Americans spend an average of 13 hours per year on hold with customer service. That's nearly two full workdays spent listening to hold music, navigating phone menus, and repeating your account number to a third person.
AI assistants can now make these calls for you — not just "press 1 for billing" automation, but actual conversations with real people on the other end. Here are five phone calls that AI handles particularly well.
1. Shipping Company Refunds
The pain: Your package was late, lost, or damaged. Getting a refund from FedEx, UPS, or any carrier means calling their customer service line, waiting on hold, explaining the situation, providing tracking numbers, and often getting transferred between departments.
How AI handles it: AI calls the carrier, navigates the phone tree, provides your tracking information, and files the refund claim. If the first agent can't help, AI requests a transfer to the appropriate department. If the call gets disconnected (which happens more than you'd think), AI calls back.
Real result: Pine spent 13 days and made 10 phone calls to FedEx to process an international shipping refund for a user. The process involved multiple departments, a local store visit (via web), and invoice waiting periods. The user didn't make a single call.
2. Doctor's Office Appointments
The pain: You need to see a specialist, but the office only takes appointments by phone. You call during your lunch break, wait 15 minutes on hold, then get told the next available is in 6 weeks. You ask about cancellation waitlists, get put on hold again...
How AI handles it: AI calls the office with your insurance info, referral details, and preferred times. If the first call doesn't connect, it retries automatically. No hold time for you.
Real result: A Pine user needed a specialist appointment. Pine called, got disconnected on the first try, automatically retried, and booked the preferred time slot — all without the user touching a phone.
3. Subscription Cancellations and Refunds
The pain: You want to cancel a subscription, but the company makes it deliberately difficult. Some require a phone call (looking at you, retention departments). The agent tries to convince you to stay, offers downgrades, and drags out the process.
How AI handles it: AI calls, declines the retention offers, confirms cancellation, and requests a refund if applicable. It's polite but firm — the perfect cancellation caller because it has zero emotional attachment to the conversation.
Real result: Pine secured a $99 refund from a subscription service that initially cited a no-refund policy. AI emphasized the user's account inactivity, which persuaded the agent to escalate and approve the refund.
4. Insurance Claims and Dealer Add-On Cancellations
The pain: Canceling car dealer add-ons like extended warranties or GAP insurance requires calling the provider, getting the right paperwork, submitting signed forms, and then following up for weeks when nothing happens.
How AI handles it: AI calls to confirm the cancellation process, identifies the required documents, helps you complete them, submits everything, and sends follow-up emails if the provider goes silent.
Real result: A Pine user needed to cancel two insurance add-ons from a car purchase. Pine handled the initial phone call, the email form submissions, and two follow-up emails over several weeks before the provider finally confirmed the cancellation.
5. Airline and Travel Issues
The pain: Your confirmation code doesn't work, your flight was changed, or you need to modify a booking made through a travel agent. Airline hold times can exceed 2 hours, and the issue might require calls to both the airline and the travel agency.
How AI handles it: AI calls both parties, waits on hold (so you don't have to), explains the issue, and gets you a definitive answer. If the phone channel isn't working, AI pivots to email.
Real result: Pine spent 2 hours on hold with an airline for a user whose third-party booking confirmation code wasn't working. When the hold didn't lead to a resolution, Pine sent a formal email and got an official written answer confirming the booking was valid.
Why AI Is Better at These Calls Than You Are
It's not about capability — you could make all these calls yourself. It's about these four things:
| Factor | You | AI |
|---|---|---|
| Hold time tolerance | Low (you have other things to do) | Unlimited |
| Emotional response to rejection | Frustration, giving up | None — retries calmly |
| Follow-up consistency | Spotty (you forget) | Automatic |
| Multi-channel switching | Exhausting | Seamless |
How to Get Started
- Pick the most annoying call on your to-do list
- Provide the AI assistant with the relevant details (account numbers, tracking numbers, dates)
- Let AI handle the call while you do literally anything else
- Get a summary of what happened and what was resolved
Bottom Line
The five phone calls above represent dozens of hours most Americans waste every year on hold, being transferred, and following up. AI assistants handle them faster, more persistently, and without the emotional toll. You don't have to sit on hold anymore — and honestly, you shouldn't.
