Building a sales team is an absolutely critical stage in the growth journey of any small business.

In the early days, you might have won a bunch of clients through your existing network and word of mouth. But at some point, you’ll need to get in front of a whole new audience – and you’ll need a sales team to help you do it.

Hiring your first salesperson is about more than just finding a fantastic cold caller or a talented email writer. They need to be completely comfortable interacting with and engaging prospects at each stage of the buying process.

They need to understand your product inside and out.

And they need the entrepreneurial ability to close deals without being able to rely on things that reps at larger organizations would take for granted – things like a tried-and-tested sales cadence, or a ton of marketing collateral, or a quality sales deck.

The fact is, not a lot of salespeople are cut out for life at a small business. They might lack the hustle, or drive, or initiative required to get deals over the line for a brand that isn’t well-known in the market.

That’s why you need your first sales hire to be a genuine A-player. Here’s how to find them:

1. Preparation is Key

Good reps are excellent closers, naturally engaging, and adept at thinking on their feet. So they tend to interview well, which means you need to go way beyond the basics to understand if they’re a true A-player.

Sure, you’ll want to discuss their previous experience – more on that in the next section – but just as important is challenging them on their preparation for the interview.

If they don’t know anything about your company beyond the stuff you reference on your homepage, that should set alarm bells ringing. If they haven’t taken the time to prepare for this interview, how can you be sure that they’ll prepare effectively to speak to potential clients?

The last thing you want is to hire a rep who ends up painting your business in a bad light because they simply haven’t done their homework.

Ask questions like:

  • Who do you think are our closest competitors?
  • Why those companies, and not X, Y, or Z?
  • What do you think sets us apart from the competition?
  • How well do you understand our products and services?

2. Previous Experience/Accomplishments

Your first sales hire needs to be able to hit the ground running. They won’t have a more experienced sales mentor to lean on when times get tough. And they’ll have to cope without the support of a dedicated marketing department churning out quality, personalized content to engage their prospects.

Experience and accomplishments are the best gauges of whether a salesperson has what it takes. That experience doesn’t necessarily have to be in exactly the same industry as yours. They’ll soon pick up the technicalities and terminologies of working in your space. What’s more important is that they have a proven track record of thriving in a small business environment. 

Don’t just take their word for it – ask for specific examples and dig into the results they’ve achieved:

  • What kinds of sales prospecting techniques have they used in the past? 
  • Have they directly managed a sales team before or been the first sales hire at a small business?
  • What sales playbooks or processes have they developed?
  • What figures were they hitting in their previous role?
  • What would they do on day one if they got the job?

3. Passionate

Because this is your first sales hire, the rep in question won’t have a line manager watching over them and offering advice every day. You’re busy running the business, so they’ll have to be autonomous and driven in their work. That means they need to be passionate about what they do.

Sales should excite them. They should wake up each day fired up to hit the phones and sell your product.

To some extent, every salesperson is motivated by making money. But the real A-players genuinely love sales and revel in the chase – finding the perfect prospect, persuading them of your value, and closing the deal.

Ask them:

  • What makes you extremely proud?
  • What’s one thing that you love to do? Why do you love it?
  • What’s your biggest life goal? And how will sales help you achieve it?

4. Necessary Skills

Personality, attitude, and drive are extremely important – but of course, you don’t want to overlook whether your potential hire has the right sales skills to succeed in your organization.

On the one hand, they need to have the necessary technical chops. But it’s not all about hard skills – they also need the ability to succeed in a small business.

Plenty of reps consistently churn out huge numbers at big enterprises but put them in a small business environment, and they’ll struggle. They’re fantastic at executing pre-existing sales processes and cadences, but they don’t have the hustle to find new ways to do things.

Entrepreneurial skills are super valuable here. You won’t be there to hold their hand every step of the way, so it’s vital that they’re comfortable taking responsibility for your whole sales operation.

You’ll want to ask questions like:

  • Do you understand the sales tech you’ll be using?
  • Do you have recommendations for new products you should adopt?
  • Do you have experience in writing email sequences and sales scripts?
  • Have you built a team from the ground up before?
  • Have you developed and run your own business?

5. Eager to Learn

You might not be a salesperson yourself. Even if you are, you likely don’t have a ton of time to invest in upskilling your first sales hire, so you need them to take responsibility for their development. 

Employee development is really important because small businesses throw up a whole bunch of new challenges, and they can also change dramatically over a relatively short space of time. 

You might launch a new product or start targeting a new audience.

Your first sales rep will have to learn to adapt, fast. And on top of that, they’ll need to build and hone your sales process over time as they learn what works and what doesn’t.

Ask them:

  • Which podcasts do you listen to?
  • What’s your favorite sales book?
  • Which blogs do you regularly read?
  • In what areas do you want to develop over the next 12 months?

6. Aligns with Cultural Values

It’s easy to ignore the importance of culture when hiring a salesperson. As long as they hit the numbers, what does it matter if they buy into your mission, vision, and values, right?


Your values shape everything about your business. They’re a reflection of how you and your co-founders view the world.

Salespeople are often the first touchpoint that a prospect will have with an organization. So if they don’t buy into your values, chances are they won’t be painting you in the right light, which can do real damage to your brand.

Ask them:

  • What do they think of your values and vision?
  • What do your cultural values mean to them?
  • What values and goals are important to them?


Sure, that’s a lot of stuff to consider – but your first salesperson is arguably the most important hire you’ll ever make. Get it wrong, and you’ll waste a lot of time and money. Get it right, and you’ll hit your targets and grow your business. You’ll win a bunch of new clients who’ll stay with you for the long term because they buy into what you do and fully understand the value of your product. More than that, you’ll build systems and processes that will help you scale your operation when it’s time to hire your second, third, and fourth salespeople.

Author Bio

Sujan Patel is a partner at Ramp Ventures & co-founder of Mailshake. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit, and many other Fortune 500 caliber companies.