I work with several business accelerators in town, facilitating sales training modules and mentoring individuals on their business. One of the questions I get asked most often, especially by brand-new startups, is "When can I hire a salesperson and stop having to sell this myself?"
My answer is simple: Never.
(It's also an answer they don't want to hear, in case you were wondering. There's never been a class where I said "Never" and everyone immediately burst into loud cheers and applause. Mostly they look at me in horror.)
But look, it's the truth. Yes, at some point, if your company gets large enough, you'll hire salespeople. I certainly have in my time at Legion. But you'll never stop selling. Your entire life as an entrepreneur and business owner is going to involve a heavy dose of sales, so you might as well get used to it.
In the beginning, it will be because there won't be anyone else to sell whatever it is that you are selling. You will be starting from scratch with an idea or a product or a service that you believe in so much that you are willing to take the risk to start a company to do it, and much of your activity in the first year(s) will be selling. Either selling your product or service to the end user, or selling the idea to investors or partners. No one else will have the passion for it that you do, so outsourcing that part of the sales process would be the height of folly. You'd be putting the future of your business into the hands of a hired gun, who might love the idea, but who does not have the skin in the game that you do.
As you grow, you'll be selling the idea of your company to potential employees, trying to convince folks to come work for you in the basement of your house (been there, done that) or in the back of your drafty warehouse. You'll be an unknown quantity, and every person you talk to will have to be sold on the potential of a career with you. If you can't sell that, people will go down the street to work for a company that actually has, like, desks and an employee handbook.
And once the company is really rolling, you'll evolve into the long-term sales role that every business owner has—selling the idea of the company, over and over. Need a bank loan? Sales. Looking for a strategic partner? Sales. Your team is trying to close a whale and needs you to come in as a heavy hitter? Sales sales sales. The company has a moment of crisis and you need to address it with the staff or, God forbid, the press? SALES.
This is why I tell all the entrepreneurship students I speak to to start their career in a sales role. You need the chops to be able to communicate persuasively to succeed as a business owner. There's no way around it. Instead of seeking to push off the sales function as quickly as you can, embrace it. Get better at it. Those are skills you'll need your entire lifespan as an entrepreneur.