Cultural Fit

Added: 2026-05-14

[00:00:00]Cultural fit is the most misused phrase in hiring. The founder say it, the recruiter say it, and the candidate, they not like they know what it means, and then everybody hires the wrong person, and act surprised if it doesn't work out. So, let me tell you what I think it means. It has nothing to do with a German or Australian culture, or yogurt, or whether we have the same taste in hardcore techno. No, it is something entirely different. Cultural fit at your stage is phase fit. That's it. That's the whole thing.

[00:00:35]You are post product market fit, you've raised some money, you have between 15 and 40 people. The job has changed. The job is no longer making the impossible happen with three people and coffee.

[00:00:50]Now, the job is turning crazy into reliable, fun into trust, and heroics into systems. And phase fit is hiring people who understand that.

[00:01:04]Someone who can feel and understand the difference between an early stage company and a scaling company, and they know what they're walking into. Phase fit is attitude, phase fit is communication, phase fit is somebody who can sit comfortably in a meeting where things are fairly uncertain, and they don't need certainty to feel safe. They also don't need the chaos to feel excited. They are somewhat in the middle.

[00:01:34]A phase fit is also not whether somebody laughs at your jokes. Phase fit is whether somebody can comfortably build a playbook without being asked twice.

[00:01:45]After your raise, you accidentally hire the wrong people.

[00:01:50]They're not bad people, they're not bad at their job, they're just really, really good at a different phase for your business. You probably hire people that are more like you, firefighters, wild cards, people who are excited about finding product market fit, jazz band members, right? People who love the chaos and love problem-solving and love uncertainty.

[00:02:17]And they're just not the people you need anymore.

[00:02:20]And then you wonder why everything sort of falls apart 9 months after a fund raise.

[00:02:26]And it's not because you hired bad people, you hired really, really good people for the company that you used to be, but not for the company that you're now.

[00:02:36]Early stage operators that thrive on chaos, they invent, they they get you from zero to something, they are brilliant in year one, and they're expensive in year three because when there is not enough chaos in your company anymore, they create some.

[00:02:55]See, in phase two operators, they look totally boring next to them. They write things down, they document stuff, they create process, but they're the ones who prevent your meltdown in the next board meeting.

[00:03:10]You don't need more wild cards.

[00:03:12]You need somebody who can turn the wild into repeatable processes.

[00:03:19]The other things founders do is hiring the title.

[00:03:24]VP of this, head of that, and 20 years at a logo that you recognize. And I get it, it feels amazing. The board loves it, LinkedIn likes it, and we sort of feel grown up now.

[00:03:41]And then they arrive, and they expect a whole team under them, they expect three reports before they do anything, they are used to executing playbooks they didn't write on tools they didn't choose on a company that's four 10 times bigger than yours.

[00:03:59]That's not a hire.

[00:04:01]That's a cost center with credentials.

[00:04:04]At your stage, you need somebody who is one phase ahead of you. Somebody who has done this before, taken a startup from scrappy to boring.

[00:04:15]Good boring. Somebody who has an experience in building the repeatable systems.

[00:04:24]Somebody who built a thing before with their hands, with a team roughly your size, and they remember what this is like.

[00:04:33]Senior enough to lead, hands-on enough to actually get done, and humble enough to happily do either.

[00:04:44]If you ask me what the first hire after product market fit should look like, I would give you two different answers depending on what it is you're selling. So, if you're a B2B, I would say hire a customer success manager.

[00:05:01]See, you have been doing all the sales, and all the customer relations ran through you. You are the CEO, and now you have to remove yourself, and have somebody creating trust relationships with your customers. So, you do a handover with each account that involves you, the new customer success manager, and the customer. And you are creating a playbook, a let's just say a notion document where you put down for each customer a single source of truth where you list everything. This is the customer, all the contact details, blah blah blah.

[00:05:41]What is the current opportunity? What is the overall? What's What's the What's the end opportunity? And then you you have an understanding in the handover who of your customers should be the most important ones.

[00:05:57]They're the ones that are most urgent and important for for handover. So, customer success manager should be your first hire.

[00:06:06]Somebody who can build trust with your existing customers and somebody who can take your proof of concept or evaluation sales or first sales into scaling sales. That's who I would hire.

[00:06:25]And that person should be somebody who understands how to operate in small teams, who is hands-on, but also somebody who can communicate very clearly. I need this by then.

[00:06:38]This is the owner and also follows up.

[00:06:41]Somebody who is kind, but also very direct and knows what they want and has a natural ability to communicate to the customer on all level from procurement to finance to security and so on.

[00:06:56]Um but also internally, they can talk to the CEO obviously, but they can also talk to the techies, the UI designer.

[00:07:04]And first hire for B2B customer success manager, 100%.

[00:07:10]And if you are B2C, I would say you should hire a CRO.

[00:07:18]A CRO is a chief revenue officer. It's basically one person that owns marketing and sales at the same time.

[00:07:27]And the the objective is revenue and you avoid those silos. You know, like if you have a chief marketing officer and a VP of sales, they run their own stories and they're often very disconnected.

[00:07:44]And they have different KPIs and it's very very difficult to to get them all, you know, pulling the the rope in the same direction.

[00:07:53]You know, suddenly the marketing department promises something that sales is confused about and engineering can't deliver and I don't know. It's it it could be very messy very quickly and you really can't afford that at a company your size. So, you have a chief revenue officer who owns the entire pipeline.

[00:08:12]And that brings everything in your company in line and and that person can talk directly to operations. That person can talk directly to engineering and clarifies and cuts red tape everywhere.

[00:08:28]And things move faster and in a higher quality.

[00:08:33]And either way, whether you're B2B or B2C, the person that you hire, they are sort of very similar personalities. They have the same culture. They have the same personality shape, so to say.

[00:08:49]They they write things down. They create playbooks. They create those playbooks for the people that come after them.

[00:08:56]They work towards being replaceable and they're totally okay with that.

[00:09:02]And that last one, um being comfortable with being replaceable, that's a massive tell. Because the early stage, um adventure seekers that you hired when you just started, they want to be irreplaceable.

[00:09:20]To the point where they hide company information, so only they have it, so they are needed longer. And that's not really a good thing at your stage anymore.

[00:09:32]You're scaling now.

[00:09:34]And here's where some people would disagree, but please stick with me for a little bit.

[00:09:40]I would always hire somebody who is a really good cultural fit, who is a really good face fit, who knows their stuff, but they might not have all the skills yet.

[00:09:54]And I always say that's a lot easier to teach somebody who has the right attitude, who is a really good cultural fit, who fits in the face, and if they're missing certain skills, they're teachable.

[00:10:12]That's time I would always always invest in them. On the flip side, if you hire somebody who is just perfect on the skill side, but is a bit of an and doesn't fit in the face, you can't change that.

[00:10:29]You can't change an and you can't change somebody who is a bad fit in the face. So, always always hire for the face. Always hire for the cultural fit is my strongest recommendation. And if they don't know your industry just yet, and if they don't really know how to use that tool or this tool, screw it.

[00:10:53]Teach them. Train them. It's It's It's worth it.

[00:10:57]You will be a lot faster with that approach than hiring somebody who is just not a good cultural fit. They will always take the ship down with them.

[00:11:09]Trust me on that one.

[00:11:12]All right, beautiful people.

[00:11:14]Before I go, there's one little trick I want to share with you. Um if you're hiring somebody right now, read the job ad.

[00:11:25]Read it out loud, and film yourself on your mobile, and then watch that, and tune into whether that that job ad talks to the persona that belongs into the startup that you used to be. You know, the firefighting, the inventor, the wearing multiple hats, you know, or does it belong to the startup that you are now? You know, you are scaling.

[00:11:57]You are um operationalizing a You want to be boring and predictable and trusted above all else. So, when you're hearing this ad read out loud, what does it feel like? Who are you talking to? And if you're talking to the old rewrite that ad.

[00:12:19]All right, beautiful people. Um have a wonderful week. And I've noticed that people don't really want to put comments um because the things I talk about, they're too close to home and people don't want to wash their dirty laundry in public and I get that. So, this time I would love to have some comments just for the algorithm. So, my question is cats or dogs?

[00:12:45]Have a good one.