worst.

[0:22:29.8] DA: Right, yeah especially like thinking back to time when you had a great manager versus the time you had a manager who was distracted and not invested in your personal success. That really makes the world a difference for your personal outlook and the energy you bring to the day.

[0:22:50.9] WJ: Yeah, I mean it could ruin a person’s job and having a terrible job can ruin a person’s life. I mean it really sucks when you have a hostile terrible manager who’s distracted and frustrated and doesn’t care about you who is actually focused on other things.

And conversely, when you have a really good manager and you feel like your career is on track and everything is going right that has ripple effects throughout your whole life.

[0:23:13.8] DA: It’s deep. Yeah, it’s true too.

[0:23:18.2] KR: I think I would just add one thing to that. I think what I try to do a lot of times is try to find deeper meaning in things that happened to you. So as an example, there was a point in my life where I thought I had the worst manager and a lot of the things that you were saying really hit me like they were hostile to you without reason, that kind of language and for me I was like, “Oh my god I remember those days.”

And at the time, I was super unhappy about it and I felt that it impacted the success of my work and all of that. As I look back on that time which were several years after, I actually now really value that manager that I had because I didn’t realize it at the time but now, I’ve learned so much from that person. You know that manager told me that I wasn’t on the path to success at my job and I could not possibly see how that could be true because I was just blind to it then.

I mean it was the reason why I left the company and now I am so, as you said, people don’t quit companies. They quit managers. But now I am so thankful to that person because that was not the right job for me and I think that going on the topic of managers having a moral obligation or sort of an ethical obligation to help people, I think helping people understand that this isn’t the job for them or this isn’t the project for them or no matter how bad they want it, I think that is an important thing and that negative experience what I perceived at the time is such a valuable lesson for me now.

[0:24:45.5] DA: Yeah, I guess it is part of also seeing what success looks like versus seeing what failure looks like. If you have never worked a terrible job then you lose some capacity to appreciate when things are going right or seeing when things are trending badly, you make way. I’ve been here for it, let’s turn the ship around.

[0:25:06.8] WJ: How do you think that becoming a manager has affected your job prospects?

[0:25:11.4] KR: Good question. I think it has raised a lot of opportunities for me personally. When I was looking for jobs after the Hilary campaign, I literary interviewed once and fell in love and just ended up there. I luckily did not have to apply, I was just connected to this company. So I had a positive experience overall.

I think that there is probably arguments to be made that there are fewer job postings for managers and more for IC engineers which makes sense because that is just the structure of a team, right? Sort of a pyramid.

But I don’t really have data on it. I’m sure there is data out there. I mean we were talking about the stack overflow survey earlier, maybe there were other surveys.

[0:25:51.9] DA: Yeah some charts there.

[0:25:53.2] KR: Yeah, I would like to believe it could be neutral or beneficial overall but everybody has their own experience and mine has been positive overall.

[0:26:02.5] DA: Yeah, I think the one thing that we saw that said it was just like managers tend to have a higher medium salary. So you’ve got to get that paper.

[0:26:11.2] WJ: Yeah, it was a good 10 or 15% more on average. Although I have heard at least anecdotally that the maximum salary that you can make is higher for an individual contributor than it is for a manager because you can get heavily specialized and become a really rare expert.

[0:26:27.7] DA: Right, you can become the [inaudible] guy at the fintech company.

[0:26:32.8] MN: The Cobalt developer.

[0:26:34.3] KR: Or just become a security engineer and you can charge a lot.

[0:26:39.9] MN: Yeah.

[0:26:40.1] DA: Right just be that one guy.

[0:26:41.9] KR: I do think that’s true. I think the more specialized you go, the higher salary you can get but I think generally speaking at most of the established tech companies, there’s a path for IC and People Manager and most of the progressions on that and the salary bends that I have seen are essentially the same for each role. The only thing ultimately that means is that everybody has to report into somebody.

And so even if you are - let’s say a principal engineer or something like that, you’re still going to report into maybe a VP or CTO or something like that and so you could argue ultimately that People Manager has more responsibility because you are managing the top IC.

[0:27:20.0] DA: Yeah, that’s interesting. I guess that opens up another question like should you even become a manager? There are opportunities in either case to excel and sometimes it seems like inevitable. The guy who’s been there longest is going to be the manager but is that the right thing to do?

[0:27:38.9] KR: No. Yeah, I think if anybody is making decisions that way, they might end up with a bad decision. Which is fine, you know mistakes happen.

Yeah, I think we talked a little bit earlier about what are some signs that might be leading you in the direction of being a manager. I think ultimately people shouldn’t be afraid to jump into it if they have curiosity about it. You can in my opinion always go back to being not a manager.

Interestingly when I was on the Hilary campaign, we ended up hiring somebody who is a VP of engineering at our company for a while and just wanted to not manage anybody, didn’t want to leave anything and just wanted to get back to writing code and so he came to the Hilary campaign just as a regular old IC engineer and was like, “I just want to write code.”

And he had been out of it for a while so he had a learning curve but that’s my example of like it can always go both ways. I don’t think that anybody has to get type cast, necessarily.

[0:28:37.6] WJ: Do you take a salary cut when you switch back?

[0:28:40.4] KR: Oh I think so if you go from VP to IC engineer especially for this job. One because campaigns do not pay really. I mean they pay but barely. It is not competitive at all.

[0:28:51.3] DA: It’s in feelings. Your hopes and dreams.

[0:28:55.0] KR: Right. You get paid by feeling good about your work and you know in this particular role that you jumped into it’s not on campaigns here like Principal Engineer or Distinguished Engineering like you would at Google and so I’m sure that for this person it was a paid job but if you are some VP is still really good at engineering and you move into a Distinguished Engineer job, I mean you know maybe the pay is not going to drop.

[0:29:19.5] DA: Yeah, I guess that goes back to what we were saying before about specialization. It’s going from a very high specialization where he’s the VP of a very specific thing and then becoming just one of all the men on women on the line writing code.

[0:29:34.6] WJ: Yeah, I think that’s probably what makes it anxiety producing. Is is the fear of losing progress when you switch back because it’s like, “Well if I had spent those two years being an individual contributor instead of trying my hand at management then I would be two years ahead on the individual contributor track and now, I am taking a pay cut in order to go back to being where I was two years ago.”

[0:29:56.6] KR: But is it a race? I just don’t feel like it is necessarily like a race. I mean maybe I guess in the financial sense of you are just trying to amass as much compensation as you can over your lifespan but -

[0:30:08.7] DA: Yep that’s the name of the game.

[0:30:13.3] KR: I guess it is the name of the game but to what detail are you so affected by it.

[0:30:19.2] DA: Yeah that’s true.

[0:30:20.0] KR: I lately have been so impressed and just the type of people that sort of like change their profession really leave an impact on me and this happens a lot in software where you have people, in my experience a lot of financial industry people who then go to a bootcamp and then start writing software and good for them. I am glad they did it and a lot of them have found out that is really their true calling, right?

So if you never try to be a manager, how could you know that it is not your true calling? Those people weren’t afraid to go into financial services. We interviewed somebody at Casper who had a PHD in pharmaceuticals and you know is now writing code and so if you look at it that way, it’s like, “Well that person went really far to come back.”

[0:31:03.0] DA: Right, pushing the boundaries of the human knowledge.

[0:31:06.4] WJ: Which one would you rather talk to at a cocktail party? The guy who has been a software developer for 20 years and never tried anything different or the pharmaceutical PHD who now works at Casper?

[0:31:17.1] KR: The latter.

[0:31:18.1] MN: Yeah.

[0:31:18.5] DA: I think that’s something that is especially interesting about like New York City tech too. I think there is a lot of path into it and that makes the people here very interesting. It is not just doing tech for tech’s sake. You know people feel passionate about it like I have friends who have made the transition from being accountants to being computer programming, a lawyer even. It’s like, “Wait, you’re making the lawyer money why do you want to write JavaScript?” is the question but yeah, there is some transition and it is a rewarding job.

[0:31:54.6] KR: Yeah, lawyer is an interesting transition I feel like I haven’t seen many lawyers that have transitioned over, have you?

[0:32:00.7] DA: Just that one guy. I am sure he’s great at naming things though.

[0:32:04.6] KR: Cool, good on him because I have the hardest problem.

[0:32:09.0] WJ: So if somebody wants to be a great manager, maybe a VP over at Casper, how do they get in touch with you?

[0:32:13.5] KR: I’m so glad you asked. This is probably not a surprise, Casper is a growing company and we are hiring. So you know if you are looking at either transitioning to management or switching management roles, we have two roles that we just opened up on our website for management and you can get to that at casper.com/jobs. There’s one that is in San Francisco for connected devices which is a very cool thing that we’re going to get into which is essentially smart products that will help you sleep better. I can tell you more one on one but it’s kind of secreted for now.

[0:32:42.3] MN: Yeah.

[0:32:43.3] KR: And the other one which in many ways is just as interesting and challenging is an Engineering Manager for our fulfillment technology which is once an order is placed, getting that package to your door which as we know, Amazon has made a whole incredible business out of and it is really hard and challenging.

So if you want to talk one on one, hit me up on Twitter and I am @kylerush. It is a very secretive name, you can’t find me, @kylerush. I am happy to chat on Twitter, grab a coffee or anything.

[0:33:11.2] DA: Nice and I guess if you are a manager and you’re looking at transitioning back to individual contributor role.

[0:33:17.0] KR: We also have that. We also have IC roles on the website, we’re hiring a lot so check it out for sure.

[0:33:23.9] DA: Nice.

[0:33:24.1] MN: Follow us now on Twitter @radiofreerabbit so we can keep the conversation going. Like what you hear? Give us a five star review. It helps developers just like you find their way into The Rabbit Hole and never miss an episode, subscribe now however you listen to your favorite podcast.

On behalf of our producer extraordinaire, William Jeffries and my amazing co-host, Dave Anderson and me, your host, Michael Nunez, thanks for listening to The Rabbit Hole.

Links and Resources:

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Python

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