Hey r/smallbusiness,

I’ve been working at my family’s business for six years now—joined right after college—and I’ve realized that we’re long overdue for an overhaul. I handle advertising sales, and while the business itself is solid, the way we operate is extremely outdated.

Without revealing too much, we print about 180 publications, and businesses pay to have their ads featured. As a sales rep, my job includes:

• Renewing current advertisers
• Finding new customers and making sales
• Collecting artwork for ads
• Gathering billing info
• Laying out the ad grid with all advertisers

The Problem:

Everything is still done with pen and paper.

• We use carbon copy paper to record business details, billing info, and ad costs.
• One copy goes to the graphic designers, the other to billing.
• The billing team manually enters everything into QuickBooks, prints invoices, stuffs envelopes, and mails them out.

We recently got new software that lets us send invoices via email and text through QuickBooks, which is a step in the right direction, but it’s just a small fix to a much bigger problem.

What I Want to Change:

• Move everything onto an app or website—no more paper.
• Digitally layout the ad grid instead of doing it manually. (For graphics team)
• Collect billing info online instead of writing it down. (Obviously to get paid faster and reduce wasted labor)
• Automate renewal emails instead of calling every single customer. (Save time)
• Find more efficient ways to generate leads for new business. (Work smarter not harder)

Honestly, the company still runs like my grandma set it up in the '90s, and it’s overwhelming trying to figure out where to start. If anyone has been through something similar or has advice on modernizing a business, I’d love to hear your thoughts! Happy to provide more details if needed.

I’ve explored some CRMs and AI tools, but I’m sure someone here has better insights or more experience with this than I do. There are other parts of the business that need improvement, but I believe this would be a big step in the right direction.

Thanks in advance!