Note: This AMA is closed for new questions, but you can check out the existing conversations below.
This January 14th, for the year’s first Relay AMA, we got to host Pilot’s co-founder and CEO, Waseem Daher. Having previously co-founded Ksplice (acquired by Oracle) and Zulip (acquired by Dropbox), Pilot is Waseem’s third foray into SaaS.
He has thus unearthed, with two equally thoughtful co-founders who’ve been with him all along, a lot of the invisible, founding scaffolding one must build upon. Sizing up a category’s adjacencies and potential. Telling apart what merely feels productive from what is. And valuing the quiet joy found in the day-to-day craft of building an org, over the ardent (ultimately exhaustible?) enthusiasm of any given startup idea.
AMA Index (Waseem’s brain-pickings) 
(founding insights, opinions, and observations; deftly examined and articulated)
— “The worst of both worlds: decentralised teams that move slowly”
— On goal-setting: “set destinations , not routes for your teams”
— Why Pilot doesn’t just sell software; neither does any other SaaS
— Technical-founder-led sales
— Acknowledging founder time as a scarce resource and how to “maximally leverage” it?
— A necessary precursor to introducing new products and what Waseem would do differently with a previous venture (a collaboration tool that predated Slack)
— The question to ask before making that first critical sales hire
— On OKRs: “it’s important for everyone at the company to understand the company’s objectives, their own objectives, and the line that exists between their objectives and the company’s objectives”
Further reading/listening/pondering from the interwebz 
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(Other insightful excerpts drawn from blog posts, interviews, and conversations)
On how most things aren’t worth fretting over:
“This sounds hard to believe, but almost all of the things you might be worrying about as a first-time founder don’t matter. I vividly remember agonizing overnights and weekends about all of these things that we thought would kill the company, and in the end, they were all irrelevant.
In particular, a lot of people (my past self included) spend a ton of time worrying about what the competition is doing, rather than worry about whether customers really love what your company is doing. If you can deliver a high-quality product that solves a very hair-on-fire problem for your customers (and they’re willing to pay you for it), you’re off to a very good start. Until you’ve done that, that’s probably the task that should occupy 100% of your mindshare.”
Source: 5 Questions with Waseem Daher, Founder of Pilot
On the world-expanding periscope doing early sales as a founder can offer:
“Ideally, you have a founder, who is just going to go all-in on sales stuff. I don’t think that requires them to be a sales person by training. But I think there’s something really, really powerful about having one of the founders operate the sales machine. Because you learn a ton about the world. Like sales is the little periscope you’re looking through to understand what is out there. And to have that information funnelled through a third party who is not empowered to make decisions, I think it’s hard. You can get that much tighter feedback loop if you have a founder doing it.
If you do have a person on the team that’s willing or capable of doing that work, I think, when you get to the point where you feel like it has started to become a process. And you’re not able to close sales at the rate you’d like to close, or you feel you’re dropping stuff on the floor, that’s probably when I’d look to say ‘well, how do we add another person to the team to give me more firepower.’ But, importantly, I don’t think that person is going to be able to figure out how to sell your thing. I think, ideally you as a founder, should have demonstrated that it’s possible to sell, and here’s the shape of how it might be sold."
Source: Fireside Chat with Waseem Daher
On a fundamental transition all CEOs must make:
“I think the specific nature of the work has changed a lot. And, I think, I’ve been a little slow to catch up with it. Which is, in the very early days of the company. And this will all sound obvious in retrospect. In the very earliest stage of the company, your job is just to do the thing that needs to be done. So sometimes that’s sales calls. Sometimes that’s taking out the trash. Sometimes it’s hiring people.
It’s just like whatever needs to be done, your job is to just do the thing. And then increasingly as the company grows, your job is less about doing the thing and more about building a company that can execute well on the things that need to be done. And so, in particular, at this stage in the company’s life if I’m doing a specific thing that’s actually a bad sign. It really means that I’m gating the growth of the company in some way.
My only jobs should be: attracting/retaining the best people, parting ways with people that don’t work out, funding initiatives and de-funding initiatives. It’s really just operating at one level of abstraction above, honestly, classically, what I’m used to. You’re used to doing things. And doing things seems so productive. Your levers as a CEO are not, ‘let me go write that line of code, let me go close that one sale.’ It’s ‘let me build a team that will close sales far better than I ever could. Or that’ll write better code than I ever could.’
It’s super hard because the first thing feels like you’re doing productive work. It’s like, ‘oh great, I closed a sale, saw the revenue number go up. Great! I actually contributed to this company today. As opposed to, ‘well, I had these five coffees with people and I didn’t fit with any of them.’ That doesn’t feel like work. Even actually the work of bucket two is likely much more impactful for the company than if you had gone and closed that incremental sale.”
Source: 20VC: Why Passion Is Overrated When It Comes to Starting Companies, Why VC Is Overrated as a Financing Mechanism & Why You Should Never Sell Your Company with Waseem Daher, Founder & CEO @ Pilot
On how existing stacks impact pricing decisions:
“With any sort of new market thing, the challenges are: educating the customer that exists and understanding where the budget is going to come from and whether it is close enough to something that already exists so that you can kind of fit into that line item. Or whether you can fit into the way they’re used to buying it. I think that also has a lot of implications on how they’d think about pricing.
For us, one of the ceilings, or at least, I believed it to be a ceiling, was how much we could charge you for our service of kSplice. Where we gave you software updates without rebooting for linux. We probably couldn’t charge you more than what Red Hat charged you for the whole Linux support contract.
Because you’re the IT buyer, [saying], ‘Well, this is a feature of Red Hat from my perspective so I can’t pay more for it than what I pay for Red Hat generally speaking… Ideally, you want to figure out the thing that is closest to your thing and try to see what lessons you can learn, either from a customer acquisition perspective. Like who buys that thing and where do they go and how to reach them. So you don’t have to create, from a whole cloth, create the whole category from scratch.”
Source: Fireside Chat with Waseem Daher
On how a thorough interview process trumps crafty interview questions:
"The thing I feel most passionately about (in the interviewing process) is just there being rigour in the process itself. In other words, before you bring in someone for an interview. Ideally, you’ve written down the role and requirements; know what the role you’re trying to hire for, you know the skills you need, and you’ve built an interview day that actually tests for those skills…
The best interview gives you a signal as you to where the candidate spikes. A mediocre interview will let you know if someone is really bad, but it wouldn’t let good ones really shine. So, I think being very very rigorous about building the process is much much more important than, [saying], ‘I have this one gotcha question or I have this one question that teases a lot about the candidate.’"
Source: 20VC: Why Passion Is Overrated When It Comes to Starting Companies, Why VC Is Overrated as a Financing Mechanism & Why You Should Never Sell Your Company with Waseem Daher, Founder & CEO @ Pilot
As an extension to my previous question on scaling Pilot’s unique model, it would also be interesting to hear how difficult was it to arrive at a scalable value metric for pricing, given the complex service-software mix?