From Seed to Series A: How to Scale Your Product Development Teams | The Pair Program Ep05

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Hey, what’s up everyone. Welcome to another episode of The Pair Program. The show that brings together two technologists from the startup world to tackle topics at the intersection of technology and career growth. I’m your host, Tim Winkler. And my co-host Mike Gruen let’s get into it. Frankie, Josh, what’s going on.

Good to see you again. Thanks for having us. I’m excited. All right. As you both know, this is The Pair Program. We love two of everything here. So let’s kick things off with a fun segment that we call Pair Me Up where each guest contributes a unique pairing. I’ll go ahead and begin.

Always been a big fan of game shows. So I’m going to go with game show host and Alex Tribec that goat, I thought long and hard about this because Bob Barker played a serious role in my life, staying home for a stick day watching prices. But I think he got to go Alex. They’re running through these rotations right now to figure out who the next house is going to be, but it’s hard to top that in my opinion.

The level that, that sweet spot of like arrogance that he brings to the, like that he brought, I think was a important aspect of jeopardy. Anything that’s going to be tough to. And I’m not saying that in a negative way. I think he, it was definitely part of the persona that came through that I thought was good.

Like when he was answering the question, like when people didn’t get the question, it can be tough to replace. And then the SNL parody is we could go on exactly. What do you got? So I’m going with chainsaws and overconfidence whole backstory there. So growing up I grew up in upstate New York, a lot of wood.

We actually had this big wood-burning stove. He did the whole house. Cutting wood with my dad was like something. We spend a lot of time. I have a chainsaw, but to use it, my neighbor recently had a tree that he wants to get rid of asked for my help assured me, he knew what he was doing and as like really, and he started getting out ropes and other things, cause he was gonna try and top the tree and bring it down like piece by piece.

And as if you know what you’re doing, that’s great. And he assured me, he did, he’d worked with in landscaping in the past Balboa, needless to say it did not go smoothly. Nobody was seriously injured, including myself, but it, the lesson I remember growing up, I was talking to my dad about this was like as soon as you’re bringing out ropes, chances are you want to actually use your wallet?

Like just go ahead and get a professional take care of, so that’s my pair. Chainsaws and overconfidence. Yeah. Bunny.

Josh, why don’t you why don’t you go next? Okay. I think artists and entrepreneurs I think the two of those have a lot in common. And the more you explore artistic endeavors, whether it’s writing or painting or poetry or whatever, or you start to realize that the bravery and the vulnerability that comes with those artistic expressions, it’s also pretty similar to what entrepreneurs have to exhibit to bring their things into that as well.

That’s something that I’ve enjoyed studying those two things in parallel and seeing the commonalities between both. That’s really interesting. Favorite artist? No, not necessarily. I enjoy riding and I enjoy some of the great novelists, Ernest Hemingway and some of those, and just enjoy the craft of writing.

I studied about that. The more, you just, you see these parallels there’s a great book called art fear. That talks about just the difficulty of putting something new into the world. A lot of the psychology that happens. And so reading that as a hobby but living in the world of startups and entrepreneurship it’s just, it’s cool to see the overlap between both cool.

Mike did you have? I was just going to say, I think that there’s a similar I’ve the creativity and artistic musician, that type of stuff. I’ve also seen a lot of correlation between that and engineering and product as well. And I was just curious if you’ve also seen that have some more.

Yeah. And the line between like brilliance and just plain crazy is obviously a very, it’s a very narrow line. And so a lot of people are misunderstood for a long time, some never fully, make the mark like they hope to but others, they see a future that people never saw and were crazy enough to pursue it.

And eventually the world caught up to them. And so it’s the parallel journey really.

What do you have for a pairing? Yeah. So my pairing is things that make us emotional for absolutely no valid reason. And those two things are immense professional sports and the bachelor nation franchise people have a huge amount of viewership and people that are in a bad mood the next day, depending on the.

Really the only difference between these two things, which both involve massive drinking parties while you watch the big events, right? Is that you can’t bet on the bachelor because it’s recorded in advance and there’s lots of websites where you can go up and look up the spoilers of the season because it’s all happening in bets.

I swear. That’s the only reason people don’t bet on the bachelor. Otherwise I think that those two things would be completely identical. It’s a very arbitrary sense of rules. Everybody’s got a role to play. You’re not ever really seeing anybody’s true face in either of these things, it’s still a job and they both just can make you irrationally upset because you’re emotionally invested in these people on your TV.

Yeah, sports and bachelor nation. It’s funny. Actually I can specifically remember walking into the office on Mondays and, being a Washington football team fan, just complete dumpster fire over here. Monday’s folks are just pissed off all season and then you get one win and you could just see like Steve.

So chipper today. I remember reading a book about the psychology of people and blah, blah, blah. And one of the things I remember from the book was like when your team wins it to your team, when they lose it’s that they lost, it’s never, we like, they lose, we won.

Oh, that’s a good one. Okay, cool. All right. That was fun. Let’s let’s segue out of this and into the meat of the discussion here. So I’ll go ahead and jump into this. All right. On today’s episode, we’re going to be covering a topic that we like to call stage fright. So this is an episode all about dissecting the unique growing pains, challenges, growth hacks that the startups experience, going from seed stage to series.

Given this as a pretty broad topic, we’re going to keep this more narrowed into, roles and how teams might change from seed to a Frankie, you’ll be the engineering perspective here, Josh, or you’re a product perspective. Frankie, let’s start with you just maybe first off for some context for the listeners, how many, seed stage startups have you been a part of, and of those, graduated into a series, a stage.

Yeah, so great question. My last company that I was at was seed-stage and we were actively raising series a to the day that this is recording. I don’t think they’ve been able to do that. Sometimes you just don’t have a product market fit, you try and experiment, and it doesn’t work. I’ve worked at a couple other companies that were essentially seed stage.

They have. Previous funding. They were either after a pivot or some sort of catastrophic problem that caused them to start from the ground level again. Cause sometimes this also works like shoots and ladders. So they had a lot of the same seed stage problems while they might have advertised that they were seeking series B.

But if you don’t have a product market fit, you’re essentially at the same place as the seed stage folks, you have a lot of the same. And Joshua, I’ve talked to you off and on, we’ve done a few interviews in the past. This is your sweet spot, right? Maybe a little context for the listeners on your back.

Yeah, so I’ve done one, one pre-seed one seed stage that was similar to what Frankie mentioned, where they actually had other funding, but do you continue to remain in that seed strata and then the other four VC backed companies I’ve been a part of have been typically one of the first product people brought in and that’s typically at the series a, so you’re right there at that transition from seed to a and so that’s really where I’ve spent most of my career.

Let’s dive into some of the, some of those topics then. So what are some of the major differences that you see from the start maybe with leadership roles and seed versus, how those evolve in a, maybe a series, a back type of startup Frankie, if maybe from your perspective on engineering, there’s actually several articles you could find on the internet about the five types of engineering leaders you need as your company scales from seeds.

To IPO because the job looks completely different. The other way you might see this laid out is, that article about handing over your Legos cause your, a job actively changes. Your first engineering leader is probably actively writing code. They’re doing a lot of things themselves.

They don’t have a lot of support. In some cases it’s been the case for me. Sometimes I have needed to act as product management. Yeah. Either because we didn’t have one or because there was too much product management work for the product management team that we had. There’s a lot of reasons why that might happen.

And that job is actively going to shift and you have some choices as you grow about whether you want to hire somebody in over top of them or whether that person is able to build the skills necessary. But your seed stage engineering leaders are usually epic Jack of all trades.

They’re writing code, they’re doing Formance management of the other engineers. They’re working closely with product. And they’re also figuring out what’s an acceptable amount of tech debt at that particular moment of time in the business. You are a lot of hats. I think I’ve lost track of the original question.

I’m curious what your thoughts are. Cause I think especially in the early days the, that. First engineer is doing so much. A lot of times they’re also trying to figure out what they want to do next in their career, right? This is this is their first or maybe second step into more of a leadership position.

Maybe at the last place they were in IC a senior dad, whatever. And now this is this is their opportunity to do a little bit of management, a little bit of this, a little bit of business ownership. I’m curious if you know what your thoughts are, because I think that’s also a big part of it as them, themselves figuring out what they want to do.

Absolutely. And I’ve been on two sides of this one is convincing engineers that they should go work at early stage startups specifically for that kind of experience. The other thing is being that person myself a couple of jobs ago, I was hired in as a team lead and they were right on the tail end of some very big change that happened and a bunch of people.

And then suddenly it was just me. I was like I guess you better give me the director title now, which I think, but you, it helps to have a goal in mind when you go work at a startup as a, as an early stage engineer, is your goal just to acquire some specific experience so that you could take that on to the next place, or do you just want to go flex your muscles and see what you can do?

That will also help you in making the decision. How long you should stay there because the earlier the startup is. And the more likely you are to experience significant change, the less need there is for you to actually be there for years and years. The engineers that you hire at the beginning who want to write the really scrappy code and just get the thing out the door, or maybe not the same ones who are capable of fixing your tech debt problems.

Six months

that’s spot on and they’re not invested, right? If you’re an early stage scrappy startup engineer and that’s what you enjoy, that’s real life hackathon happening by the time you have to start maintaining the code bases that you’ve stood up. Maybe you don’t care about that. And I think that’s a good journey to go.

And I think it’s a good question to ask yourself and I think, another thing, and I encourage people to do the same thing, which is go and try different roles. See what you like, you don’t, you won’t really know if it’s a good fit or what you enjoy doing until you try it. And it may be the case, like in my career I was pushed into a little bit of a management role pretty early on.

And I was like I liked the job, but I miss this other stuff. And so I went back and went back to engineering for a while, knowing. I enjoyed some of that management stuff. And I can get back to that if I want to. And I think that’s an important thing, as well as that it gets there’s flexibility in a startup where you can bounce back and forth between leadership, icy management.

And there can be lots of definitions of that. Yeah. Even at the same company, you can do that. Yeah. Yeah. Because when they’re ready to hire more people, you can always pipe up and say, I would like you to hire me a new boss. I just want to deal with this stuff. I want to just work on this. The reverse, make me the boss.

That’s a little bit of a harder sell, but you can always say, please hire me boss. Josh, what have you seen on from the product side of the house? Yeah, it’s it’s interesting, typically product comes in at the series a stage. So product at the seed stage is generally the founders and this.

Engineering leader quite honestly, and early customers, right? Those are the voices that are typically shaping that first version of the product. And and honestly I think that works really well. I don’t, I think there’s some advantage to having product early. But when you’re a seed stage product person, you’re wearing a lot of non product pats, like you’re typically customer success.

You’re typically operations. QA you’re typically, and some product work. So if you like that and you like, that spread, then that can work really well. But if you want to do true product stuff, that’s really starts kicking in, at least in my experience around the series eight timeframe.

Have you seen, where like a product person maybe is one of the very first senior technology type hires and it’s real and they’re. They’re technical solution is we’re going to outsource engineering, or we’re gonna, we’re going to use this third party to build the thing. We think product is really important and that’s why we want to retain this information.

But the actual engineering aspect of it is maybe less. Have you seen that? And what’s your. Yeah. Most of what I’ve seen has been actually, having the engineers as a part of the core team typically where we’re at least in with teams, I’ve been a part of the outsourcing starts when you’re ramping and you’re trying to grow quickly and you just can’t hire enough local, the folks.

And that’s where you start to augment with, folks in Europe or Asia has been at least what I’ve seen. How about you? Me personally, I’ve definitely, I know a couple of consulting companies where that’s what they do. They specialize in working with founders who don’t really know the tech side.

And then, and so they actually are the, that engineering and they bring a little bit of product. And then the first part, like one of the first hires has been a product person. It’s an interesting, it’s an interesting journey. I think. One of the things, especially engineering. Frankly, I’m curious your thoughts on this, but I think early on whatever you build, you’re just plan to replatform.

Whatever you do is probably going to be. And you need to be ready to move on. I think some of those founders that start with this, like outsourced engineering idea, like have that as like a we know, like we’re gonna, yeah, we’re going to have to move off this. In fact, actually one of the companies, I forgot where I was the first engineer hire they’d actually, they had outsourced a lot of the initial build to these other companies to build that foundation and prove out the.

That’s out there had a lot more money to self stake it. Yeah, I think that’s actually a good point, especially for those like first that really that first build, I have seen that, but a lot of times, sometimes those folks just get absorbed into that core team, if you can, and then eventually they get, get bored and decide to move to their next challenge.

But yeah. Yeah, I think you’re spot on that. That’s pretty common, at least in that like very zero to one stage. Yeah. Josh actually there’s the guys from, like a dinner rush. So I talked to them quite a bit about this because they do, they help with a lot of like early stage hiring for your first product hire.

And the common theme that they come back with is almost put your blinders on to like title because you don’t you would think you, maybe you need this chief product officer, this head of product, really what you need is like a hands-on like product manager, not really managing people, but something that’s really.

Getting their hands dirty and getting into the thick of it. You’re going to save a ton of money and you’re going to give somebody an opportunity that’s hungry and really that’s what you need in that seed phase. Or even like getting into that first product hire. Yeah, no, I think you’re, I think you’re spot on.

Especially in the seed and then the series a as long as that person can also help with hiring the first few product managers and provide leadership there and then also help getting the scaffolding for process and structure in place. Yeah, I think you can take a really, sharp IC or somebody that’s had that middle area to really fill that leadership role.

And maybe ways that’s been my journey, to be honest. Moving into that middle layer. And then at some point you can bring in the kind of hyperscale, person to build out a larger work after that back. So I think that’s spot on. Yeah. The outsourcing thing is a challenge. I’ve been engineering leadership at an early stage startup where we had folks in Europe, my team spanned from Europe to Thailand and it had not been contextualized for anybody else that was there before.

That if you have a bunch of international contractors, right? Your code base, especially if you have them do it in a tech stack, they were previously unfamiliar with you. We’re going to have to rewrite it. And so one of the challenges that I had in that role was explaining to them that what was already in GitHub was mostly garbage and it, we couldn’t debug it.

We couldn’t even solve the problems. Like it was such a mess because there had to, there was literally CRO incentive to maintain the code base that. The only, it was just push this feature out, push. It was too feature heavy. It was an overgrown MVP and it needed to be moved to another platform. And by the time we were even able to do a piece of that we actually made a mistake.

We should have just threw that rebuild up onto a sub domain that we tried to put it right up. This was an e-commerce. We tried to put it right up on the same website and the sort of local storage. Cookie stuff was so messed up, that it broke things for basically all of our customers. Oh man, we couldn’t even replicated locally.

It, this is your worst case scenario. If you hire a bunch of overseas contractors and then you don’t accept that you’re going to have to rebuild it later, that these are the kinds of problems you deal with. Within a couple of weeks of joining, I realized that there was enough information on the window.

Cause they rolled their own server side rendering to log into the database. Oh, wow. And I was like, ah, we are too big to be doing this. And then you have all, then all of a sudden this, all this tech that exists that no one else at the company even thought was going to be on the horizon.

And it was a huge surprise. So I think you can absolutely outsource successfully. But everyone needs to not be under the delusion that they’re going to build you the beginning of your final code base. I was just gonna say, yeah, it’s definitely, it’s a step you can take, but it’s I think of it as Your you’re out settling the west.

And the first thing you want to do is you want to build a shack that you can like sleep in while you build your house like this. This is going to take care of 90% of my needs in the short term, in terms of keeping me dry place to sleep place away from that. But in the end, this will eventually turn into the barn or the place I started the wood, or just turns into fire what it’s.

Yeah. And it’s okay for it to be firewood. I was sent to a tech conference once and they were talking about legacy code. Like when you’re at an early stage startup, all the code route you wrote yesterday is like C code. That’s the right attitude to have about this. When you wake up in the morning, everything from yesterday is but that’s primarily, are you saying that’s in like the seed stage?

But once you get to S to your series a, at this point, you’re I would hope you’re out. You’re off of the off shore, crutch and you’re hiring internally at this point. Yes. That’s where I was going to just piggyback on what you were saying freaky, like on the products.

I was one of the biggest challenges you have in series a is. The pace of development just slows down because you’re actually trying to do things right. And you’re trying to clean things up. And so a lot of the time like that early team is used to features just flying out the door because you’re just so scrappy.

You’re not really concerned about architecture. You’re just trying to prove to yourself that this is valuable. We can serve this customer and it’s the right. But then in, in a it takes it takes about a year and a half to really get people acclimated to this new page. That’s more consistent, more predictable.

And it’s just a lot slower. You just ship a lot less features because you’re building it for scale. So that’s one of the big challenges you have to really fight through on the product side, coming in at that series. A and you might have to have a conversation with the other leadership at the org about how you can have good quality code or you can have.

You cannot have both. I will die on this hill. Fight your mother, not me. Sliding scale. You get to pick where you are. I think there’s three things there. Speed, quality, maintainability, whatever you want to call it and predictability the predictable, like you can, we can move really quickly, or it can be predictable, but we can’t do both.

Like it’s there’s just, there’s so much time on the. How we’re going to allot it and where we’re going to allot. It is like maintainability figuring things out, predictability or shipping. Yup. Yup. And you might pull out the old mythical Man-Month essay. Like you can’t stick the nine women in a room and ask them to make a baby in a month.

Yeah. One of the things that it’s such a hard thing, because the reason used to moving so quickly, one of the things that I’ve found really useful as at series a you’re growing in a place where things start to break. And so it becomes a really good natural opportunity to just like point to those things and say, Hey, remember that outage we have last week, that’s because of XYZ.

And that’s why we want to prioritize this. Tech initiative and start to allocate some bandwidth. So instead of having the philosophical argument, those things inevitably just happen. Those quality issues just happened. Cause you’re so used to moving quickly that you point to those and that can be a more productive way to get leadership to connect the dots for them as on, on the product.

Let’s say a big thing that, plays into this in terms of, how teams kind of transition and build out is obviously going to be like from a hiring budget to, when you’re in that seat, stager, you got tight pockets, you can only do so much. And so when you think about graduating to that series, a.

You now have a lot more funds to play with. I’m curious to know what kind of trends that you’ve seen in terms of how teams start forming once there’s a little bit more in the budget, obviously there’s, squads, pods, whatever you want to call them. How have you seen those start to grow out?

Frankie on the engineering side? Yeah. Places do this very differently, depending on. Who is in charge of making those decisions. And if it’s me, it’s always going to be based around like the areas of ownership in the code base. I don’t want multiple teams to own the same code base, where if I were ever in a room and we’re having a conversation about team a owns lines, 50 through a hundred and team B owns like these other lines.

Full-stop and also the way that your features and your code bases grow and the way that your teams grow. They’re very interesting. At my last company where I was head of engineering and I got to make these choices for myself, we were going to, as we grew, this was going to be the e-commerce side.

This was going to be the warehousing side. And probably eventually fleet would be its own team. They were going to be part of warehouse for the immediate, but we had to separate the types of things that mattered to people that were basically building an internal tool from the e-commerce. Even the way the product interacts with. And by combining, like even having those two priorities on different tracks is already a benefit. Those code bases are going to grow in a way that makes sense for the engineers that are on the team. So you have to think long-term about at least for the next six months into the future, what you think is going to happen with the product.

And then how do you divide up the team so that they can be fully invested in the piece that they own, rather than giving them like little snippets. A pattern that I’ve seen that isn’t great is when teams pick up something temporarily and then put it down when it’s done. There’s no incentive to make sure that it’s easy to maintain later because you might not be the one doing it.

Also you’re probably operating on that. Let’s just get it out the door fast. And when your seed stage, and you’re just trying to figure out market fit, you can, your JIRA board might be a bunch of post-it notes on the wall and that’s fine. But the minute you start needing to be predictable to your customers that doesn’t fly anymore.

I think you, you have to create your teams in the context of the product division and also with the technical stuff, needs to be to support that product vision, and then divide it so that people can own as much of their own stuff as possible. That’s the thing that’s worked the best that I’ve seen.

Yeah, that’s spot on cranky. The other thing that really helps when you move to that model, in addition to the ownership product benefits from that ownership too, right? You break apart. The key parts are based on product line or persona or key components, whatever. It also really helps the leadership team to start to think about how we want to invest and where we want to allocate resources, because you can get a warehousing team and a e-commerce.

You can start to say, okay, we’re going to invest, five or 10 more heads over the next, period of time, where do we want to, how we want to allocate that. And that helps your roadmapping process. Cause they can start to think about it with some investment buckets to think about it makes those conversations where as if you have one kind of consolidated team, it’s way too hard to figure out how much is going to one part of the product versus the other.

And it can be really challenging. So I think you’re spot on with that. And it helps not only the engineers, but also the product to huge help. And I think there’s a product as well. I’m just gonna say I think the. It goes without saying, but at the end, I think it was implied.

Frank, can you tell me if I’m wrong, but like the idea of cross-functional right, like in the old school days back when I was an engineer, there was a front end team and the back end team and the front end, worried about the front end and gave specs to the back end of the backend, built an API and blah, blah, blah.

And it took however long it took now. It’s cross-functional you want to align things to personas, to intent, to code base and so on and so forth. And so they’re much more vertical than they are horizontal. Yeah, absolutely. I think that the front end versus back end team might still work in a handful of places, but for the most part, you’re still on incentivizing the engineers to behave the way you want them to behave.

Which is to care about the whole feature. And instead of it being parts of the code parts of the stack that we divide up, thinking about it in terms. The business units or the business separations of concern. It’s also helpful to product management, right? If one product manager can own e-commerce and one and a different product manager can own warehousing.

That’s better than one person trying to juggle those two very different concerns with very different needs against each. Or when you have two product managers that like, have those two different things and you have a pool of engineers and they’re fighting for resources. And it’s only probably knows how to do such and such.

And only Jane knows how to do blinds. Like then you’re playing all these other that’s how, that things are really bad when you’re trying to figure out who can, who should work on what whereas if the whole team is moving in the same direction and they’re all invested in getting.

Feature or that product out, they can really work together in a way that’s much better than if you were just pulling people one off because you’re like you have this special skills that if you’re at a seed stage startup, and there’s only one person that could do one thing on the engineering team, you might already have a problem.

Okay. I think it’s key for retention too. Especially in this market, if you can give somebody ownership of something and they can really own it and have some autonomy for on the product side that, the priorities and the strategy, but on the tech side, the architecture and how we want to see this thing moving forward.

I think that’s really important. And yeah, it makes a big difference. Yeah. And I think just wrapping that up in my, the idea of org structure versus team structure. I think I’ve had this conversation with any number of people where it’s like, we can have a team structure that’s this way where there’s a product person and a lead engineer and so on and so forth, but that doesn’t necessarily have to be how we’re organized from a reporting structure.

And I think that’s something that some people, especially founders who may sometimes struggle. Yeah. Th the only other thing that I think you gotta be aware of coming into series a is you gotta be patient. Like you have the vision of where you want to get to, but not all these pieces come together, right?

You might not have enough, front-end developers to really have one per team, for example, and you might need to let things balance out and you might not have product managers that can fully focus. And so it just, there is this piece where if you come from a big company and you’re used to these like nicely carved out themes, It’s going to take a little bit of time to get there and you have the vision of where you’re getting to, and you’re laying the pieces in place, but there’s definitely some patients that it’s going to be a little bit non-ideal.

But you’re moving towards where you need to get to. So what are you what do you all prefer? You prefer that seed environment or the environment? I prefer the seat environment. When we can raise here.

When you’re not just rotting fruit.

Yeah. I think I like the series a, I think that’s the more interesting piece for product managers. You’re putting the structure of the process starting to think through the strategy. And so I think that’s probably the more, a place where you come in and you feel like you can really make an impact more so than the seed stage.

If you’re a product person that sees it as you’re probably the founder is the reality.

Yeah, I don’t, I totally don’t mind also playing a little bit of product management earlier on. But the hard part about all these things is that anytime you joined a to start up, you’re making a bet, you’re making a bet that there will be product market fit. Then you can find because most startups fail.

You have to treat it like that. You can’t treat it like. This is going to be my life’s work. This is where I’m going to get rich, like getting rich on an IPO is a side effect of making really good choices about how you allocate your career time. It’s not a destination, so you have to know what kind of ride you’re willing to get on and then know what your boundaries are and what you’re trying to learn.

And then make good choices for yourself, right? The job market’s crazy right now you have a lot of choices and if you’ve never, for anybody listening, if you haven’t worked at a seed stage startup, you should absolutely give it a try. You never know you might love the chaos. Yeah. I always advise folks.

So I was going to say, I always advise folks like, if you’re interviewing Theodore series a and do a little extra homework on the leadership and kind of see like their backgrounds, see where they came from. And then, ideally you get a chance to speak with the C-suite. At least somebody, high up before making a decision so that you can buy it.

You want that buy-in and stuff to follow, a vision. If you can’t get behind the. Yeah, pro tip. If it’s an early stage tech company, you really want co-founders and you really want one of them to be technical, right? You end up with a whole host of very specific problems. If you have either a single founder or if you have a pair of co-founders who don’t know how engineering works this is why all the big VC firms look for a technical co-founder because I think statistically speaking, you’re better off.

Oh, that sounds like an awesome episode

horror stories. All any other closing remarks that you all want to throw in there before we transition to the next segment? We covered a good amount. Yeah. All right. All right. So yeah, this next segment here, we’re going to jump into it’s called round out my career. So this is a fun segment where we spend the community wheel with topics and questions that are all centered around career growth.

And these are crowdsource from the hatch pad community. So I’m gonna spend the wheel here and see what today’s topic is. Forget one lucky hatchback community member can win a free, a raspberry pie. We were land on the price.

Alright goals. Awesome.

Get hyped. Alright, here we go.

All right, so this one’s more centered around just like setting goals. So I’d love to hear just any tips that you all have when it comes around, setting some of those goals for maybe yourself, but also maybe members that are on your team. Josh, why don’t you start? Yeah. What I think is in terms of like career goals, is that what you’re talking about?

Yeah. I’d say like a specific towards like career goals. Yeah. Yeah. I think that the biggest thing I’ve found is I’ve found that when I’m setting my goals early in my career, Got a lot of insight from people that were down the road from me. Cause I didn’t really know what goals to set earlier in my career and yes, to some extent you’re always learning.

But I think a lot of those conversations with people that were, 10, 15 years down the road had already been pretty effective in their careers to circle back and say, Hey what kind of goals should I set? I had a conversation with one Startup CEO. And one of his pieces was of advice was, joined a company early for the growth potential.

And that’s what part of what pushed me into setting a goal of, Hey, I want to join an early stage seed stage company. That’s been great for my career. So I think, early in your career, as you think about career goals be sure to inform that with folks that are, have been effective in their careers and use that insight to help you.

Yeah, said, Frankie, Nia, anything specific that you’d recommend? Yeah. I always advise people, especially if you’re looking at joining early stage startups, which is what this episode has been about is to really frame it as about, this is all the information that you have that says that this is, this might be a good bet.

And maybe here are some signals that, in advance once this, if this sort of thing starts to happen, that maybe this is the writing on the wall. And you make good choices for yourself. You. Should not feel obligated to stick it out somewhere. If you are not getting what you need, a lot of companies will try to preach that you loyalty, but at the end of the day, the company is going to do what’s best for them.

And you should do what’s best for you. So you should take big risks, but also you should be willing to walk away when either you don’t think there is product market fit, or you don’t think that you’re going to get the kind of growth or coaching that you wanted out of that job. So take the big risk, but just because.

Stay light on your feet, be ready to pivot, you set goals for yourself, but they don’t have to be set in stone. And if you don’t make them, but you had a really good reason to have done something else, you should still feel good about that. Good stuff. Mike, did you have anything on that? A little bit off of what both of our guests were talking about, but with Frankie, I think one of the things like from a goals perspective, making sure that you’re communicating with leader, with your manager, your supervisor, whatever about what you want, what your.

It’s a two way thing, right? If they don’t know what you’re looking for, then they’re not going to really give you those opportunities. Similarly, if you’re constantly, I think we made it, we might’ve have even joked about this a little bit. If you’re asking for a promotion, like really find out like what it is that what is it that my boss is expecting to see from me do that from the other side of it, right when I’m promoting people.

I expect my expectations that you’ve already been doing the job for some period of time. Maybe it’s three months, six months. Depends. But you’ve proven that you’re capable of doing the role and then the title and promotion comes as a consequence of you having done it. So my advice is don’t sit on your hands.

Oh, there’ll be sorry when I’m gone. Like that type of mentality. Isn’t great either. So it’s definitely this communication and most managers, but especially in engineering, I think in product design, We really leadership really takes pride in especially early stage startup of helping people launch and develop their careers.

I don’t think any one of us thinks that this is the last job somebody who’s reporting to me is ever going to have. And I take more pride in the people who’ve gone on to great things that who worked for me at some point. And so I think it is a good conversation you can have with your leader, with leadership in general, with your boss supervisor and not to be afraid to have that conversation of.

Where’s this going to go. And maybe this isn’t the best time. I think we even talked about it a little bit in the episode oh, as the company grows and goes through these different stages what’s needed and who’s the best fit, changes over time. And that should be a conversation you’re able to have with your manager.

So definitely that. And I’ve also talk to any, I’ve always had a mentor in my life. Someone who’s a couple. Two or three stages down the road for me. Who’s helped me. And one of the mentors or two of the mentors that I’ve found most helpful or ones who actually didn’t have engineering at all, they were, one was a product person.

One’s a marketing person. But they were able to give me so much more insight and depth because they had the sort of like outside perspective. Don’t just, look for mentors of oh, another engineer and I’m going to hitch my wagon to that person, like think outside of that and look into other parts of the organization.

The other thing I’d add Tim is I think over my career, my, my goal, I never would have known what my goals were going to be like. They evolve, it’s a process of discovery, that you go through and you have a sense for where you’re going. But that starts to get clear over time.

And the only way to know is to, to Frankie’s point make some bets, and so the other thing is I think I obsess too much over my goals earlier. Whereas I probably should have just, thought about it, set some goals and then reevaluate in a quarter or six months and adapt.

And try some things. And. Worry too much about it. Is it making me better? Is it giving me some new experiences? Great. Let’s go for it. And then let’s just adjust. So that’s the other thing that I think I’ve learned along the way. It’s a good point. Like when somebody asks you so what’s your, what’s the five-year plan, I’m like, man, I’m just trying to see tomorrow.

I’ve got a year, I got a year, maybe a year goal here that I want to hit. And he started talking like three years, five years, and then there’s so much that changes when you’re in such a fluid environment and especially in the crazy ass world that we live in. And, you never know what’s going to impact how business is done.

And then your goal just got flipped on its head. So it’s like it’s being flexible with that is important. Yeah. My personal, like goal why all of my personal career goals sounds something like I would like to be able to say yes to the right thing when it is. And if you can do that and make sure it gives you, give you a future self, the ability to make decisions, you don’t have to make them all for yourself right now.

Yeah. We didn’t know there was going to be a global pandemic 10 years ago now. And then it hit us and that changes it a lot. And hopefully if five years from now, there’s no more pandemic, but also we don’t know if that’s true. So that’s your future self up for success? Good stuff. Yeah. I think unless there’s anything else that y’all want to talk on, we do have a few more minutes, but otherwise I think we covered quite a bit.

Like I mentioned, this is a good topic that I think, we just have a miniseries on and I’d also love to see it from, like series B series C or even beyond this, because there’s a lot to unpackage here. I think what’s really exciting. It’s see to a, we work a lot in that space and I think it’s one of the most dynamic changes because, and it’s one of the most high risks, so you’re going to get a lot more crazy shit happen and some good stories spit, oh, shit stories. But yeah, there’s a whole other, there’s a whole other realm of stages that have very different problems and different perspectives. So I see us building on this one. And bringing folks in that can shed some light from a different angle.

Yeah. I’m just curious on your guys. Let’s take it. It’s always seemed to me like there’s the seed stage then there’s a, to C and then there’s C plus like a and B feel very much a continuation of the same thing. Like in many ways you’re almost guaranteed to get a B, unless something, at least in this market, unless something catastrophic happens.

It seems like those are like the three phases that I’ve identified. Do you guys see the. Same thing. Or do you guys see something different? No, I would agree actually as Tim was even talking, I was thinking yeah, it’s there’s seed to a, and then a to C, C plus and Blas. I don’t know there’s this sometimes there’s a D but there’s this, then there’s this point where right.

There’s hyper-growth or whatever you want to talk, but there’s this, a and B and I’m curious, I think Frank, you probably got some pretty good experience there as well. Yeah. I think even Reddit is considering itself a start-up and they just announced like series F or something it’s come on.

I break it up into do you have product market fit, which is your pre series a and then okay, can I cuss on the show? Okay, don’t fuck that up. You have series in, just don’t fuck it up. And then you get to a point where you have so much money, at the place I’m at the company that I’m at right now.

We’ve probably raised our last Trump funding and, IPO is what we’re looking at next. And that’s a very different ball game even from like your previous rounds of funding. But I think those are really the three phases it’s get product market fit. Don’t screw it up, go public or, put a slack and let Salesforce work, whoever bought them.

Either way, lots of people get a big payout, which is great, but those are your phases. Yeah. I agree with that. Yeah. Yeah. W from a recruiting perspective, and we look at a lot of things in terms of, when is there certain departments created? For example, like we roll out a different packages that cater to, C to B, and then when you’re at C and beyond.

It’s, you’ve got a full-out recruiting team in place. We just serve as a supplement, versus like in those early stages, like we are your standalone like department because you have nothing in place. And so those are very different, requests that they’re looking for. We need a system stood up and, we need market research and we need all of these things beyond just we need candidates.

We need a pipeline. We’ve got folks on the inside that can handle. Other stuff. So like from a services perspective, yeah. We break that up between like seed to B and then the C plus. So that’s interesting, good stuff. I guess for, for the listeners, like any, anywhere on social that a guest can find you.

Yeah, I write frequently on LinkedIn. So folks are welcome to follow me there. Josh one is my handle there. I’m also on LinkedIn. I’m pretty active on Twitter, although I’m not always talking about tech, but you can find me at Frankie is Frank as I’m porny like that.

Perfect. Awesome. I’m super grateful for you all to come and spend some time. With this, I know this is a great topic and it’s going to definitely peak the interest of a lot of our listeners. So appreciate y’all thanks so much for joining us. Thanks for having me.

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