How to Hire Your First Salesperson

May 30, 2018 | Hiring, Resources, Sales Leadership

In the initial stages of a company, the leadership team does all the selling. But, there comes a time when you realize you can’t continue to grow your business even if all your time is focused on the selling. You need help. You need to hire your first salesperson. How do you do that? Knowing when to hire and how to hire the right person can be difficult.

Hiring your first salesperson can be a daunting process and you shouldn’t do it alone. We recommend that you hire expert help because hiring the wrong salesperson can waste your time and your money. I’ve seen so many failures in this area, I never recommend you do it alone. So, if you’re unsure then hire a company that specializes in recruiting and screening sales and sales management candidates.

I spoke with Jamie Crosbie, Founder, and CEO of ProActivate to get her expert answers


How do you know when it’s time to hire your first salesperson?


This question comes up a lot, especially with startups. While there is no hard and fast rule that applies across the board, here are some questions to ask yourself to determine if it’s time:

– How busy are you? Are you working 70+ hours a week and having little time for sales?

– Are you about to launch a product that will require more focus on sales?

– Do you have time to follow-up on leads or are you missing critical opportunities?

– Does the time you plan for selling continuously get interrupted by other business urgencies?

– Do you have time to travel to meet clients or prospects? Or are you hesitant to travel because you need to be in the office?

– Is your close rate sufficient to generate the sales revenue you need?

– Can you meet your revenue goals doing all the selling yourself?

– Do you have a clear job description for the sales position?

– Do you have the time and mental stamina to train someone right now?


If I have answered these questions and decide I need to hire, what should I be looking for?


There is an old saying that “All roads lead to Rome.” Your company is “Rome.” And when it comes to hiring a sales rep, the person you hire is like a road that leads inexorably back to you and your product or service.

The way they act and respond, whether they connect to the customer can alter the way your valued customers feel and think about your brand.

You are looking for someone who will represent your brand well. When you are looking for top-shelf sales talent you need to know they have the confidence and drive for it. Unlike balloons, you cannot pump them full of drive to help them fly upwards. They either have it, or have a strong potential for it, or they do not.

You should look for sales reps who are:

Engaging: They not only need to be a good storyteller, and able to emotionally synch with a customer, they also must know when to listen.

Empathetic: and see things from the customers’ viewpoint. They need to be able to meet the customer on a human level and work with them to find solutions. Not just to sell them something, but to genuinely solve a problem. That keeps customers coming back.

Resilient: They need to be able to roll with the punches and keep going.

Adaptable: They need to be able to adapt quickly to your company and to the changing sales environment.

Driven: They must be driven to succeed.

Collaborative: They should be a team player and fit your company culture too. If they do not “play well with others”, you don’t want them on your team!

Gritty: Top salespeople need fire in their belly so to speak, in other terms “grit” – that sales DNA.


So, the leader is responsible. Hiring the best sales rep can’t make up for sales leadership. I’ve seen this many times. The leader hires and then does not support the new hire. When sales are not as expected the salesperson is blamed. This causes an turnover which is quite expensive and lack of sales. What are the biggest mistakes entrepreneurs make in hiring their first salesperson?


Too many new business people just don’t know the ropes yet. As Donald Rumsfeld, the Secretary of State under George Bush famously said, “There are known knowns and unknown unknowns.” In other words, you know some things, others you learn as you go along.

Many new entrepreneurs simply do not know what to look for in a sales rep. They may hire the first warm body that comes along, only to regret it down the line. You need to find sales rock stars, not sales “rocks”.

It is very challenging to source, qualify and successfully court top sales people and often entrepreneurs don’t have the time or the knowledge to support that process successfully.


What are the costs of hiring your first salesperson and what are the costs of doing it wrong?


The cost of getting it wrong can be devastating. It can even tank your business. Over 75% of all startups fail. One of the biggest reasons is that they fail to find the right people. They either hire the wrong person or they hire a great person and can’t support them. Both are expensive mistakes.

It all starts right there when you choose the people who will either move you forward or drop you into the spin cycle. That goes for everyone you hire, not just your sales team. However, sales teams can literally make or break a company. On average, one poor hire costs you at a minimum, 30% of their yearly earnings. Add to that lost opportunities and the cost of recruiting and training a replacement, and even a small company can be looking at a loss of five figures or more. Not to mention any damage they could have done with customers and prospects out in the marketplace.

There is no cost for doing it right – it is considered an investment!

[bctt tweet=”There is no cost for doing hiring your first #salesperson right – it is considered an investment! @jmcrosbie” username=”AliceHeiman”]


Why is it important to get help from a recruiting professional?


Time, Money and Pain

A professional recruiter understands the ins and outs of sales. They can use sophisticated behavioral and mindset qualifications, and proper vetting to isolate key indicators which can predict the likelihood of future success. A multi-pronged approach considers the company’s criteria for hiring (industry experience, skillsets, education, etc.), combined with multiphase in-depth interviews, and targeted simulation evaluations. All of which gives you the candidates that are most likely to succeed.

Not only that but a recruiting professional is able to attract the top talent in the market. These are sales professionals that are working and winning and are looking for an upgrade to their career. Oftentimes, when companies do the recruiting themselves they are using resources that are focused on attracting unemployed candidates. These are typically the salespeople who got fired for not hitting quota or left before they got fired.


Thanks for sharing all these great tips for hiring your first salesperson, Jamie. A lot of them apply to hiring in general. So if you are a startup who wants to hire your first salesperson or if you have a growing business and need to hire more salespeople, I recommend you take Jamie’s advice or better yet, give her a call.

Are you building your B2B sales team? What are the challenges you’re facing besides hiring? We’d love to help! Register for our live online 8-week program, Start-Up Sales and discover how to build your sales organization from scratch! Learn more here.

Alice Heiman

Alice Heiman

Alice is nationally known for her expertise in elevating sales to increase valuation for companies with a B2B complex sale that have exceptional growth potential. She’s originally, from the widely known Miller Heiman Group. Spending her time strategizing with CEOs and their leadership teams to build the strategies that find new business and grow existing accounts is her passion.  Her clients love her spirit and the way she energizes their sales organization.


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