40-Point Accounting Software Evaluation Checklist
Score vendors on close performance, multi-entity consolidation, integration depth, security, and implementation scope. Surface hidden costs before you sign.
Scoring Framework
Rate each question 1 to 5 based on the vendor's demonstrated capability. Require live demos for technical items. Promises and documentation aren't sufficient. Vendors that consistently score below the midpoint tend to underperform projections, usually because gaps in close performance, integration, or implementation scope compound through year one.
Evaluation Criteria
Core Financial Operations
30% weightDaily accounting workflows, month-end close, and financial reporting capabilities that directly drive close timing and finance team productivity.
Sample Questions
- Demonstrate closing a month with realistic transaction volume including automated bank reconciliation, accrual entries, and financial statement generation.
- Show exception handling for cross-period adjustments, duplicate payments, and account reclassifications with complete audit trails.
- Create custom financial reports with drill-down to transaction detail and automated distribution to board members.
- Configure approval workflows for invoices over a defined dollar threshold requiring CFO sign-off while allowing recurring payments to bypass approval.
- Display real-time financial dashboard updates when posting journal entries, payments, and invoice transactions.
Multi-Entity and Consolidation
25% weightIntercompany transaction handling, consolidated reporting, and elimination entries for companies with multiple subsidiaries or business units.
Sample Questions
- Process an intercompany sale from Entity A to Entity B with automatic elimination entries and consolidated P&L generation.
- Show multi-currency consolidation with a EUR subsidiary, USD parent, and automatic translation adjustments.
- Create a consolidated cash flow statement eliminating intercompany transfers and shared expense allocations.
- Configure dimension-based reporting allowing analysis by entity, department, project, and customer segment.
- Demonstrate intercompany journal entries with automatic reversing entries and compliance documentation.
Integration and Data Management
20% weightAPI capabilities, third-party system connections, data migration tools, and backup and recovery procedures for business continuity.
Sample Questions
- Import a peak-day batch of Shopify orders in one hour showing API rate limit handling and error processing.
- Demonstrate Salesforce integration syncing opportunity data with custom fields and revenue recognition automation.
- Show Avalara tax integration handling multi-state transactions with exemption certificates and address validation.
- Execute point-in-time backup restoration showing maximum data loss and recovery time for accidental deletions.
- Import an existing chart of accounts with custom fields maintaining all relationships and historical data.
User Management and Security
15% weightRole-based access controls, audit trails, compliance documentation, and security features for financial data protection.
Sample Questions
- Configure granular permissions allowing AP clerks to post payments while restricting access to profit margin data.
- Provide a SOC 2 Type II report and explain data encryption methods for financial information at rest and in transit.
- Show user activity audit trails with IP tracking, login history, and transaction modification logging.
- Demonstrate automated user deprovisioning when employees leave with session termination and access reviews.
- Configure IP restrictions limiting financial data access to office locations and approved remote connections.
Implementation and Support
10% weightProfessional services scope, customization survival through updates, training resources, and ongoing support quality during close cycles.
Sample Questions
- Detail implementation scope including data migration, custom reporting setup, and integration configuration with fixed-price quotes.
- Show customization preservation through software updates including custom fields, reports, and workflow modifications.
- Provide implementation partner credentials with specific industry experience and customer references.
- Demonstrate support ticket prioritization during month-end close periods with guaranteed response times.
- Explain training program including user certification, ongoing education, and new feature rollout communication.
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