Starting the conversation, seeing enrollment through your team's eyes

• Tell me about your most recent open enrollment or qualifying life event window, and who ran it end to end
• In your last enrollment cycle, how many employees were included in the scope we would pilot against Options: Under 1,000, 1,000 to 5,000, 5,001 to 25,000, 25,001 to 100,000, Over 100,000
• Who on your team currently owns enrollment exceptions, carrier reconciliation, and payroll corrections Options: Benefits manager, HRIS administrator, Payroll lead, Shared responsibility, Other
• Which HRIS and payroll endpoints does your team use today for deduction files and imports, including any hosted payroll service or in house export Options: Standard batch import to payroll, API integration with payroll, Manual CSV uploads by HR, Payroll provider managed, Other
• Would a new platform reducing post enrollment corrections by half within the first cycle make you commit to a pilot within 4 weeks Options: Yes, Maybe, with conditions, No

Where the process actually trips up, and what that costs you

• If 4 percent of elections were wrong again next year, what would break first for your people or operations
• When errors surface, which downstream teams get pulled in and how do they spend their time fixing them
• How many manual corrections does your HR team average in a peak enrollment week Options: 0 to 50, 51 to 200, 201 to 1,000, Over 1,000
• Who is the first person employees contact when their coverage or insurance card is wrong Options: HR generalist, Benefits manager, Third party administrator, Carrier, Other
• Explain the step in reconciliation that takes the longest, from detection to resolution

Why the quick fixes keep recurring instead of going away

• Why do you think the issues identified in your audit kept recurring rather than being fixed permanently
• Do you have documented end to end data mappings for plan codes, employee identifiers, and dependents that are regularly used during reconciliation Options: Yes, full documentation, Partial mapping documentation, No formal mappings, Not sure
• Which part of your carrier feed or payroll file process has failed most often in past audits, for example plan code translation, dependent parsing, or deduction sync Options: Plan code mapping, Dependent matching, Salary or deduction timing, Carrier acceptance errors, Other
• Tell me how long it typically takes from the first reported mismatch to a corrected carrier feed or payroll file Options: Same day, 1 to 3 days, 4 to 10 days, More than 10 days
• Would a mandatory compliance review or legal sign off block changes to your enrollment data flows during a pilot Options: Yes, required, Maybe, depends on scope, No

How employees actually experience enrollment, not how the process is described

• Walk me through the last time an hourly employee abandoned enrollment on mobile, what happened and what consequences followed
• On a typical day in an enrollment period, which device mix do you see for employees completing enrollment Options: Mostly mobile, Mostly desktop, Even split, Not tracked
• Rate how clear your current plan descriptions are for someone who is not a benefits specialist Options: Very clear, Somewhat clear, Confusing, Very confusing
• Identify the employee segment with the lowest completion rate and whether that segment must be fully supported in the pilot for you to proceed
• How do employees currently confirm their plan code or coverage before payroll deductions start, and how often does that confirmation fail Options: Automated confirmation works, Manual HR verification, Employees call HR, No reliable confirmation

If a pilot had to prove value fast, what would it need to show

• If a pilot had to prove zero coverage gaps in the first month to convince leadership, what evidence would you need to see Options: Carrier feed audit logs, Payroll deduction confirmation, Employee completion reports, All of the above, Other
• List the carriers and specific plan types that must be included in the pilot to represent your risk profile
• Identify who would sign acceptance for the pilot results, and state whether they can approve conversion without additional executive review Options: Benefits leader can sign, People leader required, Finance required, Executive committee required, Other
• When a pilot meets its acceptance criteria, what internal action would accelerate your conversion decision to production Options: Immediate procurement sign off, Finance approval, Executive sponsor endorsement, No further approvals needed
• Estimate the internal calendar window you can reserve for a pilot cohort without conflicting with open enrollment or major HR initiatives Options: Within 2 weeks, Within 1 month, Within 2 to 3 months, Later than 3 months

Where the alternatives sit, and what would keep you with them

• What alternatives to an external enrollment platform are you actively evaluating right now Options: Keep current process, Upgrade HRIS native module, Build internal solution, Another vendor, Other
• Name the incumbent approach you would keep if it could meet three specific criteria, and list those must have criteria
• Has anyone inside your organization proposed solving this problem without an outside vendor, and if so who and what was the proposed plan Options: Yes, IT proposed build, Yes, HR proposed internal tools, No internal proposal, Not sure
• What outcome would have to be true about your current approach for you to stay with it instead of switching Options: 100% accuracy, Minimal manual intervention, Full payroll integration, Lower total cost
• Assume the incumbent offered to fix carrier feeds at no charge, point to any hidden cost or operational risk that would still make you wary

Operational readiness, the practical gates that can stop a rollout

• Does your IT or integration team already have a named owner for API access and test credentials who can commit to a timeline Options: Yes, owner and timeline available, Owner identified but timeline unclear, No owner identified, Not sure
• Are your legal, compliance, and procurement teams prepared to review a pilot agreement on an accelerated timeline Options: Yes, can review within 2 weeks, Can review within 1 month, Longer than 1 month, Not prepared
• Estimate how many dedicated internal hours your HRIS administrator can allocate to configuration, mapping, and validation during a pilot week Options: 0 to 10 hours, 11 to 25 hours, 26 to 50 hours, Over 50 hours
• Please state who will own providing sample files, test accounts, and carrier contacts during the pilot and whether they have authority to share them
• Name the single missing readiness factor that would stop this project from starting on your target timeline Options: No API access, Insufficient test data, Lack of stakeholder sign off, Budget not approved, Other

Acceptance criteria and measures that actually mean something to your leadership

• Suppose your pilot could only prove one metric to get leadership sign off, which metric would you choose and why Options: Carrier feed match rate, Payroll deduction accuracy, Employee completion rate, Time to reconcile
• Provide the measurable thresholds you require for carrier feed accuracy, payroll deduction correctness, and employee completion to call the pilot successful
• For each acceptance criterion, list the approver and the minimum threshold they require for sign off
• Describe the timing and reporting cadence you expect during the pilot for status, reconciliation, and exception lists Options: Daily, Every 48 hours, Weekly, On demand
• Point out any remaining internal approval that could delay conversion even if the pilot meets all stated thresholds Options: Finance approval, Legal sign off, Executive committee, None

Agreeing next steps, timelines, and responsibilities that get you moving

• Before we agree next steps, which unresolved risk would make you pause or stop this project entirely Options: Carrier refusal to accept feeds, Inability to map plan codes, No internal resources, Budget not approved, Other
• Assign the internal roles who must be available during pilot deployment and select when they are available Options: Benefits manager, HRIS admin, Payroll lead, IT integration owner, Legal or compliance
• Provide your expected count of test accounts and sample employee records you can deliver in the first validation batch Options: Under 50, 50 to 200, 201 to 1,000, Over 1,000
• Outline the escalation path the seller should follow if carrier reconciliation shows discrepancies during the pilot, including who to contact and SLA expectations
• Point to any commercial condition that would prevent you from signing within a week after a successful pilot, such as payment terms, indemnity, or long stop clauses Options: Payment terms, Indemnity clauses, Service level terms, Nothing would prevent signing

• Employee Experience Walkthrough

• Confirm the current state and its cost
• You confirm the demonstrated guided enrollment eliminates the rework you described in Discovery.
• Provide three representative employee records for pilot scenarios (one hourly, one salaried remote, one dependent-add) with expected elections and mobile device types.
• You confirm the mobile experience is clear and usable for both hourly and remote employees.
• Walk a salaried employee scenario end-to-end on mobile
• Share sample payroll file format and HRIS field mapping that the pilot must produce.
• Deliver the exported carrier feed lines and payroll deduction file generated during the session for the reviewed scenarios.
• You confirm that carrier feed outputs match required plan codes for the scenarios or identify specific mapping gaps to resolve before pilot.
• Walk an hourly, remote employee scenario end-to-end on mobile
• Show carrier feed mapping and plan-code output
• You agree on the remaining evidence and acceptance criteria required to run a pilot enrollment.
• Deliver a plan-code mapping document that links the platform plan IDs to the carrier plan codes used in the demo.
• Show payroll deduction file preview and HRIS field alignment
• Validation question: Is this what you meant when you said you needed the guided enrollment to eliminate plan-code errors?

• Employee Experience Walkthrough (Solution Experience)
• Solution Experience Deck
• Solution Brief - Employee Experience Walkthrough

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• Configure Benefit Plans and Contribution Structures
• Configure Eligibility Rules and Event Logic
• Set Up Employee Guided Enrollment Experience
• Deploy Mobile-First Enrollment Interface
• Connect and Map Carrier Electronic Feeds
• Implement Carrier Feed Error Handling and Reconciliation
• Integrate Payroll Deduction File and Mapping
• Synchronize Employee Demographics from HRIS
• Port Prior Enrollment Elections and Dependents
• Execute Pilot Enrollment and Carrier Validation
• Configure Decision-Support Cost Modeling
• Deploy Employee Communications and Messaging
• Train HR and Benefits Administrators on Platform Use

Configure Benefit Plans and Contribution Structures

• How many distinct benefit plans and plan codes need to be configured (include medical, dental, vision, HSA, FSA)? Options: 1-5, 6-15, 16-50, More than 50
• List the contribution tiers you require to be modeled (for example: employee only, employee + spouse, family, custom tiers). Options: Employee only, Employee + spouse, Employee + child(ren), Family, Custom tiers
• Specify the employer and employee contribution rules that must be supported (pre-tax, post-tax, percent of premium, fixed dollar per pay period). Options: Pre-tax, Post-tax, Employer % of premium, Fixed dollar contribution, Proration rules
• Indicate whether you need proration rules for mid-year enrollments and how they should behave for payroll (example: prorate to nearest pay period). Options: Yes - prorate by pay period, Yes - prorate by calendar month, No proration required
• Identify any plan-level business rules that must be enforced (evidence of insurability, waiting periods, age-banded premiums). Options: Evidence of Insurability required, Waiting period applies, Age banded premiums, No special rules
• Confirm whether legacy carrier plan code mappings must be imported and provide the source file format you will supply (for example: CSV of plan code mappings). Options: Yes - CSV mapping file, Yes - Excel mapping file, No legacy mappings to import

Configure Eligibility Rules and Event Logic

• Which eligibility triggers must be enforced from your HRIS (hire date waiting period, hours-per-week threshold, service date, union classification)? Options: Hire date waiting period, Hours-per-week threshold, Service date, Union classification, Other
• Describe any exceptions to standard eligibility (for example: variable-hour employees, seasonal staff, union seniority rules).
• Specify how qualifying life event windows should be calculated for your organization (event date vs. notification date, number of days allowed). Options: Event date basis, Notification date basis, Custom rules
• Who will approve eligibility overrides and how should approvals be recorded (email sign-off, in-platform audit log)? Options: In-platform approval workflow, Email documented approval, Other
• Indicate whether automatic termination-of-coverage rules should trigger in the platform and the required lookback period for retroactive terminations. Options: Yes - immediate termination, Yes - retroactive to termination date, No automatic termination rules
• Identify the exact HRIS fields that determine eligibility for your benefits (for example: employment status, full-time equivalency (FTE), job code, location) and provide field names.

Set Up Employee Guided Enrollment Experience

• Which employee personas must the guided flow support (example: salaried office, hourly frontline, remote contractors)? Options: Salaried office, Hourly frontline, Remote contractors, Seasonal/temporary, Other
• Provide the sample employee scenarios you will use to validate decision-support outcomes (for example: single employee, employee + spouse, family with dependents under 26).
• Specify default recommendation rules the decision engine should use for each persona (for example: recommend lowest out-of-pocket for single, recommend family plan when dependents present).
• Confirm whether you require custom help text, state-specific notices, or compliance language displayed inline for particular plans. Options: Yes - custom help text, Yes - state-specific notices, No additional notices
• Identify the plan cost components employees must see in the guided flow (employee premium, employer contribution, estimated deductible, out-of-pocket maximum). Options: Employee premium, Employer contribution, Estimated deductible, Out-of-pocket max, Network caveats
• Describe any language localization or accessibility (WCAG) requirements the enrollment UI must meet during pilot.

Deploy Mobile-First Enrollment Interface

• Which mobile platforms and versions must be validated in pilot (for example: iOS 14+, Android 10+, mobile Chrome/Safari)?
• Indicate whether offline or low-bandwidth behavior is required for field locations where employees have poor connectivity. Options: Yes - offline support, Yes - reduced assets for low bandwidth, No
• How will you measure mobile success for pilot (example: mobile completion rate threshold, time-to-complete median)? Options: Mobile completion >= 80%, Mobile completion >= 90%, Custom threshold
• Specify mobile-specific features to test such as photo upload for dependent documents, SMS verification, or push notifications. Options: Photo upload, SMS verification, Push notifications, None
• Who will provide mobile Single Sign-On or authentication settings if required (SAML/OAuth parameters)? Options: We will provide SSO details, No SSO required
• List sample employee device types and carriers to include in device compatibility testing during pilot.

Connect and Map Carrier Electronic Feeds

• Which carriers and plan codes will be included in the pilot carrier feed test (please list carrier names and their plan IDs used in the pilot)?
• What carrier feed formats must the platform support for your carriers (EDI 834, flat-file CSV, API JSON)? Options: EDI 834, Flat-file CSV, API JSON, Other
• Who is the technical carrier contact for test feed delivery and which transmission method will they use (SFTP, AS2, API)? Options: SFTP, AS2, Carrier API, Other
• Do carriers require payer ID or plan code transformations during mapping and can you provide a mapping table? Options: Yes - mapping table provided, Yes - mapping table needed, No transformations required
• What is the expected production cadence for carrier feeds (daily eligibility feed, weekly, real-time API)? Options: Daily, Weekly, Real-time/API, Other
• What acceptance criteria will confirm carrier feed mapping accuracy (for example: >= 99% plan code match between platform test 834 and carrier test data)?

Implement Carrier Feed Error Handling and Reconciliation

• Indicate the error thresholds that should trigger automated reconciliation alerts for carrier feeds (for example: missing member IDs, unmatched plan codes). Options: Any error triggers alert, Threshold at 1%+, Threshold at 5%+
• Specify the reconciliation cadence and owner for exception review during pilot (for example: daily ops team, benefits admin weekly). Options: Daily - operations team, Weekly - benefits admin, As-needed
• Identify remediation workflows you need for feed exceptions (auto-retry, manual correction with audit trail, batch resubmission). Options: Auto-retry, Manual correction with audit trail, Batch resubmission, Escalation to carrier
• Confirm whether you require carriage of carrier return files such as EDI 820 or eligibility returns and how they should be ingested. Options: Yes - ingest EDI 820, Yes - ingest carrier CSV returns, No return file ingestion required
• State the service-level expectation for resolving carrier feed exceptions during pilot (for example: 24 hours, 48 hours). Options: 24 hours, 48 hours, 72 hours, Custom SLA
• How many months of carrier feed history must be available for reconciliation during pilot (for example: 3 months, 12 months)? Options: None, 3 months, 6 months, 12 months

Integrate Payroll Deduction File and Mapping

• What payroll system generates your deduction file and which export formats will be used (for example: CSV, fixed-width, XML)?
• Which payroll cycles and effective pay dates must the deduction file align with for your employees (for example: biweekly, semimonthly, monthly)? Options: Weekly, Biweekly, Semimonthly, Monthly
• Provide the payroll file layout specifics we must map to (field names such as employee ID, pay group, deduction code).
• What acceptance criteria will define successful payroll integration during pilot (for example: fewer than 2% manual adjustments on pilot payroll runs)?
• Who will authorize pre-production payroll test runs and shadow payroll validation (name and role), and how will sign-off be documented?
• Specify how retroactive deductions or mid-pay-period enrollment changes should be represented in the payroll feed. Options: Retroactive adjustments in next payroll, Retroactive file with separate adjustment records, Manual adjustments only

Synchronize Employee Demographics from HRIS

• What is your HRIS and which export or API method will you provide for demographic synchronization (SFTP CSV export, REST API, scheduled extract)? Options: SFTP CSV export, REST API, Scheduled extract, Other
• List the exact demographic fields to synchronize from your HRIS (for example: legal name, date of birth, hire date, home address, SSN last 4).
• Specify the synchronization frequency you require during pilot (on-demand, daily, weekly). Options: On-demand, Daily, Weekly
• Which employee identifier will be authoritative for matching records (employee ID, SSN last 4, corporate email)? Options: Employee ID, SSN last 4, Corporate email, Other
• Describe the reconciliation behavior for demographic mismatches (flag and hold enrollment, auto-override with admin approval, notify HRIS owner). Options: Flag and hold, Auto-override with admin approval, Notify HRIS owner
• Confirm whether terminations, leaves of absence, and rehires will be pushed from your HRIS in real time during pilot. Options: Yes - real time, Yes - daily batch, No

Port Prior Enrollment Elections and Dependents

• How many prior enrollment election records must be migrated and what file format will you provide (CSV export, carrier enrollment summary)? Options: Less than 1,000, 1,000-5,000, 5,001-25,000, More than 25,000
• What matching keys exist between prior elections and current HRIS records (for example: SSN last 4, employee ID, DOB) and provide field names.
• Do you require dependent verification during migration (date of birth match, dependent SSN) and what proof must be retained? Options: Yes - DOB match only, Yes - SSN or other documentation, No verification required
• Specify the migration completeness target that will constitute success (for example: 98% of elections matched and imported). Options: 95%+, 98%+, 100%
• Are there legacy plan codes that require transformation during import and can you provide a plan code mapping file? Options: Mapping file provided, Mapping file required, No transformations needed
• Who will validate the migrated elections and what sign-off artifact will they deliver (for example: migration reconciliation report)?

Execute Pilot Enrollment and Carrier Validation

• Which pilot cohort will you enroll (for example: 200 hourly warehouse staff at two sites) and how will participants be selected?
• When will the pilot enrollment window run (start and end dates) and what fallback window is allowed for late completes?
• What evidence will validate pilot success for carrier reconciliation and employee completion (for example: carrier member IDs issued for >= 95% of pilot, payroll files accepted with zero rejects)?
• Who will provide day-of support for pilot enrollment (name and role) and which communication channels will they use for escalation?
• Specify the fallback process if carrier feed or payroll file failures prevent coverage at pilot go-live (for example: manual enrollments, temporary payroll codes). Options: Manual enrollments, Temporary payroll codes, Delay go-live, Other
• Confirm whether you require simulated carrier and payroll test runs prior to the pilot enrollment window and the test data you will supply. Options: Yes - simulated runs required, No simulated runs required

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• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Subscription Agreement
• Order Form
• Service Level Agreement (SLA)
• Acceptance Certificate
• Change Order Agreement
• Data Processing Addendum (DPA) / HIPAA BAA (conditional)
• Operational Handover and Roles Matrix
• Payment Schedule and Invoice Terms

• Go-live Health Check (weeks 1-4)
• First Measurement Review (weeks 4-10)
• Acceptance Gate Decision (around day 90)
• Quarterly Success Review

• Deliver a short training refresh for HR teams addressing any recurring user or configuration errors identified this quarter.
• Restate acceptance criteria from Solution Scope
• Produce a documented pass or fail for each acceptance criterion recorded in Solution Scope.
• Capture a formal acceptance decision with the named signatory for the buyer where applicable, or a documented owner decision for self-serve motions.
• Agree remediation items for any failed criteria with fixed resolution dates and verification requirements.
• Confirm legacy system wind-down status and archive completion or establish final retention plan.
• Publish the acceptance decision record and attached evidence package to the shared workspace.
• Deliver carrier reconciliation reports for all plans flagged as failed and schedule re-validation runs.
• Complete legacy system archive and confirm that read-only access or contract termination steps are documented.
• Trend review of core metrics
• Confirm whether the primary metrics are sustaining at or improving toward the Solution Scope targets.
• Have a prioritized backlog for the next quarter with target dates and verification steps for each high-priority item.
• Identify any process or configuration changes required to prevent recurrence of the top two root causes.
• Publish the prioritized quarterly backlog with resolution targets and required verification evidence.
• Run the monthly carrier reconciliation for the quarter and post the summary of discrepancies and fixes.
• Re-confirm acceptance criteria and owners
• Deployment validation checklist completed and signed as reviewed, with any failed items documented.
• List of critical defects with reproducible steps and target resolution dates agreed.
• Owners confirmed for each acceptance criterion recorded in Solution Scope.
• Produce a deployment validation log that includes sample carrier feed files and payroll file exchange confirmations.
• Publish the initial defects register with reproducible steps and proposed fix timelines.
• Run a reconciliation of the first carrier feed batch and report any mismatches within 3 business days.
• Present first-period outcome data
• Determine whether carrier feed accuracy rate and payroll deduction file match rate are progressing toward the Solution Scope targets, and identify any blockers.
• Agree a timebound remediation plan with verification steps and a confirmed path to the acceptance gate.
• Confirm the data extracts and reconciliation reports required for the acceptance decision are identified and owners assigned.
• Deliver a root-cause analysis for the top three error types observed in carrier feeds and payroll files.
• Publish corrected field mappings and a test plan for re-running the affected carrier feed batches.
• Schedule a verification run of payroll deduction files and capture a signed comparison report for the acceptance packet.
• Present evidence against each criterion
• Deployment and integration validation
• Backlog and blocker burn-down
• Root-cause diagnosis for gaps
• Carrier and payroll reconciliation review
• Early adoption and usage signals
• Document pass/fail per criterion and formal acceptance decision
• Operational exceptions and recurring root causes
• Agree corrective actions and timeline to acceptance gate
• Next quarter action plan
• Carrier and payroll discrepancy reconciliation
• Open defects and blockers
• Confirm acceptance gate readiness criteria
• Immediate remediation plan
• Incumbent system wind-down confirmation