Why enterprise startup founders shouldn’t rush into hiring their first sales leader

When is the right time to hire your first sales leader?

This is a critical question for every startup founder, especially those who come from a technical background. Jyoti Bansal, co-founder of 3 software companies, explains that he “learned the hard way that having an effective sales strategy matters just as much as creating a great product.” For Jyoti, finding product-sales fit, especially in the initial days is solely the founder’s responsibility. Once founders have built the initial “sales machine” themselves, they’ll be in a much better position to hire the right talent to keep innovating. 

We recently chatted with Hector Hernandez, a go-to-market leader who has scaled revenue organizations at companies like LaunchDarkly, Teleport, Traceable, and Speakeasy. Hector’s path to tech sales wasn’t traditional. After working as an analyst in oil and gas, he went to grad school and partnered with a Silicon Valley CEO. This experience sparked his interest in tech and led him to a role at a small startup. He’s worn many hats, from SDR to AE, and has learned the ins and outs of scaling revenue organizations. 

Hector provides great advice to technical founders about making those first critical sales hires. Like Jyoti, Hector emphasizes the importance of direct founder involvement in the early sales process and knowing when it’s time to bring on your first sales hire. He also emphasizes the importance of genuine, transparent relationships, particularly when selling to developers.

What should founders do before hiring a sales leader?

One of the most important things for technical founders to do is to go through the sales process themselves first. 

Here’s what Hector advises:

1. ‍Don’t rush to hire a salesperson thinking they’ll magically solve your sales problems. If you can’t close those first few deals, it will be difficult for a new sales hire to succeed. You know the product and the company best, and you need to understand the sales process yourself.
2. It’s critical to have direct conversations with early users yourself. You need to know the difference between someone saying, “This is cool,” and “I need this now”. This will help you develop a trained ear for genuine interest and enthusiasm for your product.
3. Hire a sales leader when you’re at capacity and you’ve become the bottleneck. When you are missing customer communications, and are falling behind with leads, then it might be time to bring in a sales hire.

When you finally hire a sales leader, you will have a new perspective on sales because they will close deals, and you will realize what “good” looks like.

Founders are almost always the best salespeople, even at large companies. If there is a big deal to close, a founder’s involvement can help get the deal done. Early customers will believe in you and your passion for your product and will be personally invested in seeing you succeed.

Hector has seen many founders try to hire too early, thinking a sales leader will solve initial sales issues. This often leads to frustration for both the founder and the new hire, leading to what Unusual investor Lars Albright describes as the “false hope sales cycle.” These situations can result in lost time, and a lack of customer feedback, which is crucial for finding product-market fit.

What should sales leaders look for before joining an early stage startup?‍

According to Hector, the most important factors when considering a startup are:

• ‍The Founders: He emphasizes the importance of a strong personal connection with the founders. Can you have honest, sometimes heated, discussions and agree to disagree? Are these the founders you want to be in the trenches with?
• ‍The Space/Product: Is it a problem that you want to solve? Is it something that you believe has a good shot at becoming a giant company?

Key takeaways for enterprise founders‍

Sales is like running,” says Hector. “It never gets easier, you just get better at it. You can hand the baton to a sales hire, but they can’t run the race for you. You need to take the first few steps yourself.

Before you make your first sales hire, make sure you’ve gone through the sales motions yourself. Understand what it takes to close a deal. Focus on direct customer conversations. Find the right words for your offering. Then, when you bring on your first sales hire, you’ll be better equipped to guide them and set them up for success.