Win! vs ConnectBooster

A Different Philosophy on How Invoice Payments Should Work

ConnectBooster is built for the MSP ecosystem. Win! is built on the belief that any business invoicing through QuickBooks Online or Xero deserves merchant-owned payment infrastructure, transparent pricing, and automation that runs entirely without manual follow-up.

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Why we built Win!

Win! started with a simple belief: the merchant should own their payment infrastructure. Your Stripe account, your customer relationships, your rate — not a platform's. And payment automation should work for any business that invoices through Xero or QBO, not just those in a specific vertical.

Merchant ownership

Your Stripe account. Your rate. Your customer relationship. Win! processes payments through your account — not ours.

Any invoicing business

Win! works for any company that invoices through Xero or QuickBooks Online — HVAC, electrical, plumbing, professional services, and MSPs.

Transparent pricing

Published plans from $85/mo. No sales call required. Start a free trial in minutes and see exactly what you're paying.

Mobile-first collection

Technicians create invoices and collect payment from any smartphone browser — no app download, no version management.

Different philosophies

Every product reflects a set of choices. Here's how Win! and ConnectBooster approach the same problems from different angles.

DimensionWin!ConnectBooster
Payment infrastructureYour own Stripe account — direct charges, direct payoutsManaged payment processing through ConnectBooster
Accounting scopeQuickBooks Online + Xero simultaneouslyQuickBooks Online — Xero not supported
Platform purposeAR automation for any QBO or Xero invoicing businessPayment collection for MSPs on PSA platforms
Pricing modelPublished flat monthly plan from $85/moCustom pricing — contact sales
Mobile field invoicingBrowser-based Field Tech App — no download neededDesktop-optimised platform
Surcharge complianceBuilt-in, state-aware engine — one toggleManual compliance management

Feature comparison

A factual look at what each platform includes.

FeatureWin!ConnectBooster
Works with QuickBooks Online
Works with Xero
Use your own Stripe account
Rule-based AutoPay
Apple Pay & Google PayNative (via Stripe)Varies by processor
ACH / bank account payments
Field Tech App (on-site invoicing)
Built-in surcharge compliance
Instant invoice reconciliation
Self-serve customer portal
Branded payment pages
Automated payment reminders
SMS payment links
Pay multiple invoices in one checkout
Customer updates payment method self-serve
30-day free trial

Based on publicly available product information as of July 2026.

Where the philosophies diverge

Both platforms automate invoice collection. Here's how the underlying approach differs on the dimensions that matter most.

Merchant ownership: your Stripe account vs. managed processing

Win!'s approach

Win! uses Stripe Connect direct charges. Every payment goes straight to your own Stripe account from the first dollar. You own the account, the rate, and the customer relationship — and you keep any negotiated rate advantage as your volume grows.

ConnectBooster's approach

ConnectBooster operates through its own payment processing relationships. Funds flow through its system before reaching you — a model that works well for many MSPs, but one where the processing account and relationship belong to the platform, not to you.

Accounting scope: Xero + QuickBooks vs. QuickBooks only

Win!'s approach

Win! connects to Xero and QuickBooks Online simultaneously. Every payment marks the exact invoice paid in whichever accounting platform you use — within seconds of the charge. If you ever switch accounting software, Win! moves with you.

ConnectBooster's approach

ConnectBooster is purpose-built for the MSP ecosystem, integrating deeply with PSA platforms like ConnectWise, Autotask, and HaloPSA alongside QuickBooks. That depth serves MSPs well — but Xero isn't in the picture, and the platform is optimised for the MSP workflow specifically.

Reach: any invoicing business vs. MSP ecosystem

Win!'s approach

Win! works for any business that invoices through Xero or QuickBooks Online: HVAC, electrical, plumbing, professional services, and MSPs. The Field Tech App means businesses with field crews can also invoice and collect on-site before leaving the job.

ConnectBooster's approach

ConnectBooster is designed for the MSP and IT service sector. It's an excellent fit for that world — deep PSA integrations, client billing workflows tuned to managed services, and a feature set shaped around the IT support relationship. For businesses outside that ecosystem, Win! is the more natural fit.

Getting started with Win! takes about 15 minutes

No data exports. No bulk uploads. Win! reads your open invoices directly from Xero or QuickBooks.

1

Connect your accounting platform

Authorise Win! to read invoices and contacts from Xero or QuickBooks Online. Open AR syncs immediately.

2

Connect your Stripe account

Link your existing Stripe account (or create a new one in minutes). You own the account — Win! charges through it.

3

Send payment links or enable autopay

Send a branded payment link in one click, or enrol customers in autopay so future invoices charge automatically.

4

Transition on your own timeline

Once autopay is running and your open invoices are being collected, transition at the pace that works for your business.

See how Win! fits your business.

Connect Xero or QuickBooks, link your own Stripe account, and send your first payment link — all in under 15 minutes. No credit card required for the 30-day trial.

Feature comparison is based on publicly available product information as of July 2026. Features and pricing may change. ConnectBooster and all other company names and trademarks referenced on this page belong to their respective owners. Win! is not affiliated with ConnectBooster.

Built on infrastructure you already trust

StripePayment infrastructure
XeroAccounting
QuickBooks OnlineAccounting
Your own Stripe account — funds settle directly to you
Works with Xero and QuickBooks Online
No platform percentage on payments
30-day free trial, no credit card required

What businesses say about Win!

"We switched from QBO Payments and saved more on ACH fees in the first month than Win! cost us. The autopay enrollment alone cut our AR follow-up by 80%."

— Owner, Commercial HVAC contractor

"My accountant was nervous at first. After seeing that Xero reconciliation happened in real time — not end of month — she was sold. Now she recommends it to other clients."

— Director, Managed IT / MSP

"The field tech app is what got us. Techs invoice on-site, customers pay before they leave. We used to wait 45 days for service calls. Now most pay the same day."

— Operations Manager, Electrical Contractor