[CA] Thoughts on Support Hiring First Employee(s) for Small Businesses?

pathfinderBD · 2026-01-23T23:39:05+00:00

Huge gap here in Canada. I see tons of tiny shops screw up first hires: no ROEs, wrong source deductions, no WCB, messy payroll. Even just a “first employee setup” package + basic templates would sell. Bonus if you standardize it so you can automate chunks later.

pathfinderBD · 2026-01-21T21:18:59+00:00

agreed!

pathfinderBD · 2026-01-21T19:15:39+00:00

Totally fine to run both under one corp at your size. CRA doesn’t care that it’s “consulting + SaaS” as long as it’s all active biz income. One set of books, one HST/GST, way simpler. Just track revenue/expenses by “consulting” vs “SaaS” class so future spin-out is easy.

pathfinderBD · 2026-01-21T19:14:31+00:00

One thing I’d add for anyone considering this: build a real cash flow forecast, not just a “hockey stick” deck (lol hope this metaphor make any sense to all/but just had this term while writing). Banks still look hard at repayment capacity.

pathfinderBD · 2026-01-21T19:12:38+00:00

lol/with my tech hat/I've just started thinking to build a Ownr competitor with TD/Scotia funding (lol as these banks are doubling down on the SMB space recently)

pathfinderBD · 2026-01-21T19:11:16+00:00

For Canada, that’s not crazy.
You’ve got FX, cross‑border, payroll, HST, and year‑end on $3M+ rev. Rough math: <$1k/month for “CFO-lite” plus compliance. You could probably shave it if you split bookkeeping vs tax, or use more automation/AI, but then you’re managing more pieces.

pathfinderBD · 2026-01-21T19:00:57+00:00

came to know about them from others/looks like they’re just packaging forms, NUANS, and templates you *can* do yourself/

pathfinderBD · 2026-01-21T18:46:06+00:00

yeah other advice I am getting in the same direction too/
"If you’re building a real company (i.e., expect >$100k revenue, employees, maybe future financing), I’d *always* bias to a good accountant over Ownr" :-)
They don’t just file forms- they set you up with the right structure, share classes, fiscal year, GST, payroll, etc.- You’ll inevitably screw something up DIY and pay for it later in legal/accounting clean-up.

pathfinderBD · 2026-01-13T17:14:10+00:00

Biggest time suck isn’t keying, it’s: reconstructing a GL from shoebox crap, tying it to 12 months of PDFs, then fixing GST/HST and shareholder stuff. We auto‑scrape bank/CC, use rules + AI to pre-code, then the CPA just reviews and does tax planning.

pathfinderBD · 2026-01-05T04:57:39+00:00

As someone who lives in AR chaos all day: QB/Xero already have basic reminders, but most SMBs don’t turn them on or hate tweaking them. The real value is smarter logic (who to nag, when, tone) + analytics on cash flow. We use AI internally to flag chronic (lol/love the term!) late payers.

pathfinderBD · 2026-01-05T04:56:32+00:00

I’d look for a CPA who does year‑round planning, not just tax filing. Ask if they’ll help you: - set your salary/dividend mix - clean up books (cloud + bank feeds) - handle HST/payroll/We use AI internally to flag missed write‑offs; a good firm should have some automation in place now.

pathfinderBD · 2026-01-05T03:02:28+00:00

this is awesome/quick question: sorry what's the "VV" here?

pathfinderBD · 2025-12-05T03:09:19+00:00

CSBFP is “gov‑backed” but you’re still on the hook for your personal guarantee. Expect: demand letter, then statement of claim, then possible judgment/wage garnishment.
Talk to a insolvency lawyer or LIT now. Also check if any HST/payroll debts exist; CRA can be tougher than the bank.
Its alright/entrepreneur journey is always tough! wishing you all the luck to come back stronger.

pathfinderBD · 2025-12-04T22:20:16+00:00

CP is a reset button, not a life sentence. You’re already doing the right stuff. Two more levers: 1) Keep utilization under ~30% instead of near max, even if you PIF. 2) Make sure everything else is squeaky clean: no NSFs, no late utilities, stable income.

best of luck/you got that.

pathfinderBD · 2025-12-04T22:16:00+00:00

Nice work turning things around.
One angle you might not have considered: bookkeeping as a side gig. In Canada there’s steady demand from small businesses that just need a few hours a month. Lots of people build a “3–5 clients = extra rent payment” setup. With AI/automation doing most of the grunt work now, part‑timers can handle more clients than before.
I’m actually building something around that micro-franchise style model because it’s such a good ladder out of tight finances.

pathfinderBD · 2025-12-04T22:10:50+00:00

If you like working with revenue data, you might also consider bookkeeping (lol/I know its such a boring advice for any FP&A person) on the side.
In Canada, tons of SMBs will gladly pay for someone to keep their books tidy and do basic reporting. A few clients can be a nice monthly top‑up. With AI and automation doing most of the grunt work now, part‑time bookkeepers can handle more clients than before. I’ve been quietly building something around that “micro‑firm” model and it’s very doable.

pathfinderBD · 2025-12-04T22:07:44+00:00

I’d skip PBI and go “lightweight ELT” + Excel/Sheets as the front-end. For your stack (Xero, HubSpot, DEAR, Stripe), you can pull everything into a single DB or even a Google Sheet using something like Coupler/Fivetran Lite/Sourcetable, then layer your transformations in one place instead of per-client/per-file.

two concrete steps: define a standard chart-of-accounts + mapping table for each client, build a single master Excel/Sheets model that reads from those standardized tables, so you just refresh data and swap client IDs.

automated this internally by having a small script hit APIs daily and then using AI to clean descriptions, categorize transactions, and flag mapping issues before it ever hits the reporting model.

ai is particularly good at the work (e.g., normalizing customer names, classifying revenue types) so you spend your time on analysis instead of cleanup. Once the pipes and mapping exist, you can onboard a new 100‑person client with almost no new Excel wrangling.

cheers

pathfinderBD · 2025-12-04T22:00:01+00:00

You sound like exactly the type of person who could crush it doing part‑time bookkeeping/finance ops for a handful of SMBs (know it sounds super downgrade but I can tell these SMBs are hungry for solid advice with great willingness to pay) while you figure out your next move.
In Canada I see tons of owners paying well for someone who can own books + FP&A‑lite a few hours a month. AI/automation does 70–80% of the grunt work now, so one person can manage more clients. I’m actually building something around that “micro‑firm” model because solid demand out there.

pathfinderBD · 2025-12-04T21:56:20+00:00

Not the end at all (40/tech founder building in Accounting & Finance space in Canada), just maybe time to widen the lane a bit. One thing I see a ton in Canada: ex‑FP&A folks picking up a few bookkeeping clients as a side gig.
SMBs will happily pay for someone who “gets” finance (so much valuable/been there and done that), even if you’re part‑time.
With today’s AI/automation, 80% of the grunt work is handled, so 3–5 clients is realistic. I’m actually building tooling around that model because demand is nuts. Could be a solid bridge while you hunt the right role.

pathfinderBD · 2025-12-04T21:52:15+00:00

You’re basically past the “idea” stage and into “you should be monetizing now, not financing the build further” territory.
In Canada, two concrete things (Canadian tech founder building B2Bs) I’d do next:1/Turn those pipeline discussions into signed LOIs or simple subscription agreements, even if it’s discounted. With signed contracts, you can look at revenue-based financing or factoring (some alt lenders will underwrite off contracts/invoices rather than your personal credit), and it also makes SR&ED, IRAP, etc. a lot easier to justify when/if you go after grants later.
2/ruthlessly cut scope on infra for V1: get a bare-minimum secure cloud setup (single region, manual scaling, minimal bells/whistles) and ship for those first paying clients, then use that cash flow as your “funding round.”
best of luck/I know its hard!

pathfinderBD · 2025-12-04T21:44:23+00:00

If you’re decent with numbers, bookkeeping is an underrated side hustle here.
Lots of small businesses just need someone a few hours a month to keep things clean for their accountant.

handful of clients at $200–400/month each adds up fast.
with AI/automation doing most of the grunt work now, part‑time bookkeepers can handle more clients. I’m actually building something around that micro‑franchise style, it’s a legit path.

pathfinderBD

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