In the eighth episode of Business Banter by SkillsLab’s Jack Kosakowski, we speak with Andi Vanetta Smith, Founder of Vanetta Partners. Jack and Andi discuss everything you need to know about hiring your first five salespeople.

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Most startups are deeply immersed in the frenzy of getting their feet on the ground.

This makes it difficult to find perfect salespeople for rapid (and sustainable) growth.

The true cost of hiring the wrong salesperson can be financially detrimental.

To make the right decision, you need to talk to experts and leverage their experiences.

That’s precisely why we are super-stoked to present a real pro today.

Andi Vanetta Smith is the founder & CEO of Vanetta Partners, which is a specialty firm that helps find sales talent for fast-growing businesses.

Along with Jack Kosakowski, Andi is ready to share her unique insights into what you should be looking for when you plan your first sales hire.

Hopefully, you’ll walk away with a few actionable items so you can ramp up your business.

What to consider when hiring the first few salespeople?

While focusing mostly on SaaS companies, Andi has learned fast by being next to founders during their time of growth and struggle.

Many factors come into play. To begin with, it comes down to self-awareness to attract real talent more holistically, whether you’re hiring 10, 50, or 100 employees.

Having said that, it’s never easy to know when to hire the first salesperson. Ideally, it should happen when founders are tired of devoting a significant chunk of their time on sales-related activities (and their desk is already overloaded.)

It all starts with reverse engineering your revenue goals. When you sort of hit a ceiling, you got to duplicate yourself. When you find that you’re doing all of it, you will realize that you need to find somebody that’s going to come in and understand the operational aspects.

Also, your first hires need to have a business mind and entrepreneurial DNA. It’s more about being a human brand (… and less about your product.) It’s important to know that your sales team has to embody what your brand is, right from day one.

How to understand the salary aspect?

Here’s the problem. As an early-stage founder, you can’t afford to go out and hire a salesperson with a $100k salary right away, but at the same time, you can’t afford to hire the $50k one that sucks.

Ideally, you should be attracting people that want to work on a heavy commission model. For long-term involvement, you have to cut them on a larger revenue goal (for them to be attached.)

Also, this is where the concept of remote work becomes exciting. You can’t put a price tag on allowing someone to have the flexibility to be at home. It is the perfect option for a person looking to achieve the work-life balance.

You can potentially have a completely remote team. This is one step that’ll help you manage the “crazy inflated salaries” problem that most startups face.

There are a lot of great workers who’d love to walk away from that extra $25-50k variable to have their sanity and health back.

The ability to set their own schedule has a fantastic impact on employee productivity. So working from a remote location is a masterstroke that helps you handle many variables.

(Just a word of caution. Don’t micromanage as long as they are on the right track and doing fine.)

How to hire top salespeople when you’re still figuring out your position in the market?

Clarity matters. So it’s essential to make sure that you let a prospective employee know about your job expectations if they are going to be more intensive.

Inform them about the evolving customer profile as the company gets more experience. Just let them know what’s the direction in which your company is moving.

Tell them they might have to bear some bumps and bruises while you are identifying your target market. It’s crucial to prepare your early salespeople for growth and patience.

Your recruiting team should talk about a broader context of career opportunities. Give them an option to contribute to the growth of an early-stage company. Fostering an environment where someone can have their own identity within their brand is important.

It is the age of influencers. Allowing everybody to have their own identity is good for career self-esteem, so they know they’re building something. It’s a world where you should encourage your new hires to consolidate their positioning.

How should you interview for a role?

Here’s how the normal process goes. You meet a person. The interview goes smooth. You get excited. There’s some synergy that you thought was right… and then after a few weeks, nothing turns out to be perfect. ZERO results.

This is why recruiting is such a unique process because it requires a panel of experts. It requires comparison. It involves iteration. In fact, it is surprising to know that recruiters are incredibly undervalued when it comes to the process piece of their role.

There’s a need for a lot of conversation, and that’s where the expertise of a recruiter comes in handy. There’s a chain of communication that eventually leads up to the top management.

Clearly, you need an educated and experienced recruiting team to steer your company in the right direction (experienced being the operative word here!)

It’s all about holistic planning

As a leader, you need to plan well. You also need to look for characteristics like loyalty and dedication; rather than over-romanticizing the “so-called” unicorn talent.

There are unfortunate times when a startup doesn’t value the candidates that are specifically looking for them. Instead, they want to work with a highly specialized talent that’s difficult to retain.

This is a wrong approach since loyalty is critical at an early stage. You can bring in a top performer by spending extra money. But, it’s not always easy to turn potential into results. Sometimes these proven performers can take a large chunk out of your resources with no guarantee for success.

Instead, you can mentor, coach, and develop young talent. You can hire the inexperienced reps and prepare them accordingly. You can instill the company values and create a workforce that is loyal to your brand.

Obviously, this approach requires more investment in the training department. You’d also need to hire a coach that knows your industry pretty well. But, this is a huge piece that’s been missing, and executives have finally started hiring the trainers, coaches, and mentors.

Why are companies struggling to hire women in sales?

To begin with, don’t be hung up on the exact job description with a “certain amount of years” of experience coming from a particular industry. Such job descriptions are usually written for men and act as a hurdle.

First, analyze whether your company is creating an opportunity for women to come onboard. This whole expecting to be “experienced enough” is a bit of a hindrance.

The solution is to reframe this narrative and attract women by creating real career opportunities. Also, you need to change the expectations for the role.

“Years of experience” is just like a college degree in an application – it doesn’t matter. There’s simply a ZERO correlation between a college degree, level of experience, and results.


Most industries have matured after the last Silicon Valley bubble. There has been enormous learning at each level.

Salespeople today are looking for real opportunities with a healthy work-life balance. They’re looking for a stable career with rapid upward growth.

In the current environment, there has to be a value alignment between what you offer and the salesperson you want to hire. Prospective candidates want to work with a boss whom you can respect and a brand in which they believe.

The digital age is allowing us to do that more and more. So don’t get stuck behind a logo and stay ready to bring in the human element in your hiring processes. That’s what matters in the end.

And now we’d like to hear what you have to say,

What’s your main takeaway lesson from today’s post?

Or maybe you have a question.

Either way, please go ahead and leave a comment below with your thoughts.


Jack is known for leading the charge in sales innovation. He has a proven track record of working with top organizations to help them integrate social into their traditional sales process.

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