Hiring Your First Salesperson: When and How to Hire a Sales Team

Hiring Your First Salesperson: When and How to Hire a Sales Team

If you’re the founder (or one of the first employees) of a small company, you have to wear a lot of hats — including sales.

You have revenue goals. And as your company grows, your goals do too.

You can’t do it all on your own. You need help selling your products or services, so you can spend time working on the things that only you can do.

It might be time to hire your first salesperson. (Or even a whole sales team.)

If you do most of the selling for your business, handing over the reins to a new salesperson can be daunting. But when you hire the right salesperson — one you trust; one who gets results — they can help your business grow in unprecedented ways.

Keep reading to learn:

  1. When to hire your first sales rep
  2. How to hire the right salesperson
  3. How to measure sales hire success
  4. When to expand your sales team

When to hire your first sales rep

When you get to a point where you can’t hit your sales goals without hiring a dedicated salesperson, it’s time to hire your first sales rep.

Ask yourself:

  • What numbers are you trying to reach? What’s the annual recurring revenue (ARR) you’re looking to hit?
  • Can you get there with your current headcount?
  • As a business owner, where do you want to be spending your time?
  • Do you want to run sales for your company, or do you want someone else to take it on?

Many small companies will hire a VP of Sales as the first member of their sales team. A VP of Sales helps you define:

  • Which sales methodologies you want to follow
  • What your sales process will look like

Whether you hire a VP of Sales or a sales development representative (SDR) first, make sure you have a goal in mind. What do you plan to accomplish by bringing on a new employee? What new revenue goal can you set?

Many companies hire salespeople too early and often, which results in adding more people in the hopes that they solve all of your problems — without addressing the root cause of the problems. Put clear goals and processes for new sales reps in place before you decide whether to hire more people.

How to hire the right salesperson

Before you post a job description, figure out how you define a successful salesperson. If you don’t know what you need, it makes it hard to narrow down the candidate pool (and to write a job description that brings in the best potential employees).

Here’s what to look for when hiring a salesperson:

  1. Values
  2. Sales skills
  3. Authenticity
  4. Coachability
  5. Past experience
  6. Resourcefulness

1. Values: Does this person align with your company’s core values and how you operate? What type of work environment motivates them to excel? Does that match your company (and sales team) culture?

2. Sales skills: What makes this candidate different? There are a lot of salespeople out there — it’s important to know that the person you hire will elevate the team.

3. Authenticity: People buy from people they trust. When you appear authentic during the sales process, prospects feel like they know who they’re buying from. Look for someone comfortable with sales calls and objection handling.

“It’s not just that people want to deal with someone they like. It’s that they want to deal with someone who likes them, and who is like them. People trust that those who like them won’t steer them wrong.” – Robert Cialdini, Pre-Suasion: A Revolutionary Way to Influence and Persuade

4. Coachability: Humility is the foundation of coachability. A coachable salesperson is:

  • Humble
  • Hungry for feedback
  • Eager to learn

Coachable sales employees take feedback and run with it to improve their performance and the team’s processes.

5. Past experience: The level of salesperson you plan to hire helps determine how much past experience you require.

Your first salesperson should have sales experience. They’ll be responsible for forming your sales processes and culture — you want someone who’s done this before!

If you choose to hire for a more entry-level sales role, like an SDR, that salesperson might be learning sales skills for the first time. You don’t need to focus on past sales experience.

Just make sure you have the sales resources, tools, and training in place to help them succeed.

If you hire for an account executive role, make sure your candidates have sales experience. Account executives nurture leads, demo services, and close deals; the learning curve in this role is too steep for a brand-new salesperson.

6. Resourcefulness: Your first hires need to be resourceful and scrappy. When you’re the first of anything at any company, you end up doing more than your job description. As you look to hire your first salesperson, find someone comfortable dealing with ambiguity and thinking outside of the box.

What to ask during a sales interview

Many recruiters use behavioral interviewing, and it’s a great tool — when used sparingly. Behavioral interviews ask questions that use past behavior as an indicator of future performance. These are situational, “tell me about a time when…” questions.

Behavioral interviews can be stressful for candidates, so limit yourself to 3 behavior-based questions. Figure out the top 3 qualities you want your sales hire to have, like:

  • Good at navigating ambiguity
  • Past experience with a specific industry or kind of customer
  • Ability to think on their feet

You have to understand a role before you can hire for it! Make a list of core competencies for each role before you interview candidates. This helps you do 2 important things:

  1. Come up with questions that tell you whether candidates have those core skills
  2. Evaluate each candidate against the same set of expectations

Red flags for sales hiring

Now that you know what to look for, what are some warning signs when interviewing salespeople?

Lack of humility: Even amazing salespeople won’t be number one everywhere they go. Watch out for candidates who claim that they’ve always been the top salesperson at their company. Push them to explain a bit more about their success.

Humility is the foundation of coachability; if a candidate believes that they know it all, what can you teach them? Will they be open to learning from you?

No focus on metrics: Sales numbers define sales success. A salesperson’s resume should include metrics; if they can’t articulate how they were compensated or how they performed against quota, they probably didn’t outperform the rest of their team.

Inconsistency: In an interview, ask a candidate the same question in different ways — not to trick them, but to ensure that they understand the question and give a consistent answer.

Inconsistency and hitting sales goals do not go well together; salespeople need to follow processes and get consistent results.

Trust your gut

Experienced recruiters develop what I call a “spidey sense:” If you feel like something might be amiss during an interview, don’t be afraid to ask clarifying questions and dig deeper. Trust your instincts. How do you feel about working with this person?

Important: Don’t expect everyone you interview to be your best friend. You don’t have to “like” somebody to hire them.

Instead, evaluate them as holistically as possible:

  • Do they share our company values?
  • Do they fit the company culture?
  • Will they elevate their team?
  • Will they make a positive impact on the future of the company?

How to measure sales hire success

Once you hire a new salesperson, how do you know if you made the right choice?

Sales is a numbers game: You either reach your quota or you don’t. But success often goes beyond hitting quota. Here are 3 questions to gauge your sales hires’ success:

1. Consistency: It’s not enough to hit their goal every once in a while. Are they consistently making quota?

2. Collaboration: Do other teammates go to them for advice? Do they go above and beyond to help their teammates? How do they elevate the team?

3. Process: Successful salespeople understand what goes into being successful in the role — especially as the first person on the team. If they hit quota but don’t know how they hit quota, they won’t be able to repeat the process or teach others. They can’t grow the team if they don’t know what makes you successful.

Conclusion: When to expand your sales team

When should you expand your sales team?

Everyone’s favorite answer: It depends!

Work with your current team and executives to answer these questions:

  • Why do you want to expand your sales team?
  • Are you throwing people at problems instead of addressing the root cause?
  • Can you make your current processes more efficient without hiring more people?

Don’t add people for the sake of adding people. Tie hiring to a business goal. Look at your revenue goal: Do you need more leads to hit that goal? If you have more leads than your current team can work, it might be time to hire more salespeople to handle those leads.

If you expand your sales team, make sure you have the bandwidth and resources to support the new business they bring on. If you bring on 5 new agency clients, do you have the ability to complete the work for those clients? Do you have account management in place to continue to support them?

If not, you risk paying a sales team to bring in clients who will have a negative experience and won’t stick around.

As you expand your team, you may worry about “maintaining the culture” during growth. But as your company grows and changes, your company culture will, too. Processes will change, and people might be uncomfortable with that.

But when you hire the right team — both in sales and across the organization — your company culture will only get better.

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