Hire Hyper-Inventive Generalists and Don’t Overcomplicate Things: Lessons on Early-Stage Sales Hiring with Airplane’s Co-Founder, Ravi Parikh


Placed firmly at the core of early-stage startup hesitations, is an on-off unease that surrounds setting up sales. Reading by some founder descriptions — “my co-founder and I thought sales was evil; a dark art that separates people from their money" — it takes a real perspective-shift to even begin dispelling those early inhibitions, let alone designing a path for the foundational, first hires.

In the following conversation, Airplane’s co-founder, Ravi Parikh (@ravi), draws from his time at a previous SaaS startup (Heap) he co-founded, paints precisely what the sales learning curve demanded from him as a technical founder, and delivers clear-eyed recommendations on:

Arriving at the deeper logic of founder-led selling,
Searching for those early candidates (“I didn’t know what I was looking for in the first sales rep, but I knew how I sold”),
The single most important trait to interview for when selling a technical product,
Why the first few sales reps need to creatively double as sales engineers and product marketers (and what else separates them from late-stage hires),
How people tend to overrate “relevant” experience (faster ramp times offer scant basis for overall success),
The biggest sales hiring constraint you’ll likely grapple with,
And why founders — undeniably — overcomplicate early-stage sales processes.


Figuring founder-led sales:

We started the company in 2013. My co-founder and I are both engineers by background. But once the company started growing, I naturally moved over onto the customer facing side.

I was the person doing all the sales from more or less day one of the company. And so I hired our first few sales reps. I hired our first VP of sales. I basically helped build that team. So yeah, I’ve hired a lot of people in sales roles over my time at Heap, including all the early people.

And I’ve seen what successful people have looked like, what unsuccessful people have looked like, and, you know, what led people to grow in their career over time. And also what traits made someone really good early versus what traits mean, someone really good later stage.

I just had a fair amount of experience, that, now, going into my second company with Airplane, I have a fairly clear vision of what we’re going to need from that first sales hire. Even though it’s a very different product, different sort of company. I’ve seen over time what things matter and what things don’t I guess.

We were a self-serve SaaS product. People would just come in, sign up for the product on the website. And honestly, our approach to go-to-market was very reactive. People would come in, use the product, they could chat with us via email if they wanted support. And then we would answer those support questions.

But inevitably, sometimes we would have sales questions.

‘Hey, what is the pricing?’ Or ‘how does it scale over time?’ Or ‘do you have this feature?’ And then we got on the phone and talked about those questions. And honestly, our first 20, 30, 50 customers were actually just leading the process themselves.

And then I just figured out patterns for, ‘hey, maybe I should be trying to give them a demo initially, instead of just waiting for them to ask for one. Maybe if someone comes in and they’re from a big company, I should reach out to them proactively.’

It sounds very basic and very stupid. But you know, as first-time founders who are just engineers by background, our instinct was to engineer every system. And as basic and simple as it sounds, just the idea that a human being should be proactive in sort of getting in touch with people was sort of, in and of itself, a big revelation.

Then I realized, ‘oh, what I’m doing is sales.’

So I went on Hacker News and saw a comment from some guy who was like, ‘oh, I used to be an engineer, but I became a sales person. And I was like, ‘oh, who’s this person?’ So I clicked on his profile. I reached out to him.

Turns out that that person was the first sales rep at PagerDuty. And so I met up with him for coffee, and just asked him some questions, really basic stuff about sales.

And this guy was out there closing million-dollar deals. I happened to be reaching out to someone who was a very successful sales rep.

And then he introduced me to their head of sales.

I met up with them. And basically from them, I kind of downloaded the playbook of how they approached sales. A lot of it was actually very different from what we were doing, because our business was way smaller and we were way earlier stage than PagerDuty at the time.

A lot of it was learning that didn’t actually become relevant for a while. I actually kept up in touch with those folks for quite a while and continually sort of refined our sales processes based on us just being a couple steps behind PagerDuty from a company lifecycle perspective.

The search:

The first few sales hires, none of them came through my network, interestingly. Because my network indexes very heavily on engineers. I studied computer science, my co-founder studied computer science, we both knew each other from college.

We had a bunch of friends from college, but they all studied computer science as well. And we hired a few engineers that way, from our personal networks, but in sort of non-engineering roles, I didn’t yet have an established network of folks I could draw from.

I do now, by virtue of having built Heap, and having been in the industry for a while. But at the time, I didn’t. I actually tried everything really, we went on AngelList and started sourcing random people there.

I reached out to that guy from PagerDuty, ‘hey, you want to come here?’ And he’s like, ‘no, way too much money to do that.’

I went on Hired.com. And then there was like a clone of Hired.com called Gogohire, which was for sales. That’s where I hired my first sales rep from.

And we probably interviewed 30 or 40 people. And we had no idea what we were looking for. I mean, I asked David, the PagerDuty guy, how I should recruit for sales, as I didn’t really know what we were looking for.

And in the end we defaulted to… the way I thought about it was: I didn’t know what I was looking for in the first sales rep. But I knew how I sold.

By this point, we had closed about a million dollars in ARR. We had some sort of process. We had at least a few customers paying us 50K-100k. Thus we had enough data to say, ‘here’s how we’ve closed deals in the past.’

What I usually do is I default to a very demo-heavy process, like showing the product a lot. I didn’t even have terms like qualification and all that kind of stuff in my vocabulary.

The definitive trait to assess:

So I really optimized for hiring someone who themselves, I felt confident, could learn our product deeply. Because, you know, at scale, you have these sales engineering roles, and you have marketing collateral and all that stuff.

We didn’t have all that at the early stage.

And you’re probably not going to have a lot of support for your first sales rep. They’re probably just going to be by themselves. Having to be both the account executive and the sales engineer, and the product marketer and everything all baked into one.

Because you don’t have that specialization yet.

So we defaulted to asking, what is the hardest of those skills to learn?

Probably the product stuff. Because Heap is a technical product. It’s not the most technical product in the world. But we do get lots of questions about HTML, JavaScript, CSS, and SQL, and how it integrates with other products and all that kind of stuff.

And that’s stuff that would be much harder to teach, if you didn’t come up with it. I wanted to have a sense that this person could learn that stuff. So we optimized the interview around their ability to do that. What I did was I gave them access to a sample Heap account and said, ‘hey, you give us a demo of the product.’

And we hired a person who did a really great job giving a demo of Heap. And he even took his sample Heap account and installed it on some website and got some fake traffic into it. Stuff that you didn’t need to do.

But he got a Squarespace page and installed it there. So that gave me some confidence. ‘Hey, this guy, I don’t know if he’s good at selling, actually, but I know he’s good enough to do all this stuff.’ And then he had had some success at Square before.

We brought him on board. And he was really good. It turned out I hired someone way better than I had any right to hire. But, in retrospect, the demo ask was a good thing.

Although, I don’t think it’s a way to hire at scale.

Because a lot of people are not really going to want to go into your product and learn the details of it before they come on site. But if you’re selling a technical product, like Heap, or an API company, or what Airplane is (we’re a developer tool), they have to be able to learn the product decently well.

It’s just a non-negotiable aspect of it. Everything else can be taught. But if they can’t get up to speed on the product in three to six months, it’s going to be really, really hard for them to be an impactful first hire before you have all that infrastructure to help support them.

That’s number one.

The other (hard-to-define, must-have) trait:

And then this person came in and he actually ended up being really good in many other ways we didn’t interview for and, in retrospect, I should have interviewed for. Because of how impactful it turned out to be.

He was really good at sort of maximizing the value we got out of every lead. A good sales rep is going to do that. Our deal size was basically 4X when he came in. And our second sales rep, Becca, came in as well.

We hired two sales reps, in very quick succession, using a very similar process. Both of them came in with not a tonne of experience, probably two or three years of experience before they joined us.

But both of them immediately increased our deal sizes significantly.

And they were just very good at sort of asking for money. Whereas I was not very good at that thing. I gave discounts very readily. And I had a pricing sheet that I just kind of stuck to. I didn’t do an effective job of price discrimination or upselling features and things like that.

And one thing that distinguished them from the later reps that we hired, who were also very good, but probably not the right fit for us at that early stage, was that they were very creative people.

By ‘creative,’ I mean, they would sort of think, ‘oh, a customer came in, they’re in a different industry or vertical than we’re used to selling to, let me redo our pitch deck a little bit, to sort of tailor it to this particular industry or this particular person.’

And like, ‘oh, like this person has a lot of traffic, but they’re not actually that big of a company, let’s tailor our pricing a little bit to what they need.’

They just had that sort of proactive lens of thinking through, ‘Okay, for this particular conversation, I’m heading into what’s the optimal way to approach it.’

I don’t know how to interview for that creativity.

But that was massively, massively, massively impactful in the early days of Heap.

So that’s something I’m thinking through now, we’re probably going to hire our first sales rep in the next two or three months here at Airplane. I’m also thinking about that creativity piece, because it’s so important early.

It doesn’t matter at scale.

Because, you kind of know, ‘well, we sell really well on these three verticals.’ A good sales rep at scale is good at executing a playbook over and over again and executing it optimally.

And it might not even be the same person who was good in the early days at the creative stuff. And so over time, those two people, they stayed with the company for 6-8 years, but they became managers. People in more creative-ish roles where they were moulding things.

They didn’t really want to do individual selling that much anymore, once we were at scale. Both have gone off into different companies and are doing very interesting things.

So. The ability to learn the product quickly. Ability to be creative. And understand that even if you’ve closed a fair amount of deals already, it’s not a tried and true process yet. You don’t need them to just implement a process you’ve created. You need them to improve upon it.

And then, also from a sort of personal standpoint, neither of them were there just to maximize their paychecks. Partially, obviously, if you’re in sales, at some point, you’re money-driven.

But they were also quite good at things such as mentoring new people we added to the team, documenting things that they found out that worked, sharing that knowledge a little bit.

They joined early because they wanted to help build the team, even if they weren’t in a leadership role in an explicit sense. That’s important as well.

And so whereas for later sales rep, you might get some lone-wolf AE, who’s just trying to get a million-dollar paycheck, which is great when you’re at scale.

When you’re really big, having someone who’s in there who’s like, really just trying to maximize their paycheck, if you’ve created the incentives correctly, and you’ve created a comp structure correctly, that will result in your company also making tonnes of money.

It’s the sort of way they want to fit onto the team that has to be a little bit different early than if they join at a later stage.

Why hiring for similarities (deal sizes/categories) doesn’t yield much:

I believe people overrate relevant experience in the same field. It’s really tempting to be like, ‘oh, we’re Heap, we should hire reps from Mixpanel or Amplitude or something like that.’

That’s great. They’ll perhaps ramp a little bit faster.

But the right reps honestly can learn most products pretty quickly.

If you hire, let’s suppose, I’m making things up here a little bit, but let’s say you hire someone from a direct competitor, who’s in the same space as you.

They’ll probably do a great job in your interview process, especially if it’s sort of product centric, but you don’t actually know their ability to ramp on your product. You only know their ability to have existing current knowledge of the space.

Your product is inevitably going to be somewhat different from the product they’re coming from. So I don’t want to give too much detail because I don’t want to name specific people, but we have hired people who had a lot of ‘relevant’ experience.

And then their ability to just get that 20% more to learn Heap, specifically, was actually a lot more difficult than I thought it would be.

I don’t know if it took them two years to learn all that stuff. Whereas there’s other people that may have come totally out of the industry. Todd, our first sales rep came from Square. Square and Heap have no relationship with each other. Different deal sizes. Different products.

Yet he figured Heap out within a couple of weeks.

And to me, it’s that slope, that rate of learning that matters a lot more than the knowledge that they come in with today. Especially for your early sales reps, who don’t have all that scaffolding and support.

If you hire from the same industry, you’ve actually diminished your own ability to discover their rate of learning, in some sense. Because they will come in and feel very knowledgeable compared to the average person you’re interviewing.

That’s not to say that you shouldn’t hire from the industry. It’s just that you should have that potential shortcoming in mind. And then sort of interview around that. Design an interview where they have to demonstrate their ability to learn something quickly.

Maybe it’s some sort of behavioural interview like what we did. Which is, ‘learn our product and demo it to us.’ Go through their past experiences, try to figure out situations where they’ve had to learn or ramp up on stuff really quickly.

Todd, our first sales rep, was a very early sales rep at Square. I don’t think they even had a sales team. And then they created one. And then he was one of the first people hired onto it.

And he talked a lot about his experiences, experimenting with, who to sell Square to and how to position the company as a whole. Even though it was a pretty late stage company, it was building that sort of sales process from the ground up.

There was some of that creativity exhibited during the interview process. And it was a lot more important than I gave it credit for. I didn’t realize how much that mattered to how good he was going to end up being for our company.

A lot of other people will say, ‘oh, you want people who’ve worked at the same deal sizes, or people who have had a certain quota attainment or something like that’ That stuff’s all great. At scale, those metrics matter a lot more. When you’re early, you’re looking for a very different type of person.

To be clear, you want someone good.

You don’t want someone who was ranked at the bottom of whatever company they were at previously. You want someone who has a history of quota attainment and excelling. You want someone who’s in the top quartile of their peers at their previous company.

But there are plenty of people who were in the top quartile of their previous company and still are not the right fit early for you. Because they don’t have those other traits.

The capital constraint (that’s mostly good for you):

For sales hiring specifically, one constraint that you’re really going to feel when you’re hiring your first sales rep or your first couple sales reps is: money.

Sales is a job where if you’re good at it, you make a lot of money.

If you’re trying to hire someone with, let’s say, eight years of experience. And they’ve been in sales that whole time. They’re not like transitioning to sales from a different career. They likely are getting paid a lot of money at whatever they’re doing currently.

And you’re probably not going to be able to match that. As an early stage company hiring their first sales rep, inherently (unless you’re super well-capitalized) you’re just going to have less money to spend than other companies.

And unlike engineering roles where you can say, well, we’re not going to have as high compensation as Facebook, but we have equity that we’re giving out.

You can give out equity to your first sales reps if you want to, but I’ve found that most sales reps are more motivated by cash compensation than equity. So it’s going to be harder to compete. You’re going to be usually hiring more junior people, or hiring people who’re transitioning to sales from a different career.

And that is just a constraint you’re going to have to live with a little bit. And arguably, that selects for some of the things you want anyways. The high rate of learning and the creativity.

If they’re making tonnes and tonnes of money at their current opportunity, they probably shouldn’t be joining an early stage company.

Even if you’re one of these well-funded companies that has tonnes of seed funding. You still probably don’t want to spend tonnes of money on your first couple of sales reps. Because what’ll end up happening is they might have the wrong picture of what it’s like to sell for your company.

Usually the people who are over at, say, Datadog, earning a million dollars a year in cash compensation, they’re doing so because they’re really great at executing a mature playbook. And with a product that has a brand behind it and lots of resources.

That’s what an account executive does at scale. And sometimes they might think, ‘oh, I want to go early and build from the ground up,’ but they might really not really realize what that entails.

And even if the comp looks good on paper they might join and be like, ‘oh, wow, there’s actually a lot of things here to figure out that I didn’t quite realize.’ It’s not to say that they have the wrong traits. I would just say that, that [realization] constrains them.

Don’t juggle sales specializations just because you’ve been told so:

I would not overcomplicate your sales process early.

In 2013, when we were starting Heap, SaaS was a lot less mature. In some sense, we didn’t have the luxury of even knowing that we could overcomplicate things, we just said, ‘hey, we need sales.’ So we hired a sales rep. And I feel that was the right thing to do.

These days, you might have had a lot more exposure to the SaaS business model. And you just might know a lot more. You’ve read more SaaStr.com or whatever. And you just might learn that you can have a BDR and an AE and a sales engineer, and this and that, and an account manager and a customer success person.’

And at scale, you’ll have all those things. You’ll have a process where customers are touching like 18 different roles over the course of their journey.

Don’t do that early.

I’ve seen a lot of founders overcomplicate things and say create a wreck with a BDR and an AE and a sales engineer and like another thing. Just hire one role at a time.

Hire your first AE and make them do all the roles you can specialize in later. Hire generalists who don’t need to be pigeonholed in a very small box. Until you get that one thing right and then specialize the thing when you need to. The point of specializations is to get more efficiency out of a given role.

But the cost of specialization is that it’s a management overhead for you. And it’s also like communication overhead internally. You don’t want to pay those overhead costs until you absolutely have to.

Keep the specialization as low as possible for as long as possible. Or like until you’ve hired a VP of Sales who can manage the specializations. They’ve done it five times before. They can.

If you’ve never managed that specialization yourself, you’re probably going to mess things up. You’re probably going to get the boundaries wrong. And you’re going to be spending your time fighting fires internally instead of improving the customer experience.


Editors’ note: We hope @Ravi’s thoughts help expand your sense of the composition that makes a great, early sales team. If you have any questions for him, please ask away in the comments below. Also, we cannot recommend highly enough, @Ravi’s writings on the Airplane blog; where he returns repeatedly to recollect similar lessons on wide-ranging SaaS subjects such as pricing’s real value and why merely being enterprise-ready isn’t enough.

Related reading from the Relay archives:

Chameleon’s co-founder, Pulkit Agrawal, on how to transition from founder-led sales
Pipedrive’s co-founder, Timo Rein, on sustaining a competitive yet healthy sales environment
Founder notes on how to contemplate, develop, and scale an early-stage, B2B sales process


Hey @Ravi,

Thanks for sharing your take on early-stage sales hiring!

So many interesting valuable lessons, here.

A precursor (and in some cases, a parallel) to founder-led sales, is of course, founder-led marketing. Or rather early demand gen. It’ll be helpful for early-stage Relay founders to hear briefly, how differently/similarly you’re approaching that with Airplane.


Hey @Ravi,

Thanks for taking the time to do this!

It’ll be great to learn, on the culture side, what were some of the things you did, accidentally or not, that allowed for that early-stage sales creativity to flourish?

And congrats on starting up your second SaaS journey. Wish you tremendous success with this one, too! :slight_smile: