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Knuckle Up with Nakul · 7 min · Oct 13, 2026
Railway uses a six-week onboarding to build ownership
Jake Cooper
Founder & CEO, Railway

Nakul MandanHost · Host, Knuckle Up with Nakul
General partner at Audacious Ventures; his show goes deep with founder CEOs on how they build.
About this segment
New hires move through trust, clarity and judgment, starting with scoped tasks and progressing to open-ended problems. The structure gives people context while testing their ability to decide what the business needs.
From “How Railway says no to 90% of ideas and keeps winning | Jake Cooper (Founder, CEO)”, Oct 13, 2026. Watch the full episode
Thanks. We'll look at and fix what's off.
“Trust, clarity, judgment. That's like two weeks of trust, two weeks of clarity, two weeks of judgment.”
Takeaways
- The first two weeks focus on building trust through small tasks.
- Next, hires propose solutions to open-ended problems.
- The final stage asks what the business needs now.
In this episode
Full episode- 3:00Railway rebuilt its free tier around better infrastructure economics3:02
35:29Railway uses a six-week onboarding to build ownership7:02
- 22:30Railway says no until the timing and need are clear3:04Up next
- 5 more moments in the full episode
Transcript
Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.
- 35:34
Going back on the people side for four years, I think you had no onboarding. People start and... It's like, hey, welcome to Railway, grab a shovel. Yeah. And now you've shifted. Tell us why that did not work and what made you feel like, hey, you know, we need some kind of an onboarding. And then I think you have a pretty unique onboarding even now. So we'll dive into that six week onboarding thing that you have now.
- 35:57
The success of any individual at the organization is measured by like, can you get that person to do the best work of their life? And how quickly can you get them to do the best work of their life? And so I think originally it was like easy because the code base was small and the context was like pretty like whatever. And then over time, like that context would like grow and grow and grow. Right. And like there's various different sections of I think I don't think we're unique in this sense.
- 36:18
Like, but I think every company has various sections of like some parts of your company are more well formed than others. Right. Maybe like the basement isn't like renovated or whatever. And you're like, yeah, it's kind of like dicey. Right. And in some parts, actually just like you're just like, oh, there's tech debt or there's landmines or whatever. Right. Like you should probably not be in there. Setting people up with their own devices or whatever to be like, all right, figure it out or whatever. Like they just don't have that context. Right. And there's like, in my mind, I don't say there's no amount of excellence because any amount of excellence, you can figure it out.
- 36:44
But we were basically like, well, like, why are people, why are excellent people using their time? Like, if we're saying we're going to recruit and pull in these excellent people, why are they using it to like navigate this thing that like will take us literally, I don't know, an hour and a half on like a Sunday to like put together a really, really structured, awesome six to, you know, eight week onboarding plan that we can go and sit down with them based on their background, based where we are in a company, right?
- 37:06
If we want to go in and hire fewer, more amazing, amazing folks, like how do we set them up for as much success out of the gate and then push more as excellent? But the thing that was interesting is that even when there was no onboarding, you were like, you'd let the person who's joining figure out what the company needs and then run with it. Now it's the third part of the onboarding. So that was the interesting thing where it wasn't just pick a shovel and do.
- 37:30
It's more like you were letting the person decide what does the company need? You figure it out and then go and solve that. right? That was the initial onboarding. It's just three things. And now it's three things, yeah. Yeah, I'm a big three things person, just broadly speaking. Trust, clarity, judgment. That's like two weeks of trust, two weeks of clarity, two weeks of judgment. What does two weeks of trust and two weeks of clarity mean in onboarding?
- 37:52
So these are tasks, small tickets or anything else like that. They're really straightforward. You give them the tasks. Yeah, we just basically like, hey, here's five things. Roughly around your zone of excellence that you want to go in and move towards. If you join us on the infrastructure side and you say you want to work on networking, we will say you have to go in and build networking. We have had people join and then, you know, within nine, 12 months, et cetera, they were owning the entire edge network. Right. So those like five things to just start like boom, boom, boom, you can just crank those out. Right. And we were just like, great. These should be easy. Two weeks worth of whatever. Right. Allows you like get your sea legs, like that's earning your trust as a company.
- 38:26
Yeah, it's like seeing those reps kind of close, right? Where everybody's like, great, this person's moving. I can see what they're working on. I can see how they're working. I can see all these other things. Oh, amazing. I'm so excited that somebody is going and joining us to work on trust and safety. I've had so many ideas. That's awesome. I can go in and grab time with this person, right? And we say, okay, cool, grab some time with some folks, right?
- 38:47
And then internally, we also say, you know, we have an onboarding channel and the onboarding channel gets broadcast to basically the entire company. So everybody can kind of see we try and help people out as they're kind of joining. Right. And it gets trust on both sides. Right. Because like just joining a new job is never it's just never easy. And you should just acknowledge that. Right. And it'd be like, oh, OK, cool. You should feel good. You should get reps. You should feel awesome and comfortable. And then you kind of move on to these like what we call problems. Right. Which is instead of a task, which you're like, OK, it's like pretty straightforward to go in and do this. A problem is like there's multiple solutions. Right. You'll you'll have to figure something something out. Right.
- 39:17
right, set up some trade-offs, some benefits, like all of those other things, right? And so we have people write internally a request for comment, which is just like a little bit of background. What's the problem? What am I going to go in and do? And then like, what are alternative solutions to go in and do this? And then we can go and talk with this person, right? And we can say, okay, well, like, actually that's like probably like, you know, that looks like eight weeks worth of work, right?
- 39:36
Like, here's how we can trim that down to like just the stuff that we need. Because again, we're a big, let's do the 10%, maybe 20% that matters, right? And the other stuff we can bring later, right? And incidentally, that's actually a really, really good thing for onboardings, because if you leave those 80 percent, it's actually very, very clear the jobs to be done when somebody joins your organization.
- 39:54
It's very, very clear how you can build an onboarding plan when most of the P2 requirements just have not been completed. Right. And then so then we move folks, you know, from the trust to the clarity and then to the judgment, which is what do you think the business needs at this point in time? That is the only prompt. That's it. Right. And then you're basically like, OK, well, like we should be doing this.
- 40:15
our observability story is, you know, dog water, and we need to go and improve these things. Like, great, we think that that's correct, right? And we also kind of, you know, we will give this this kind of like structure ahead of time. And we, you know, tell people to use that thing internally called a scratch pad, we just use Notion. And you just like, dump ideas into this. And so by the time you end up with this thing, you have a bunch of, you know, things that either people have been like, oh, you wanted to work on trust and safety again, I had these kind of thoughts or whatever.
- 40:39
And then you kind of have these like cards that you can kind of go through and be like, oh yeah, I want to do like, I'm going to do this and this, right? Or I'm going to do just this one thing because it's like going to take me probably like three or four weeks. Boom, right? And what that sets people up to do is they basically get, you know, in university back in Canada, you would have almost like a capstone project, right? Where you just like put something together, right? And it was like impressive and you like build something from scratch, all this other stuff. You do the same thing basically internally. Does each person then eventually end up having their own zone? You call it zone, right? The agency thing. So is it like 40 people all running on projects that they chose that the company needs?
- 41:13
No, because that would be a total tire fire because there is a bunch of stuff that just has to go in and get done, right? You would just have disproportionate amounts of people working on all the hype, hot AI, whatever kind of things. We try and make sure that folks are set up to take shots unilaterally as part of onboarding because we want those folks to be like, drag us to the new frontier. You know, you're new and there's a specific time in which, you know, you can join an organization and not be like brainwashed, right?
- 41:38
Because then after a certain point, You're just like, you know, the culture, these are the norms, all of that other stuff, right? And so we want people to kind of drag us towards those things. But, you know, that kind of pulls back to like the planning phase where we're like, okay, here's the things that have to get done this quarter, right? And maybe you're just like, you know, on the product side, you're like, oh, man, you know, like I want to work on these things.
- 41:55
And the infrastructure is like, hey, man, like we still have problems with the crypto miners, you know, and you're letting these people in the front door or whatever, right? We need this kind of work to be done, right? And then we go into the product zone and say, well, listen, 70% of this stuff is steak. 30% of it is vegetables. Let's break it down. We're each going to have a vertical. We're going to go in and do that.
- 42:12
We're all going to sign our names on the things that we're going to go and get done. And by the end of the quarter, we're going to go in and complete those things, right? Hell or high water, we're going to go in and complete those things, right? And so it's a blend between having people go in and drive those things and also, again, jobs to be done. Let's shift towards overall.