Let's talk about the who, when, and how of moving on from founder-led sales.

Successfully landing your first sales hire takes more than luck.

It takes a thoughtful and intentional approach to hiring the right person at the right time.

Not only do you need to figure out who to hire and when to do it, but also how to find them and how to convince them to join.

Daunting? Maybe.

Rocket science? Not exactly.

So, grab your coffee, and let's get into the who, how, and when of making your first sales hire.

When is it right time?

Before we dive into the "when," let's get a couple of obvious but necessary points out of the way.

1. Start with founder-led sales before you ever consider hiring a dedicated sales rep.
2. Sales should (probably) not be your first hire.

We say probably because you can't assume every company out there. However, data from some of the most successful founders point to the fact that sales is most definitely not the first hire they make.

Who was your first hire?

Source: Lenny’s Newsletter, 2023

Rather, the sales hire falls somewhere between the 4th-9th hire. However, when you zoom out and look at hires 1-10, sales falls right behind engineering. This signals that while it isn't one of the first hires you should make, it has a solid spot in your first ten team members (see full data here).

Distribution of first 10 hires

Source: Lenny’s Newsletter, 2023

Okay, so you should start with founder-led sales but make a sales hire within your first 10.

This is why, early on in your team's growth, it will be time to pass the torch to someone who can work to talk with customers and close deals. But moving from founder-led sales to your first sales hire is a big jump - and knowing if you should make it at hire 2 or 10 can feel daunting.

If you make it too soon? You're paying big bucks for a sales rep who doesn't have the docs, training, network, and insight needed to close deals.

If you make it too late? You might struggle to hand over responsibility - and you're giving the new hire the unreasonable task of decoding a messy, non-scalable process where revenue and client satisfaction are on the line.

There isn't an exact formula you can use to figure out if now is the right time, but here are a few tell-tell signs that usually indicate it's time to get the recruitment process rolling.

1. You have established product-market fit with a clearly defined (and profitable) target audience. If you don't have PMF or your target audience is too small for profitability, you should strongly reconsider your need to make this hire.
2. You are consistently selling to those outside your network.

There are other metrics, like revenue targets, recent funding, or even the size of your customer base, that you can use to help you decide. However, establishing sustainable demand for your solution and bringing in revenue outside of your network are two green flags that now is the right time.

All of that is to say, get your product right first. Then start selling it.

What profile should you look for?

Before you even start thinking about what persona you should be looking for, you need to ask yourself two key questions:

1. Is this person a Manager or an IC who can eventually move into a leadership role? Hint: this will depend on your runway.
2. What are the outcomes this person expected to achieve? In other words, what does success look like in this role? Is it to build a repeatable sales process or close deals immediately? Again, this will also depend on the runway.

Answering the first question will help set the tone for seniority. Do you already have sales traction but need someone with five years of experience to take over the reins? Or do you want to maintain control over the sales operations but offload the actual mechanics behind closing?

Typically, if you only have a few months of runway, you'll need a closer. But if you have 2-3 years to work with, you can hire someone more senior to build the foundations for scale.

Source: Captivate Talent

Answering the second question will help you craft your job description, crystalize your pitch, and understand what a great candidate looks like. The metrics, job description, and pitch for an IC will naturally differ from that of a leadership hire.

For an IC role, such as a BDR, your pitch might focus on the commission on closing and the possibility of growing into new roles. On the other hand, pitching to a Sales Manager might focus on establishing strategy, repeatability, and building a team under them.

Candidate Persona

Regardless of how senior you want your hire to be, you will want to build an ideal candidate profile to help you operationalize your job description, outreach strategy, and assessment.

Profiles consist of the tangible (i.e., what you put on the job description) and the intangible (i.e., innate qualities), and can help your team align on who is a good for the role. Craig Burel from Reciprocal Ventures defines a sales persona as:

A 'salesperson persona' is an aggregate view of a candidate and is comprised of many factors: their years of experience, the types of products they've sold, the types of customers they've sold to, their expertise in sales management, and past roles in sales operations.

Tangible Attributes

Let's get into the tangible characteristics first. The list of tangibles can go far beyond what's listed below. But here are a few "must have's" when you start thinking about your ideal candidate profile.

• Seniority. This is pretty straightforward - how many years of experience should they have? It can be a range. It can be implied in the job description. However, you need to know where the person fits into your current organization. If you follow a bottom-up approach, they will be a junior resource helping you book meetings and get momentum. If you want a top-down approach, they will be a senior resource who has "done this before" and can set long-term strategy. We recommend checking out this situational analysis to get more context around seniority and GTM status.
• Previous industry. Are they coming from a low-cost, frequently purchased SaaS company? Or a high-ticket item manufacturing supplier? This will dictate the type and volume of accounts they are used to working with, the sales cycle lengths they're accustomed to, and their relationships with other departments (i.e., product, marketing, etc.).
• Previous experience. As with any hire, what is this person expected to have worked on before? Is there experience in a PLG organization or a traditionally sales-led one? All of this will shape how they tackle your current sales problems and can help you outline development opportunities in their new role.
• Stage fit. What type of company and journey the candidate is coming from might be often overlooked. But thinking about what environment the person should (ideally) be coming from is telling for what type and impact they'll have on your team. Should they have experience with a startup? Have you been with a company as it scaled from 10 to 100? Or 100 to 1000? This should align with where you are - or even better, where you want the hire to take the company. Another thing to consider is whether or not the candidate is coming from an industry-leading company or an underdog. If it's the latter, and they were still a top performer, it shows they can close even without a brand name behind them.
  
  Source: JooBee Yeow
• Company-specific requirements. Last but not least, basic necessities like time zone, language, and openness to remote work must be agreed upon before you start the recruitment project. This might differ in the sales team from the entire company since they have so much face-time with customers. For example, even if your internal working language is English, your sales hire might need to speak German since if they are expected to sell in the Austrian market.

Intangible Attributes

Here are a few intangible attributes that a first sales hire typically has, regardless of seniority or previous experience. No matter junior or senior, successful hires usually have the following characteristics (and then some).

• They have builder qualities. This applies to both teams and systems. Even if they are junior, they will need to build out formal docs and processes. If they're senior, they will need to do that and make a game plan for how they want to build a team around them.
• They can work autonomously. As the first sales hire, they'll be reporting to a founder with limited capacity. This means they'll need to be confident in making localized decisions and working with processes and accounts independently, regardless of seniority.
• They can balance strategy with execution. You don't want to hire someone who lives and breathes brainstorming sessions and whiteboard charts (unless you have years of runway). But you also don't want someone so execution-oriented that they become near-sighted and build tech debt. That's why many first-time salespeople have enough experience to see the bigger picture but are still junior enough to roll up their sleeves.
• They're quick to earn trust. This is important for gaining insight from colleagues/teams, just as much as it is about gaining trust with new leads and existing accounts. Curiosity, openness, and accountability can be useful proxies for understanding how quickly a candidate can earn the trust of others (in addition to scenario-based questions). During interviews, try to imagine putting this person in front of customers.
• Willingness to test. If you're in a high-growth phase, processes that got you to $1 million ARR might not get you to $3 million ARR. If you have a diverse customer base, what converted segment A might not convert segment B. And so on. The willingness to systematically and intentionally test new ideas, processes, and systems is a great skill for your first sales hire.

Where do you find them?

You can take a few routes when it comes to accessing the right candidate. There isn't a single right approach, and you might use a combination of all techniques to bring candidates into your pipeline.

1. Your friends, ex-colleagues, and network
2. Your employees' friends, ex-colleagues, and network
3. Cold outreach (by you or a recruiter)
4. Job boards

Using your own network or your employees' network is probably the most common since network recruitment is low-cost, efficient, and fairly reliable while you're in your early stages. The problem is that it's not scalable and is more open to bias than other recruitment methods.

The second approach mirrors that of more traditional recruitment. It's about doing active sourcing through LinkedIn, social media, and various job boards. You can either do this on your own or with the help of a recruitment agency if you have the funding available.

Regardless of your path, you will need a solid outreach plan to convince the best to join an early-stage startup. You'll need a clear idea of how you'll assess candidates once they've been brought into the recruitment process. After all, you don't want to hire someone just because they were in your network or you were roommates in college. You still have the right to be systematic in hiring, even in the early stages of growth.

Here are a few tips on crafting your outreach and a few things to look for when assessing candidates.

Outreach Tips

• Deliver a vision and sell a sense of purpose. Basically, have a clear and concise pitch of your vision and how you plan to get there. If you can sell them on the vision and purpose, they will be more excited for the journey.
• Don't over-glamorize the startup life, but do communicate the benefits of being an early joiner. Emphasize their role's impact, the growth opportunities you plan for them, and what development opportunities they can expect.
• Top talent attracts top talent. Make sure any hires made before your sales rep are top-notch. Their background and network can do a lot for your employer brand.
• If you opt for outreach, create a short and sweet outbound sequence that you can push via LinkedIn Recruiter.

Green Flags

• They build rapport with the interviewer from the first "hello." Salespeople should be easy to talk to, and they should work on establishing trust from the get-go, even if you're not the one they're selling to.
• They follow up with you after the interview. Follow-up is a key skill for a sales hire - even if you're not the one they are selling to. Taking the time to send a thank you note speaks volumes to their attentiveness.
• They have a track record of expansion. Whether it's accounts, territories, or responsibilities, they should have a strong track record of progression. This, of course, demonstrated that they are likely a high performer but also that they are eager to adapt to change.
• They align with your culture. This goes for any hire, but it's imperative with early hires since they will help shape your culture as you grow, and for setting subcultures within their teams.

Red Flags

• They are overly focused on compensation. Yes, OTE and targets are a big part of the equation, but if it's the only thing that keeps them selling, they're likely to land poorly fit customers to hit quota.
• They lack process and structure. Your first hire will be responsible for setting up the customer journey, documentation, and outreach tactics - all of which require a decent level of structure and process (even if they don't always have the tools to do so).
• Their experience is exclusively in companies with well-established processes and/or big names. This might not be a red flag in every sales hire, but it's definitely something to note for your first sales hire - don't let industry-leading brand experience blind you.
• They are unable to translate customer feedback to the product team. Your sales reps - especially the first one - are an essential link between customers and product development - which is why showing customer empathy and successfully translating complaints into impactful product changes is a critical skill to have as an early sales hire.

Onboarding and Long-term Success

If you're making your first sales hire, it means you're most likely coming from two different situations: you've been doing founder-led sales or you've outsourced sales to an agency.

If you're coming from the first scenario (founder-led), your docs and processes might be all over the place. After all, many departments (if not all) are founder-led initially, and you don't have time to write down all the knowledge inside your head.

But now is the time to start.

How do you find new leads? How do you do outreach? What does your sales process look like? How long are your sales cycles on average? How do you know if an inbound customer is worth meeting with? What terms are non-negotiable?

Answers to these questions (either directly or through shadowing) will make up your sales playbook that your new hire can get up to speed and start selling with repeatability.

As a founder, you might not be the best person to build the sales playbook needed for long-term success (even if you're great at closing deals). While this responsibility will likely fall on someone with more capacity and structure, you do need to formalize some notes and be hands-on in the early days to answer questions when they arise. Hopefully, your sales hire will have the structure to standardize these processes into a playbook(s) that they can use to build their team.

In addition to building our processes, here are few other things to keep in mind during those first few months and quarters.

1. What got you here won't (always) get you there. However, you've been doing sales in the past probably won't be how your company will be doing sales moving forward - and that's okay. The most important thing is that you give them the support and freedom to see their ideas through (with scale in mind).
2. Remember that your expectations might not be realistic. After you factor in OTE, your first sales hire might be the most expensive hire you've made so far. Which means there are high expectations for your hire to deliver. Having high expectations is okay, but don't be afraid to recalibrate those expectations based on reality. With that said, if you have to recalibrate too often or too much, they might not be the right fit.

Hiring your first sales team member is one of the most pivotal hires you will make, given their direct impact on your growth trajectory. So, take your time, use your network, look for red flags, and stand firm on your vision and culture.

Good luck!

References and additional resources:

Job title means s**t. Understanding the 4 types of management role, JooBee Yeow (2023)

Hiring your early team, Lenny’s Newsletter (2023)

A founder’s guide to your first sales hire, Craig Burel (2017)

First sales hire guide for SaaS founders (2023)

The Enterprise Sales Learning Curve

The Sales Acceleration Formula

Predictable Revenue