Hiring Your First Salesperson at a SaaS Startup

Hiring your first salesperson is one of the most critical decisions you’ll make in your first year as a SaaS founder.

Get it right and you can start to build a consistent, scalable revenue stream and grow your business. Get it wrong and you’ll burn a ton of time and money, then have to start all over again.

I’ve founded a bunch of SaaS startups, so I’ve been through this process multiple times. Here’s what I’ve learned along the way.

When Should You Hire Your First Salesperson?

I always advise founders to do the sales job themselves for 30-90 days before making that key hire. 

Why?

Because that way, you get to know customer friction points and the process for yourself, rather than just having a theoretical idea of how things should work.

I also prefer to develop a basic sales process and tracking so the sales hire isn’t starting completely from scratch.

When you start seeing some traction and have enough to outline a simple process that can be changed and optimized, that’s a good time to hire a salesperson.

What Are the Challenges of Hiring Your First Salesperson?

No one said hiring your first salesperson is easy – if it was, you likely wouldn’t be reading this article in the first place. There are a lot of challenges to consider, such as:

• Your own inexperience: You likely haven’t been a sales pro yourself, so you don’t really know how a salesperson’s workflow should be structured.
• Your preconceptions: Entrepreneurs are idea people. Chances are, you have a lot of views about how to sell your product. But those views might be completely wrong!
• Your expectations: You want to ramp up fast. A great salesperson will help you do that, but they’re not a magician. If your goals aren’t grounded in reality, this can create a lot of tension and pressure.
• A lack of leads: You need to be producing a decent volume of inbound leads – say around 50 qualified leads a month – to keep your salesperson busy.
• The cost of your hire: In the early days of a startup, your first salesperson might be your most highly paid employee, which puts even greater pressure on you (and them) to get it right.
• Needing well-rounded experience: It’s not enough to hire a great cold caller – they also need to turn their hands to prospecting, qualification, demoing your product, closing deals, and much more besides. That’s a tough gap to fill.

Should You Hire Two Reps Instead of One?

If you’ve read up on this subject, or listened to podcasts about hiring a salesperson, you’ll know the conventional wisdom is to hire two reps instead of one. The idea being that you can pit them against each other, and they can learn from one another too.

I agree with that advice up to a point. But what if you don’t have enough budget, or leads, for two reps?

That’s been the case at all my companies, and generally we’ve managed to make it work. I’d say in two-thirds of cases, our first sales hire was successful. So don’t worry if hiring two reps just isn’t an option for you right now.

However, that begs a question: if you only hire one rep, where do they get their motivation? After all, they don’t have anyone to compete against.

Well, that’s another reason why I recommend doing the sales job yourself for the first couple months. That way, their motivation is to beat you.

If you’re a founder, you likely suck at sales. Even if you don’t, you’re probably not the greatest. So if a sales rep isn’t doing a better job than you, something’s wrong.

It also pays to have a little insurance in place. Prepare yourself for the fact that things might not work out with your first sales hire, and have a shortlist of other candidates on standby. That way, if you need to bring in a replacement, you can hopefully do it fast.

5 Tips for Hiring Your First Sales Rep

You’ve laid the groundwork. You’ve been your own salesperson for a month or two, built some basic processes, and you’re now in a place to make that crucial hire. Here are five things to bear in mind along the way.

1. Passion Trumps Reputation

Obviously, you don’t want your first hire to be awful at sales.

But they don’t necessarily need to have a world-beating track record either.

In my experience, you’re far more likely to succeed if you hire someone who’s decent at sales, but who truly buys into your product and mission.

The fact is, they’ll have to put in a ton of work in the early days of your SaaS startup. If they don’t genuinely believe in your business, there’s little incentive for them to go the extra mile for you.

Also, keep in mind that a lot of top-performing salespeople have big teams behind them and access to all the marketing collateral they could ever need. They just won’t get that at a startup – if they need something, they’ll have to figure out a way to do it themselves.

2. Storytelling is Essential

If you’ve followed my advice and been your own salesperson for 30-90 days, you should already have a good idea of the messaging and narrative that has the greatest impact on your customers.

Your first salesperson should be able to take your findings and elevate them to create something even more impactful.

So how do you find someone who can do that?

Justin Welsh has some good advice on this topic: he gives all his salespeople – not just first hires – a little information about his product and a profile of his typical customer, then asks them to craft a narrative that compels the prospect to learn more.

Typically, he’ll allow them 24 hours to prepare, then they’ll run through the results as a role-playing exercise.

If they just rattle off a bunch of features, they’re not the right person for the role. As a minimum, you want them to connect features with benefits, and understand how those benefits tie into your customer’s pain points.

3. Hire a Doer

As I’ve already mentioned, your first sales hire will need to do all the heavy lifting themselves, because they likely won’t have a marketing team or an account executive to lean on.

At the same time, you need someone who’s prepared to step out of their lane. On any given day, they might need to write and design a one-pager, edit together a video testimonial, or speak at a business breakfast.

It’s a cliche, but they need that entrepreneurial edge to thrive in a startup environment. You likely don’t have the time to manage them day in, day out, so you can’t afford to have them waiting to be told how to do something, or what to do next.

4. Be Realistic

There’s nothing wrong with being ambitious – in fact, if you don’t have big plans, you probably shouldn’t have founded a business in the first place.

But your sales targets need to be realistic. It’s not unreasonable to expect your sales hire to start generating enough revenue to effectively cover their own salary within 90 days, but it’ll likely take time for them to ramp further.

Be generous with your targets in those first three months. You don’t want to risk losing a talented salesperson who’s a great fit for your business, just because your goals were totally unachievable.

5. Remember Why You’re Hiring Them

I’ve already spoken about the importance of your first sales hire being prepared to get stuck in and do a bit of everything.

But never lose sight of the reason you hired them in the first place: to sell your product.

What I mean by this is, it’s fine for them to spend a couple months bogged down in qualifying leads and building their own collateral. But the sooner you get them some support – whether that’s a marketing executive, or a BDR, or an account exec – the quicker they’ll start generating results.