| Primary billing job | Focused PSA billingA focused Microsoft billing layer for licences, Azure, managed users, contacts, and custom recurring services while the supported PSA remains the invoicing system of record.[6][2][5] | Broader revenue platformWork 365: broader Power Platform CSP revenue operations across subscriptions, provisioning, invoices, payments, renewals and customer self-service.[11][16] | Start with the operational problem each product is designed to own before comparing individual features. |
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| Published entry price and rollout | From $73.50 monthlyAt the 10-tenant minimum, Sync 365's published USD rate is $7.35 per customer tenant, or $73.50 a month before tax. The 30-day free trial requires no credit card, and the per-tenant rate falls at higher volumes.[7][8] | From $699 monthlyWork 365 publishes plans from $699 a month for its broader platform and says guided onboarding is included. Its typical rollout is four to six weeks, with customer-owned data cleanup and Power Apps licensing or role prerequisites to confirm.[12][18][15] | The published small-MSP entry points differ by $625.50 a month. This is not an equal-scope quote: Work 365 covers a broader revenue platform, so compare the transformation you need as well as price. |
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| New subscription mapping | Reusable AutoMap rulesAutoMap applies reusable Microsoft licence and commitment-term rules to matching new subscriptions, routing each to the configured billing profile and PSA destination automatically or pending review.[1] | Mapped platform rolloutWork 365's broader onboarding configures accounts, contracts, products, billing and optional PSA mappings before trial invoices and validation. Its ConnectWise and Autotask paths then send resolved billing records from Work 365 through one-way integrations.[17][16][14][18] | Compare what happens after setup: where the rule lives, how a new commitment term is routed, whether review is optional, and which system owns the billing record. |
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| Custom recurring services | Derived MSP servicesA configured Microsoft or managed-user count can keep support, backup, antivirus, security, filtering, and other related recurring PSA lines aligned.[2] | Platform contract billingWork 365 manages broad subscription and contract billing inside its revenue platform. The comparison question is whether custom MSP service quantities should live there or be derived beside the existing PSA.[11][17] | MSPs often sell a service bundle around each user, not only the underlying Microsoft licence. |
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| Calculated quantities and overage | Flexible quantity formulasCalculated custom licences add and subtract Microsoft licences, subscriptions, users, custom licences, or fixed values to produce bundles, included-seat deductions, and overage quantities.[3] | Contract calculationsWork 365 can calculate additions for ConnectWise contracts. Buyers should test whether its contract model expresses their user-derived bundles, deductions, deduplication, minimums, and overage rules in the preferred system.[17][19] | The correct quantity may be a formula—such as protected mailboxes minus users already included in the bundle—not a copied vendor count. |
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| Location, department, and split billing | Attribute-driven split billingOffice, city, state, country, department, company, domain, Entra group, and custom attributes can split one tenant into separate billable populations and PSA records.[4] | Contract-led structureThe reviewed Work 365 material covers billing contracts and provider subscriptions; it does not describe the same office, department, domain, group, and custom-attribute population builder feeding separate PSA records.[19][20] | One Microsoft tenant can represent several sites, departments, franchises, cost centres, or legal billing entities. |
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| Azure consumption workflow | PSA-first usage workflowAzure consumption can move through billing profiles, markup, billing-period review, approval or configured auto-approval, and supported PSA posting.[5] | Platform usage billingWork 365 provides Azure usage billing inside its broader revenue platform, including CSP billing workflows. Compare system ownership and approval design rather than treating Azure as absent.[21][11] | Azure comparison should include data timing, markup, period review, approval, exception handling, and the final PSA record—not only ingestion. |
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| PSA ownership and scope | PSA stays in controlSync 365 supports ConnectWise Manage, Autotask PSA, and HaloPSA workflows while the PSA remains responsible for invoices.[6] | Work 365 owns billingWork 365 documents both ConnectWise and Autotask integrations as one-way paths with Work 365 as the source of truth. The ConnectWise path pushes calculated agreement additions after a Work 365 invoice; Autotask receives queued service adjustments after review.[17][16][14] | Clear system ownership prevents overlapping automations and keeps finance confident about which record becomes the invoice. |
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