Taxes into Rewards - CRA, Property etc

One of the biggest regular expenses we encounter as self employed Canadians is Taxes. While I've already outlined how you can use the unique bill paying feature of a Canadian Tire Mastercard to pay property taxes without any fees, the rewards are pretty lackluster and the scale of property taxes could be small compared to payroll and installments. In this article we will instead be looking at Paysimply, a service that lets you pay the CRA and many other payees, and discussing when the benefit is worth the fee. Update March 2025 - ChexyTax has launched covering personal taxes with an even lower fee of 1.75%, signing up with my link will earn us both $15, this makes paying personal taxes by credit card to earn rewards and sign up bonuses a viable strategy. Edit After an initial period of only supporting Visa for taxes, Chexy now appears to support Amex as well. Edit 2, as of Aug 2025 Chexy now beta supports corporate taxes making it my defactor choice for business tax spend.

Referrals and disclaimers at the bottom, and as is always the case with business/tax, be sure to talk to your accountant if you're unsure. Just looking for the steps? Jump down to Implementation.

Cost Versus Benefit

It's not uncommon to hear people talking about optimizing their "organic spend", getting the most from money they were going to spend anyways. This might be simply by using credit instead of debit, or by selecting the "right" card (eg. cobalt for food). But for many of us there are expenses that we brush off as "not eligible" for credit cards. You may be aware of services that let you use your credit card for some of these expenses but their fees eat away at your return.

So first of all we need to establish what sort of return we can expect by doing this - can we reliable exceed the 2.49% fee Paysimply charges for corp tax paid with any card and 1.75% ChexyTax charges for individual tax paid with Visa or Amex?

Using common point value estimates you'll find that there are a couple of cards that can earn 2.5% or higher return on uncategorized spending.

Amex Business Platinum 1.25x MR points

TD/CIBC Aeroplan Visa Infinite Privilege 1.25x AP points

Amex Aeroplan Reserve 1.25x AP Points

Amex Business Aeroplan Reserve 1.25x AP Points

RBC Avion Visa Infinite Privilege 1.25x Avion Points

RBC Avion Visa Infinite Business 1.25x Avion Points up to 75k/yr

Each of these cards earns points often valued at 2c so a 1.25x earn rate is effectively 2.5% back. If you're a bit more savvy in your redemptions you may get significantly more value than this, with my redemptions averaging out around 3c each, making 1.25x effectively 3.75%. Certainly, if I reserved my points only for business class travel I could do far better still.

Rogers Red World Elite Mastercard is the only Canadian cash back card worth mentioning for Paysimply. While it earns only 1.5% back base, it earns 2% back if you have at least 1 qualifying service from Rogers, Fido, or Shaw, and if you redeem that cash back against those bills you get 1.5x value. This means provided you have enough Rogers/Fido/Shaw bills, you can get 3% back, but unlike travel points there is no potential outsized upside with savvy redemptions. Unfortunately as a mastercard product it can not be used with Chexy at this time.

With the introduction of Chexy Tax we have another set of cards to consider however, as their platform actually codes as recurring payment. Expect a full article comparing options here but I would highlight one of the best choices below:

Scotia Momentum - 4% back on recurring payments up to $25k/yr spent, and currently available with no first year annual fee

There is also one other card that is certainly worth considering provided your spending is at the "right" level, the Amex Business Gold.

Golden Opportunity

The Amex Business Gold card is a core level card with a manageable annual fee of $199 and a base earn rate of 1x. It doesn't come with all the fancy lounge perks of the Platinum series, but under the surface is an incredible power.

While the advertised 1x rate is nothing special, it has a perpetual spend bonus which can amp up the return over critical thresholds for the right people.

Namely, spend over $20k in a quarter and you get an extra 10k points. That means that if you were to perfectly spend $20k every quarter you'd end up with 120k total for your $80k spend, a return of 1.5x on uncategorized spend. A higher earn rate than the most premium cards with an annual fee that is hundreds of dollars lower - certainly worth considering if your spend could be in that range.

Realistically most people won't be able to perfectly target $20k per quarter so let's consider the breakpoints:

• At $10k/q you earn 10k points or 1x

• At $20k/q you earn 30k points or 1.5x

• At $30k/q you earn 40k points or 1.33x

• At $40k/q you earn 50k points or 1.25x

• At $50k/q you earn 60k points or 1.2x

As you go higher the effective earn rate drops and at 40k/q you're at the same 1.25x you'd get with the business platinum or the premium Aeroplan/Avion cards. But consider that even at 40k, you are still ahead by the difference in annual fee, so depending on other benefits it could make sense.

To put it more clearly, given the Business Gold's ability to generate as much as 1.5x return, if valued at 2 cents per point, this is a 3% return, greater than the fees and the highest uncategorized earn rate in Canada giving the greatest potential for arbitrage with Paysimply.

Is It Really Worth It?

If you're following along you might be thinking that spending 2.5% for 2.5 or 3% doesn't seem worth the effort (and until 22/March/2025 there wasn't the lower fee Chexy Tax option for personal taxes). I'd be inclined to agree but there are some important considerations that this misses. First of all, this can make it very easy to hit the large sign up bonuses that these premium cards frequently carry. For example the Amex Business Platinum has a public SUB of 80k points for $15k spend in 3 months (message me to discuss the best offers that may be available at your spend level). These sign up bonuses significantly increase the return of the approach. For example, if you spent $15k in corp taxes on a newly opened Amex Business platinum, you'd pay $375 in fees but earn ~89k in points worth ~$1800 in travel. Similar math applies for the other premium cards which routinely have SUBs that require $10k+ in spending which you may otherwise not hit. Note that there may be options you aren't aware of as a business owner, feel free to message me to take advantage of my expertise. This also doesn't include the potential for spend related benefits such as Aeroplan cards spending towards frequent flyer status and companion passes, or spending on various US cards that come with benefits like the Southwest companion pass, Hyatt globalist status, hotel free night credits and others. As a specific example, if it is December and you find yourself just short of the SQM necessary to qualify for a meaningful Aeroplan status tier or threshold gift, the additional perk of getting SQM for the tax payment can significantly move the needle.

Between sign up bonuses and spend related benefits, a strong case can be made that paying 1.75-2.49% fee is worth it if you otherwise wouldn't reach those rewards.

Even better, if you're paying business taxes, the transaction fees can reasonably be considered business expenses. This means that even without the boost of sign up bonuses or spend related benefits, spending 2.49% from the corp to earn 2.5% for personal could still be desirable. Discuss with your accountant if this sort of approach matches their interpretation of CRA statements and precedent on the topic, and consider that the more cashlike the reward the less likely it is to be "kosher" so I would personally avoid the Rogers card mentioned above unless you're using it to pay personal taxes and consider the 0.5% arbitrage sufficient for the effort.

You might be wondering why I put such an emphasis on getting at least 2.5% back if this is a corp cost versus personal benefit - wouldn't it still be a win below par? Well I have several reasons

1. This takes time, not much, but some to log in and click around whether it's once a quarter or once a month

2. This takes effort to track, not much, but some to keep track to make sure you don't double pay

How much benefit is enough to merit it is ultimately up to you to decide, and for people looking for clear net positive benefit I would look to the Business Gold or sign up bonuses to get higher than 2.5% return.

Implementation

Let's walk through a simple example step by step for paying business taxes with Paysimply (the approach is similar for other payees). In this example I start off with having my payments made automatically from the CRA and I choose to skip them individually instead of cancelling the PAD to reduce the chance of a missed payment - this is not required. Also note that the more recent launch of the Paysimply app allows you to schedule notifications and save your payment info (Paysimply does not want to have to manage this info themselves, so on their website it is not stored, while it is stored on your phone itself)

• Log into your business CRA account

• Click on managed pre-authorized debits

• Copy down the relevant alphanumeric tax account number

• Select the relevant autopay and click skip next payment, note I don't currently have the skip option visible as I already skipped the next payment but it should be there unless you're within 5 days of scheduled payment

• Go to Paysimply's website and click the button for paying the CRA

• Paste in the account number you copied and select the correct payment type (ie is this an installment or an amount owing).

• Enter the relevant amounts, dates, credit info, and submit.

• Assuming you're paying business taxes, save a copy of the receipt for tax purposes

Still Not Convinced?

The good news is, even if you're unsure about this, it is a low risk thing to try out. The Business gold for example has a sign up bonus of 40k points for $7.5k spend. So long as you can make that minimum you could bail on the whole strategy and still be well ahead of the $199 annual fee. So give it a try for the first quarter, make sure to at least put through $7.5k to get your SUB, but ideally $20k to get the 10k bonus (40k sub + 20k from spend +10k bonus). Was it all too much work to earn that 70k points or do you maybe want to start daydreaming about where they can already take you by Maximizing your Redemptions.

Portugal in business class eh? And maybe you can't help but imagining where you could go next year if you just keep at it for one year.... I mean you already paid the annual fee, so why not? A year in you should have 160k from this card paying your taxes...

Business class with Emirates direct to Dubai. I don't know about you, but that's an experience I know I'd never have otherwise, especially when this is the cash price:

If you're willing to commit a little more than the annual fee of the Business Gold, instead I'd recommend starting with the Amex Business Platinum. Yes the annual fee is higher, but the massive sign up bonus will get you flying even faster. Just reach out and I can help you make sure you're making the right decision and getting the best offer for your situation with a no cost consult.

If you are a particularly big spender, and/or have high taxes, reach out to me to discuss a plan to optimize that is specific to your scenario.

Conclusion

While the right card for you should be tailored to your exact spend amount and the perks that you prioritize, many people can benefit from using Chexy Tax or Paysimply to hit sign up bonuses and unlock spend related perks. Business owners in particular have the most to benefit given their high tax bills and potential tax deductibility of the fees. Broadly speaking the parameters to consider are:

1. How many points can you earn (base multiplier and sign up bonus)

2. How highly you value those points

3. Are there other spend related bonuses that you value (ex. SQM for aeroplan status)

4. What is the transaction fee (2.49% corp, 1.75% individual visa and amex only)

5. Are you able to write off the transaction fee as a business expense

   
   

Also, while taxes are the prime candidate here due to their large scale and potential deductibility of fees, with ChexyTax bringing a lower fee option to many payees, suddenly there is arbitrage opportunity for many things like utilities and property taxes.

If you're considering a business Amex card (gold, platinum, or aeroplan reserve), reach out to me and we can discuss the best card and offers for your circumstance.

Referral links

Use my referral for Chexy to get a $15 credit towards your payments.

If you're interested in the best offers for Amex business cards or to find out what card is the best for your spend pattern and personal values, reach out to me free consult. If you sign up for a card through my referrals, then be assured that I will give personalized advice to help you get the maximum benefit both from earning and redeeming points - getting your travel journey going faster than you ever thought possible.

Search all cards on our platform here.

Check out my Keeper Cards series to see other cards worth exploring

Disclaimer

These posts are all made in good intentions and are to the best of my ability accurate at the time of writing. That said, the official terms and conditions and current sign up bonuses should be verified and interpreted in the context of your personal financial situation. Also, any business and tax related concerns should be considered in the context of you and your accountant's priorities and interpretation of CRA statements.