RFP/RFI Questions to Evaluate Modern Tax Software
Modernize your stack without regrets. Use these ready‑to‑paste RFP/RFI questions to compare vendors on the essentials for small tax practices. The goal: one hub that eliminates re‑entry, delivers fast search, and handles high‑volume document intake with reliable extraction.
1) Integrations & Zero Re‑Entry
Questions
Which accounting systems are natively supported (e.g., QuickBooks Online, Xero)? What’s the sync direction (push, pull, or both)?
After a single update, which downstream records auto‑refresh (workpapers, client profile, returns)?
How do you prevent version drift between ledgers and tax forms?
What’s your field‑level mapping strategy (GL → tax forms) for common entity types (1065/1120‑S)?
What good looks like
True “one hub” behavior: one‑update sync across modules with no copy‑paste.
Clear mapping documentation and conflict detection.
2) Automation, Reminders & Workflow
Questions
Which follow‑ups can be automated (missing docs, signature requests, status nudges)?
Can cadence, timing, and message templates be customized by client segment or return type?
Can automations pause/resume based on client activity?
What good looks like
Built‑in reminders tied to workflow states; little to no manual chasing.
3) Document Intake, OCR & Accuracy
Questions
Which document types are reliably parsed (e.g., W‑2, 1099, bank statements) and what accuracy benchmarks can you share?
Can staff review/approve extracted fields before posting to ledgers/returns?
How are exceptions flagged and routed? Is there a queue with SLA reporting?
What good looks like
Review‑first workflows, reliable extraction for high‑volume documents (including bank statements), and clear exception handling.
4) Client Experience & Portal
Questions
Is the portal mobile‑first with step‑by‑step tasks for clients?
Can clients upload, e‑sign (if supported by the vendor), and view status in one place?
What’s the average client time‑to‑complete a standard request (e.g., W‑2 + 1099 + bank statements)?
What good looks like
Guided tasks, fewer “How do I upload?” tickets, and clear status visibility.
5) Search, Auditability & Controls
Questions
Is search instant across clients, documents, messages, and tasks? Can we scope by entity, year, or document type?
Do you log every change (who/what/when) with exportable audit trails?
Do you support role‑based access with field‑level permissions?
What good looks like
Sub‑second global search; complete audit trails and granular permissions.
6) Security, Compliance & Reliability
Questions
How do you handle encryption in transit/at rest? Any third‑party attestations (e.g., SOC 2) or roadmaps?
Which authentication options are available (SSO, MFA)?
Uptime SLAs, incident history, and data‑retention policies?
What good looks like
Transparent security posture with documented processes and clear SLAs.
7) Pricing, Support & Implementation
Questions
What’s included in base pricing? What variables drive overages (users, storage, e‑signature/KBA, extraction cycles, support tiers)?
Busy‑season support hours and median first‑response time?
Typical time‑to‑value for a 2–15 person firm (from sign‑up to first return or deliverable)?
What good looks like
No hidden fees; responsive support that scales during peak season; clearly defined onboarding steps.
A Sample Scenario to Demo (Clock the Clicks)
Ask vendors to run this end‑to‑end in a live environment using redacted sample docs:
Intake: W‑2 + 1099 + bank statements → document recognition/extraction.
Review: Staff reviews extracted fields; exceptions are flagged and resolved.
Sync: Post approved data to the accounting system; verify no re‑entry.
Prepare: Generate the needed schedules/workpapers; confirm mappings.
Finalize: Client completes outstanding tasks in the portal; status updates automatically.
Track: number of clicks, hand‑offs, exception time, and total cycle time. Favor platforms that minimize manual steps and surface errors early.
At‑a‑Glance RFP Checklist
Native integrations with one‑update sync (no re‑entry)
Automation for reminders/follow‑ups tied to workflow states
Reliable OCR/extraction for high‑volume docs (incl. bank statements)
Mobile‑friendly client portal with guided tasks
Instant, global search
Full audit trail and granular permissions
Transparent pricing; in‑season live support
FAQ
RFP vs. RFI—what’s the difference?
Use the RFI to explore capabilities and narrow the field. Use the RFP to lock requirements, timelines, and pricing.
How many vendors should we compare?
Two to three is enough to spot patterns without analysis paralysis.
How do we validate AI claims?
Request a live workflow demo using your sample documents. Measure clicks, time, exception handling, and search performance.
How to Use This Checklist
Objective: Select a single hub that reduces tools, eliminates re‑entry, and speeds up staff work with fast search and reliable document intake.