Operational fit and scale

• To make sure this engagement is the right scale, which range best describes the number of covered lives you expect to include? Options: Under 2,000 (below supported range), 2,000 to 10,000, 10,001 to 50,000, 50,001 to 100,000, Over 100,000 (above supported range)
• Thinking about the next 12 months, do you expect your covered lives to change materially? Options: Stable, Grow under 10%, Grow 10% to 30%, Expect to exceed 100,000 in 12 months (may disqualify)

Technical and compliance dependencies

• How many active carrier EDI feeds or unique vendor integrations does your enrollment environment currently maintain? Options: 0 to 2, 3 to 5, 6 to 10, More than 10 (increases integration complexity)
• Do you process or store protected health information or have data residency or other regulatory constraints we should know about? Options: No, Yes, PHI is processed or stored, Yes, data residency or other regulatory constraints apply
• Please briefly describe the complexity of your most complex plan that you would expect us to validate in tests (one to two sentences).

Budget, decision authority, and timing

• Is there an allocated budget range for outsourcing benefits administration for this initiative? Options: Yes, under $250,000/year, Yes, $250,000 to $1,000,000/year, Yes, over $1,000,000/year, Not yet allocated
• Who will sign the contract and which roles influence the decision? Select all that apply. Options: CHRO or Head of HR, CFO or Finance lead, Procurement, Benefits Head or Total Rewards leader, Cross-functional steering committee, Unsure / need to identify
• What is your target decision or go-live timeframe that would make a full discovery conversation timely? Options: Within 1 to 2 months (urgent), 3 to 6 months (typical renewal window), 7 to 12 months, No defined timeline yet

A quick enrollment snapshot

• Tell me, how many covered lives were included in your most recent open enrollment? Options: 2,000–9,999, 10,000–24,999, 25,000–49,999, 50,000–99,999, 100,000+
• Describe the teams that own benefits enrollment, eligibility, and carrier reconciliation today.
• Which system is the source of truth for your enrollment records, and what other data sources feed it? Options: Your HRIS, Payroll system, A vendor platform, Carrier portals/feeds, Manual spreadsheets, Other
• Walk through a recent new-hire to active coverage timeline, noting the key handoffs and decision points.
• Estimate the monthly volume of enrollment changes you process, including hires, life events, and terminations. Options: <100, 100–499, 500–1,499, 1,500–4,999, 5,000+

Where the process breaks and who notices first

• What single enrollment failure in the last two years triggered executive escalation, and why did it draw that level of attention?
• In that incident, who first detected the problem and how long passed before the CHRO or executive team was informed? Options: Within hours, Same day, 1–3 days, More than 3 days
• Which carrier acknowledgments or EDI exchanges failed most often, and how do you currently surface those errors? Options: EDI acknowledgments, Missing enrollments, Duplicate enrollments, Incorrect coverage tier, Other
• How many employees were impacted by the most recent coverage gap or claim denial event? Options: <10, 10–49, 50–299, 300–999, 1,000+
• If the same failure pattern recurred tomorrow, what would have to change for you to feel comfortable moving core administration to an external managed service?

Who owns escalations and why that matters

• Who is authorized to escalate eligibility exceptions to legal or procurement, and what threshold triggers that escalation?
• List the roles and typical experience level of staff handling benefits calls during peak open enrollment. Options: Call center agents, entry level, Onshore specialists, mid-level, In-house benefits team, senior, Third-party partner staff, mixed
• Do you track first-call resolution, carrier error closure time, and caller satisfaction today? Options: We track all three, We track two of three, We track one metric, We track none of these
• Walk me through a recent escalation from the employee call to final resolution, including who owned each step and the elapsed times.
• What single people-related gap—training, staffing level, or escalation authority—would stop you from selecting an outsourcer?

The metrics that will decide the deal

• What measurable pilot outcome would cause your CFO to approve a contract within 30 days?
• List the SLA targets you need for first-call resolution, carrier error remediation, and enrollment processing time. Options: FCR 95%+, FCR 85–94%, Carrier error remediation <48 hours, Carrier error remediation 48–96 hours, Enrollment active within 4 hours
• How do you currently validate a vendor's platform against your most complex plan design before advancing procurement approval?
• Provide three reports or datasets the finance team requires to model net savings versus internal headcount.
• If pilot metrics meet your targets, what remaining approvals or blockers would still prevent a signature?

Other paths you're weighing

• Who else are you actively evaluating for benefits administration, including internal 'fix-it' plans? Options: Incumbent vendor, Another external outsourcer, Enhance in-house team, Hybrid model
• For each alternative, what single advantage do they claim that most appeals to your stakeholders?
• Should you keep the current in-house approach, what one operational reality would need to be true?
• Has any internal sponsor proposed solving this without an external vendor, and who would champion that position? Options: Yes, benefits leader, Yes, HRIS/IT, Yes, CFO/Finance, No one has proposed it
• Rank the commercial priorities that will sway procurement: price, contract length, exit rights, SLA guarantees, implementation risk. Options: Price, Contract length, Exit rights, SLA guarantees, Implementation risk

Readiness, constraints, and integration blockers

• Name the single integration dependency that would halt migration if it could not be resolved.
• Please enumerate the third-party systems (HRIS, payroll, carrier portals) that must be reconfigured or approved before data extracts begin.
• Identify the person or role who controls the APIs, feeds, or vendor contracts and whether they will be available during onboarding.
• Are your employee data extracts normalized to a single employee identifier across systems today? Options: Yes, normalized, Partially normalized, No, multiple identifiers, Not sure
• How many dedicated IT or HR FTEs can you commit to a three-month parallel run and migration window? Options: 0, 1–2, 3–5, 6–10, 10+
• Identify the single regulatory, legal, or vendor approval most likely to delay go-live and a realistic timeline for that review.

Pilot signals and cutover acceptance

• Assuming a parallel run demonstrates 99% enrollment accuracy and 95% first-call resolution, what internal evidence would still stop sign-off?
• Provide the reconciliation steps and carrier confirmations that must pass before you will accept cutover.
• Name the stakeholders who must sign cutover acceptance and the timeframe they need to review evidence.
• Please specify the dashboards or SLA reports you will require during the first 90 days of live service. Options: Eligibility reconciliation summary, Carrier EDI health, Call center FCR and hold time, SLA incident log, Monthly executive scorecard
• Should the pilot fail to meet a critical acceptance criterion, what remediation or exit options would you expect to see in contract terms? Options: Defined remediation plan with timelines, Financial penalties/credits, Right to exit after cure period, Extend pilot at vendor cost, Other

Decision triggers and next steps

• What single decision or event would accelerate the timeline from evaluation to signature in your organization?
• Which internal stakeholders must be present for an acceptance review to be decisive (legal, procurement, CHRO, finance, benefits operations)? Options: Legal, Procurement, CHRO, CFO/Finance, Benefits operations, IT
• What would you need from the seller in the next two weeks to move to a pilot agreement? Options: Detailed SLA proposal, Carrier EDI test plan, Reference data from similar customers, Security documentation (SOC 2), Cost and commercial terms
• Who should we schedule the next alignment meeting with from your side, and what is the best decision window to aim for? Options: CHRO, Head of Benefits, CFO, Procurement lead, IT integration lead

• Solution Experience: Preventing Coverage Gaps and Meeting SLA Targets

• Confirm the current state and its cost
• You confirm the demonstrated workflow eliminates the specific coverage gap that caused the two-week loss of coverage.
• Deliver SLA performance reports from three comparable employers for review within five business days.
• You validate that the reconciliations and SLA timelines shown meet your risk threshold and reduce executive and litigation exposure.
• Walk a representative failed-enrollment case end-to-end
• Run a platform configuration test against the provided complex plan design and deliver test logs and remediation timelines.
• Demonstrate the error reconciliation and SLA timelines
• Provide the most complex plan design file, recent eligibility error logs, and a sample affected participant case for the end-to-end run.
• You agree on the remaining evidence and tests needed to complete procurement and legal review.
• Run a mock-call audit for first-call resolution
• Schedule a carrier EDI test window and confirm required carrier contacts and endpoint details.
• Validate carrier EDI and complex plan configuration
• Confirm this maps to your required future state
• Agree next evidence and test windows

• Solution Experience: Preventing Coverage Gaps
• Solution Experience Deck
• Solution Brief

• meeting
• slides
• document

• current_state
• decision_readiness
• success_criteria
• desired_state
• gaps
• stakeholders
• gaps
• stakeholders
• desired_state
• success_criteria
• decision_readiness
• current_state
• gaps
• current_state
• desired_state
• success_criteria
• stakeholders
• decision_readiness
• decision_readiness
• decision_readiness
• decision_readiness
• decision_readiness

• Configure Plan Administration in Platform
• Migrate HRIS and Enrollment Records
• Reconfigure Carrier EDI Feeds
• Enable Real-Time Eligibility Activation
• Reconcile Carrier Eligibility and Resolve Discrepancies
• Operate Participant Call Center
• Administer COBRA Continuation Coverage
• Prepare and File ACA Reporting
• Issue Employee Communications and Enrollment Notices
• Execute Parallel Service Run and Cutover
• Handle Service Center Escalations and Case Management
• Deliver Monthly SLA and Operational Reporting
• Implement Annual Plan Change Configurations

Configure Plan Administration in Platform

• Confirm which benefit plan types (medical, dental, vision, FSA, HSA, life, disability) you require configured by plan ID Options: Medical, Dental, Vision, FSA, HSA, Basic Life, Voluntary Life, Short-Term Disability, Long-Term Disability, Other
• List the plan-level rules that must be enforced by the platform (eligibility by service date, waiting period in days, hourly FTE threshold, age-banded rates)
• Provide the naming convention and plan codes from your benefits snapshot or carrier plan sheet used to map plan IDs
• Specify the premium billing split rules required for each plan (employee only, employer contribution percent, company-paid tiers) and indicate any variance by employee class Options: Standard employer contribution, Class-based contribution, Employee-paid only, Variable by location, Other
• Identify approved pay-cycle mapping for premium deductions (biweekly, semimonthly, monthly) and any retro deduction rules Options: Weekly, Biweekly, Semimonthly, Monthly, Custom
• Attach or describe required eligibility rules tied to job codes or bargaining units from your current HRIS

Migrate HRIS and Enrollment Records

• Provide the primary HRIS export artifact you will supply (employee census CSV, full benefits enrollment extract, payroll deduction file) and its expected cadence Options: Employee census CSV, Benefits enrollment extract, Payroll deduction file, Other
• Name the key fields in your HRIS extract that must map to the platform (employee ID, SSN last 4, hire date, hours, job code, home ZIP, email)
• Specify the record volumes for migration: active employees, dependents, terminated with COBRA-eligible, and historical enrollments (example: 12,000 active / 3,500 dependents) Options: <5,000, 5,000-20,000, 20,000-50,000, >50,000
• Identify any data quality issues present in your HRIS extract that will require remediation (duplicate SSNs, missing plan codes, invalid hire dates) Options: Duplicates, Missing plan codes, Invalid dates, Missing contact info, None identified
• Describe your payroll vendor linkage needs for deduction reconciliation (file format, frequency, vendor name type) without naming vendor brands
• Indicate whether terminated employees with COBRA rights should be migrated as active or staged for an administrative handoff Options: Migrated as active, Staged for handoff, Exclude terminated

Reconfigure Carrier EDI Feeds

• Which carrier EDI transaction sets must be established or reconfigured (834 enrollment, 820 premium payment, 276/277 eligibility, 834 reverse feed) and list carrier endpoints you currently exchange with Options: 834 Enrollment, 820 Payment, 276/277 Eligibility, 834 Reverse
• Provide the carrier test plan artifact you can share (test cases matrix, carrier connectivity checklist, sample 834 test file) Options: Test cases matrix, Connectivity checklist, Sample test file, None
• Identify the required transport and security for each feed (SFTP, AS2, secure web service) and whether you have existing certificates to transfer Options: SFTP, AS2, HTTPS API, Other
• Specify acceptance threshold for carrier EDI test runs (number of successfully processed test 834s without reject over N attempts) Options: 1 successful run, 3 consecutive successful runs, No rejects on pilot batch
• Indicate the typical carrier turnaround time for acknowledging test 834s and the external contact point we should use from your carrier list
• Describe any non-standard carrier requirements (plan-specific fields, custom member ID formats, COBRA-specific segment usage) from your carrier addenda

Enable Real-Time Eligibility Activation

• Confirm whether real-time activation is required on a per-plan basis and list which plan codes must turn active within 4 hours of enrollment Options: All plans, Selected plans only, None
• List the integration endpoints that must support real-time confirmation (carrier API endpoints, employer HRIS webhook, payroll API) and their expected availability windows
• Specify the business rule for eligibility confirmation latency you require (example: confirmation within 4 hours for new enrollments) Options: Within 1 hour, Within 4 hours, Within 24 hours, Custom
• Identify fallback behavior if a carrier fails to acknowledge a real-time activation (queue for batch 834, manual carrier reconciliation, notify benefits manager) Options: Queue for batch, Manual reconciliation, Notify benefits manager, Other
• Describe required data elements for the eligibility confirmation payload (member ID, plan code, effective date, employee SSN last 4, enrollment source)
• Estimate peak concurrent enrollments during open enrollment that the real-time activation pipeline must support Options: <100/hr, 100-1,000/hr, 1,000-5,000/hr, >5,000/hr

Reconcile Carrier Eligibility and Resolve Discrepancies

• Identify the reconciliation frequency you require between platform records and carrier files (daily 834 reconciliation, weekly net-change, monthly full file) Options: Daily net-change, Weekly, Monthly full file, Real-time where available
• Provide the maximum acceptable reconciliation divergence rate (for example: <0.5% mismatched member records per pay period) Options: <0.1%, <0.5%, <1%, Custom
• List the top three discrepancy types you expect us to resolve (member ID mismatch, missing dependents, incorrect effective date) and give examples from prior reconciliations
• Indicate who in your team will approve carrier change requests when we require carrier-side corrections and provide their email role (benefits manager, payroll lead)
• Describe the priority and SLA for resolving carrier rejects that cause claim denials (example: P1 within 8 business hours) Options: P1: 8 business hours, P2: 24 business hours, P3: 5 business days, Custom
• State the evidence that will validate successful reconciliation for a given month (reconciliation report with zero unresolved rejects and carrier confirmation)

Operate Participant Call Center

• Specify the service hours required for participant support (examples: 8am–8pm ET during open enrollment, 9am–5pm ET off-season) Options: Business hours only, Extended hours, 24/7
• Indicate the first-call resolution target you require for benefits inquiries (Head of Benefits requires 95% target) Options: >95%, 90-95%, 80-90%, <80%
• List the call types that require agent script and knowledge-base coverage at go-live (enrollment change, eligibility verification, COBRA eligibility, carrier coordination)
• Identify any language support needs beyond English and the expected volumes per language Options: Spanish, Other languages, No additional languages
• Describe performance evidence you will request during evaluation (mock call audits, recorded call samples, average handle time reports) Options: Mock call audits, Recorded samples, AHT reports, All of the above
• Provide required integration points for the call center (case management ticketing system, single sign-on for agents, CRM pop-up) and desired routing rules

Administer COBRA Continuation Coverage

• Confirm whether COBRA administration includes notices generation, premium billing, and beneficiary communications Options: Notices only, Notices + billing, Full administration including payment remittance
• Specify required COBRA notice templates you currently use (initial COBRA notice, election notice, early termination notice) and whether custom legal wording is needed Options: Standard templates, Custom legal wording required, Employer-provided templates
• Identify the census extraction rules for COBRA-eligible events (involuntary termination, reduction in hours) and how you tag qualifying events in HRIS
• Indicate required payment channels for COBRA premiums (lockbox ACH, credit card portal, invoicing) and expected remittance cadence Options: Invoicing, ACH, Credit card portal, Lockbox
• Describe reporting you need for COBRA (active electees, premium aging, electee churn) and required delivery frequency Options: Weekly, Monthly, Quarterly, On-demand
• Identify any state-specific continuation rules or notices we must support (list states with unique forms)

Prepare and File ACA Reporting

• List the employee populations and months of coverage to include on ACA 1095 reports (full-time equivalents by month, stability period definitions)
• Specify whether you require draft ACA forms for internal review before IRS/transmittal filing and the expected review turnaround Options: Draft for review, Direct file without draft, Draft optional
• Provide the payroll and HR data fields required for ACA compliance (monthly hours, offer of coverage code, IRS-required employer info)
• Indicate whether you need reconciliation of monthly FTE counts against payroll and a threshold tolerance for discrepancies Options: Yes, with <1% tolerance, Yes, custom tolerance, No
• Describe the evidence you require for SOC 2 handling of ACA data during transmission to the IRS (encrypted file transfer logs, access audit)
• Identify preferred filing method for ACA transmittal (bulk XML upload, IRS AIR endpoint, third-party transmitter) and whether we should onboard a transmit vendor Options: IRS AIR/XML, Third-party transmitter, Other

Issue Employee Communications and Enrollment Notices

• Specify the enrollment notices required at each phase (pre-enrollment campaign, confirmation emails, proof of coverage letters) and delivery channels Options: Email, Printed mail, SMS, Intranet
• Provide your branding and template requirements for employee communications (logo, legal footer, required disclaimers)
• Indicate whether you require multi-language versions of all enrollment notices and list the languages Options: Spanish, Other languages, English only
• Identify the enrollment confirmation content elements that must appear in notices (plan code, effective date, premium share, carrier contact)
• Describe approval workflow and SLA for communications sign-off (who approves draft and typical review window)
• Estimate the number of employees who will receive paper notices vs. digital only during go-live Options: <5%, 5-20%, 20-50%, >50%

Execute Parallel Service Run and Cutover

• Identify the start and end dates you propose for the parallel run and cutover window including any blackout dates
• List the exact named owners for migration tasks (platform migration lead, payroll coordinator, carrier technical contact) including role email aliases
• Specify the parallel-run acceptance criteria that will gate cutover (example: 99.5% eligibility match, zero high‑priority unresolved carrier rejects) Options: 99.5% eligibility match, Zero P1 unresolved rejects, Custom acceptance
• Describe the rollback plan triggers during parallel run (evidence of claim denials, unreconciled payroll deductions, carrier feed failure) and required approvals
• Indicate required parallel-run artifacts to be delivered (test 834s, reconciliation report, pilot SLA metrics) and their delivery cadence Options: Daily, Weekly, At checkpoints only
• Name carrier and payroll contacts we will call during cutover and confirm availability windows for live support

• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Service Level Agreement (SLA)
• Order Form / Subscription Agreement
• Data Processing Addendum & Security Addendum (DPA)
• HIPAA Business Associate Addendum (BAA) — conditional
• Transition and Exit Services Schedule
• Governance and Reporting Addendum
• Commercial Terms Summary

• Go-live Health Check
• First Measurement Review
• Acceptance Gate Review
• Monthly Operational Review
• Annual Service Quality and Continuous Improvement Review

• Update the monthly SLA report and circulate to stakeholders.
• Agree remediation actions and deadlines for any failed acceptance criteria.
• Publish the acceptance decision document including pass/fail per criterion and the named signatory.
• Open remediation tasks for any failed criteria with target verification steps.
• Execute incumbent decommission or archival steps and confirm completion with evidence.
• SLA performance dashboard review
• Validate current SLA performance against targets recorded in Solution Scope and identify any breaches.
• Close or replan remediation items and confirm next-step deadlines.
• Agree any immediate training or staffing adjustments needed to improve metric performance.
• Re-confirm success criteria and owners
• Refresh the remediation tracker and mark items complete or reassign with new dates.
• Schedule targeted training sessions for identified knowledge gaps.
• Annual SLA trends and benchmarking
• Confirm whether annual performance for first-call resolution rate and eligibility reconciliation accuracy met targets recorded in Solution Scope.
• Agree a prioritized continuous improvement plan with timelines to sustain or improve service quality.
• Confirm compliance posture and schedule for the next SOC 2 evidence review.
• Publish the annual SLA and escalations report with recommended improvement initiatives.
• Kick off the top three agreed improvement initiatives with timelines and verification criteria.
• Confirm upcoming SOC 2 evidence delivery dates and responsible contacts for documentation.
• Confirm the deployment completed to plan and any deviations are logged and owned.
• Agree a short list of immediate remediation actions with resolution dates.
• Establish the cadence and owner for the first measurement review.
• Publish the deployment validation report with all noted discrepancies.
• Compile the initial adoption metrics export for review at the first measurement meeting.
• Open tickets for each blocker with target resolution dates and escalation path.
• Present first measurement data
• Determine whether first-call resolution rate and eligibility reconciliation accuracy are on a path to meet targets recorded in Solution Scope.
• Agree specific corrective actions with completion dates to address any shortfalls.
• Confirm evidence required for the acceptance gate and the date for the acceptance meeting.
• Produce a root-cause report for each underperforming metric with recommended fixes.
• Schedule targeted carrier EDI test runs and revalidation exercises.
• Update the remediation tracker with deadlines and progress checkpoints.
• Restate acceptance criteria and numeric targets
• Record a formal acceptance decision with a named buyer signatory for the managed service deliverable.
• Confirm incumbent system is either decommissioned or retained read-only with data archived or migrated complete.
• Deployment and migration validation
• Cumulative escalations and remediation effectiveness
• Present outcome data against each criterion
• Root-cause diagnosis for metric gaps
• Escalations and repeat-failure analysis
• Remediation burn-down and action tracking
• Document pass or fail per criterion and collect acceptance decision
• Prioritized continuous improvement plan
• Escalations and remediation progress
• Early adoption signals and usage patterns
• Training and staffing adjustments
• Blockers and open issues with owners
• Confirm timeline to acceptance gate
• Compliance and security posture review
• Incumbent system wind-down confirmation
• Immediate remediation actions and next steps
• Agree corrective actions and deadlines
• Agree remediation plan for any failed criteria