Every small business owner starts by handling customer support themselves. And for a while, that works. You know the product better than anyone. You care more than any hire ever could. But there comes a point where doing support yourself is costing the business more than hiring someone would. Here is how to recognize that point and make the transition well.

The real signals, not the obvious ones

The obvious signal is volume. But most owners wait too long if they only watch volume. The earlier signals are subtler: you are answering support emails at 11pm because there is no other time. You are rushing responses because you have a meeting in five minutes. Customers are waiting 24+ hours for a first reply. You have stopped proactively reaching out to unhappy customers because you do not have time. Any two of these mean you are already past due.

The cost of doing it yourself

Calculate what your time is worth per hour as a founder or business owner. Now calculate how many hours per week you spend on support. If you are spending 15 hours a week at an effective rate of $100/hour, that is $6,500 a month of founder time on support. A dedicated rep at $45,000 a year costs $3,750 a month and frees your most expensive resource: your own attention.

Full-time vs part-time vs outsourced

For most small businesses, the first hire should be part-time or a contractor who can grow into full-time. You need someone who can cover your peak hours and handle the volume that is currently falling through the cracks. Outsourcing to a support agency works if you have well-documented processes. If your knowledge is mostly in your head, an outsourced team will struggle.

What to look for in your first hire

Writing ability matters more than technical knowledge. You can teach someone your product. You cannot teach someone to write a clear, empathetic response under pressure. Look for: clear written communication, patience with repetitive questions, curiosity about why things break, and the ability to say "I don't know, let me find out" without anxiety.

Set them up to succeed

Before your first rep starts, document your 20 most common questions and answers. Set up a proper helpdesk tool so they have a system, not a shared inbox. Write down your tone guidelines: do you use first names? How formal are your replies? What is your refund policy? The time you invest in onboarding documentation pays back tenfold.