The Transition from Founder Sales to First Sales Hire

The Transition from Founder Sales to First Sales Hire

The hardest transition B2B startups go through is moving from founder-led sales to a hired sales person. Unfortunately, almost everyone gets this wrong.

A founder has several advantages when selling. Beyond knowing the product inside and out, they control the product roadmap. This gives founders the power to adjust the pitch and even promise features on the fly. While helpful in the early days as a way of building for the customer, this approach clearly does not scale beyond the founder.

The first sales hire you bring on, no matter the seniority or experience, cannot be driving your roadmap. They likely also aren't intimately aware of exactly how the product was built. As a result, they can't mimic the founders product-led and adaptable approach to sales. And even if they could, playing quasi-product manager isn't really how most salespeople thrive.

The way to ensure that your first professional salesperson succeeds is to make sure you have a defined value prop, a structured sales pitch, and a clear product to sell. When they have this they can leverage all of their sales experience and knowhow to dramatically accelerate revenue.

And this brings me to why the transition from founder-led sales to the first sales hire fails so often. It is not just a change from one person selling to another. It is a total transformation of the sales process.

So how do you avoid the mistakes so many of us have made during this transition?

I have seen two things work. But both of them require an explicit understanding that everything sales needs to change for the transition to work.

Option a: Start by changing how you as the founder sells. Define the sales pitch, put structure around the product, show that you can sell without leaning into the founder advantages. When you can bring on new customers in this way you are ready to hire your first professional salesperson.

Option b: My preferred option is to hire someone as a bridge to go through this transition. I have found that a generalist with a product bent and lots of hustle, can start selling in a way that is a hybrid of what a founder does and what a sales person does. The focus should be on adjusting the sales motion and focusing on how to turn the founders unconstrained pitch into a more structured one.