When Do You Hire Your First Salesperson?

Alan Pentz says lots of businesses (including his) make the mistake of hiring one too soon.

Good Morning!

Here are today’s highlights:

• This is a consumer-driven economy, and consumer confidence is plunging.

• A tech columnist explains what happened when she switched to AI search.

• Is it possible that not all PE firms deserve the bad rap?

• Expectations are mounting that President Trump’s next tariff target will be copper.

SALES

Alan Pentz warns against hiring a salesperson too early: “Fair warning: If you're struggling to grow past $1-2 million and think hiring a salesperson is the answer to working fewer hours, you're not going to like what I'm about to say. I've watched dozens of business owners make this exact move while trying to escape the daily grind. Hell, I did it myself. And it almost always ends the same way—with a fired salesperson, wasted money, and a business that's still completely dependent on you.”

• “Here's how it usually goes: Your business hits $1-2 million with you as the primary (or only) salesperson. You're drowning in work and think, ‘I need to clone myself.’ You hire a sales person with a hefty base salary and commission structure. Six months later, they've closed little to nothing. You fire them and start over. I went through THREE salespeople this way. Each one was a great person who I genuinely liked. And each one failed spectacularly.”

• “Stage 1: Optimize your time ($0-1M): Don't try to hire a salesperson yet. Instead focus on effective delegation: Get an assistant to handle your calendar and email. Delegate all non-sales tasks. Create simple follow-up systems. Say no to non-ideal clients to focus on better ones.”

• “Stage 2: Document and systemize ($1-5M): Before you can hire someone, you need to know what actually works: Hire a sales admin to do all the logistics to free up your time. Track every lead and what happened to it. Get a CRM system. Identify your actual sales process (not what you think it is). Create sales collateral that explains what you do. Start building a reputation beyond just you.”

• “Stage 3: Hire for support, not replacement ($5-10M): Don't try to replace yourself yet: Bring on junior people (beyond the admin) who can handle parts of the process. This helps scale founder sales. Document your sales conversations. What works? What doesn’t work? Start to document and refine the sales process that works. Keep doing the critical customer/client meetings yourself. You’re still the closer, but you don’t have to be in every step of the way.” READ MORE