Helping SMB's with Their Top Challenges: Can AI Help Solve?

By: Mike Caprio

I have friends and family who run small businesses — restaurants, service companies, medical offices. When we catch up, I hear pretty consistent feedback on their challenges:

1. Cash flow is unpredictable — especially as vendors stretch out payments.

2. Hiring takes too much time and doesn’t always work out.

3. Finding new customers is harder than ever.

Occasionally I get asked, “Caprio, what would you do?”

So I took some time to dig into the best practices and practical applications for collections, hiring, and lead generation. My goal: keep it actionable for most businesses — something you can test for 30 days and then automate if it works. If any of these ideas help you, or your friends and family who face similar challenges, all the better. 

Let’s Start with Collections.  This is a Big Problem.

Cash flow issues impact nearly 90% of small businesses each year (ASBN). Late payments strain payroll, force emergency borrowing at painful rates, and age owner-operators considerably (you know who you are).

What Most Businesses Do Today (Using Data Manually)

• Pull an aging report from QuickBooks or another system.

• Call or email overdue customers when they remember.

• Offer a small discount for early pay or tack on a late fee.

• Negotiate with vendors to buy time.

These tactics work, but they’re inconsistent. Reminders get skipped, tone isn’t curated, and there’s no time to analyze which customers are most likely to pay late in advance.

Start with the Data: You Already Have 90% of What You Need

Every invoice you’ve sent and payment you’ve received is a signal. With a little discipline, you can make your collections more predictable and effective:

• Segment customers by behavior: who always pays on time, who drifts 30–60 days, who’s chronic.

• Forecast cash flow: if you know slow payers usually take 60+ days, you can plan ahead for payroll or financing.

• Set predictable outreach: Day 30, Day 45, Day 60 — the same cadence for everyone.

Even without automation, this structure makes a difference.

Where AI and Automation Come In

This is the shift: instead of doing all of that manually, AI and automation can make it faster, cleaner, and more consistent.

• AI Reminder Cadence: Tools like Tesorio and Gaviti generate polite, scheduled reminders that mirror your tone. Users report 25% faster collections and up to 70% less staff time wasted chasing invoices. But you can just as easily use ChatGPT, Grok or Google’s Gemini.

• Risk Scoring: AI analyzes past payment history to flag who’s likely to be late this cycle. That way, you focus personal calls where they matter most and even factor that risk into pricing.

• Forecasting Models: QuickBooks AI, Float, or Pulse project your 30/60/90-day outlook automatically, giving you warning before shortfalls.

Practical Example

Say your AR report shows:

• 15 customers always pay net 30.

• 8 customers drift to 45–60.

• 3 customers push past 90.

You could:

1. Feed that data into AI — to auto-score them.

2. Set rules:

   • Net 30 customers → automated friendly reminders.

   • Drifters → firmer notices at Day 30 + a call at Day 45.

   • Chronic → immediate flag for human outreach.

3. Let AI handle the rest: drafting, sending, tracking replies, escalating only what needs you.

Now your staff isn’t chasing every invoice — just the 20% that cause 80% of the pain.

Sample AI Prompt for Collections Email

“Write a professional but firm reminder email for a customer who is 45 days overdue on a $1,500 invoice. Keep it polite, reference our strong relationship, and include a link to pay online.”

30-Day Action Plan — Just Try It

1. Pull your AR aging report.

2. Tag customers into 3 groups: on-time, late, very late.

3. Use AI/automation to schedule reminders for the first two groups.

4. Reserve human calls for the last group.

5. Track your DSO (Days Sales Outstanding) this month vs last.

If this helps you — or helps a friend or family member avoid paying unnecessary points to their lender — that’s a win.

Running a small business is hard, and it’s the lifeblood of our economy. Let’s Pay it Forward.