Episode 41: Piloting Sales at Pilot.com with Founder, Waseem Daher

Waseem Daher (Ex-Dropbox and Founder of Pilot.com) sits down with Peter Ahn and Alex Allain of Decoding Sales to discuss learnings from his founder-led sales journey. 

They discuss:
• The importance of founders being involved in closing a startup's first customers
• How to think through hiring your first salesperson
• What the right profile is for sales hire #1
• How to know when to fire salespeople who aren't working out
• Lead gen tactics for startups and the power of word of mouth

Transcript

Episode 41: Piloting Sales at Pilot.com
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[00:00:00] 

Alex Allain: Welcome to Decoding Sales, a podcast where an engineer, that's me, Alex, and salesperson. 

Peter: That's me, Peter.

Alex Allain: Talk about the art and science of sales as it relates to life and business. In this episode, we have another guest. Very excited to welcome Waseem to the show. Waseem is the co founder and executive chair of pilot.

com, a company that does accounting and tax prep for startups and growing businesses in a tech enabled way. Prior to pilot, Waseem also co founded Kslice, which. Updated your software without rebooting. And it was acquired by Oracle in 2011 and Zulip, a group chat for business, which was acquired by Dropbox in 2014, which is how Peter and I know Wassim.

And prior to that, of course, graduated from MIT. So Wassim, welcome to the show. We're very excited to have you. 

Waseem: First of all, thanks for having me on the show. Great to be here. I'm a big fan of both of you. [00:01:00] And so it's, it's really a pleasure to kind of be able to chat with you all. I mean, we all met at Dropbox, right?

And I think the thing that was interesting about my time at Dropbox was. It was the first time that I really got to see a high growth startup, like from the inside at the scale it was operating at, like our prior companies were, you know, 10 or 20 people. So I had a fairly good read on the super early stage.

And then my first company was acquired by Oracle. So I guess I had a good read on like the a hundred thousand plus person stage or however it is. However, big Oracle is, but you know, when I joined Dropbox, it was 600 people when I left Dropbox, it was 1200 people. And it was really interesting to kind of observe that in a hyper growth across a bunch of different functions.

And in particular, I think one of the things that was really exciting is that I, as a product manager at the time, actually did get to spend a bunch of time with Peter and the sales team to see sort of like how the go to market side of the machine worked. 

Alex Allain: Terrific. And that was a really intense time at Dropbox.

And, um, so most recently you've been at Pilot and I'd love [00:02:00] to hear a little bit, just tell us a 

bit more about Pilot, what you saw in the marketplace and kind of maybe just a little insight into that's the sales process at Pilot and what you've learned from that. 

Waseem: Sure. So the kind of two insights that underpin.

What we're doing at pilot both really stem from our own prior experience running our previous companies. And so for us, and this is true for anyone who has a business of any kind, you know, you start your company because there's some product or service you want 

to bring into the world. And you're excited to do it.

You're excited to kind of devote your skills to making that happen. And as soon as you start, you realize actually there's a lot more to running the company than just providing that product or service. There's all of this back office stuff. And the thing that's so tricky about the back office stuff is you don't know how to do it.

But it's also important, you can't actually ignore it, like big companies have enormous teams that do all like finance, legal and HR and IT, they do that because it's important because it's valuable. So you as the business owner, the founder [00:03:00] kind of stuck, it's like, there's this hard thing you need to do, you don't know how to do it, you don't want to have to kind of reinvent it from scratch, you want a trusted resource that can actually do this for you.

So insight number one is like, look, founders, business owners really need help kind of running their back offices and specifically on the accounting and tax side. We felt a lot of pain there in our previous ventures. Insight number two is if you look at the work that actually goes into doing the accounting, a lot of it is very mechanical.

A lot of it is very error prone. A lot of it is very well suited for software to do. And, you know, we were all engineers by background. We said, Oh, we were pretty confident. We can write some software to do this stuff. You know, going back to the first point, no business owner has ever said, I want to buy accounting software.

What the business owner says is I want someone to solve the problem for me. So I said, we're going to do a really weird thing for a tech company. It's, it's less weird now, but when we started in 2017, I think it was quite weird. We said, we will be a tech enabled service. We will actually be your accounting firm.

We're going to employ [00:04:00] a bunch of accountants are full time us based employees of ours. They're going to do your accounting and tax prep. And under the hood, we're going to kind of build the iron man suit for them. Software that lets us do the work more accurately, more reliably, more consistently, more efficiently.

And so what does that imply about our sales process? your accountants, not of your B2B SaaS software vendor, meaning like people want to talk to us. They want to get a feel for like, Oh, do these people know what they're talking about? Do they know about businesses like mine? And I can be able to trust they're going to do a good job.

And one of the things that I think is especially interesting is if you think about a piece of software, let's say you're talking to Peter and Peter is, you know, selling you Dropbox. First of all, you have an amazing Experience with Peter, but even if you didn't, your conclusion would not be, Oh, the software isn't very good.

It must not like sink the bits correctly. Your conclusion would be like, I didn't really like that guy. He's a jerk, but probably the software is fine. Whereas if you talk to our sales reps, and if they sound like they don't know what they're talking about, your assumption is, [00:05:00] Oh, These people don't know about accounting or they don't know about my business.

Like there is a direct implication about the quality of the product from the actual 

conversation with the sales rep, which is more true for what we do than I think it is in other industries.

Alex Allain: How 

did you approach this? Seems like the kind of place where being a founder, I assume leading some of the sale and early sales efforts was very valuable because obviously, you know, the business and you know, the software I'm curious to hear about that and also about how you thought about. hiring a sales team over time to do that when you really need that sort of domain expertise as well as that sales skill.

Waseem: Sure. So I'm a super, super, super big proponent of this kind of founder led sales. I think it's so healthy for your business for one of the founders to really own the sales function in the early days. And just because like you don't have a sales background doesn't mean you can't do it. Meaning. You [00:06:00] know, I'm a software engineer by training.

Like I said, computer science. I didn't know anything about sales. The stuff I learned about sales, I learned by figuring out how to and failing at doing sales in the early days of the company. Um, but a pilot, I sold probably the first 100 accounts. And I think that was super valuable because one, you can really credibly and earnestly Present the case for the business.

Like it's a compelling sales conversation. And two, you're actually getting very valuable feedback about what about your pitches resonating? What isn't like what features you might need to build, what things don't resonate, like as a very concrete example, in the earliest days of the business, the way we pitched it is, Oh, we have software.

And the software is going to do all the accounting for you. And yeah, there's a human that like helps you out when you have questions, but like the computer beep beep boop boop is going to do all the accounting. And what we heard very viscerally is from customers was like, well, I don't want that. I want a person like I want to know that someone like has my back is like kind of piece.

[00:07:00] Piece of feedback. Number one, a piece of feedback. Number two, we heard as well. If the computer is really doing all the work and to be clear, it's not, but if the computer is really doing all the work, why does it cost as much as a, you know, legacy accountant, shouldn't it cost, you know, 60 a month. And being able to just like rapidly iterate on the messaging was possible because like I heard it directly.

It wasn't disintermediated through someone that we had brought on where you sort of have to wonder, well, like how much of the true messages necessarily getting through. 

Peter: Love that. Um, I have another question about the early days, actually, because one of the things that we had to really come to grips with at Twingate was that we were not cybersecurity experts, right?

We came in to replace VPN. As folks who had come from Dropbox, right? A very usable piece of end user technology. And so in the early pitches, you know, I felt this imposter syndrome, but then I leaned into the fact that we were different and fresh [00:08:00] as bringing in a new perspective, right? So I wonder if you could talk to that.

Cause you said, you know, you were your technical founder, you weren't an accountant, so what was your superpower coming into pilot and how did you engage knowing that your background didn't scream, you know, accountant? 

Waseem: Totally. It's a great question. And it's, it's one of these things, which is really interesting, which is I think the average business owner and certainly the average tech founder and, you know, tech founders is really where we got our start.

Probably half of the customer base today is technology companies of various sizes and stages, like the ability to just talk to someone who gets what you're about. is so powerful. In fact, it's, it's in some ways more powerful than proving on the call that you know a ton about accounting. And here's a, here's an analogy I really like.

I think there are certain things that you buy where the buyer is very sophisticated about kind of what performance they're looking for. It's like you're buying a camera and you're a camera nerd, [00:09:00] like you're going to look at the specs or whatever. Right. And you'll go pretty deep on, well, does this meet my specific requirements?

Like that's what you're shopping for. Hiring the accountant is actually much more like finding a doctor. Like, when you go and you're picking your, you know, primary care physician, you're not like, oh, tell me about the endocrine system, or like, what does this gland, you don't quiz them, you're not like testing their domain knowledge.

In fact, you're evaluating them on these sort of secondary signals that candidly have almost nothing to do with whether they're good at medicine. That's like, is the office clean? Like, do they wear a white coat? Do my friends go here? Were they on time? Like, none of those have anything to do with like, are they going to be a good doctor for you necessarily.

They're really secondary signals. They're kind of like the brand, if you like. And these buying decisions tend to actually be made very much based on like, Okay, is my sense that this person Is for me, do they serve people like [00:10:00] me? And this is actually what you're saying, Peter. Like, you really leaned into like, listen, we're the company you should go with.

If you are also a modern company, if you, like, like the kind of Dropbox style ethos, like, if you want something really usable and friendly that, like, end users are going to know how to deal with, like, that's what we're about. Like, I think leaning into that is really a strength. And for us, we were like, well, listen, we're founders like you.

Like we understand what it's about. We're going to take care of it for you. I really like that. It reminds me a lot, Peter, of some of what we've talked about, sales being kind of a relationship building process. And I think we've seen what I'm hearing you say is like, you know, part of the relationship is like, well, we're kind of like each other.

Like we should be able to get along. Like we're on the same wavelength, which I think really translates to at least thinking about it as a. Buyer for a minute as like, Oh, I trust that if I come to you with feedback, I know I can model your reaction to it. I can say, Oh yeah, I think you're going to care about this sort of thing and not just dismiss what I care about.

Alex Allain: Which kind of goes to this thing that Peter and [00:11:00] I have talked about of like, that's kind of the point in an early stage company. You're not getting the full product at the start. You're getting the promise of the product over time. Does that resonate with, with your experience? 

Waseem: Totally. It's like, is this for me?

Do these people care what I care about? Like am I actually a sweet spot customer for you? Because if I'm not and I buy, as you said, I like, I'm, I'm probably gonna find myself in some trouble. Like maybe I have some weird edge case that you don't really care about. Whereas if I'm like right down the fairway for you, that's very powerful.

Or even like relatedly, I think there's a little bit of. You know, founders ask me all the time, like, how do I sell against like these big companies that are dominant in the space? And the like, way to win is very counterintuitive. You're, you basically are like, listen, we're a small company and you're a huge account for us.

Like, you're not going to be a big account for the other guys. Like I'm, you know, I'm one of the founders and I'm on the phone with you. Like, that's how much I care about like [00:12:00] winning your business. Like, that's a very, you know, reassuring and positive message that I think you can. You can use to your advantage, even though like you in some ways have no right to win that deal.

Peter: Totally. I, I use that all the time, especially cause they're buying your brain power too. Right. They're not just buying the product for what it is today. They're buying it for what it could be and how their fingerprints are going to be reflected on the roadmap. Right. So I used to use that all the time, even though I wasn't the founder, I would say, Hey, like the founder is on the call.

Cause Tony was on a lot of calls with me at twin gate. Right. So super powerful, I think message that you're surfacing. 

Alex Allain: So one thing I'd be curious to dive into, uh, here, Waseem, is, you know, I imagine that it took a, you, you talked about needing to iterate on this sales message. And I imagine you're also iterating on just your knowledge of sales.

What advice or what do you want to share with founders who are in this like, ah, I've got to figure this thing out. I get the idea of iterating, but how do I actually do it? How do I learn this baseline set of skills? What worked for you? 

Waseem: Yeah. So in [00:13:00] our very first company that we did, we were basically all technical founders and not, it's not that we literally drew straws, but essentially we were like, okay, someone needs to do sales.

And I was like, well, I don't know. That's like, sounds kind of interesting. Like I, I like talking to people, like I want to do it. And I think people approach it. With sort of weird preconceptions about what it is. I think people have these stereotypes of what are basically bad sales experiences. Mm-hmm . And they're like, oh, that's sales.

It's like, uh, a used car sales person or like the pushy person trying to like, get me to buy life insurance or whatever, like mm-hmm . That's example. Those are examples of like sales that are not done well and I think the thing that it. It took me a little while to like really grasp was listen, you're in the job of helping people and ideally the way you're helping them is they like actually derive real value from your product, but your orientation has to be OK.

Listen, I'm getting on the phone with you. I'm I'm really trying to learn about what your deal is, what's working for [00:14:00] you, what isn't working for you, where you need help. And then if my thing happens to be a thing that can help you like let's talk about how it can help you. And if it's not like I should actually just tell you that I should say, Hey, listen, based on what you've said, like, I actually don't think pilots gonna be a good fit for you.

But you might want to consider thing ABC or whatever. And like, that's really powerful because you're, you're building a very solid relationship there. Like that person is going to trust you even more when you're not selling them your thing. And they'll go and tell their friends like, Oh, you know, actually I talked to a seam and pilot wasn't a fit for us, but actually like, I really liked him.

It seems like they're doing great stuff. Like you should talk to them. Like, that's really powerful.

Peter: Yep. Yeah. The word of mouth, I think you wrote. Don't take it personally. And that blog post you wrote about founder led sales. Right. And I think, yeah, what you said is a perfect example of that. And the word of mouth is so powerful too.

And I think ironically, when you say no, it makes you look more confident because they're like, Oh, this person has enough business. They're confident in what they can offer. They don't need me to, you know, get to the next [00:15:00] month. Right. So I think it builds this like confidence psychologically. Totally.

Waseem: Totally. And then, yeah, the. It's a numbers game to some extent at the end of the day too, which is, I think if your win rate is, you know, 20, 30%, you're like doing great. And so you, you do have to develop some thick skin about being told no. And the orientation we always had was like not getting the salest fine.

As long as you understand why you didn't get it and that you're ideally, you're learning something from like, okay, well, maybe this type of customer is actually not a good fit for us, or maybe this part of the talk track like didn't work very well, or maybe I could position differently against competitor X, Y, Z, like the learning is actually the more important thing to optimize for in the early days than the actual like dollars booked.

Alex Allain: Oh, I really liked that. Cause actually one of the questions I was 

going to ask you is like, as the person who's drawn the straw, if you will, to do the sales, you kind of have to go back to your team every time [00:16:00] something doesn't come through. And that seems hard, you know, you don't, and it seems like if you're, you could push too hard to make that sale rather than to say no.

So I think that framing of like, well, look, I have something to bring back to the team. It might not be the deal. It's an insight. It's a tweak. It's something that there's every. Every interaction has a value to it might not be the deal. It might be something else. I think that that really helps answer that question for me.

So I love the way you put that. 

Waseem: And I just think it's like iterative refinement of your own process. Like one question that folks ask me all the time is like, when should I hire my first sales rep? And my response is, well, have you figured out the process 

yet? Like, do you actually feel like you understand the repeatable motion of how to get people to buy your thing?

And if you do, cool, then you might be ready to scale it up. Like you might be ready to add some folks to the team or whatever. But if you're still like figuring out how it's going to go, like you kind of owe it to yourself and the company to keep that feedback loop super tight. 

Peter: [00:17:00] Salesperson can't figure out product market fit for you, right?

So yeah, that's the job of the founder. I completely agree. 

Waseem: Well, and even worse, I think it can really throw you off because what ends up happening is like you hire someone great and then like it doesn't work. And then you can't tell why it didn't work. You can't tell, well, did I make the wrong hire or is the product bad or is the messaging wrong?

It's just like you've introduced more variables about why it is or isn't working. And I think until you've really feel like you've nailed at least the initial message to the initial audience, like you want to keep the feedback loop really tight. I really like that. 

Alex Allain: Yeah. I'm thinking back to the episode with, with Tito, where he was, I think, encouraging people to hire a salesperson earlier in the process than they might otherwise.

Think about it because having somebody who's dedicated to that iterative refinement and really knows how to do it, uh, can be really powerful. So I'm curious kind of how you would. Which sounds a [00:18:00] little bit different from what you're describing. So I'm actually kind of curious if you have a reaction to that sort of like alternative framing.

I



Waseem: sort of disagree with Tito with deep respect to Tito. And I think it depends. It look, it also depends on the disposition of the founders. I think some folks like 

thrive doing this more than other folks do. I think for me, the things we've always optimized for are like, I want to keep the feedbacks loop super tight.

I want to make sure that I'm really nailing the messaging. I want to understand like what product tweaks need to be made. And the best way to do that is to just like hear it from the horse's mouth directly. Like, yes, you can listen to call recordings, all that good stuff. But like, there is no substitute for just like actually being on the call.

Those are all the arguments in favor of doing it yourself. The arguments against. Or listen, like skilled salespeople are incredibly valuable because there is a real skill there that you probably don't have. And like, yeah, if you had Peter on your team, you're going to get there faster. I think that the [00:19:00] thing you cannot do, and maybe this is how we kind of merge these feedback points of feedback together.

You cannot abdicate responsibility. Or you can't be like, well, I brought in the sales rep and like, they'll figure it out. Like to your point, if you don't have product market fit, like that's really not going to work for you. 

Peter: The other option of course is to hire a coach, right? So you could do it that way, right?

So that you have somebody who's sidecar ing with you, right? 

Waseem: Yeah, totally. We lean very, very heavily on our advisors, especially in the early days as I was trying to figure out like, well, what even is sales? Oh, we had a series of like extremely one on one in retrospect. Like level conversations about, okay, how, how do you do this?

Totally. What are things I need to be tracking? What are things I need to be thinking about? Like how do I structure a call? Like what, you know, is this buyer like actually gonna buy? Like there's definitely, you do not need to invent all of this stuff from first principles, and in fact you probably shouldn't.

Yeah. So there is, I think, a best of both world where it's like, okay, [00:20:00] can we get the advice of someone who's done it before? While also making sure that you are still like in that kind of like information stream of what are customers saying about your thing? Because the other note is no two sales processes, or maybe I should say the sales process for each product or each company.

is not the exact same as the sales process from every other company. And there is a certain danger of like just trying to copy paste. Well, if it works for them, it may or may not work for you. Like it's a function of like your buyer and your price point and your sales motion and like the competitive landscape and like, and the, the probability that all of those things perfectly line up.

And that you can just use someone else's playbook outright is actually like not that high. 

Peter: Yeah. And I tell founders like when you're looking to hire first go to market folks, even when you have product market fit, it's actually not a true sales job. It's almost like a GM, a project manager, right? Because there's no playbook that is just going to stay the [00:21:00] same for a month.

Right. You have to iterate, you have to go back to the team. A lot of salespeople, they're not used to talking to the CTO about what needs to be changed, right? So I do think there's a lot under the hood that goes beyond sales, which is why when you look at like large company sellers, they tend to know how to operate within systems, but maybe not within ambiguity, right?

So I wonder if you agree with that. It seems like you do from what you just said. 

Waseem: Like, you know, there's the AE at Salesforce who's consistently crushed quota, you know, quarter over quarter and the president's club, like on paper, they're like the perfect rep. They're probably actually not going to do very well at your super early stage company because it is very different to write the playbook than it is to do a stellar job.

at executing against the playbook. And I'm not demeaning anyone's skill here. Like that is, those are both very valuable skills, but they're not very transposable. The person who's a great first sales rep is probably not going to thrive in that environment. And the person who crushes it in that [00:22:00] environment, like it's, there are question marks about how well they will do in the, in the unknown environment.

Alex Allain: There's sort of a Nassim Tlaib, uh, view of this, which is like anyone who's like the best in any particular regime is probably not adapted well to being adaptable because they put all their resources into like being really, really good at like the thing. And so that really resonates. So like, if you've crushed like the, you know, Salesforce scaled AE experience, like you probably put all your resources into doing that.

Not into like, how do I be a generically good like salesperson? Across like all environments, and that doesn't mean anything bad about that person. It just means like they invested in one thing. So 

Waseem: well, in the flip side is your first 80 or whatever you want to call the first sales hire who really helps you kind of like write the playbook and master the motion and all that good stuff may or may not be the right VP of sales for 

you, which is like, it's very different to write the playbook than to scale the team and then [00:23:00] to scale to a team, you know, manager managers.

It's like, Those are, those are pretty different skill sets and they're, you know, the, the skill sets are not necessarily transferable in either direction. Yeah, I'd actually love to, uh, transition a little bit here to actually the hiring of the first sales person. I think this is a really interesting topic for founders who are listening because there are many different views on this.

Alex Allain: I'm curious, like what's your mental model or like advice for what, like what role to hire for? Are you hiring like the VP of sales first? Are you hiring the AE first? Like, how do you think about that? And then what are you looking for in that person? 

Waseem: Yeah, I think there are a couple of different approaches here.

And I think it again, it depends on the disposition of the founder. But if you have a kind of like, let's say, sales interested founder, which doesn't mean that you're necessarily like awesome at sales, but you like, you want to engage, right? You want to talk to customers, you get energy from talking to customers, and you have mastered the initial motion yourself.

What you should probably do is hire someone who, [00:24:00] who can free up or who can add to whatever the limiting reagent is in the reaction right now. Like if your shortage is of. Booked meetings and you know you could book more meetings if you spent more time like doing some outbound email or whatever Like you should hire someone to like plug that gap Meaning like your presence as a founder on like the closing call is actually like very high ROI And so you probably should, like, keep doing that for a long time.

Like, I still hop on customer calls today, like, in year eight of the company, because I think it's, well, one, it's, like, fun and interesting for me. And two, I think it's, like, valuable, and it's, like, kind of refreshing and unique for the prospect. And so in some ways, I think the question is, like, fine, what is the thing where if you had more of that input, you would be able to get more revenue?

And I would try to hire to kind of, like, plug that gap. And so, for me, that suggests hiring, like, the IC. You know, it's the former sales rep somewhere else or like the [00:25:00] scrappy person who's excited to just like really hustle for you or whatever. It probably does not look like hiring this season VP of sales.

And the reason is because the season VP of sales job is to build the sales org. And you're not ready to build the sales org yet. Like if you're thinking about should I make my first hire, like you are not ready to go and like build the machine. You want to just like more, you know, more rigorously test your existing hypotheses about who the buyer is and how they buy and like what they care about and what they want and how it's priced now it's packaged and all that stuff on the hiring.

So if you are looking at an IC, the other question we asked was, do you hire to, you know, to de risk and compare and have some healthy competition or do you hire one, right? And so where kind of on the spectrum, did you lie there? And what did you do when you first hired this IC? Yeah, great question. In the very earliest days, I hired just one person [00:26:00] and like she and I were on.

Every call together for some number of months, like shadow reverse shadow, it's like I drove the call like she was there and like took notes basically and then after she sort of felt like she'd mastered it, she drove the calls, but I was still on the call. Like in other words, I knew what was going on because I was still super close to it.

And I like developed a lot of conviction about is it working or is it not working now? Another way to do that. And one of the things that definitely I advise kind of After that point for your early sales hires, definitely is you want to hire them in pairs or in cohorts because it allows you to de risk it.

It lets you ask the question, is this not working because something is broken in the process or actually because like this person is stronger than this other person? Like it is nice to have that reference point. And if you don't have it and again, it's not working, you're sort of left wondering why. Well, is it the product?

Is it the messaging? Is it the rep? So I think you want to do things to eliminate uncertainty. One way to eliminate uncertainty is to hire in pairs or [00:27:00] cohorts, which is awesome because it's like, it's like an AB test in a way. Right. Another is you just have to remain super, super, super close to it. Makes sense.

Peter: Makes sense. I'm sure for that first hire too, she wasn't just doing sales. She was taking ownership of a lot of different things as well. I'm guessing. Right. And yeah, the reason why I also suggest founders for the first hire, just to hire one is because there's clarity and ownership and then also less management overhead, right?

Because even one extra person, one extra one on one a week, that's a lot of your time as a founder. Right. So, um, I like that you took that approach. 

Alex Allain: Yeah, I think this is great. I'd love to hear, um, Wasim a bit about. So just your thoughts on hiring sales execs, both like when to hire, but also how do you think about evaluating them?

Waseem: Sure. So the, the nice thing about evaluation in sales generally is there like there is a scoreboard, right? It's like, okay, how much revenue did you add? [00:28:00] You know, did you hit quota? Did you exceed quota by how much? And there's like, there is a refreshing honesty that comes from that. And this is like. You know, by contrast to like, you know, again, my background as an engineer, it's like, how, how do you assess whether your engineers are good or not?

Like, it's, you guys like sort of vibes, right? It's like, well, I don't know. They seem good. The sales, it's like, listen, the number is either good or it isn't good. And the number being good. Does not mean that you are a good rep, but it is a necessary condition. You cannot be a good rep without the number also being good.

The number has to be good. And you need to be a team player and needs to be aligned to the company. And dah, dah, dah, dah, dah, dah. But there is like, everyone knows what the score is. And so the nice thing is like, unless something has gone pretty wrong, like people know where they stand. And that actually makes kind of management of the team a lot easier because you are all on the same page.

You're all pretty eyes open about, is it working? Is it not working? Um, so I think the hardest part on sales management, [00:29:00] generally speaking, is when it becomes clear that it's not working. Do you act aggressively enough? Do you act fast enough? And I think especially for like, I mean, for any kind of like first time or early founder or any new manager, it's like the motion of like parting ways with someone who's like awkward and uncomfortable.

And there's a lot of, well, actually I like, I really like working with XYZ and like, maybe I'll be able to turn it around next quarter or whatever. And it's like, Probably not though, like probably not like usually, you know, sometimes you're like, okay, yeah, there was a big whiff here because our product was blah, blah, blah, blah.

And it's like, actually not the reps fault. The whole team missed the whole team missed and therefore like, it's not on the team. It's like we messed up as a company, but sometimes just like, well, that, that person is just like not. Getting it and you like listen to the calls and you're like, oh, I don't like I don't really want this person on the phone Like representing my company like, you know what you need to do.

You just like need to do it so I think [00:30:00] that's actually probably the place that like Folks get sales management most wrong is just like you you frequently know what you need to do and you just like need to actually Do it 

Peter: Yeah. And how, how quick is that timeline for you? Right? Like what's the fastest you've said, okay, this isn't working.

This 

person's gone. And what's like on the flip side, the longest you've waited to make that decision. Um, you know, traditionally I hear, Hey, three quarters of missing you're out, but that's also a lot of time in startup land, right? So I'm curious how you think about the time horizon of that assessment.

Waseem: Yeah. It's super tough because it's exactly, as you said, in the early days. It's like, well, are they, they're ramping, right? They like, there's Scott here. They don't really know how to sell a product yet. There's a certain amount of like, well, is this just like the normal ramp or is this person just not getting it?

And that's actually where the cohorts help. Right. If you're like, well, this person is pacing super far behind and I listened to her call and she's crushing it. And this guy is not getting it. Like that, that [00:31:00] helps you kind of get to conviction there. I don't think you need to wait three quarters if the early, if the early data is showing a clear sort of separation in your cohort.

It's in your interest and the reps interest to just like wind it down as quickly as you can, to be honest, I think, again, most people probably wait too long because they're like, Well, I don't know, maybe, maybe I'll turn the corner on it. I agree with you. Three quarters is like too long. Yeah, like the life of a startup.

I'd say like, if there's like a big miss in a given quarter, and you don't have confidence in the person anymore, like you should just part ways. If there's a big mess and you like, you really truly believe that they can do it and you have reason to believe that you've listened to the calls and you like, um, like then, you know, fine, like, let's let it, let's let it ride.

But I think it's a combination of the numbers and your own sort of. 

Peter: Yeah, I think the call also is a key portion of this, right? Because you have to trust that they're emitting the [00:32:00] right, like brand values. Um, because they're one of one or one of two who are talking about your product publicly, right? So the stakes are even higher than missing a quarter.

I would say there's like reputational damage as well. One other question, actually, if you can ask Wasim about hiring, um, I think a lot of firings are about communication and interpersonal relationships as well. So I wonder what you think about that. I coach a lot of first time go to market hires, and I know we have a lot of listeners who are also first time, um, you know, go to market hires at a startup.

That's like 10 or so people. Like what I want to ask is what is the communication pattern that works for a technical founder? Because a lot of these folks struggle with like, what do I share in Slack? What do I not? And so before I give my answer, I'd love your thoughts on. What that's like, because it's very, very different than reporting to a VP of sales at Oracle, right?

That's a very different communication pattern. So can you talk a little bit about that? Like what you like to see if you're managing Salesforce directly as a [00:33:00] technical founder? 

Waseem: Yeah, it's a it's a good question. You, I think you want folks who are gonna be real with you about What's happening, like, is it working?

Is it not working? You want people who are going to own the outcome to like, I'm not that interested in hearing like a laundry list of excuses about why we lost the deal. So I think you want like real talk. And you want like real ownership and by the way, like it is a two way street, meaning that you is a non sales founder have to earn like your credibility with your reps to like your reps have to believe one that your product is good and two that you know how to sell it.

And like if you, if, if they don't believe the product is good, they're not gonna be able to sell it. And if they don't have like any conviction and like your ability to do it. It becomes much harder for them to learn how to do it as well. So my approach kind [00:34:00] of like in trying to build rapport with our reps in the early days has always been like a little bit lead from the front.

It's like, well, let's do calls together and like, let's make sure we both feel good about like how it's going. But I'm, I'm curious to get your reaction, Peter. Like, what do you, what do you frequently tell folks on this? 

Peter: Yeah, I think what I tell first go to market hires is your job is not just as a sales leader.

It's also as somebody who's educating the company on the market and the product. Right. So I think the communication can't be like you said, it can't be a laundry list of like, here's what my pipeline looks like that doesn't tell a CEO anything. Right. I think a level deeper is here's what my pipeline is here.

The buckets of people we're talking to, and here are the biggest gaps in the product. And we tried these workarounds. They didn't work by the way, competitor ABC is also doing another thing. I think that conversation is very different because you're actually learning something versus saying I'm going to hit 80 percent to a goal, right?

So that's what I coach a lot of folks because quotas are also [00:35:00] crap shoots in the early days. So there are 70 percent Dakota and still be a star if they're teaching the business how to move forward the next quarter in the next year. Right. So that's kind of how I coach, um, go to market hires on how to engage with like technical founders.

Right. Cause I think, you know, folks like you and Alex, you just want to learn, right. And you want to move forward. Like you don't necessarily care about a miss in one quarter, but you will if it's four quarters in a row. Right. So I agree with that. I mean, I think just in general, and this kind of goes back to like why I think sales is so valuable.

Waseem: Like, yes, it's about revenue. But it's also like you're in the submarine and it's like the periscope that's like looking around at the real world, it's like actually where you're getting a lot of valuable input data about what's happening in market, what messages are resonating, what aren't like, you know, you're competing against et cetera, et cetera.

Peter: Yeah. I love, you have the great, greatest analogies, man. I don't know if you like, think about these beforehand, but they're so natural and authentic. 

Alex Allain: I think this is like super, super interesting and hopefully a few [00:36:00] good takeaways for our audience in terms of what to look for in a rep and how to think about, uh, I mean, honestly, like whether or not you want to keep them around, uh, cause that's, that's, it's always tough when you're hanging for a skillset that you're, you don't know yourself.

And I think we're seeing one of what, one of the things I'm taking from this is like, we kind of, you build up that skillset. So you have some way to like, get close to it and understand. 

Waseem: You have an unfair advantage as a founder. Which is like you bring a sort of an instant sort of like credibility to the call by virtue of being a founder and yeah, you're not going to be as good as the sales rep you hire at like the raw sales skills.

It would be surprising if you were, but you also have like an advantage. You have like some tricks that they like can't really use. And so the blend of that should actually be that you're like a fairly effective seller. That's a great message. Actually, I think people should really Take that to heart. 

Alex Allain: Um, well, why don't we shift gears one more time?

And, um, you [00:37:00] know, I think founders are always trying to make the number get bigger, which means it's not just about closing the deals that you currently have, but also how do you build your pipeline? So I'd love to hear if you have any, what are your creative tactics? What have you, uh, So, what have you seen work 

or what have you tried to pilot that's been, uh, that you're willing to share?

Waseem: Yeah. So this is interesting because it has a lot to do with the type of business you have and like how long your sales cycles are. Like if you have a super long sales cycle, a product or service. You might know a quarter out, two quarters out, three quarters 

Alex Allain: out, like whether you have enough pipeline coverage to actually hit the number or not.

If it's a super slow sales process, by contrast, if it's a super fast sales process, like if the lead shows up tomorrow, like they could still hit in quarter. And so actually forecasting this stuff is tough. It's actually like quite hard depending on kind of the nature of the business. And then you kind of have two Sort of inputs or like constraints you have to balance or make sure you have [00:38:00] coverage on and again It depends on kind of if this is a marketing led motion or a sales led motion Like are your reps?

Responding to kind of inbound form fills that come in through the website And if you had more of those you get more revenue or your reps actually out there like hunting for deals themselves Because again, the question is kind of like, what is the limiting reagent in the reaction, right? Do you need more leads or do you actually need more reps?

And actually, if, if any of those like get out of balance, it like stops working. If you have too many leads and like not enough reps, like you drop a bunch of leads on the floor that could have otherwise been good sales. If you have too many reps and not enough leads and there isn't an outbound motion, like they.

They go hungry and they like get unhappy and then they leave because you haven't given them enough to do. You don't, you haven't given them a real path to kind of like hitting their number, which like doesn't work. And so you need to kind of like take all of these factors together. You have to ask like, do I have the right number of people taking into account how they're going to ramp?

Do I have the right number of like leads or opportunities? Like from what is my marketing team [00:39:00] doing? And like, how do I get coverage there? And I think the, the best way to like get folks Kind of in, in the process is very, very specific to your business. It's like, you want to sort of ask yourself, well, who do I sell to?

Where do they hang out? How do they hear about other products to buy? And like, how can I get there? And so there, there are some standard things, right? You'll do like cold email or whatever. You'll do some podcast advertising or you'll post on LinkedIn or whatever. Like there is like generic stuff that yeah, probably like does work, but I think the thing that's really going to pop for your business is probably.

A function specifically of like what your business is and how it operates and like, you know, how you grow,

Peter: what is the most creative thing you've seen with pilot? Like maybe that you tried or one of your reps tried, or maybe it's your marketing leader to really attract leads. It could be something where you thought, you know, maybe it wouldn't work, but it was surprisingly good.

I'm curious, like what that might be. 

Waseem: Yeah. I'm going to give us kind [00:40:00] of like a C C plus on this a pilot. I think we're like, not that creative about this stuff. 

Peter: Okay. Okay. I appreciate the transparency 

Waseem: has really worked. And this is, this is a good thing and a bad thing. And I obviously I'm painting it as a bad thing here.

A lot of pilots growth has been organic word of mouth. Like founders talk, business owners, talk to other business owners, founders, talk to other founders. And the reason you like that is like, okay, it means the product is good. They're telling people they like it. And the cost of customer acquisition is very low.

Like you're not spending money to acquire those customers. The obvious downside is. The, you know, that flywheel spins at the rate that flywheel is going to spin. And there's not a lot I can really do to like get even more organic word of mouth going. I don't know. I could try to make the customer experience even better, but it's like, okay.

So we think about how to supplement that. Like, okay. Is there like some paid ad stuff? Is there event stuff? Is there like, are there other useful things we can do targeted to this audience? I talked to [00:41:00] the CMO at Rippling. Once about kind of how they think about their customer acquisition. And he said, listen, you can.

You either have to fish where no one else is fishing or you need to fish where everyone else is fishing, but you need to fish differently. Like doing the exact same thing as everyone else in the exact same population that everyone else is targeting will get you the, you know, median result. Which is like not, it's pretty mediocre, right?

It's not going to be that interesting for your business. So I think ideally you want to find something that's like your secret weapon. And I know like a Dropbox, it was like the domain tool, right? It was like, you could just see, oh, this company already has XYZ free users. And like, let me call up the IT person and say, listen, you, you're already using Dropbox.

Like, let's get, get you on a real plan. Like, that's not something another company could really do. That's pretty specific to how the product operated. 

Peter: Totally. Yeah. And it goes back to like the product just working flawlessly actually. Right. And so I actually think that's a really cool message that your [00:42:00] lead gen was the fact that you spent so much intentional time with your early customers to make it right and to care because I don't want to make a blanket statement about accounting firms, but I've worked with a few of them and a lot of them don't really.

Care about me, I would say, and so I think that's actually a really cool message that even if you give yourself a C plus that word of mouth started somewhere, which was intentionality for the early customers. So that's cool. 

Alex Allain: Yeah, I love this. I love the point, actually, just like figure out where your audience.

It might be Reddit or a forum or a trade show, or, you know, like it's very audience and industry specific. And of course, if you can get some champions there who will talk about you from your customer base, like that can be some real, we saw this at USDR, that was our, our like secret sauce was word of mouth lever, like accelerated by those, like, sort of like.

Get a lot of people talking together moments. 

Waseem: Well, and this goes back to kind of what I was saying in the beginning, right? It's [00:43:00] like you want to buy from people who get you who sell to people like you, who understand what you're about. And how do I like, understand 

if you're like from my tribe or whatever, it's like, well, are you showing up in the spaces?

I go to like, Learn or to hang out or to like, talk about the thing that I do. Yeah. Yeah, that's right. I love that point actually. It's like, that's where the tribe is meeting. Go there. 

Peter: Can I ask one more question actually on Legion? I know we're coming up on time. Um, you have like, I think now north of 50, 000 followers on LinkedIn.

Wasim and I, I, I see your content all the time. I love it. Especially the one today really resonated about, you know, finding innovators. You're not just solving a pain. You need to find customers who are willing to lean into. So I love that. But can you talk about that as a lead gen machine? Has that worked for you?

Um, over time, obviously like the first post, you probably weren't getting a bunch of people being like, let me buy pilot. But can you [00:44:00] talk about that? Cause I am a firm believer in just personal branding and having that drive a lot of your company identity too. So has that helped for you in, in similar ways?

Waseem: I think so. And the reason I'm giving you such a vague answer here is it's like, it's very difficult to attribute because you can't really directly track it to like, Oh, this person saw my post on LinkedIn and then they went to the website and they bought. But anecdotally, yeah, 

my sense is that like increasingly, you know, founders and business owners are like, Oh, I saw your stuff on LinkedIn and I saw it a bunch of times and it was like mostly pretty smart.

And then if you want like, Oh, I guess I do need some accounting and tax prep. Well, I like, you know, seeing this guy's stuff. And so like, I'll give it a shot. So I, I definitely, I mean. I was spending time on it because I have conviction that it's valuable. And furthermore, I think that like, and this is like, you know, the marketing influencers have already, this is like very well trodden territory.

I think people want to hear from real people. They don't want to hear from brands. And so I think there is actually something really powerful [00:45:00] when it's like one of the founders or whatever, it's just like someone at the company being like, I am a real person. And like, These are my opinions about the XYZ.

I think the stuff you see from brands on LinkedIn or social media, like with some exception, they just tend to be very generic. And it's like, that's not that interesting. Yeah. Yeah. They can't be as edgy as like a human can be. Right. Yeah. That's my experience too. I even have like founders come to me or like, Oh, I saw a video from eight months ago and I'm like, well, that video had like seven likes, but you know, you're creating this, I like your stuff.

Peter: Thanks. So you appreciate it, man. Throw up some more likes for me. Well, yeah, it's some comments, but no, I think you're generating that like rabbit hole of research. And 

yeah, it builds that trust, which you mentioned in the beginning too, right? Between you and like your potential prospect, whether it's tomorrow or like six months or a year from now.

Waseem: And I think it has to be given mostly not get like my posts are almost never like, Oh, come by pilot accounting. [00:46:00] We're the best at accounting. They're usually like, okay, you are a startup founder or whatever. Like here are some things that will help you help make you a better startup founder. Yes. I love that.

Alex Allain: If people want your stuff, they'll find out how to buy Pilot from you. Right. They'll know that you're interesting and smart and they'll do some research and it makes a big difference. All right. Well, Waseem, this was fantastic. Thank you for joining us for our audience. First of all, if you want to learn more about Pilot, you can go to pilot.

com. Follow Waseem on LinkedIn for lots more, uh, not just sales, but general founder advice. I know a lot of you. Probably benefit from that. I've read his stuff. It's great. Um, and, uh, we'd also appreciate, uh, for decoding sales, hit the like, like button or the subscribe button or whatever, you know, the primary action is that PMs get, uh, promotions.

If you do them on these various apps that you use for us, um, that'll help us out and make us feel good. And, uh, probably make it more likely that you see our next episode. 

[00:47:00] Mhm.