Jun 20, 2026 · 1 hr 23 min · 12 segments
This is a conversation with Jeff Escalante, who’s currently a Director of Engineering at Clerk, where he spends more than 80% of his time writing code. Before that, Jeff was an early engineer at…
Jeff EscalanteGuest
Arjay McCandlessHost
So were you already in a leadership position before you joined Vercel, or did you kind of join as a leader?
I've always, like, drifted in and out of leadership positions since HashiCorp.
I mean, even since, like, halfway through my time at the agency, which is called Carrot.
Um, I don't feel like I deserve a leadership position if I don't know what's going on, and I think that's the hardest part of leadership positions, is you get put in one, and the second you do, the clock starts ticking before you're-
You got put in that position because you presumably knew what was going on and were good at directing things and were trustworthy, and then you stop doing all the things.
[chuckles] And things change, and now you're more out of touch, and so, like, are you still a good leader? Um, uh, it's...
I mean, for me, I had gone back and forth throughout the whole time in HashiCorp.
And I think the key was, like, um, if you have a bunch of ICs that are working for you as a manager who are really good, um, it's easier to be a manager.
You know? Because what you could do is just keep stuff off their plate that distracts them.
There's tons of stuff that just comes up all the time that you have to deal with, um, that takes you away from getting work done.
So were you already in a leadership position before you joined Vercel, or did you kind of join as a leader?
I've always, like, drifted in and out of leadership positions since HashiCorp.
I mean, even since, like, halfway through my time at the agency, which is called Carrot.
Um, I don't feel like I deserve a leadership position if I don't know what's going on, and I think that's the hardest part of leadership positions, is you get put in one, and the second you do, the clock starts ticking before you're-
You got put in that position because you presumably knew what was going on and were good at directing things and were trustworthy, and then you stop doing all the things.
[chuckles] And things change, and now you're more out of touch, and so, like, are you still a good leader? Um, uh, it's...
I mean, for me, I had gone back and forth throughout the whole time in HashiCorp.
And I think the key was, like, um, if you have a bunch of ICs that are working for you as a manager who are really good, um, it's easier to be a manager.
You know? Because what you could do is just keep stuff off their plate that distracts them.
There's tons of stuff that just comes up all the time that you have to deal with, um, that takes you away from getting work done.
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