A quick snapshot of your benefits landscape

• Tell me about the account types you offer today and the approximate number of active participants in each (HSA, FSA, HRA, commuter)
• Describe how your annual enrollment cadence works, including any midyear eligibility events Options: Open enrollment only, Open enrollment plus life events, Rolling enrollment year round, Other
• Share which payroll connectivity approach you currently use for benefits deductions Options: Batch payroll files (SFTP), Direct API integration, Payroll export via broker, Manual payroll entries, Not integrated
• Which of these account administration activities are handled in-house versus outsourced Options: Enrollment administration, Contribution reconciliation, Participant servicing, Debit card provisioning, Compliance testing
• How do new hires typically get set up for accounts, and how long until they can access their funds

Where employees actually get stuck

• If participation and engagement don't improve this year, which business outcome would be most affected for your team or finance partners Options: Benefits value perception, Employer budget forecasting, Payroll reconciliation load, Regulatory exposure, Nothing critical
• Identify the top three participant friction points you hear about most from employees Options: Account activation, Card declines at point of sale, Claims submission, Receipt management, Investment enrollment, Balance visibility
• How often does your team receive participant tickets that require manual substantiation or paper documentation Options: Daily, A few times a week, Weekly, Monthly, Rarely
• Give a recent example of a participant issue that required cross-team escalation and tell me why it escalated
• Which single operational failure would make you pause supplier selection or an implementation immediately

Compliance risks that carry real consequences

• Describe a situation where a compliance lapse or audit finding changed how you thought about your vendor choices
• List the IRS or regulatory requirements you consider nonnegotiable for any admin platform Options: Contribution limit enforcement, Eligibility validation, Substantiation tracking, Non-discrimination testing, Audit-ready reporting, Data retention policies
• Does your benefits team run internal audits or compliance checks on plan data, and how often Options: Quarterly, Biannually, Annually, Ad hoc / event-driven, No formal audits
• Who in your organization must sign off on plan design changes, compliance exceptions, or audit responses Options: Benefits manager, HR leadership, CFO/Finance, Legal/Compliance, Broker/Consultant
• Would an inability to provide audit-ready reports within 30 days rule a vendor out of consideration Options: Yes, No, Maybe, depends on scope

Payroll and integrations, where timelines break

• Pinpoint the single integration failure that has caused the longest delay in prior benefit rollouts
• Select the payroll systems or payroll delivery methods you must support for a successful integration Options: Hosted payroll with API, Hosted payroll with file feeds, Custom payroll system, Global payroll provider, No payroll integration required
• Who owns the payroll connection at your company and who do we need to contact to validate access
• Identify which participant data fields must be present in the first feed for activation Options: Employee ID, SSN or alternate ID, Hire date, Payroll deduction amount, Eligibility code, Email and phone
• Are there any contractual or security rules from your payroll vendor that could block exchanging participant files Options: Yes, strict vendor restrictions, Yes, limited windows or formats, No formal restrictions, Not sure

Who decides and how success gets measured

• Name the one executive or committee whose buy-in would accelerate a signed agreement
• Outline the top three metrics your team uses to evaluate benefits vendor performance Options: Participation rate, Time to activate, Reduction in manual claims, Participant satisfaction score, Reconciliation accuracy
• Rank these outcomes by priority for the next 12 months Options: Increase HSA adoption, Reduce FSA forfeiture, Improve participant service, Automate substantiation, Shorten payroll reconciliation
• Suppose a pilot reaches your target adoption numbers, describe any internal approvals that would still be required before full rollout
• Would achieving your numeric pilot goals remove procurement or budget obstacles and allow signing within your desired timeline Options: Yes, Maybe, depending on final terms, No

Operational readiness and the data reality

• Pinpoint the single data quality issue that would stop a launch if it remains unresolved
• Estimate how complete and clean your employee roster and eligibility data are today Options: >95% ready, 80-95% ready, 50-80% ready, <50% ready
• Does your team have a dedicated technical lead and at least one resource available to support integration and testing Options: Yes, dedicated resources, Yes, but limited bandwidth, No dedicated resources
• Provide the typical timeline your IT team needs to approve API credentials or file exchange access Options: 1-2 weeks, 3-4 weeks, 1-2 months, Longer than 2 months
• Name any regulatory approvals, union agreements, or legal reviews that could materially delay an implementation

Alternatives on the table and why they might win

• Share the other solutions you are actively evaluating, including your incumbent and any internal build options Options: Incumbent vendor, Internal build, Broker-managed solution, New market vendors, Other
• Select the single reason you might prefer to stay with your current provider Options: Lower perceived transition risk, Better pricing, Existing integrations, Familiar support model, Contractual obligations
• Would anyone on your team advocate for an in-house solution instead of a vendor, and who would that be Options: Yes, IT, Yes, HR Ops, Yes, Finance, No one currently advocating for in-house, Unsure
• Are there contract terms or legacy data constraints from your incumbent that would keep you from switching even if the new platform met your targets Options: Yes, significant constraints, Some constraints that can be negotiated, No significant constraints, Unsure
• Why would your benefits broker or consultant recommend staying with the current approach rather than moving to a new partner

Acceptance criteria that will make procurement sign

• List the single measurable outcome that would allow you to commit to a vendor within 30 days of pilot completion
• Set numeric targets for the following, if applicable: participation lift, time to activate, reconciliation error rate Options: Participation lift (%), Activation time (days), Reconciliation error rate (%)
• Suppose the platform cannot meet one of your top three metrics during pilot, describe the threshold or contingency that would still allow a go/no-go decision
• Rate how flexible you are on commercial terms if the solution delivers above-target operational results Options: Highly flexible, Some flexibility, Minimal flexibility, No flexibility
• Confirm whether procurement or finance has pre-set deal-size limits that require executive approval Options: Yes, executive approval required, No, procurement can sign, Unsure

Timeline, blockers, and clear next steps

• When is your target launch date for a new benefits administrator, and is that date fixed Options: Within 30 days, Within 2-3 months, Within 3-6 months, No fixed deadline
• Estimate how long your legal and data security review process usually takes for a new vendor Options: 1-2 weeks, 3-4 weeks, 1-2 months, Longer than 2 months
• Summarize any internal initiatives or technology projects that could block implementation during your desired window
• Flag the single person or committee that will raise the final objection if the project stalls
• Specify the next action you want from the seller after this discovery to move toward a decision Options: Technical scoping call, Contract terms draft, Pilot proposal, Reference checks, Proof of concept demo

• Solution Experience Session

• Confirm the current state and its cost
• You confirm the demonstrated payroll integration removes the manual upload and reconciliation steps you described.
• Provide a representative payroll file, the current enrollment export, and a list of 3 participant service scenarios to test before the session.
• Walk through payroll-to-account scenario with your data
• You confirm the participant workflows shown reduce support handling time and map to the adoption improvements you need.
• Identify a pilot cohort and define 2 success metrics and their measurement windows for the pilot.
• Prove participant-service scenario
• Run the provided sample payroll and enrollment scenarios in a test environment and deliver the scenario runbook, results, and a recording before the follow-up session.
• You agree on a concrete set of evidence items and acceptance criteria required before a deployment decision.
• Provide plan rules for contribution limits and eligibility exceptions to validate compliance controls against your design.
• Show compliance and eligibility controls against your plan rules
• Validate the future state
• Agree on remaining evidence and next steps

• Solution Experience Session
• Solution Experience Deck
• Solution Brief

• meeting
• slides
• document

• Configure plan designs and IRS contribution limits
• Provision participant accounts and enrollment
• Integrate payroll for pre-tax contributions
• Issue and activate healthcare debit cards
• Enable mobile app and web access
• Deploy auto-substantiation for point-of-sale expenses
• Set up HSA investment portal and custodial options
• Manage claims submission, adjudication, and reimbursements
• Establish custodial banking and funds settlement
• Run non-discrimination testing and compliance monitoring
• Migrate participant and payroll data from prior provider
• Activate employer admin portal and reporting dashboards
• Configure real-time eligibility verification
• Operate participant customer service and dispute resolution

Configure plan designs and IRS contribution limits

• Which account types will you offer at launch (select all that apply: health savings account HSA, flexible spending account FSA, health reimbursement arrangement HRA, dependent care account, commuter)? Options: HSA, FSA, HRA, Dependent care, Commuter
• How many plan variations (distinct benefit designs) do you require for the initial go-live (for example: single HSA plan, dual HSA/FSA option across employee classes)? Options: 1, 2-3, 4-6, More than 6
• Who on your benefits team owns plan design decisions and will sign off on IRS limit configurations?
• When configuring HSA limits do you require automatic annual updates tied to IRS published limits or manual annual adjustment by your admin team? Options: Automatic annual update to IRS limit, Manual update by admin each year, Hybrid - notify then update manually
• Provide the eligibility classes that affect plan enrollment (for example: full-time hourly, salaried exempt, part-time 20+ hours, union employees) and indicate which account types each class may elect.
• Select which IRS-related compliance artifacts must be generated for your plans: contribution limit audit report, annual Form 5500 inputs, participant year-end statements, or other. Options: Contribution limit audit report, Form 5500 inputs, Participant year-end statements, Other

Provision participant accounts and enrollment

• How will employees enroll: through single-sign-on from your HRIS, a separate enrollment portal, or paper forms to be uploaded? Options: SSO from HRIS, Separate enrollment portal, Paper forms to upload, Combination
• Approximately how many participant accounts must be provisioned at go-live (headcount or estimated active participants)? Options: Less than 500, 500-2,000, 2,001-10,000, More than 10,000
• Describe the data fields required for account provisioning (for example: legal name, SSN last 4, date of birth, hire date, eligibility status) and indicate any fields that are currently missing from your source feed.
• Which enrollment events should trigger account provisioning or changes (new hire enrollment, life event, rehire, QLE documentation)? Options: New hire, Life event, Rehire, Annual enrollment, Other
• Are there multi-company or multi-division hierarchies that require separate employer IDs for accounts and reporting? Options: Yes separate employer IDs, No single employer ID, Need guidance
• Do you expect we should handle participant welcome communications and initial enrollment confirmations or will you provide those messages? Options: We handle communications, You provide messages, We provide templates and you edit

Integrate payroll for pre-tax contributions

• Which payroll provider or system will supply contribution files and ongoing payroll feeds? (name your current payroll system or indicate if using a payroll bureau)
• Which payroll file formats and transport methods will be used for sending contribution files or receiving payroll confirmations (for example NACHA ACH file, CSV payline export, SFTP delivery, API endpoint)? Options: NACHA ACH, CSV export, SFTP, API endpoint, Other
• How often do you process payroll contributions that need to flow to the accounts (each payroll run frequency e.g., weekly, biweekly, semi-monthly, monthly)? Options: Weekly, Biweekly, Semi-monthly, Monthly, Other
• Identify the primary payroll contact who can provision API keys, SFTP access, or scheduled file transfers for initial integration and ongoing troubleshooting.
• Which payroll deduction fields must map to account types (for example: pre-tax HSA elective amount, pretax FSA contribution code, employer HRA funding code)?
• What defines successful payroll integration acceptance for your payroll team (for example: two consecutive payroll cycles processed with zero contribution reconciliation exceptions)? Options: One successful payroll cycle, Two consecutive cycles with zero exceptions, Three cycles with reconciliation within tolerance

Issue and activate healthcare debit cards

• How many physical debit cards should be issued at launch and how many participants should receive virtual cards only? Options: All physical, Some physical and some virtual, Virtual only
• Which card activation methods do you require: phone IVR, mobile app activation, web activation, or employer pre-activated distribution? Options: Phone IVR, Mobile app, Web activation, Employer pre-activation
• List any card controls you require at go-live (for example: MCC blocking for non-medical merchants, single-merchant exclusion, per-transaction limits, ATM restrictions).
• Who will own card dispute escalation within your HR or finance teams and what is the expected SLA for initial dispute acknowledgement?
• Are you expecting cardholder funding to be real-time at point-of-sale or batched settlement from employer-funded accounts? Options: Real-time point-of-sale, Batched settlement, Hybrid
• Specify the acceptance criteria for card issuance and activation (for example: X% of distributed cards activated within 14 days and no more than Y% returned undelivered). Options: Activate rate target 60%+ in 14 days, Activate rate target 75%+ in 14 days, Custom target to be defined

Enable mobile app and web access

• Which authentication methods must be supported for participant access (for example: SSO via SAML/OAuth, email/password, biometric unlock on mobile)? Options: SSO SAML/OAuth, Email and password, Biometric unlock, Multi-factor authentication MFA
• What participant features are mandatory in the mobile app at launch (balance view, transaction history, receipt upload, claims submission, investment portal access)? Options: Balance view, Transaction history, Receipt upload, Claims submission, Investment portal
• Describe any corporate branding or text changes required in the portal and whether you will provide brand assets (logo, color hex codes, copy) prior to configuration. Options: We will provide assets, We need templates provided, No custom branding
• When do you expect mobile app store provisioning and what is your timeline requirement for iOS and Android availability? Options: Both at launch, Android first then iOS, iOS first then Android, Store provisioning not required
• Identify required accessibility standards or corporate policies the portal must meet (for example: WCAG 2.1 AA, mobile accessibility guidelines). Options: WCAG 2.1 AA, WCAG 2.0, No formal accessibility requirement, Other
• Are push notifications and transactional SMS messages required for card activity and claims updates, and do you have an SMS consent policy to share? Options: Push and SMS required, Push only, SMS only, Neither

Deploy auto-substantiation for point-of-sale expenses

• Which merchant categories or point-of-sale data sources should be prioritized for auto-substantiation (for example: pharmacies, urgent care, dental offices, eligible medical merchant category codes MCCs)?
• How do you want the platform to handle transactions missing merchant category codes or with ambiguous MCC assignments? Options: Request manual receipt, Flag for adjudication, Attempt enhanced merchant lookup
• Provide any existing rules your plan uses for auto-adjudicating transactions (for example: threshold amounts auto-approved, recurring prescriptions auto-approved).
• Which participant communications are required when a transaction is auto-substantiated versus when manual receipt is requested? Options: Auto approved notification, Request receipt message, Escalation to adjudication team, All of the above
• Specify the acceptance test for auto-substantiation accuracy (for example: 95% correct auto-approval rate on sampled pharmacy transactions across 30 days). Options: 95% accuracy target, 90% accuracy target, Custom target
• Who will own exception adjudication for transactions that fail auto-substantiation and what turnaround time do you expect?

Set up HSA investment portal and custodial options

• Which investment features must be available at launch (for example: self-directed brokerage, employer default investment menu, automatic sweep to investments at a balance threshold)? Options: Self-directed brokerage, Default investment menu, Automatic sweep, No investments at launch
• Do you have a preferred custodian or do you require a vendor-agnostic integration that supports multiple custodians? Options: Preferred custodian, Support multiple custodians, No custodial investments
• List acceptable investment account minimums and any participant eligibility rules for investing (for example: minimum HSA balance $1,000, enrolled employees only).
• How should investment reporting be delivered to participants and to your finance team (daily NAV feeds, quarterly statements, API access)? Options: Daily NAV/API, Quarterly statements, Participant portal only, Custom reporting
• Identify the custodian onboarding documents we should expect from your side (W9, organizational resolution, custody agreement) and whether they are already available. Options: Available now, Need to procure, Not applicable
• Are employer HSA matching or employer-directed investment contributions planned and how frequently should they post? Options: Yes employer match, No employer match, Match but deferred schedule

Manage claims submission, adjudication, and reimbursements

• Which claims submission channels do you want enabled at go-live (mobile receipt upload, web claims form, mail-in paper claims, vendor EDI)? Options: Mobile upload, Web form, Mail-in paper, Vendor EDI
• What adjudication SLA do you require for typical FSA claims and for escalated HRA reimbursements (for example: 3 business days for standard claims)? Options: 1 business day, 3 business days, 5 business days, Custom SLA
• Describe your desired reimbursement methods for approved claims (direct deposit ACH to employee bank, reimbursement to payroll, check mailed). Options: Direct deposit ACH, Reimbursement to payroll, Paper check mailed
• Are subrogation or coordination-of-benefits workflows required for claims adjudication and do you have existing vendors to integrate for COB? Options: Yes subrogation required, No subrogation, We have an external vendor
• Provide any required document retention periods or evidence rules for substantiation (for example: retain receipts for 6 years per IRS documentation expectations). Options: 6 years, 3 years, Other
• Who on your compliance or benefits team will review adjudication exception reports and what is the expected review cadence?

Establish custodial banking and funds settlement

• Which bank relationship will be used for custodial accounts or do you require us to provision a new custodial bank account? Options: Use existing bank, Provision new custodial account, Undecided
• Which settlement method do you require for employer funding and participant reimbursements (ACH debit/credit, wire transfers, same-day ACH)? Options: ACH debit/credit, Wire transfers, Same-day ACH, Other
• Identify the bank account and routing data fields we will need from your treasury team and whether micro-deposit verification is permitted.
• Specify the expected reconciliation tolerance between payroll remittances and custodial settlements (for example: net variance less than 0.5% per cycle). Options: 0.5% tolerance, 1% tolerance, Custom tolerance
• Are there required fund float rules for your organization (for example: employer holds float for X days before settlement) or fiduciary constraints to observe? Options: No float rules, Employer float days required, Fiduciary constraints exist
• Who is the treasury contact for bank onboarding and ACH authorization (name and role)?

Run non-discrimination testing and compliance monitoring

• Which nondiscrimination tests do you require at go-live and on what cadence (for example: IRC Section 125 eligibility testing for FSAs annually)? Options: IRC Section 125 annual, HSA testing if applicable, Other
• How should failed nondiscrimination test results be remediated and who on your team approves remediation options (for example: corrective contributions, participant refund)?
• Provide the compliance monitoring reports you need for HR and finance (for example: eligibility exception report, contribution limit violations, substantiation failure rates).
• Are you subject to any additional regulatory regimes that affect plan operation (for example: state-level mandates, collective bargaining agreements)? Options: Yes state mandates/CBA, No, Unsure - need review
• Identify the frequency you want compliance checks run (daily transaction scanning, weekly summaries, monthly audit reports). Options: Daily, Weekly, Monthly, Quarterly
• Who will be the designated compliance owner for receiving exception alerts and taking corrective action?

• Order Form / Subscription Agreement
• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Service Level Agreement (SLA)
• Data Processing Agreement (DPA)
• HIPAA Business Associate Addendum (BAA)
• Go-Live Acceptance Certificate
• Roles & Responsibilities and Escalation Matrix

• Go-live health check (week 1-4)
• First measurement review (week 4-10)
• Acceptance gate and formal acceptance (around day 90)
• Ongoing quarterly success review

• Close any remaining compliance exceptions and confirm remediation evidence in the shared channel.
• Implement payroll reconciliation fixes to address missing or mis-mapped deduction records.
• Launch targeted participant communications or training to improve enrollment and contribution setup rates.
• Restate acceptance criteria and numeric targets
• Produce a documented pass/fail decision for each acceptance criterion listed in Solution Scope.
• Agree remediation actions and a timeline to resolve any failed criteria, with verification checkpoints.
• If replacing an incumbent, confirm the legacy system's decommission or retained-read-only status and data migration completion.
• Publish the acceptance decision record with pass/fail results and any remediation plans.
• Schedule remediation verification checkpoints prior to final acceptance closeout if criteria failed.
• Complete archival or migration steps for legacy system data and confirm access status of retired system if incumbent is decommissioned.
• Quarterly metrics trends
• Confirm the solution remains on track against participant adoption and auto-substantiation targets in Solution Scope.
• Ensure open issues are being actively worked and remediation is progressing or completed.
• Agree prioritized enhancement requests and concrete actions for the next quarter.
• Update the shared dashboard with the latest quarterly metrics and circulate for async review.
• Assign owners and target dates for the top three enhancement requests to be addressed next quarter.
• Confirm success criteria and owners
• All deployment validation checks completed and documented with owners for unresolved items.
• Early adoption signals captured and classified as healthy or requiring remediation.
• Issue tracker populated with owners and dates for all high-priority blockers.
• Publish the hypercare issue tracker with owners and target resolution dates.
• Provide a one-page status of payroll feed confirmations and card provisioning counts for the first 7 days.
• Execute the agreed immediate remediation tasks and report status before the first measurement meeting.
• Identify root causes for any metric shortfalls and document specific remediation actions with deadlines.
• Confirm timeline and readiness criteria for the acceptance gate meeting.
• Present first-period outcome data
• Determine if participant adoption rate and payroll contribution setup completion rate are trending toward Solution Scope targets.
• Publish the measurement dataset and dashboard used in the meeting for ongoing tracking.
• Service performance review
• Review transaction integrity metrics
• Present outcome data against each criterion
• Deployment and data migration validation
• Early onboarding and usage signals
• Root-cause analysis for gaps
• Open issues burn-down
• Document pass/fail per criterion and record decision
• Agree corrective actions, owners, and dates
• Blockers and open issues triage
• Enhancement requests and backlog status
• Agree remediation plan for any failed criteria
• Agree immediate remediation actions
• Incumbent system wind-down verification (if applicable)
• Confirm acceptance gate timeline
• Agree next-quarter actions and checkpoints