I'm Waseem Daher, Cofounder and CEO at pilot.com. AMA!

Hey Waseem,

Thanks for doing this!

Being a technical founder, what were some of the misconceptions (and fears) that you had to overcome in order to run those early enterprise sales? Also, what are the two-three key steps you’d have your younger self at Ksplice, approach differently today, to build the right base for the future sales org?

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Hi Waseem,

Thanks for taking timeout to do this AMA. I loved your piece around transitioning from working in the business to working on the business.

As co-founders of a bootstrapped business that now just closed a seed round, we’ll be making this transition over the coming years.

To me it feels like hitting PMF is the inflection point where you focus your energy to working “on the business”. I think this stems from not wanting to burn through investment before we have reassurance of PMF, user love and MRR going up and to the right.

In your experience what have been the key moments when these transitions start? Do you think about different streams of work differently e.g the role of the CEO on sales and CTO in development? How do you balance staying lean and frugal but not losing out on leverage?

Looking forward to hearing your thoughts!

Neil

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Hey Waseem,

Thanks for taking the time to share your lessons!

You had mentioned in an interview, how you felt that Zulip’s (which remarkably preceded Slack in the group chat category) GTM execution could have been better. If you were starting out today, within a new category, what are some of the early GTM wins you’d definitely want to score?

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Dear Waseem,

Thanks so much for doing this AMA with us. It was great to read about your journey thus far. Congratulations on your success.

We are kriyadocs, a document workflow automation company focused on the publishing industry. We have transitioned from a services business to a product-led services business. We believe that we have achieved PMF and are ready to scale and grow. In the true spirit of transition that you talk about, I have pulled myself out of several roles including development and operations. However, I am still heavily involved in sales and am our chief sales guy. I am currently building out our sales playbook to allow us to replicate what I do but am still struggling with the decision on when to hire a head of sales. What are your thoughts and experiences on how to manage this critical function?

I look forward to your insights.
Best regards
Ravi

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Hi Waseem,

Thanks for doing this.
Would love to hear your thoughts/ practices that have worked for you around org structure, goal setting and clarity for individuals in a team and creating alignment across various teams - especially at the stage when scaling the org beyond the 30-40 people.

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Hey Waseem,

I’ve got another one. :slightly_smiling_face: 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?

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This is super-hard. The most elegant solution is: if you can keep the team as small as possible, you actually get both—you get centralized decision-making but high velocity.

I’ve always been impressed by how much a small but dedicated team can accomplish, and arguably the best strategy is “Can we figure out how to do this without having to add a bunch of heads to the team?”

Absent that, I’m a fan of Amazon/Jeff Bezos’s strategy of “Two Pizza teams” on this (a team that’s small enough that it can be fed with two pizzas): can you assemble a small team with a clear mandate and clear decision-making authority and point them at the problem?

I think the place this gets frustrating is when you get the worst of both worlds: decentralized teams that move slowly because of their significant coordination overhead (because they’re not actually empowered to do the things they need to do)

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To be frank, we’re not perfect about this—but I think one of the big things that helps here is: clear goal-setting, where the person or team that is accountable to the goal is also decides how the goal is achieved. (In other words, set destinations, not routes for your teams.)

The second piece that helps is just good hygiene around communication: write down and share out decisions. We’ve had two offices (SF and Nashville) for a while, so that forced us ot get into this habit early—things that are decided in hallway conversations that aren’t shared out make it hard for teams to collaborate.

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I just thought about my own experience, and the experience of business owners like me. No one has ever said “I really want to buy accounting software!” — the sentiment is “I want this problem solved for me, end-to-end.”

What we’re really in the business of selling isn’t software. It isn’t even “monthly financials.” In many ways, it’s “peace of mind knowing that Pilot is taking care of you,” and I don’t think you can get that without being willing to own the problem end-to-end.

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Yes, there’s a lot of operational complexity that we have to contend with that a pure-software company doesn’t have to—so in general I don’t really recommend this approach if you can avoid it :slight_smile:

In this case, I’m not convinced it actually can be avoided, though.

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Don’t underestimate your own sales ability—you’re more passionate and knowledgeable about the space you’re playing in and the product you’re building than anyone else out there.

I wrote some very tactical tips on technical-founder-led sales on Quora a while back, which I’d encourage you to take a look at if you’re curious.

Don’t try to step out of the role too soon. It’s tempting to hand off sales to someone else early, but don’t. You’ll want to do it because you want to get that unfiltered feedback from your customers and potential customers—it’ll help you improve the product!

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I think about this a bit as: founder time is my scarcest resource—how can I maximally leverage it?

  • If we’re in the early days of being bootstrapped, I will just necessarily do a lot myself (because you have to). In that way, I’m converting founder time into $ saved, which is a high-leverage activity at this point in the company’s life.
  • If we’ve raised some money, the highest-leverage thing I can do is help the business grow. So if I can thoughtfully deploy dollars to buy time (especially in places where hiring the expert will do it in a higher-quality way anyway), I’ll do that
  • If we’ve started to achieve scale, the highest-leverage place for me to use my time is to help the organization work on the right things, move faster, etc. To do that, that generally means that I can’t do the thing—I have to help build the machine capable of doing the thing, and then I spend my time trying to adjust the machine.

Easier said than done, of course.

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I think the challenges of Zulip were more product challenges than GTM challenges, per se—in particular:

  1. I think we could have benefited from a strong visual designer as a cofounder—the product never really popped from a UI perspective, which I think hindered its adoption

  2. Our model was really different than what people were expecting. Now, it happens to be really different in a way that’s actually much more productive—but it requires you to use the system for ~two weeks to get the hang of it, to see that that’s true.

My feeling for any new thing is that you either need to:

  • Meet your users where they are (so it’s obvious on day 1 how to use the product, and it already fits into your established workflows, etc.), OR
  • Ask the user to do something new, but demonstrate to them in the first 30 seconds why this new way of doing things is going to be much better for them than the old way of doing things.

At Zulip, we asked you to do something in a new, different way, but the payoff was fairly delayed, which was challenging.

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This is absolutely one of the hardest hires to make—a good head of sales will dramatically accelerate the revenue trajectory of the company, and a bad head of sales will significantly slow your growth. So it’s definitely a high-stakes hire.

The question I’d probably ask is: is your playbook mature enough that you think you can hand it to someone and have them run with it & scale it up? Or are you constantly iterating on it?

If you’re still constantly making tweaks, what you may want is a sales manager to manage all of your sales reps, but you probably still need to stay close to the machine.

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We do annual company goals and quarterly OKRs, at the company level, and then at the team level as well.

I think 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. (In other words, does the work I do actually matter to the company?)

I think if people don’t understand the why of what they’re being asked to spend time on, you get bad results.

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To be honest I still don’t think we’ve perfected this :slight_smile:

We’re probably one of the only firms in the world that can actually lose money doing bookkeeping/accounting work for our clients, which is a consequence of our flat-rate model.

Having said that, I think customers appreciate the transparency/straightforwardness of the approach.

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Hey @waseem,

Thanks so much for taking the time to join us today and sharing some great thinking that has informed your journey. Along with other ideas, you pointed at a much-needed, nuanced reality with this:

“I think the place this gets frustrating is when you get the worst of both worlds: decentralized teams that move slowly because of their significant coordination overhead (because they’re not actually empowered to do the things they need to do).

Thanks, again, for doing this!

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And, as always, thanks to our wonderful members @aditi1002, @ncameron, @Akhilesh, @raviramani, and @Vengat, for joining in today, yet again, with ever-thoughtful questions! :slight_smile:

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Thanks Waseem,
That’s a great way to put it. People are always seeking better end-to-end solutions to problems and aren’t necessarily concerned with paths, guess hence the rise of various unique ways in which software is being deployed these days. Thank you for patiently answering all the questions.

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Thanks Waseem,

That makes total sense. Not as obvious at first and not often considered, but decentralized teams that move slowly can actually be the worst outcome here. And your point about empowering people to pursue destinations not routes fits right in.

Thanks again for doing this. Cheers.

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