How and When to Hire a Great Sales Rep in The Early Days of your Startup

I had the good fortune of starting my career off as a salesperson. Not too long ago, my first ever boss, Bartosz Mozyrko gave a complete amateur (me) a shot.

Since then I’ve worked with several companies that further instilled my love for sales. All thanks to Bart!

I was going through my old emails and I stumbled across the email thread where Bartosz offered me the job as an SDR. To call it one of the best days of my life, would be a gross understatement.

And yes, I’m ashamed to write this but I was going through the emails because I wanted to delete that email account. Why, you ask? 

Well, my email address was Sigh. Yes I know. I mean who didn’t like Gladiator? right? 

Moving swiftly along…

That email got me to think about the early days at UsabilityTools. When we were just starting to build out our sales team and were a relatively small company (doing just under $10K in MRR). We thought a lot about the kind of sales reps we wanted to hire, the qualities they needed to have.

Just like everyone, we went through the whole interviewing process, screening the potential hires, looking at their background, and eventually having a video chat with them to get the “feel” and see if there is a mutual fit.

However, looking back now, none of the things worked as well as having the top candidates demo our own product to us. This method worked really well for us. There are three main reasons why it did, let’s dig in!

You can learn a lot from seeing what “others” think of your product

They don’t have the same access or experience with the product that you do, which means almost always you will learn something from those sessions.

That feedback can help your product grow and can often give great pointers to the marketing team to make changes around the website to communicate the USP of the product better. It’s a great way to see how the product is perceived by someone who’s just trying it out for the first time.

They almost always add their own “unique spin” to the demo and that helps you analyze how the candidate thinks. If this indeed is a product that they can sink their teeth into.

There have been times where I ended up using a lot of the things the candidate was trying to pitch because it gave me a new perspective on how to improve my demo delivery.

It helps the candidates get out of their comfort zone

At this point, I can give a demo of the current product that I’m selling in my sleep. It’s because I have done over a 1000 demos of the same product and yes practice makes you perfect.

Chances are that the candidates you’re interviewing are not very familiar with your product. They don’t know all the features or how folks can make the most use out of them. Simply put they don’t have the same experience selling the same product as you do – and they know that. 

Salespeople love the sound of their own voice. Well, most of them do. They talk the talk. Getting them out of their comfort zone for a “quick test” is a great way to see if they can back up all that talk. 

I’m not looking for immaculate execution of a demo. What I try to look for here is the way the candidate approaches the demo, their style, and their ability to showcase the benefit of the product in their own unique way.

Bonus points for anyone that asks questions and engages the attendees in the demo presentation and does not act as a brochure of the product!

Third, and most importantly: It helps you asses if you’d buy your product if they were selling

Only hire someone that you would buy your own product from. Period.

If you are not willing to buy the product from that candidate. What makes you think that your prospects will?

In the early days of a startup, your marketing is probably not so great. Every demo and pricing request that does come in is extremely precious. If you give that lead to someone that you wouldn’t buy your product from, they will end up doing worse then you. 

The goal here is to make sure you hire someone that you’d be willing to buy your product from. Someone that makes you excited about the product they are selling. The same product that is bug-ridden, does some things really well and others not so well. It does not have the most pleasing UI in the market but shows promise. 

That vision, an idea is what you’re trying to sell in the early days. Would you buy that from the person if they were the ones selling you? 

Most founders hire salespeople who cannot do that.

Instead, they hire someone with a great sales background, who worked for well-known companies and closed a crap-ton of deals. They talk really well and since you think “you can’t sell really well” and believe they do, you go ahead and hire them.

If you have a single paying customer, you indeed can sell. Granted, you’re probably not the best person for it but you CAN SELL!

Just because one person was good at selling a certain product it does not mean they would be equally as good selling your product.

Understand the dynamics of selling in the early days

In the early days, every single sale is different. 

You’re offering discounts, selling on the fact that you can build a feature just for a single client. Almost every single sale will be unique until you find that product-market fit. Not all the sales will go through the same sales process as the last one.

There will be ample time to build a proper sales process and a sales team down the line.

Later, you’ll probably need a village. All types of reps. Once you hire a real Head of Sales, don’t be so rigid about this test. Let them figure it out. Just use it as a gut check.

Right now, it’s about making sure you don’t flush those precious leads down the drain!

Now that we talked a bit about what you need to focus and look for in a new hire. Let’s take a step back and find out when is the right time to hire that sales rep?

I cannot say it enough. Timing is everything! 

Especially with limited capital, you want to make sure you get the first hire right.

Why timing is important?

Before you even start thinking about hiring a salesperson. You need to step into the ring yourself and sell. 

Your company’s first salesperson should be YOU. Period.

I can’t emphasize enough how important it is for you to have sold the product as the founder. You need to validate that the customers are willing to buy your product from you and you will learn a great deal about their needs along the way.

Once you have sold your product a few times and have hit the 10 customer mark. It’s time to bring on a salesperson, whose job will be to focus on selling while you can go ahead and do what founders do.

As Jason Lemkin said:

If you hire a salesperson before 10 customers. It never works. You’re looking for them to do something you haven’t proven out yourself, at all yet.

They can’t be successful at selling if you have an unsellable product. Salespeople aren’t magicians. They are process-scalers.

If you hire prematurely, you will only end up having to fire people and losing money. Bottomline, timing goes hand in hand with the type of sales rep you hire.

Finding a great sales rep in the early days can be challenging but top performers can really help you grow in the early days. Just like the salesperson is “selling” you the product, you should sell them on your vision. 

If they can get behind that and believe in the product, it’s a win-win. Just make sure that you’re putting candidates through an interview process that clearly uncovers whether you’d buy your own product from them or not. 

And timing. You nail those two things and you have a much higher likelihood of success.

Happy hiring!

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