3 Mistakes Founders Make When Hiring Salespeople

Highlights from my panel at the Inc. 5000 Conference

In October, I was honored to join Inc. Editor-in-Chief Mike Hofman, Salesforce EVP Adam Alfano and David Jarrett, CEO of Rootstrap, on the main stage at the Inc. 5000 Conference to discuss The Secrets of America’s Best Sales Teams.

I’m incredibly passionate about helping founders make smart, strategic decisions—especially around those crucial first sales hires and structuring effective sales teams.

Our conversation got me thinking about the common missteps I see when founders usually consider hiring sales support.

In this post, I’m sharing impactful steps to avoid common hiring pitfalls and build a strong sales team from the ground up.

Let’s jump right in.

Mistake #1: Rushing to Hire

The founders I work with walk a tricky tightrope as they grow. They balance an enormous workload: managing business development, delivering client services, and handling the demands of being CEO. 

Understandably, because they desperately need to get things off their plates — and let’s face it, business development and sales can be daunting — they look to offload those tasks first.

Before handing over the reins, I invite you to consider the following:

• Do you fully understand how sales work within your business? Without this, you can’t effectively write job descriptions, onboard, set expectations, measure or manage.

• Is it really the right time to make your first sales hire? If you run a low-volume, service-based business, chances are you’re going to be the best salesperson for the job for a long while — especially if all your leads currently come through your relationships. 

My Advice? 

Delegate other tasks first. Of course, there are exceptions to that rule, but not many. 

Bringing in a sales consultant can be a worthwhile investment if you want to strengthen sales results and start preparing to build a team in the future.. 

A consultant can help you create a strong sales strategy, document your process, and refine it over time, providing valuable insights and expertise that can accelerate your sales efforts.

By bringing in a sales consultant, you can create a strong sales strategy, document your process, and refine it over time. This means that when you’re ready to hire, you’ll have a streamlined process ready for your team to execute. 

In the next section, we’ll consider another critical aspect that founders tend to overlook when hiring.

Mistake #2: No Strategy Before Hiring

It’s crucial to have a well-crafted sales plan and strategy in place before hiring, unless you plan to hire a seasoned sales leader — but let’s face it, that’s likely not in the budget. 

WIthout a sales plan and strategy in place, a more junior or subject-matter expert hire will have a diminished shot at success. 

Repeat after me: Hiring a salesperson is not a sales strategy!

When I work with clients, whether they’ve hired sales support or not, I always start with a detailed sales plan that serves as a roadmap to success. It outlines how your business will achieve its goals, including a business development strategy and a clear sales process.

Your plan should answer questions like: 

• What is the right revenue goal, based on past performance, market conditions and other factors?
• What’s the right offer mix to get you to goal profitably?
• Which client avatars are you targeting for which offers?
• How many new leads will you need, and how will you develop them?
• How much of your goal needs to be covered by existing accounts, and how will you ensure this number is reached?

Because without this foundation, you won’t have clarity on:

• The roles and responsibilities you need to hire for
• The talent you need
• The demonstrated abilities you’re looking to bring on board

For instance, many founders quickly hire Business Development Representatives (BDRs) to drum up leads. However, if all your leads have typically come through your network and word-of-mouth, how will you set that hire up for success?

With that in mind, let’s move on to the third common mistake. 

Mistake #3: Not Hiring The *Right* Person

As the founder who has been the one selling premium services to companies, your subject-matter expertise naturally bleeds into your sales calls. 

So, when thinking about hiring, it’s natural to wonder whether you should hire someone with the same expertise or someone gifted at sales.  

During our panel discussion at Inc. 5000, David Jarrett, Founder of Rootstrap, shared that he hired experienced salespeople, but it didn’t pan out. 

Here’s what he shared about the experience:

“Ultimately, we [went] down this road where we wanted to emulate the best practices of the types of companies we aspired to be. That meant trying to recruit sales and marketing people from those kinds of companies and get them excited and knowledgeable about what Rootstrap had to offer. This turned out to be the wrong strategy and required a pivot. They didn’t have that adaptability and sort of entrepreneurial spirit that we needed. … We ended up kind of deciding that we wanted everybody in our company to be a salesperson. I don’t want to minimize it. Like, it was an incredibly, incredibly painful decision for us to make. … But, we ultimately had to make a difficult decision.”

In today’s world, buyers are more educated than ever. They’ve researched the problem, the solution, and everything about you and your company. 

So, sales calls need to be additive.

Here’s what I mean:

Buyers don’t want a sales pitch — they want a strategic partner who can offer clarity and guidance to help them navigate the best way to a solution.

They’re also wary of making mistakes, which can lead to buyer indecision, so the more you challenge them and bring them to greater clarity and decisiveness about the right way forward, the better.

So, considering all of this, I invite you to ask yourself: Who is best suited to do this in my business? A salesperson who is skilled at closing deals and managing the sales process, or a subject-matter expert who can provide in-depth knowledge and insights about your service? Me or someone else?

Here’s what I shared with Inc.:

A solution to that challenge is to present buyers with highly knowledgeable sellers — often, subject matter experts — who can cultivate an experience that “creates not only safety, but brings a greater sense of clarity and propels that sale forward.”

Now that we’ve covered the three common mistakes I see when founders make their first hire, let’s recap some best practices in the concluding section.

Your Sales Team: The Key to Hiring Success

I was thrilled to be a panelist on the Inc. 5000 Conference stage, sharing my insights with an incredible community of ambitious founders and CEOs building the next wave of mission and value-driven companies. 

Building a good sales team takes patience, strategy, and a deep understanding of your company’s unique needs. 

By clarifying your sales approach, documenting your strategy, and hiring people who can speak to your services with the same level of expertise as you can, you’ll have a team to help grow your business.

More Resources:

Click here for the complete article, Why Everyone In Your Company Should Be a Salesperson.

Click here to read the complete article, 3 Key Strategies to Sell More to The People Who Matter Most.