One of the most critical aspects of a young company’s life is deciding to go all in, step on the gas and hire a salesperson. It’s one of the most frequently asked questions I get from founders that are finally getting a bit of traction or are pre-revenue and looking to push out their product to the masses. It typically comes up when your week is too packed with CEO activities that you can no longer think about sales on your own.

The answer (like most answers in the startup world) is: it depends.

I know what you are thinking, that’s a cop out answer. But hear me out, because hiring too soon is one of the biggest mistakes an entrepreneur can make. Answer the following three questions before making your first sales hire to ensure you know exactly what you need.

Have you closed 10 unaffiliated customers?

There is a lot of content out there speaking about the importance of having 10 unaffiliated customers. This means you have moved on from selling to your friends, families, and close network and found 10 customers who are willing to pay you for your product each and every month.

When you have those 10 unaffiliated customers and you start seeing a bit of success, consider putting a seller in that role. They now have a chance to accelerate your growth and get you to 20, 30, 40 customers and beyond.

You now have proof points and can get feedback on the value of your product through the lens of your customers, which makes it easier to speak in terms that future customers will understand.


Can you close deals?

If you are a natural salesperson, or have been a successful salesperson in the past, your first sales hire might not need to be a closer. You can close a lot of the early deals on your own, and you may need someone who can source more potential customers for you.

This means you are trying to find a “hunter,” which in the sales world is often known as a sales development rep (SDR) or business development rep (BDR). A BDR can help you build up a pipeline and develop your bullpen for the first closer that you have in the future. Overtime, they can run shotgun and eventually take over the full sales cycle.

If you are not a salesperson and feel like you struggle to message your product in a way that people can understand, hire a sales veteran that has a proven track record of closing deals.

This hire can be tough to find, because he or she needs to be someone who understands the environment of selling without any methodology, structure, message, or support from other departments. Hiring from big name employees in your community may seem tempting, but those employees may not fully understand how to be successful in a bootstrapped situation. Instead, trust your gut and hire someone with a proven track record who fits into the culture you’re building.


Do you know what you are looking for in a sales person?

This is usually my first follow-up question when someone asks me if they should hire a salesperson. Your sales team, and anyone in your first 10 hires, make up a big portion of the culture that you’re building. It is important to know what qualities you are looking for in a candidate.

One of my favorite founders, Kyle Porter, frequently mentions this piece of advice from his mentor, Mark Suster, “Only hire A players that punch above their weight class.”

This means finding the person who not only wants to grow themselves in a sales role, but also has the drive and ability to do it.


You need to find sales people that have soft skills and can build an organization. The type of people that you want to spend time with for countless hours in the early days, and can also see yourself buying from in the future. Someone who is willing to put in the work that an early stage company needs to see success. They need to be able to check their ego at the door each day, and get things done.

There is no perfect time to make your first sales hire. It’s something you will feel comfortable doing once you’re able to confidently answer the three questions above. When you do make that first hire, find the person that your gut says will outwork the others and has the potential to scale as your business grows.


About the Author: Phill Keene is the Director of Marketing at Octiv and co-host of #RealSalesTalk podcast. Through his experience as a sales professional, he has learned how to be a strategic resource to companies trying to reach their revenue goals and attain quota. Phill brings commitment to learning and development to the inside sales space, and was named one of 2017’s Top 25 Most Influential Inside Sales Professionals by AA-ISP. His expertise is in best practices around sales productivity, marketing, lead generation, business development and technology.