Choosing a rollover analysis software is both a compliance decision and a workflow investment, so it deserves careful scrutiny. Making the wrong pick could leave you with documentation gaps, problems at audit time, or surrounded by hidden costs buried in multi-year contracts. The good news: with the right checklist, you can quickly separate software that may check boxes on paper from solutions that actually support your business and keep you audit-ready for the long term.

What True PTE 2020-02 Compliance Looks Like in Practice

The Department of Labor's PTE 2020-02 regulation sets a clear (and tough) standard for documenting every rollover recommendation. Plenty of tools claim compliance, but you want proof that all four regulatory pillars are addressed—not just a disclosure template:

Best interest analysis. The system walks you through each relevant factor: comparing current plans, evaluating all alternatives (including leaving assets where they are), and tying everything back to your client's goals and needs.
Fee and service comparison. You'll be able to clearly outline plan-level and investment-level fees (admin, expense ratios, advisory), along with key features like advice, digital access, and distribution options.
Impartial conduct documentation. Built-in fields prompt you to address compensation, potential conflicts, and your process for unbiased analysis in language that is clear and customizable for your firm.
Full documentation and audit trail. Not just a form to sign, but a client-ready written analysis plus an electronic record of every recommendation and change, time-stamped and secure.

Your litmus test: During evaluation, ask to see precisely where the product covers each required pillar in both workflow and generated reports. If it isn't evident, that's a red flag.

Plan Data: Form 5500 Integration and Flexible Intake

Plan data delays drag down the analysis process. Good rollover tools make finding this information easy. Real Form 5500 integration makes a huge difference:

Breadth matters: Access to 500,000+ employer retirement plans, instantly searchable by company name, and immediately returning critical plan attributes (fees, participants, assets).
Flexible intake: Because real-life is messy, you want three ways to get data: automated 5500 look-up, document upload (with OCR to extract from fee disclosure PDFs), and, when necessary, simple manual entry fields.

We've experienced how a system that supports all three reduces friction not just for us, but for our clients.

Cost, Service, and Investment Comparisons: Going Beyond Fees

Regulators (and best practice) demand more than just a table of fees. Each recommendation should show cost, service, and investment fit side-by-side, tailored to client priorities. Here is what to verify:

You can input and compare plan-level costs, investment costs, and your own advisory/planning fees.
The platform creates clear, multi-year visual comparisons—not just single-year snapshots—so clients understand the bigger picture.
Service analysis is structured. Can you document which features and services are available in each scenario, and which matter most to your client?
Investment fit analysis is explicit. There should be a place to articulate risk tolerance, goals, time horizon, and suitability—not a catch-all note box.

Audit-Ready Documentation: Surviving Regulatory Scrutiny

The best tools make your documentation review-proof, building a bridge from intake to a defensible, professional PDF. What should that really look like?

A comprehensive, plain-English client summary—no industry jargon or fill-in-the-blank boilerplate.
Side-by-side tables or visual charts comparing cost and services across all rollover options.
All required disclosures, conflict documentation, and client acknowledgments included by default.
Full audit trail: Time-stamped records for every recommendation, edits, and the ability to track who did what.
Data retention and security: Confirm AES-256 encryption (or higher) and at least seven years of secure record retention. Ask if you can export your data, too.

This isn't just ticking boxes; it's risk management for your business and reputation.

Efficiency: Real Time Savings and Usability

If compliance takes all day, nobody will use it. Modern rollover analysis should reduce your cycles from hours to minutes:

Manual methods can devour six to eleven hours per case, while automated tools should get you across the finish line in ten to fifteen minutes (or less once you're trained).
The workflow covers all case types (Plan to IRA, IRA to IRA, Plan to Plan), so you're never cornered by limitations.

During any free trial, time yourself on three real-world cases. If you're consistently delivering full, audit-ready analysis and reports in under twenty minutes, you've hit the mark.

Pricing and Contract Considerations

Don't just look at sticker price. Dig into how pricing works—how much do unlimited analyses cost, is there a required contract, any setup or data-access fees, and is public pricing available for easy reference?

Look for transparent, contract-free subscriptions: public pricing (not "contact sales"), true month-to-month flexibility, and all core features (like unlimited analyses and Form 5500 access) included on every plan.
Annual plans should deliver material savings and include enhanced support rather than just bundling a long-term commitment.

Many advisors are shocked to learn the same compliance value can be had for a fraction of the cost charged by legacy platforms—if you choose a right-sized, modern solution.

Testing Before You Commit: A Checklist for Evaluation

How you trial a tool gives you real insight into your future support experience. The ideal: no forced sales call, full access in under a minute, use of all features, and the ability to generate actual reports (not watermarked samples) before you buy. Here's a one-page checklist for effective evaluation:

Compliance: All four PTE 2020-02 regulatory requirements are clearly addressed.
Data integration: Access to 500,000+ employer plans, document upload, and manual data entry all available.
Report quality: Fully audit-ready, professional PDFs, not just data dumps.
Security: Seven-year record retention, strong encryption, and export capability.
Usability: End-to-end time per analysis is 10-20 minutes after brief training.
Pricing: Public, all-inclusive, no-fee pricing at under $1,000/year for most use cases, with no forced multi-year contract.
Trial experience: Free 14-day trial requiring no credit card and no sales call to start.

Considerations for Firm Type and Growth

The right solution flexes with your needs:

RIAs and solo advisors: You want professional documentation, time efficiency, and predictable, publicly posted pricing. Unlimited analyses and fast setup (five minutes or less) are make-or-break features.
Broker-dealers and compliance officers: Team oversight matters. Tools should include user management, role-based controls, dashboards, risk pattern detection, and centralized regulatory reporting. Implementation should still be quick—not months—and pricing should scale much less steeply than with legacy enterprise offerings.

If you're curious about compliance requirements for fiduciary rollover recommendations, our in-depth resource explores PTE 2020-02 documentation in detail.

Reporting, Branding, and Integration Roadmap

Your client and regulatory deliverables should reinforce your firm brand and ensure a seamless workflow. In evaluation, confirm that reports can be generated instantly in clear, client-friendly formats and (if needed) look for planned features like custom branding and multi-user permissions. Secure, robust integration with your CRM or documentation system is a problem worth solving early—ask vendors about available API or SSO offerings and their current roadmap.

Summary: Bringing It All Together

In our experience, the best results come from a rigorous but practical evaluation. Take a live or sample case, run it through the platform you're testing, and see if you're able to document all required PTE 2020-02 elements, generate a professional report, and be confident you could survive a DOL audit—all in a fraction of the time it once took.

If your workflow still includes manual data entry, scattered fee disclosures, or cobbled-together PDF templates, it may be time to invest in a process that lets you focus on advising, not paperwork risk. And if you want to understand exactly how modern automated rollover analysis streamlines your workflow while ensuring compliance, you can always start a free 14-day trial with Simple Advisor Tools—no credit card and no sales call required.

For advisors wanting more hands-on troubleshooting tips around rollovers, our practical guide walks through common rollover analysis errors and workflow enhancements.

Rollover Analysis Software: What to Look for Before You Commit (A Practical Checklist)