Hiring your early team

Welcome to part six of our ongoing series on how to kickstart and scale a B2B business. Here’s where we’re at:

- **Part 1:** [How to come up with a great B2B startup idea](https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups)
- **Part 2:** [How to validate your idea](https://www.lennysnewsletter.com/p/how-to-validate-your-b2b-startup)
- **Part 3:** [How to identify your ICP](https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer)
- **Part 4**: [How to find and win your first 10 customers](https://www.lennysnewsletter.com/p/how-to-win-your-first-10-b2b-customers)
- **Part 5:** [A guide for finding product-market fit](https://www.lennysnewsletter.com/p/finding-product-market-fit)
- **Part 6:** How, and when, to hire your early team *← This post*
- **Part 7:** [How to scale your growth engine](https://www.lennysnewsletter.com/p/scaling-your-b2b-growth-engine)

*A huge thank-you to **[Akshay Kothari](https://www.linkedin.com/in/akothari/)** (COO of Notion), **[Ali Ghodsi](https://www.linkedin.com/in/alighodsi/)** (CEO of Databricks), **[Andrew Ofstad](https://www.linkedin.com/in/aofstad/)** (co-founder of Airtable), **[Barry McCardel](https://www.linkedin.com/in/barrymccardel/)** (CEO of Hex), **[Boris Jabes](https://www.linkedin.com/in/borisjabes/)** (CEO of Census), **[Calvin French-Owen](https://www.linkedin.com/in/calvinfo/)** (co-founder of Segment), **[Cameron Adams](https://www.linkedin.com/in/themaninblue/)** (co-founder and CPO of Canva), **[Christina Cacioppo](https://www.linkedin.com/in/ccacioppo/)** (CEO of Vanta), **[David Hsu](https://www.linkedin.com/in/dvdhsu/)** (CEO of Retool), **[Eilon Reshef](https://www.linkedin.com/in/eilonreshef/)** (CPO of Gong), **[Eric Glyman](https://www.linkedin.com/in/eglyman/)** (CEO of Ramp), **[Guy Podjarny](https://www.linkedin.com/in/guypo/)** (CEO of Snyk), **[Jori Lallo](https://www.linkedin.com/in/jorilallo/)** (co-founder of Linear), **[Julianna Lamb](https://www.linkedin.com/in/juliannaelamb/)** and **[Reed McGinley-Stempel](https://www.linkedin.com/in/reed-mcginley-stempel-17362245/)** (co-founders of Stytch), **[Keenan Rice](https://www.linkedin.com/in/keenanrice/)** (founding team), **[Mathilde Collin](https://www.linkedin.com/in/mathilde-collin-bb59492a/en/)** (CEO of Front), **[Rick Song](https://www.linkedin.com/in/rick-song-25198b24/)** (CEO of Persona), **[Rujul Zaparde](https://www.linkedin.com/in/rujulz/)** and **[Lu Cheng](https://www.linkedin.com/in/lu-cheng-973b7830/)** (co-founders of Zip), **[Ryan Glasgow](https://www.linkedin.com/in/ryanglasgow/)** (CEO of Sprig), **[Shahed Khan](https://www.linkedin.com/in/shahedkhan/)** (co-founder of Loom), **[Shishir Mehrotra](https://www.linkedin.com/in/shishirmehrotra/)** (CEO of Coda), **[Sho Kuwamoto](https://www.linkedin.com/in/shokuwamoto/)** (VP of Product of Figma), **[Spenser Skates](https://www.linkedin.com/in/spenserskates/)** (co-founder and CEO of Amplitude), **[Tom Preston-Werner](https://www.linkedin.com/in/mojombo/)** (co-founder of GitHub), and **[Tomer London](https://www.linkedin.com/in/tomerlondon/)** (co-founder and CPO of Gusto) for contributing to this series. Art by [Natalie Harney](https://www.natalieharney.com/).*

For this step, I’ll focus on the four most common hiring questions I get from early-stage founders:

1. **Who should I hire first?**
2. **Where do I find them?**
3. **How do I convince them to join?**
4. **When should I hire a salesperson (and what should I look for)?**

## 1. Who to hire

I asked all the founders I interviewed who their first 10 hires were:

Let’s break this down by your first hire, first three hires, and first 10.

### Who to hire as employee #1

**Takeaway:** Developers, developers, developers, developers. Over two-thirds of the companies hired an engineer as employee #1. Not a big surprise.

In the rare case when an engineer wasn’t the first hire, it usually came down to the founding team having enough horsepower to build the V1.

> “**Having four founders who could stretch across the business helped a** ***lot*** **here.** Each of us could write code, handle customer success, write product specs, and work across the stack.” —[Calvin French-Owen](https://www.linkedin.com/in/calvinfo/), co-founder of Segment

Founders were instead able to de-risk, or un-bottleneck, something else. **Vanta** hired a compliance subject-matter expert as their first employee:

> “**We could build, but we wanted the check on are we building the right thing**, given our background wasn’t in the space. The worst case would have been promising to get a company ‘secure and compliant’ and then failing to do so!”
>
> —[Christina Cacioppo](https://www.linkedin.com/in/ccacioppo/), co-founder and CEO of Vanta

**Coda** hired a recruiter:

> “I’d say that our first hires were all fairly typical, except for hiring a Head of Recruiting at such an early stage of development. It was earlier than anticipated, but a good friend introduced me to [Kenny Mendes](https://www.linkedin.com/in/kennymendes) and said, **‘I know it’s early, but people like Kenny don’t come along often, so you should probably pull him in.**’That turned out to be a fantastic choice, as Kenny has turned out to be an amazing generalist and quickly became chief operating officer for us.” —[Shishir Mehrotra](https://www.linkedin.com/in/shishirmehrotra/), co-founder and CEO

**Sprig** hired an AI data scientist, and **Segment** and **Amplitude** hired a customer success/support person as employee #1. Here’s [Calvin French-Owen](https://www.linkedin.com/in/calvinfo/) (co-founder of Segment) on why they did this:

> “**There’s something really magical when you write in to a startup and they fix your issue within a few hours. It’s something you’d never, ever expect from a big company, and it was one way for us to differentiate.**
>
> So initially, the four of us basically round-robined support. We’d log in to Help Scout and answer as many emails as possible. We’d switch off whoever answered the handful of Olark live chats that would pop in throughout the day. By the middle of the year, we were getting slammed with fairly technical support requests from users. They’d run the gamut from the relatively easy ‘What analytics tool should I use?’ to the more technical ‘I’m running Python on App Engine; why aren’t my events making it to Segment?’
>
> To give us extra engineering bandwidth, Peter [Reinhardt, the CEO] spent about eight weeks handling all the support volume on his own. But it basically meant he couldn’t do anything else.
>
> **We wanted to find someone who could handle most of these requests on their own and synthesize any new requests. Jake [Peterson] (who we hired for the role) was a bit of a unicorn in that respect. He had run his own analytics consultancy that was focused on helping customers reduce their costs and had a little bit of technical ability to read code. He wrote good docs and authored a bunch of our early blog content.**
>
> Given the breadth of integrations we supported, and the fact that we had four technical co-founders, we hired early here.”

### The first three hires

**Takeaways:**

1. Engineers continued to be the predominant function across the first three hires. Not shown in the chart, but **100% of companies hired at least one engineer among their first three hires**.
2. Interestingly, customer success/support continues to be a popular role for the first three hires. **Of the non-engineer hires, almost a quarter of them are customer success/support.** For me, this ties directly to the core lesson from part five—[get companies to love your product](https://www.lennysnewsletter.com/i/119122450/step-get-one-company-to-love-your-product).
3. **Subject-matter experts also continue to be a surprisingly common early hire**, particularly for startups building in a complex regulatory-oriented market (e.g. Gusto, Zip, and Vanta).
4. Although only 10% of hires were designers, and this isn’t shown in the pie chart above, **over 40% of companies hired a designer in their first three hires, or had a designer co-founder.**
5. **Very few companies hired a salesperson among the first three.**
6. **Three companies hired a PM within their first three hires**: Coda, Persona, and Snyk. Here’s [Guy Podjarny](https://www.linkedin.com/in/guypo/), founder and CEO of Snyk, on why they hired a PM so early:

> “I believed the fact that security products weren’t fit for developers **was a product problem, not a tech problem**, needing breakthroughs more in the UX world than tech algorithms. Furthermore, I had two technical co-founders that I knew would lead the security and tech aspects well, so felt I’m well-covered there.
>
> **I could have done the product work myself (and in practice, I did a portion of it), but I wanted to free myself up to build the company as a whole, and not be too focused on one aspect of it. I did hire someone with deep UX skills, better than mine, who complemented me, not just offloaded work.**
>
> In general, I intentionally took the path of building a strong leadership team early on. It was always a very hands-on leadership team, who initially spent most of their time as ICs but were also building teams and practices. This is a personal choice, and many founders prefer to directly manage most of the team until it grows. For me, however, I perceive myself as a better leader and innovator than I am a manager, and I wanted to focus my attention there.”

And here’s [Rick Song](https://www.linkedin.com/in/rick-song-25198b24/), founder and CEO of Persona, on hiring a PM as employee #1:

> “We hired Vincent [Tsao] because Charles and I believed his professional experience and willingness to give it his all were a perfect fit. We would’ve wanted to work with him whether at Persona or elsewhere, and that speaks highly of our rapport. He had experience from a previous startup and understood the fluid nature of a company’s early stages—he wasn’t tied to a specific role, title, or set of responsibilities and understood that we were all going to do whatever it took to succeed. In fact, his very first project had nothing to do with product- he spent the first evening setting up payroll!
>
> **We also believe that many founders, in their eagerness to launch and iterate, often swing too far on the pendulum of no documentation or process. While Charles and I were confident in our product and market insights as well as our ability as engineers to create a MVP, we were also self-aware about our shortcomings.** We knew we needed someone with not only sharp product intuition but also someone who could anchor our product operations and knowledge base, synthesizing insights from chaos and ultimately helping us move faster. Vincent was invaluable in building the foundation that enabled us to smoothly go from MVP to product market fit, and eventually, to scaling our team.”

### The first 10 hires

**Takeaways:**

1. **Sales becomes the second most common hire**, after engineering.
2. **A quarter of companies hired a product manager** at this point.
3. **Recruiters become a surprisingly common hire.** I did not expect that. This is particularly true across some of the most unique startups, like Linear, Figma, Ramp, and Coda. Here’s [Jori Lallo](https://www.linkedin.com/in/jorilallo/), co-founder of Linear, on why they hired a recruiter so early:

> “Initially all of us three founders ran the recruiting process, and while it worked for a little while, it wasn’t something we were necessarily particularly good at or passionate about. **We cared about hiring the best people, not about the first person who came knocking at our door. Also, we didn’t really have the tools or the time to reach outside our own networks, so we needed help to expand outside the inbound applicant pool.**
>
> At first we experimented with a couple of external boutique recruiting agencies, but it didn’t feel natural. This was mainly due to a consulting recruitment model where incentives are often tied to closed hires, so the recruiters are incentivized to make the hires as fast as possible. This is good for growing the team fast but hard when you want to hire only the best talent. The best and most sought-after people are often hard and slow to hire, and the process looks more like leadership recruiting.
>
> So building the function in-house and investing into it made sense to us. We probably weren’t great at it at first but have since come a long way. Today we have a four-person recruiting function at a 50-person company.”

## 2. Where to find your early employees

Once you have a sense of which roles to hire, how (and where) do you find amazing people? I asked each founder how they found their early employees. Their answers all fell into four channels:

#### **Channel 1: Friends and former colleagues**

Unsurprisingly, hiring friends and former colleagues was by far the biggest channel. This also in part explains why multi-time founders, and anyone with a large network (e.g. Y Combinator), have an advantage:

> “All of our early hires were friends/ex-coworkers.”

> “First hires were practically all former colleagues. Several people who worked with me in my previous company reached out when they heard I was into something new, with my co-founder.”

> “About half the early hires came from my personal network (friends from school, ex-coworkers, etc.).”

> “I thought about the hardest-working people I knew and reached out to them.”

But not so fast. There’s also a downside to this path, as shared by **Segment** and **Linear**:

> “We tried for a long time to hire former classmates (we were fresh out of college, so had no former colleagues), but we had pretty rotten luck. **Believe it or not, there was little appetite to join four crazy guys in a room who had been failing for two years straight** :)” —[Calvin French-Owen](https://www.linkedin.com/in/calvinfo/), co-founder of Segment

> “We didn’t end up hiring people from our past jobs, which might be more common for others. **All of us founders worked for more established startups before Linear, and we looked for people who would do well in an early-stage environment**. Among our first 10 hires were several founders (including two who had gone through YC). We still look for generalists and people with experience and who deeply care about their craft.” —[Jori Lallo](https://www.linkedin.com/in/jorilallo/), co-founder of Linear

#### **Channel 2: Cold outreach**

I was surprised to learn that the second most common channel for finding early employees is cold outreach—finding people you want to hire and reaching out to them directly. These outreaches happened mostly through LinkedIn and GitHub, and unlike channel #1, this is something anyone can do.

> “We filled many roles through **cold hard outbound on LinkedIn**.”

> “**We reached out directly to people (mainly engineering) that had significant public experience** with parts of the product we were developing, i.e. visualizations.”

> “**We had great luck finding people off GitHub**. These were folks who had contributed to repos we were watching, and we had decent evidence that they were good. They didn’t come from FAANG, they had solid contributions in open-source land, they paid a lot of attention to abstractions and were really productive. Most of them had worked at one or two prior startups, but in general we bet on people looking to make their next big leap.”

#### **Channel 3: Job boards**

Also, surprisingly, a lot of early hires were found by posting roles on public job boards—again, something every founder can do. By far the most mentioned job board was AngelList. Also mentioned were Triplebyte, Facebook groups, and VCs’ internal job boards. Shoutout: If you’re looking for the best jobs in town, check out [Lenny’s Job Board](https://www.lennysjobs.com/)! 😅

#### **Channel 4: Friends and former colleagues of your** ***employees***

A final channel, which, if you recall, was also useful for [finding your early customers](https://www.lennysnewsletter.com/i/115245373/start-by-reaching-out-to-your-personal-network-looking-for-people-who-match-your-icp), was tapping the networks of your early employees.

> “Many of our early hires were people from my network or the n**etwork of the very first employees.**”

> “Our second sales hire was a **former colleague of our first salesperson.**”

I didn’t get many interesting quotes for this channel, but it was a fruitful one for many founders, and worth spending time on.

## 3. How to convince people to join your startup

[I actually researched and covered this in a previous issue](https://www.lennysnewsletter.com/p/early-stage-hiring), so go read that post. Here’s the high-level summary of what you need to get right:

1. **Captivating vision**—Make it easy for candidates to visualize what you are building toward and to feel like their work will be meaningful.
2. **A++ early team**—The best talent attracts the best talent.
3. **Put in the time—**Be prepared to commit 50 to 100 hours for each hire you make.
4. **Grow your network**—It’ll be an easier sell if they know you (or know someone who knows you).
5. **Love bomb—**Go the extra mile when trying to close a candidate:

> “We see the actual offer stage as a big place you can stand out. We do a Zoom to surprise the candidate with everyone from their interview panel to share why they’re excited about the candidate potentially joining.”
>
> —[Julianna Lamb](https://www.linkedin.com/in/juliannaelamb/), co-founder and CTO of Stytch

## 4. When to hire a salesperson, and what to look for

#### Always start with founder-led sales

Every founder I spoke to started with founder-led sales—doing the sales themselves until they reached a certain milestone.

[David Hsu](https://www.linkedin.com/in/dvdhsu/) (founder and CEO of **Retool**) shared why he found this so valuable:

> “**The main thing you get from doing sales yourself is that you have a very good sense of how customers think about the product, the pros and cons of your product in the market versus competition. It’s actually very hard to scale sales if you haven’t done that yourself. If you talk to most people, most SaaS people will say the CEO generally is the best salesperson for the product, at least when you’re under $10 million ARR. And you should be. If you’re not, that’s actually kind of a problem.**
>
> I don’t think you should view sales as like, ‘Oh, let me go hire someone who will magically distribute my product to everyone for me.’ Instead, you have to go figure out how to distribute it. You can hire other people to help you scale the distribution, but you have to figure out what your market is, you have to go figure out how to price, stuff like that. The direct experience is so helpful and is not really reproducible by anything else. Especially for a new category, it requires a lot of first-principles thinking.”

I heard exactly the same advice from [Ryan Glasgow](https://www.linkedin.com/in/ryanglasgow/) (founder and CEO of **Sprig)**, among others:

> “I remember not loving sales and wondering why I was doing sales for as long as I was. **But I do think the business is much, much better off because of it.** I learned how to sell.”

#### Four signs it’s time to turn over the reins to a full-time salesperson

**Sign 1:** You can sell consistently.

> **“We hired our first salesperson when we were able to grow it consistently. We had a pitch, it was working, and we got to the point where I could do something repeatable and I thought I could teach it to someone else.**
>
> We also didn’t know, as ex-consumer founders, what we were talking about in sales. And so we were really hopeful at the time we could find someone who could help us do that and figure it out. And we did.”
>
> —[Eric Glyman](https://www.linkedin.com/in/eglyman/), co-founder and CEO of Ramp

> **“We hired our first salesperson when I was consistently selling**. Basically, I hired someone to do my job versus hired someone to figure out sales. We had 200 customers already.”
>
> —[Mathilde Collin](https://www.linkedin.com/in/mathilde-collin-bb59492a/en/), founder and CEO of Front

**Sign 2:** It gets boring, and you’re not learning.

> “The impetus for hiring a salesperson wasn’t actually a dollar amount. **What it actually was, was the sales calls were repeatable and boring: you get on, say your script, turn your brain off, get off, send the DocuSign**.I was spending all this time on sales calls, and it was working, but it felt repeatable and boring, and that seemed to mean someone else would be able to take the calls. That was actually the thing.”
>
> —[Christina Cacioppo](https://www.linkedin.com/in/ccacioppo/), co-founder and CEO of Vanta

> “It was at a point where basically I was doing sales while I was building the product, and **it was like, okay, it feels like I’m not learning more now, I’m just trying to awkwardly turn these calls into sales calls from advice**.Because that was the only way we could get the meetings.
>
> I felt that it would be irresponsible of me to spend all my time just doing more of these calls by myself. It’s time to go get somebody. Then you slowly fire yourself from the most simple building up to the most complex part of the sales cycle.”
>
> —[Rujul Zaparde](https://www.linkedin.com/in/rujulz/), co-founder and CEO of Zip

**Sign 3:** You’re overwhelmed with inbound.

> “Our first salesperson didn’t come on until, honestly, **there was more deal flow than I could deal with.** We were getting a lot of inbound. We did our launch ourself, and we were getting enough in that I was realizing I was just really underwater, and I wanted someone to help figure it out.”
>
> —[Barry McCardel](https://www.linkedin.com/in/barrymccardel/), founder and CEO of Hex

**Sign 4:** You hit $300-500k ARR.

#### Try to wait until $300-500k ARR before hiring your first full-time salesperson

This is where nearly every founder I spoke with brought in a full-time salesperson. [Ryan Glasgow](https://www.linkedin.com/in/ryanglasgow/) (CEO of Sprig) got this advice from his lead investor, [Bill Trenchard](https://firstround.com/person/bill-trenchard/#mystory):

> “**Don’t consider marketing or sales until you get to a million in ARR**. We’re going to meet every week, talk through the feedback you’re getting from prospects, and see what’s working and not working. We’ll do this until you get the company to a million ARR.”

Ryan didn’t fully follow his advice, but got past **$300k (with a large pipeline)**:

> “I was talking to several late-stage founders, hearing at $200k, or $300k, you should hire a salesperson. So what I did was I got to $300k ARR, and I had $700k in late-stage procurement, and so when she joined a month later, it was essentially a million in ARR. It was kind of penciled in, because sales deals, it takes 90 days, and kind of knew, ‘Okay, this is working. Let’s bring someone in.’ ”

[Christina Cacioppo](https://www.linkedin.com/in/ccacioppo/) (co-founder and CEO of **Vanta)** hired her first salesperson at **$500k ARR** (her 9th employee):

> “I sold the first $500k for about 50 customers, and that’s when the first salesperson came on. I think I probably started to figure out what a salesperson is and how you recruit one at $250k.”

[Spenser Skates](https://www.linkedin.com/in/spenserskates/) (co-founder and CEO of **Amplitude)** hired his first salesperson at ~**$300k ARR** (2nd employee):

> “Once you get to a few $100k in ARR, that’s a great time to bring on sales reps. That’s when we brought on ours.
>
> We brought on one and then we brought on a second one at the end of the year when we were closer to a million-dollar mark. Which was too slow; we should have done it much earlier. And then we brought on two more the following year. We should’ve ramped that up faster. I remember we got to about 8 million in ARR with four sales reps, which is the stupidest thing ever.
>
> We hired one guy, Marcus Ratzlaff, who did $2.3 million in his first year, and then Bryan Parman, who did $2.7 in his first year. We were at the right place at the right time at the right thing. Got very, very lucky on that front.”

[Julianna Lamb](https://www.linkedin.com/in/juliannaelamb/) and [Reed McGinley-Stempel](https://www.linkedin.com/in/reed-mcginley-stempel-17362245/) (co-founders of **Stytch**) hired their first salesperson at “**low six figures” ARR** (8th employee):

> “If I had to describe my skill set, I think I’m actually pretty good at pitching, and I can sell you on things. I don’t think I’m great at running a sales process. When you see a great salesperson figure out who the champion is, how to fully get their buy-in, how to navigate all the different stakeholders, really, it’s a massive coordination effort and it’s a different skill set than what I would say is one of my best.”

[Ali Ghodsi](https://www.linkedin.com/in/alighodsi/) (founder and CEO of **Databricks)** hired their first salespersonat **under $1m ARR:**

> “In 2015, the year we did $1 million revenue, we had already hired something like three salespeople, might have actually been four. Three of them were focused on startups and they were doing okay. They were closing all these startups, and the startups were not paying us that much. Typically they were paying us $15,000 to $20,000 a year. You can do the math; it was adding up to a million. We had a bunch of those. We had one salesperson that focused on enterprises.”

[Tomer London](https://www.linkedin.com/in/tomerlondon/), co-founder and CPO of **Gusto,** alsohired his first salesperson at **under $1m** (~20th employee):

> “Gusto was primarily, and is still today, a self-service motion. So sales is mostly for the channel side of things, for accountants and then a little bit on the inbound side, so we didn’t hire our first salesperson for a while.”

**Other data points:**

- Zip at $200k ARR (4th employee)
- Census at “mid-six figures” ARR (4th employee)
- Hex at $250k ARR (8th employee)

**Takeaway:** Past $200k ARR, start looking; before $1m, you should probably have someone.

#### Some founders went founder-led for longer, mostly because growth was going so well

**Retool hired their first salesperson at $2-3m ARR:**

> “Initially, it was all me, up until probably $3 million or so, then I gave it to my co-founder, who ran it to $5 million, and then I think we started hiring AEs at that point.” —[David Hsu](https://www.linkedin.com/in/dvdhsu/), founder and CEO

**Linear at a couple million in ARR:**

> “We brought in Casey [Bertenthal] as head of sales, and he was only salesperson for years. The second person, under him, only joined a few months ago.
>
> His main job has been product growth. That’s been our path to get companies, through our product. And now that we work with medium to large startups, **he’s there mainly helping them adopt Linear and navigate their internal structures and so on.** We don’t do any outbound sales. It’s all about enabling these teams to get on board and figuring out securing reviews and procurement and contracts if there are some.” —[Jori Lallo](https://www.linkedin.com/in/jorilallo/), co-founder

#### Some went an incredibly long time 🤯

**Notion went past $10-15 million in ARR before bringing on a salesperson:**

> “**I basically made a rule that said that no salesperson should touch companies less than 100 employees because I felt like product needed to do that work.**
>
> **We got to $10-15 million in ARR just with startups and SMBs.** And then what ended up happening was some of them started to grow. I remember one of our early customers was a U.K. bank that went to 400 employees. And I used to do biweekly meetings with them because I was like, ‘Oh my God, tell me how is Notion even working for you? We are 20, 30 people and we have all these problems, and you’re using it for 400 people.’ And they actually had a full-time person whose entire job was to make Notion work. And I was like, ‘Why do you have that?’ I remember the founders basically said, ‘Actually, if everybody can use this tool to do their work and everybody used it in a specific way I want them to work, we are at least 50% more productive.’ And so they built internal templates for how they wanted to write their PRDs and internal templates for how they want their sales. I don’t know, they sort of built everything inside Notion.
>
> **And then that’s when we realized, okay, well these kinds of companies will churn unless there’s a human involved in really sort of making sure their experience is growing with Notion. And so that’s that.**
>
> The first six, nine months of my journey, when I was in the support pit, was essentially when I met a lot of the sales folks. Ivan [Zhao, co-founder and CEO] and I both did a lot of these interviews together, because we were both trying to understand what will make Notion sales successful. We have this ideal view of product and sales working together as opposed to product versus sales. And so it took some time, but I think our DNA is quite good. Nobody’s walking around asking why we have salespeople, and also salespeople are very empathetic for how we think about product roadmap at Notion.”
>
> —[Akshay Kothari](https://www.linkedin.com/in/akothari/), co-founder and COO

**Canva went past something around $120m ARR 🤯🤯🤯**

> “For most of our life, we haven’t been very sales-led. Our sales organization has mostly developed in the last three years as we started to focus more on enterprise and large teams. And you could even apply that question to marketing. We weren’t a very marketing-led company either. **I think in terms of spending real marketing dollars, we only started doing that in about year six or seven. Prior to that, we had a very SEO-driven strategy, and it wasn’t even paid—it wasn’t SEM, wasn’t paying money to search engines. It was mostly very much in the vein of content marketing and jobs-to-be-done. For the first two years, we relied a lot on organic word of mouth.** And then year two, or probably to the end of year two, we actually met a guy called Andre [Andrianes Pinantoan].
>
> Andre just brought a whole bunch of knowledge and experience about how to leverage landing pages, SEO, keyword analysis to drive customers to the right place at the right time in Canva. And he set up this whole strategy around a number of jobs to be done, targeting keywords and getting people into the right flow within Canva. An example for this might be typing ‘poster maker’ into Google and surfacing the right landing page that showed a great poster gave people the confidence that Canva was the right tool for it, and then easily let them jump into the product and start building their first poster. And he did this for posters, presentations, flyers, business cards, whole swaths of different things that you could create in Canva. And that probably drove the second phase of growth in Canva, so this was not just about people telling other people, this was about people discovering Canva without any other social pressure. And that would’ve driven our growth from year three to year six and really accelerated the curve of our growth.
>
> Then, as we started getting more revenue ourselves and as we got a little bit more later-stage investment, then we started thinking about marketing. Firstly, we did keyword marketing, SEM, that type of stuff, and **it’s only in the last two years that we’ve started doing more brand marketing, billboards, all that kind of thing.**”
>
> —[Cameron Adams](https://www.linkedin.com/in/themaninblue/), co-founder and CPO

#### On the other extreme, some companies hired a salesperson before they had any revenue

Sometimes this was a customer success person who essentially did sales, as with **Coda**:

> “**We hired our first salesperson before we had monetization at all.** So there was no ARR, and his job was basically just to help companies get activated. These days you’d probably call it customer success, although I would argue that for products like Coda, getting a commitment to use the product, the dollar figure matters. But the commitment to use it, actually it’s sales. You have to get them to actually commit. I don’t want to minimize what is really hard work from our sales team, but it’s one of those products where if you use it, you’ll value it. Most of what we do is focused on helping teams get set up using it well, happy with it, and then worry about paying for it.” —[Shishir Mehrotra](https://www.linkedin.com/in/shishirmehrotra/), co-founder and CEO

Sometimes this hire was most useful for tapping into the existing latent demand, as with **Segment**:

> “We hired our first sales rep, Raphael Parker, about 10 months after launch. We had a lot of latent demand to pay for Segment, and my co-founder Peter [Reinhardt] was trying to navigate sales. We weren’t very good at it, so we hired a Raphael.
>
> Raphael honestly had no way of evaluating us, and we had very little way of evaluating him. He went on to close our first $1.5m in revenue.”
>
> —[Calvin French-Owen](https://www.linkedin.com/in/calvinfo/), co-founder

#### Pro tip: Consider hiring a coach or consultant early on

This idea came up a number of times and seems like a great one to me.

Here’s **Gong**’s experience, from [Eilon Reshef](https://www.linkedin.com/in/eilonreshef/) (co-founder and CPO):

> “We hired a part-time consultant initially who used to be the VP of sales at various companies. It’s always a gamble for a salesperson. Do you bring a VP? Do you bring an IC? Nothing works, because you bring an IC, they have no idea what to do. We bring a VP. They want to hire a team. There’s no playbook. So that one actually worked well for us because that guy was VP-level but still dialing.
>
> He got us, out of the 12 first customers, probably half. And then after we saw things working, we started hiring salespeople. I think the first two or three are still with us after so many years.”

And also for **Amplitude**:

> “You don’t want to learn sales out of a book or reading. You’ve got to go through the motions and get the reps. If you look at how the best salespeople learn, they get someone who’s really good at sales, aka a sales manager, to coach them regularly. So we hired this guy, Mitch Morando, to meet with us once a week and walk me through stuff. He helped sort the wheat from the chaff in the existing customers and pipeline very, very quickly. And after that, we really started taking off.
>
> A lot of engineers that go to sales, it’s not that hard; it’s actually just as deep and complex as an important problem to the success of a business as the engineering. But it’s also very solvable. The best salespeople are very much like the best engineers; we’re able to take some problem that seems almost impossible to solve and figure out how to absolutely go crush that.”
>
> —[Spenser Skates](https://www.linkedin.com/in/spenserskates/), co-founder and CEO

#### **Final tip: Be careful about assuming you can make PLG work**

Here’s **Databricks**’scautionary tale:

> “The whole vision of Databricks was we don’t want to have sales in the company. It’s going to all be product-led growth. So it’s a hundred percent product-led-growth motion. And in 2015, we kind of doubled down on it. We actually said, ‘Let’s do what Amazon did. Let’s just make it really slick, and you swipe your credit card and you can start using this stuff.’ We called it the zero-touch effort. We were going to touch the customers zero times from a sales perspective. No human needed to touch the customer. We’re very excited about that and we built it all, we automated it all. And I think around Q2 of 2015, we told sales, ‘Stop engaging with the customers. This is going to be zero-touch. Focus all your attention on automating this stuff and let’s set it up for that kind of motion.’
>
> **And actually, revenue flatlined. Revenue was growing, and then in Q2, Q3 of 2015, it started flattening. So around Q4 it was starting to become kind of clear that, okay, this product-led-growth thing—nice story, but in practice, it doesn’t really work.** Which is actually, by the way, my view. I think for all practical purposes, it doesn’t work. Maybe it works for Atlassian. Maybe there’s another company out there that nailed it, but a ‘don’t try it at home’ kind of thing.”
>
> —[Ali Ghodsi](https://www.linkedin.com/in/alighodsi/), founder and CEO

### Who to hire as your first sales hire

Across all of my interviews, one of the most recurring themes is to hire what I’ll describe as “**hungry senior AEs**.” Somewhat experienced early-career salespeople who can help you “break through the snow”:

> “**Be very mindful when you’re bringing on early go-to-market/sales hires of the difference between someone you’re bringing on who helps you break through the snow and figure out new things, versus someone who’s there to just do a repeatable process.**
>
> A lot of people who have been successful salespeople at later-stage companies are really good at those repeatable processes and playbooks, but it’s really, really, really, really, super-duper important that you see the evidence in their resume and in the interviews that they’re able to break new ground.” —Anonymous

[Tomer London](https://www.linkedin.com/in/tomerlondon/) (co-founder and CPO at **Gusto**) learned the same lesson early on:

> “An article I recommend all the time is Mark Leslie’s [‘The Sales Learning Curve’](https://hbr.org/2006/07/the-sales-learning-curve) in *HBR*. It teaches you that the job of a salesperson is different in a startup in three different phases across the maturity. **In the beginning, you really are looking for a product person that’s all about generating insights.** You [Lenny] are talking with 20 people and then you generate insights from that. That’s what you want your early salesperson, and the marketer, to do. Their job in the beginning is to experiment. To be a super-entrepreneur. Just experiment with a bunch of stuff, see where the opportunity is, and get ahead of the curve of the newest technologies, newest stuff, etc.”

[Ali Ghodsi](https://www.linkedin.com/in/alighodsi/) (founder and CEO of Databricks) went through this pain himself:

> “**Early on, we had four salespeople, three of them young kids who just had maybe finished being SDRs, who were focusing on small and medium businesses. They were closing $10-20k deals, doing very well. Two of them are still at the company.**
>
> **We also had an early-enterprise salesperson, a very senior big-enterprise salesperson, who had been at a very successful billion-dollar-revenue company, and he really felt like he was a sort of fish out of water.** This kind of felt like, will he fit in at Databricks? Will this work out? He was not having much success that first year. Eventually, the success started coming in, and eventually we hired more and more and more, and eventually sales became a normal thing at Databricks. Eventually we had a huge sales force, and it is now half of the company. But this part started slow.”

At **Vanta**, they hired “**a senior AE who had been a founder in a prior life, and super-entrepreneurial**”:

> “He **thought of himself as a marketer as well, loves to recruit, loves doing all the things needed to build a company**. He wanted a leadership role from the start and is still advancing at Vanta. It’s awesome. From a temperament perspective, he was very willing to roll with the punches. He kind of knew, as much as anyone can, what he was doing and what walking into a 10-person company meant. The other piece that was very clear is he’s the sort of seller who literally and figuratively makes friends with the people he sells to and then invites them into his Burning Man camp. It was clear he would do right by customers.” —[Christina Cacioppo](https://www.linkedin.com/in/ccacioppo/), co-founder and CEO of Vanta

At **Stytch**, it was an “**AE who had a mix of more mature sales org experience at Plaid but had also been the first AE on the ground as Plaid opened up a Europe office**”:

> “We needed someone who could be boots on the ground, working deals. We wanted someone that could be autonomous and could navigate the ambiguity of an early-stage startup. This person played more of a player-coach role opening up the Europe office, and so for us it was a good mix of someone who was senior enough to be autonomous but not so senior that they didn’t want to be in the weeds on deals.” —[Reed McGinley-Stempel](https://www.linkedin.com/in/reed-mcginley-stempel-17362245/), co-founder and CTO of Stytch

At **Zip**, they hired an AE who had “**experience working at a large company as an AE but also in other cross-functional roles (programs, enablement, etc.)**”:

> “He did an incredible job scaling the early sales motion and teams.” —[Rujul Zaparde](https://www.linkedin.com/in/rujulz/), co-founder and CEO

At **Sprig**, their first sales hire was “**one of the top AEs at Box**”:

> “**She was the enterprise account executive, selling to large companies. Very experienced.** What’s tricky for founders to consider is that you could take a star AE to be your first AE, but don’t assume they grow into a head of sales. I got to talk to so many founders where their first AE does great, but then they don’t do so great as a head of sales.” —[Ryan Glasgow](https://www.linkedin.com/in/ryanglasgow/), founder and CEO

At **Census**, they hired two salespeople relatively close together, both “**senior AEs who could instantly be doing deals and learning and bringing back that information**”:

> “I hired two salespeople in quick succession, which is helpful to do a comparison, because it’s like you don’t know what you don’t know at that point when you’re managing these people.” —[Boris Jabes](https://www.linkedin.com/in/borisjabes/), co-founder and CEO

At **Gusto**, their first salesperson was a former investment banker—but creative, smart, collaborative, and ready to hustle:

> **We were really hiring for creativity, raw intelligence, ability to work together with engineers, product managers.** That was basically it, because their first job is to help evolve the product roadmap. The second job is to help build the go-to-market motion. Both of these things are creative endeavors. They’re not repetitive, sales-y, close-close-close, create-FOMO roles. This is about actually creating something. That was really the focus, and was really helpful for us to understand.”

#### Takeaways on hiring your first full-time salesperson:

1. Start with founder-led sales—do the selling yourself until you can sell consistently, it gets too boring, or you’re overwhelmed with demand.
2. Consider bringing on a sales consultant/coach (normally a former VP of Sales) to help you during the early period.
3. Once you hit $300-500k ARR, it’s probably time to bring on a full-time salesperson.
4. Your first hire should probably be a hungry senior AE. If not, they should act like one: dialing, gathering insights to inform the product/GTM, and closing deals themselves.

## Takeaways on hiring your early team

To close, here’s a quick recap of my biggest takeaways:

1. Developers, developers, developers, developers.
2. If your founding team has enough horsepower to build the V1, consider hiring to de-risk, un-bottleneck, or lean into a part of the business that can differentiate you (e.g. customer success, subject-matter expert, design).
3. Within your first 10 hires, in addition to engineers and designers, consider a recruiter, a PM, or a GTM person.
4. To find your early employees, spend time in these four channels:

1. Friends and former colleagues
   2. Cold outreach (mostly through LinkedIn and GitHub)
   3. Job boards
   4. Friends and former colleagues of your *employees*
5. To convince candidates to join your risky startup, invest in:

1. A captivating vision
   2. An A++ early team
   3. Putting in the time
   4. Growing your network
   5. Love bombing

For even more tactical advice, and inspiration, don’t miss my conversation with [Pete Kazanjy](https://www.linkedin.com/in/kazanjy/) (author of my favorite founder sales book, *[Founding Sales](https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1)*[)](https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1):

[Watch on YouTube](https://www.youtube.com/watch?v=cZd5234Eem0)

I’d love to spend more time in this area, so if you have additional questions about hiring your early team, or insight from your experience, please leave a comment 🙏

[Leave a comment](https://www.lennysnewsletter.com/p/hiring-your-early-team-b2b/comments)

### Next week: Scaling your growth engines 🚀

*Have a fulfilling and productive week 🙏*

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