How and When to Hire Your First Sales Rep

July 9, 2018

When starting a business, the responsibility falls on the CEO to wear multiple hats, one of which is being a sales rep. At first, this can be hard – especially if you have no prior background in the art of selling.

As a founder, however, you have one vital advantage: Vision.

It’s your product, and people are buying into your vision. If you can convince them to do just that, then your sales skills are better than you thought. Through sheer will, trial and error, and a great product or service, you soon begin finding the right market fit.

As demand increases so does the need to widen your reach. And you need sales reps to push the brand forward and expand. However, it can be hard sourcing people that are the best fit if you don’t come from a sales-driven environment.

We’re Hiring

Hiring good sales reps is more than merely sifting through the best CVs. There are several factors to consider. Identifying them isn’t always straightforward.

You want to build a sales team to reproduce – and surpass – the success already achieved. The process hasn’t reached full industrialization, but it’s the beginning of the path.

Here are some essential tips to help you determine which sales reps are best suited to your company.

Game Recognize Game

Those first hires are the most important. You start building a team and the reputation of your company and don’t want to ruin it by taking on bad salespeople. A good first step is to think about your own experiences as a consumer with salespeople. What did a rep do that made you feel good about a product or service?

It is also important to reflect on your own sales skills. The company has grown to the point where you have closed several customers and have some revenue, which indicates you have found a solution that returns an element of success.

Draw on your own experiences of being a salesperson and what went well and what didn’t when you pitched your company. Identifying these traits places you in a healthier position when it comes to hiring your own sales staff.

It’s important to teach your new reps about the company but also be open to learn from them and their experiences.

What Type of Reps do you Need?

At this stage, it’s important not to get too ahead of yourself and hire a Vice President of Sales. You are expanding, but unless your revenue is north of $1 million, essentially you need someone who you will work with on a frequent basis. You aren’t going to stop selling, but you want them to eventually have the capability to manage a small team.

Even if you’re not 100 percent comfortable with the selling aspect, you managed to get this far and scaled a product that fits the market, so it’s important to build on that success. Hiring reps to help with increasing demand is where you should focus your efforts.

The First Hires

Finding the right reps that are a good fit for your company is imperative. Initially, you may be tempted to cut costs and go for people with little or no sales experience but with lots of ambition. If you don’t have a vast knowledge of sales, however, it’s best to avoid going down this route.

The first bona fide sales reps to walk through the door don’t have to be all-star sellers. But it’s helpful if they have previous experience and a grasp of what a sales process entails. Four to five years of experience is ideal. Even if that’s not possible, try and steer clear of someone with little or no prior understanding of selling.

Be Bold

Finding the right person with previous experience can be a struggle in itself. The temptation might be high to go to a Fortune 100 company and hire the top reps, budget permitting. But even if you do have the money for this kind of hire, it’s best to avoid these salespeople.

While reps from blue-chip companies are likely to be good at selling, they also benefit from the safety blanket of working for a huge brand. Placed in a market where you are still establishing yourself could be a step too far out of their comfort zone.

It will also cost too much money if it fails. It can take between six and nine months to establish whether or not a sales rep is a poor fit. Such a wait could have negative ramifications on your company.

Finding reps that have previously struggled with an inferior product might be a better route. They’ve had to work harder for their leads and will have an appreciation of grinding as opposed to those who were served everything on a silver platter.

Enthusiasm is Key

As well as experience, it’s important to find people that fit the culture and personality of the company – or will at least help to define it. You want people that have intellectual curiosity – reps that are curious about the world and are interested in more than just themselves.

Those traits will help them emphasize and relate to prospects and listen when dealing with leads.

Above all else, a willingness to learn is the most important aspect of hiring sales reps. The ones who are willing to act as a sponge and absorb information about the company are more likely to prosper and increase success.

You’re at the beginning of your company, and the product/service will evolve, so you need to find someone capable of evolving with it and who can help you push it in the right direction. You’re not yet at a place where you set up your final sales process; you need to discover it first.

And it’s not just from a learning perspective where reps need to be listeners. The most important part of selling is listening after all. If you want to close deals, you need to listen to the problems of the customer and find solutions.

Many reps believe the way to successful selling is by talking continuously. This isn’t the case, however. As Debussy once said: “music is what happens between the notes”. Listening is the key to success.

How Many Reps

While you might think that hiring one rep is a good starting point, in reality, you should aim for two.

The idea of hiring two can seem daunting, especially if money is tight. But reps aren’t as expensive as many believe. Salespeople don’t get their bonus unless they close revenue, and closing revenue is a sign of growth.

Hiring two allows you to A/B test and improve your process. If you just have one – even if they are performing above expectations – you don’t have anything to measure against. It is hard to tell why they are successful.

Two reps who perform well help you better understand your sales process and make you more confident when it comes to future hires. Aim for one with four to six years of experience and another with one to two years. Also if one is bad, the good thing is that you can rely on the other one to lessen the possibility of losing six months’ worth of time.

Bonus tip when recruiting:

  • Don’t believe the Rolodex. Do not hire someone because they have a network. People don’t buy a product because they know the seller; they buy because the product solves their problem.
  • When interviewing, if your internal alarm is ringing, believe in your gut instincts. You will not find the perfect person, but don’t underestimate the warning signs. Don’t think that because something is easy for you it is the same for other people.

Build a Culture and Hire a VP

Word travels fast in industries, which is why you want people to talk positively about your working setup. A good culture will lend itself to others wishing to be part of the company and join the journey.

If you scale quickly and revenue increases beyond $1 million, the final piece of the puzzle is hiring a Vice President of Sales. Whether through promoting from within or hiring externally, the VP will round out your team.

In the end…

By hiring people who are hungry, ready to listen and learn, and all pull in the same direction, you will be well on your way to creating a lasting culture that will define your company.

And all that starts with a couple of sales reps who are ready to win.

Sunny Paris


Sunny Paris is the CEO of <a href=""></a>, a SaaS lead management software designed specifically for sales reps. Founded in 2013, simplifies the process for salespeople, allowing them to easily track and convert leads as they move through the pipeline, focusing on the next step. Sunny is a serial entrepreneur with a background in developing innovative IT startups, including Weborama, which was listed on the French market.