Is customer loyalty dead or did you just negotiate with the wrong person when bills creep up? Here's the 1 person Kevin O'Leary says Canadians need to call to get a deal

If you’ve noticed your internet bill creeping up, your airline miles shrinking in value or your streaming subscription suddenly costing $5 more, you’re not imagining things.

Across sectors, companies are quietly extracting more money from long-time customers while rolling out deals to newcomers. Experts call it the “loyalty penalty” — and it could cost you hundreds or even thousands of dollars a year.

However, superstar investor Kevin O'Leary has a tip for Canadians looking to trim their monthly budgets and stick it to these corporations that are pillaging more money from loyal customers.

The loyalty penalty

From airline miles to home internet plans, companies have learned that keeping you hooked is cheaper than winning new customers. But instead of rewarding your loyalty, many quietly raise prices.

• Streaming services: Major players like Netflix and Disney+ have raised subscription costs in Canada, so you pay more when you remain loyal to a subscription service.

• Internet and cable plans: Canadians pay among the highest telecom rates in the world (1). However, customers can negotiate discounts of 15% to 25% off prices.

• Car insurance inflation: Car insurance premiums were up 8.7% by December 2024. In Ontario, increases soared by roughly 11.9% (2).

• Airline loyalty programs: Popular programs like Aeroplan have seen the value of points decline. Even long-time frequent flyers find it harder to redeem rewards without paying extra fees.

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Why you should always ask for a retention officer

In a recent video, Kevin O’Leary revealed his negotiation playbook.

“I always call on a bill and say, ‘Let me speak to your retention officer.’ Avoid dealing with the sales rep, because only the retention officer can cut the deal.” He said.

A retention officer is responsible for reducing customer turnover. Their job is to keep you from leaving, often by offering exclusive discounts, fee waivers or bonus perks.

According to a report by Outbound Engine (3), customer acquisition can cost five times more than retaining your current patronage. In addition, Think Impact reports that 65% of company revenue comes from loyal customers, so many businesses offer perks to maintain their following (4).

How to Negotiate Like a Pro

You should come prepared when calling your provider. Here’s how to maximize your chances:

1. Pick the right moment. Pick the right time to switch. If you’re under contract, negotiate your rate just before it expires. Another option is choose a month that’s convenient for you or a time of year when providers typically offer the best deals, like Boxing Day or Black Friday.

2. Ask for your old rate. You can request your previous promotional rate. Many companies are willing to extend a discount rather than risk losing a customer.

3. Negotiate add-ons. If they won’t lower your subscription cost, ask for benefits. Perks like free months of service, waived upgrade fees or bonus loyalty points help make up for the cost.

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Other ways to save on your bills

When a company refuses to negotiate, there are still options.

You can switch providers altogether. Major companies like Bell, Rogers and TELUS let you bundle mobile, internet and TV services to unlock discounts. Some savvy Canadians will rotate account holders among family members to re-qualify for introductory pricing.

Companies are counting on you not to notice rising costs — or not to bother fighting back. But by asking for the right person, doing your research and being willing to walk away, you can turn the loyalty penalty into real savings.

Article sources

CBC: Why are Canadians' cellphone bills higher than other countries? by Katie Pedersen, Virginia Smart and David Common (1); Mychoice: Canada’s Auto Insurance Is Under Pressure from All Sides (2); Outbound Engine: Customer Retention Marketing vs. Customer Acquisition Marketing (3); Think Impact: Customer Retention Statistics (4)