Starting Simple: Your Current COBRA Snapshot

• Tell me briefly how your COBRA process is currently owned and staffed.
• How many employees are on your benefits roster, and how many qualifying events do you see in an average month? Options: Fewer than 500 employees, 500 to 1,000, 1,001 to 5,000, 5,001 to 10,000, More than 10,000
• Which benefits plans do you offer that trigger continuation obligations, select all that apply. Options: Medical, Dental, Vision, Flexible spending account, Health reimbursement account, Other
• Roughly what percentage of your qualifying events come from terminations versus reductions in hours or other reasons? Options: Mostly terminations (over 70%), More terminations than reductions (50-70%), Balanced (30-50% each), More reductions than terminations, Mostly reductions or other
• Who is the primary point of contact for COBRA on your HR side, and which teams in payroll or finance are also involved? Options: HR operations, Benefits team, Payroll team, Finance/accounts payable, Outsourced HR/PEO, Other
• Describe the last time a qualifying event created an exception to your standard process, what went wrong, and how you resolved it.

If Regulators Looked Back at Your Notices

• If a regulator audited last year, what single notice or eligibility finding would make you most concerned? Options: Late election notices, Incorrect eligibility determinations, Missing proof of mailing, Incorrect termination dates, Carrier remittance errors, Other
• How often in the past two years have you experienced notice timing errors, eligibility mistakes, or missed mailings? Options: None, Once, A few times (2-5), Several times (6-12), Frequent (monthly)
• When one of those incidents happened, what was the most immediate operational or financial consequence for your team? Options: Regulatory fine or penalty, Broker or legal escalation, Participant complaints and manual fixes, Material administrative overtime, No measurable consequence
• Who typically uncovers compliance gaps and how do you currently document corrective actions? Options: HR team discovers and tracks, Payroll discovers and tracks, Broker or carrier discovers and escalates, External auditor finds issues, No formal documentation process
• If you had to pick one metric that, if it stayed below target, would make you stop the project immediately, which metric would that be? Options: Notices on time (%), Notice accuracy (%), Payment collection rate (%), Carrier remittance on time (%), Participant enrollment rate (%)

Where Your Current Handoffs Break

• Which handoff between HR, payroll, and benefits produces the most delays or data errors? Options: Termination capture to HRIS, HRIS to payroll, Payroll to benefits enrollment, Enrollment to carrier updates, Other
• Walk me through the exact steps from an employee termination to election notice generation in your current setup.
• How are qualifying event triggers recorded today, and what required fields are captured (for example, termination date, reason, benefit elections)? Options: Minimum fields captured, Moderate detail captured, Full event detail and attachments captured, Inconsistent across teams
• Do you have a standard owner who verifies coverage dates and dependent eligibility before notices are mailed? Options: Yes, HR operations, Yes, benefits administrator, Yes, payroll, No single owner, ad hoc review, Other
• What breaks downstream when a notice is late or an election is mis-recorded? Options: Participant coverage gaps, Carrier disputes, Regulatory exposure, Billing and remittance reconciliation, Broker escalations, All of the above

Which Systems Must Work for Automation to Win

• Point to the single system whose integration is most critical for reliable notice generation and why. Options: HRIS, Payroll, Benefits enrollment system, Third-party timekeeping, Other
• List the HRIS, payroll, and enrollment platforms that currently hold the source of truth for eligibility and termination data.
• Are APIs, secure FTP, or flat file exports available from those systems, and who on your side manages access? Options: APIs available and IT owner identified, SFTP available and IT owner identified, Flat file exports only, No automated export available
• How often are employee and termination files updated, and do you have backfills available for historical events? Options: Real time or near real time, Daily batch, Weekly, Ad hoc/manual updates, No historical backfill
• If granting integration access requires IT approval, what approval timelines and gates could push your go live beyond the quarter? Options: Less than 2 weeks, 2 to 4 weeks, 4 to 8 weeks, More than 8 weeks, Unknown

Who Will Own This When Things Go Wrong

• Name the roles that sign off on compliance exceptions and who can authorize service level decisions.
• List the internal stakeholders who expect regular reporting on notices, enrollments, and payment status. Options: HR leadership, Benefits manager, Payroll, Finance, Legal, Broker/advisor
• Tell me how your benefits broker or third-party advisor is involved in vendor selection and escalation handling today. Options: Broker manages vendor selection, Broker consulted but not owning, Broker handles escalations, No broker involvement
• If a participant disputes enrollment or payment, what is the current escalation path and typical timeline to resolution? Options: Resolved in under 3 business days, 3 to 10 business days, More than 10 business days, No formal escalation path
• Identify the person or role with final authority to pause participant billing or change remittance routing in an emergency.

Alternatives You Are Seriously Considering

• Imagine you keep your current approach, what would that cost you in time, money, or risk over the next 12 months?
• Describe the options you are actively evaluating today, including incumbents, other vendors, broker-managed paths, or internal solutions. Options: Staying with incumbent vendor, Switching to another vendor, Broker-managed solution, Do it internally, PEO or outsourced HR partner, Other
• What would have to be true about your current approach for you to choose to stay with it instead of switching? Options: Lower cost, No change in workflow, Improved SLAs, Better reporting, Vendor commitment to custom work, Other
• Has anyone within HR, finance, or legal proposed solving COBRA without an outside vendor, and what path did they suggest? Options: Yes, internal build suggested, Yes, use existing payroll vendor, No internal proposal, Other
• Which single concern about switching vendors, if unresolved, would make you cancel the selection process? Options: Data security and privacy, Integration complexity, Cost, Service continuity, Carrier acceptance, Other

Budget, Timing, and the Things That Stop Deals

• What single timing or budget constraint would stop this project from moving forward this quarter? Options: No allocated budget this quarter, Procurement freeze, Key stakeholder unavailable, Compliance audit in progress, Other
• Identify the budget owner for benefits operations and the person who signs vendor contracts.
• Provide your target timeline for pilot start, pilot evaluation period, and full production rollout. Options: Pilot in 2 weeks, Pilot in 1 month, Pilot in 2 to 3 months, Pilot in 3+ months, No timeline set
• Are there procurement or legal review steps that regularly add weeks to your vendor onboarding, and if so how long do they usually take? Options: No formal reviews, Legal review only, 1-2 weeks, Procurement and legal, 2-6 weeks, Enterprise procurement 6+ weeks, Unknown
• Should a pilot hit the key metrics, what internal approvals and timing would allow you to sign within seven days?

The Numbers That Will Decide This

• Name the measurable outcome by month three that would make you call the engagement a clear success. Options: Notice timeliness, Notice accuracy, Participant enrollment rate, Payment collection rate, Carrier remittance accuracy, Participant portal adoption
• Select the KPIs you care about most from this list. Options: Notices on time (%), Notice accuracy (%), Election/enrollment rate (%), Participant payment collection rate (%), Carrier remittance on time (%), Participant portal activation (%), Number of compliance incidents
• For the top KPI you chose, what is your target threshold in the first 90 days? Options: Above 95%, 90% to 95%, 80% to 90%, Below 80%, No target set
• If performance falls below targets, who on your side can require remediation and what remediation timeline would satisfy your team? Options: HR leadership, Benefits manager, Finance, Legal, Procurement
• Which SLA failure would be immediate grounds to pause new enrollments or escalate to your legal team? Options: Repeated late notices, Notice accuracy below threshold, Missed carrier remittances, Material data breach, Other

Practical Readiness: Files, Test Windows, and Who Does the Work

• Should we schedule a test window next month, what is the one missing item on your side that would block it immediately? Options: No sample files, No IT availability, No test data, No carrier test access, No internal approver
• Do you have sample termination and enrollment files available for an initial mapping exercise? Options: Yes, sample files ready, Files available after request, Need to generate samples, No sample files available
• Please name the person or team on your side who will run acceptance tests and estimate how many hours per week they can commit.
• Confirm whether carrier remittance instructions and ACH routing are ready to test, and whether your finance team can share a sample remittance file. Options: Ready and sample available, Ready but need request, Not ready, Unsure
• When a data mapping reveals incompatible fields, do you have a fallback manual process that can be sustained during remediation? Options: Yes, manual process defined, Partial manual workarounds, No fallback process, Unsure

If This Moves Fast, What Happens Next

• If the pilot proves the numbers, what stops you from signing the contract that same week? Options: Final legal terms, Budget approval, Procurement gating, Executive sign off, Nothing, we could sign quickly
• What would your ideal go live date be, and what timeline feels realistic given other priorities? Options: Within 30 days, 30 to 60 days, 60 to 90 days, 90+ days, No firm date
• Provide the names and roles of people who need to be in the contract approval loop from legal, procurement, HR, and finance, and indicate who signs.
• Are there non negotiable contract terms or data handling requirements that must be included before you will run a pilot? Options: Data processing addendum required, Specific SLA thresholds, Background checks or SOC report, Carrier integration guarantees, None
• If we agree on scope and pricing today, what is the single next internal approval you need and how fast can it be obtained? Options: Legal approval in 1-2 days, Procurement approval in 1-2 weeks, Executive approval in 1-2 weeks, Budget cycle delay, Other

• Solution Experience Session

• Confirm the current state and cost
• You confirm the demonstrated workflow eliminates the risk of missed statutory election notices for the shown scenarios.
• Run the buyer's three provided qualifying event scenarios in the sandbox and deliver an annotated event timeline and evidence package before the next meeting.
• You confirm the enrollment and premium collection flow reduces manual handoffs and produces audit-ready evidence acceptable for your compliance needs.
• End-to-end scenario walkthrough, intake to notice
• Provide 2-3 redacted real qualifying event records, your current election notice templates, and your HRIS event feed specification.
• Enrollment and premium collection walkthrough
• Confirm decision criteria and target procurement timeline for this service.
• You agree on the remaining evidence required to reach a purchasing decision and a target timeline for that evidence delivery.
• Carrier remittance and reporting proof
• Schedule a follow-up decision review with the buying committee after evidence delivery.
• Operational exceptions and escalation handling
• Validate the future state
• Agree remaining evidence and next steps

• Solution Experience Session
• Solution Experience Deck
• Solution Brief

• meeting
• slides
• document

• HRIS Event Integration and Intake
• Multichannel Election Notice Distribution
• Election Notice Proof and Service Records
• Participant Enrollment Processing
• Premium Invoicing and Online Payment Portal
• Payment Processing and Reconciliation
• Carrier Premium Remittance and Reconciliation
• Coverage Termination for Nonpayment
• State Mini-COBRA Compliance Administration
• Participant Support and Case Management
• Secure Participant Portal and Document Upload
• Reporting Dashboard and Exportable Reports

HRIS Event Integration and Intake

• Do you currently generate a qualifying event file from your HRIS or payroll system? Options: Yes, No
• How does the qualifying event feed reach your vendors today (SFTP batch, API push, secure email, manual spreadsheet)? Options: SFTP batch file, API push/webhook, Secure email with attachment, Manual spreadsheet upload, Other
• Which HRIS fields are included on your feed for each terminated employee (last day worked, termination reason code, dependent list, plan tier, COBRA eligible flag)?
• When should we consider an event 'received' for start of the 14-day notice window (timestamp on file, HRIS effective date, payroll termination date)? Options: Timestamp on file, HRIS effective date, Payroll termination date, Other
• Identify the person or role in your HR team who will approve inbound event reconciliation exceptions.
• Provide any connector coverage requirements (list of HRIS platforms to connect and minimum connector availability percentage e.g., 99.5%).

Multichannel Election Notice Distribution

• Please list the notice delivery channels you require for COBRA election notices (first class mail, certified mail, email with link, SMS opt-in). Options: First class mail, Certified mail, Email with secure link, SMS notification
• Provide the statutory mailing/notice windows that must be met for your workforce and any state-specific shorter windows we should enforce.
• Specify the return-mail handling preference (scan and attach images to case, forward to a distribution address, discard after upload). Options: Scan and attach images, Forward physical mail to address, Discard after upload
• Indicate if you require bilingual or translated notice templates for specific states or workforce segments and which languages. Options: English only, Spanish, Other languages (specify)
• Select the address verification approach we should use for mailed notices. Options: Use employer-supplied addresses as-is, Validate and correct against postal database (USPS), Use a combination with review
• Identify any business rule exceptions that should pause automatic notice generation (e.g., disputed termination, pending FMLA return).

Election Notice Proof and Service Records

• Describe the evidence you require to accept that a notice was sent within the 14-day federal COBRA window (postage date, USPS certificate, electronic delivery timestamp).
• Choose the proof artifacts you need stored on each participant record for audit readiness. Options: PDF of mailed notice with USPS certificate, Email delivery receipt with timestamp, SMS delivery logs, All of the above
• Confirm the retention period for notice service records and whether records must be exportable in bulk for audits (e.g., 7 years). Options: Retention 3 years, Retention 7 years, Retention 10 years, Custom retention period
• What measurable acceptance criteria will validate notice timeliness and proof for go/no-go (e.g., 100% of sampled notices have postmarked date within 14 days, 0% late notices in pilot of 200 events)?
• Indicate the owner on your side who will verify notice proofs during deployment testing.
• Attach or describe any legal wording or company-specific notice language that must be included in the election notice template.

Participant Enrollment Processing

• Select how participants will submit elections and enrollments back to the platform. Options: Online secure portal, Returned paper form scanned, Email with secure upload, Phone-assisted enrollment
• Describe required enrollment data elements we must capture to enroll a participant into the carrier (plan code, effective date, SSN last 4, dependent DOBs).
• Specify whether you require automatic enrollment mapping to your carrier plan codes or a manual enrollment handoff. Options: Automatic mapping to carrier plan codes, Manual enrollment handoff
• Indicate the turnaround SLA you expect for processing a completed election into an enrollment (e.g., within 2 business days). Options: Same day, 1 business day, 2 business days, 3+ business days
• Identify any eligibility rules we must enforce before accepting an election (e.g., dependent verification, COBRA qualifying event types excluded).
• Describe how enrollment corrections should be handled post-submission (edit with audit trail, require re-submission, contact support). Options: Edit with audit trail, Require re-submission, Contact support for manual change

Premium Invoicing and Online Payment Portal

• Which billing cadence do you require for participant invoicing (monthly in advance, monthly in arrears, custom cycle tied to termination date)? Options: Monthly in advance, Monthly in arrears, Custom termination-date-based cycle
• Specify the payment methods you will accept through the portal (ACH debit, credit card, lockbox check remittance). Options: ACH debit, Credit card, Lockbox check, Other
• Indicate whether you require invoice branding with your employer logo and any specific invoice line-item requirements. Options: Use employer branding, Use vendor branding, Hybrid (employer logo only)
• Estimate the expected monthly participant billing volume at go-live and at 12 months. Options: Less than 100, 100-1,000, 1,000-5,000, More than 5,000
• Describe required retry and late-fee rules for failed payments and the days-to-delinquent thresholds to apply.
• Provide any special payment reconciliation needs such as employer-paid COBRA segments or retroactive premium adjustments.

Payment Processing and Reconciliation

• Identify the ACH or merchant processor arrangements you plan to use or need us to integrate with (bank ACH originator, merchant gateway via API).
• Specify the expected settlement timeline for participant payments to reach the employer or carrier settlement account (T+0, T+1, T+2). Options: T+0 same day, T+1, T+2, Other
• Choose the reconciliation artifacts you need delivered (daily settlement file, transaction-level CSV, exception report). Options: Daily settlement file, Transaction-level CSV, Exception report, All of the above
• What measurable acceptance criteria will confirm payment processing accuracy for deployment (e.g., 99.9% matching of receipts to invoices on 30-day pilot)?
• Describe your desired process for handling unapplied or unidentified payments and who on your team will investigate.
• Indicate whether you require daily notification of payment exceptions and the preferred delivery method. Options: Daily email report, Daily dashboard alert, Both

Carrier Premium Remittance and Reconciliation

• Which remittance format do your carriers accept (EFT with 835-like remittance file, lockbox check, carrier portal upload CSV)? Options: EFT with remittance file, Lockbox check, Carrier portal CSV upload, Other
• Specify the carrier acceptance rules we must enforce on remits (per-participant payment mapping, batch-level only, separation by plan). Options: Per-participant mapping, Batch-level remittance, Separated by plan
• Indicate the reconciliation cadence you require between remitted amounts and carrier acknowledgments (daily, weekly, monthly). Options: Daily, Weekly, Monthly
• What measurable acceptance criteria will validate successful carrier remittance and reconciliation during pilot (e.g., 100% carrier acknowledgments for 30-day pilot, zero misapplied remits)?
• Identify any carrier-specific onboarding artifacts we must produce (test files, connectivity certificates, carrier mapping spreadsheets).
• Describe the escalation path if a carrier rejects a remittance or reports a payment discrepancy.

Coverage Termination for Nonpayment

• Specify the grace period and delinquency rules before coverage termination (e.g., 30-day grace, 60 days then terminate). Options: 14-day grace, 30-day grace, 60-day grace, Custom (specify)
• Describe required notice cadence to participants before termination and whether notices must be mailed and emailed.
• Identify any state statutes that require extended notice or special handling for nonpayment in your jurisdictions of operation.
• Indicate whether retroactive reinstatement after termination is allowed and the conditions for reinstatement. Options: Allow reinstatement with catch-up payment, No reinstatement allowed, Case-by-case
• List the downstream systems that must receive termination events (carrier feed, employer HRIS, participant portal). Options: Carrier feed, Employer HRIS, Participant portal, All of the above
• Provide the person or role who will approve terminations for nonpayment on your side.

State Mini-COBRA Compliance Administration

• Name the states where you operate that have mini-COBRA rules we must support.
• Describe any state-specific timelines or notice language differences we must enforce for those states (example: 10-day notice requirement in State X).
• Indicate whether you need automated statute lookup per participant based on worksite state or employer location. Options: Yes, automate by worksite state, No, we will provide state rules manually
• Specify how you prefer statute updates to be handled and communicated (automatic rule updates, monthly change log, notification emails). Options: Automatic rule updates, Monthly change log, Notification emails
• Identify any state-mandated premium caps, coverage durations, or special election pathways we must implement.
• Provide sample state-specific notice text or references to statutory citations we should validate against.

Participant Support and Case Management

• Select the support channels you require for participants (phone support, email, in-portal chat, scheduled callbacks). Options: Phone support, Email support, In-portal chat, Scheduled callbacks
• Describe SLA targets for participant inquiries (first response time, resolution time) you expect us to meet. Options: First response within 24 hours, First response within 48 hours, Custom SLA
• Indicate whether participant interactions must be recorded and attached to the participant case file for audit purposes. Options: Yes, attach to case file, No, summary only
• Identify common case types to triage (enrollment issues, billing disputes, notice receipt confirmations) and routing preferences.
• Provide the escalation contacts and business hours for urgent participant issues affecting coverage.
• Specify any language support or accessibility accommodations your participant population requires.

• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Order Form / Service Order
• Service Level Agreement (SLA)
• Data Processing Agreement (DPA)
• HIPAA Business Associate Addendum (BAA) — conditional
• Service Commencement & Go‑Live Conditions
• Transition & Offboarding Addendum

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

• Produce a quarter-over-quarter metrics summary for distribution to the buyer's benefits leadership team.
• Execute agreed corrective tasks and document test results for the acceptance review.
• Prepare an issues tracker entry for any unresolved item and set re-test dates.
• Restate numeric acceptance criteria from Solution Scope
• Record a documented acceptance decision for each Solution Scope criterion, with pass/fail outcomes and a formal acceptance record if applicable.
• Create a remediation plan with clear timelines for any failed criteria and a verification method.
• Confirm the operational ownership, escalation paths, and that audit-ready documentation is accessible.
• Publish the acceptance decision record, including pass/fail per criterion and the named signatory where required.
• Open remediation tickets for failed criteria with target resolution dates and verification steps.
• Deliver final runbooks and the audit documentation index to the agreed document repository.
• Trend review for notice timeliness and carrier remittance accuracy
• Confirm that notice timeliness rate and carrier remittance accuracy remain within acceptable ranges or that remediation plans exist for deviations.
• Ensure audit-ready documentation is current and that any compliance incidents are closed or on a defined remediation path.
• Agree prioritized enhancement items and the next steps to evaluate or implement them.
• Update the compliance documentation index and attach evidence for any recent changes or incidents.
• Add agreed enhancement requests to the backlog with priority and expected evaluation or delivery dates.
• Re-confirm success criteria and owners
• Confirm the deployment components are functional and aligned with the values captured in Solution Scope.
• Produce a prioritized list of open issues with owners and target resolution dates.
• Agree the near-term remediation plan and the next checkpoint for verifying fixes.
• Publish the deployment validation checklist and test evidence for buyer review.
• Create a prioritized issue list with reproduction steps, owners, and target resolution dates.
• Schedule the first measurement meeting and circulate required data extracts to attendees.
• Present outcomes for notice timeliness rate and premium collection success rate
• Determine whether notice timeliness rate and premium collection success rate are on track to meet Solution Scope targets.
• Produce a root-cause summary for any gaps and a corrective action plan with clear dates to reach acceptance.
• Confirm the acceptance gate date and the required evidence to be presented at that meeting.
• Provide an exported dataset and dashboard slices used to validate notice timeliness and collection rates.
• Present outcome data against each criterion
• Premium collection performance and participant support metrics
• Deployment and data migration validation
• Review enrollment election rate and participant portal adoption
• Document pass/fail per criterion and capture acceptance decision
• Early adoption and usage signals
• Audit readiness and compliance incidents
• Root-cause diagnosis for metric gaps
• Enhancement requests and backlog prioritization
• Agree remediation plan and resolution timelines for failed criteria
• Blockers and open issues triage
• Agree corrective actions, owners, and dates
• Confirm timeline and criteria for the acceptance gate
• Confirm operational handover and runbook availability
• Close ongoing items and set next quarter checkpoints
• Agree remediation actions and near-term checkpoints