Starting with your team and how benefits work today

• How many employees do you have enrolled or eligible for benefits? Options: 2-9, 10-24, 25-49, 50-99, 100-200, More than 200
• Tell me which roles at your company are involved in making benefits decisions Options: Owner/CEO, Office manager, HR generalist, Finance/Controller, Broker, Other
• Who currently manages enrollment and carrier communications day to day Options: Office manager, External broker, HR generalist, Payroll provider, Other
• Describe any prior experience your team has with running open enrollment and ongoing eligibility maintenance
• Which employee groups in your company have the most variable schedules or part-time status Options: Hourly or part-time, Remote employees, Seasonal staff, Field staff, All staff are stable, Other
• Estimate how your workforce splits between employees who live locally versus employees who live across states Options: Mostly local, Mostly across states, Roughly even split, Unsure / mixed

Where cost and access collide

• If premium increases forced you to cut benefits, which employee group would be hit hardest Options: Frontline hourly staff, Managers, Employees with chronic conditions, Part-time or seasonal staff, Executives, All groups equally
• Why would that group be more affected than others
• On a typical month, how many employees file claims that exceed your current plan's deductible Options: None or very few, 1-3, 4-10, More than 10, We do not track this
• Do you track unexpected assessments, reconciliations, or retro premium adjustments from carriers Options: Yes, regularly, Occasionally, Rarely, Never
• Tell me about the last time a benefits cost surprised you, what happened, and what changed afterward

Providers your people rely on

• Who would lose access to their primary doctor if you moved to a narrower network Options: Large portion of staff, A small handful, No one, Unsure
• Walk me through how an employee checks whether a doctor is in-network today
• Which medical specialties or clinics show up most often on your team's claims Options: Primary care, Behavioral health, OB/GYN, Cardiology, Orthopedics, Urgent care, Other
• When an employee needs a specialist referral, how long does it usually take from request to appointment Options: Same week, 1-2 weeks, 3-4 weeks, Longer than a month, Varies widely
• Describe how often employees call out surprise out-of-network charges and give an example if you can

Budget, contributions, and the real funding limits

• When you set your benefit budget, what is the hard monthly employer contribution cap you cannot exceed Options: Under $500, $500-$1,000, $1,000-$2,500, Over $2,500
• Do you currently offer tiered employer contributions by employee class, for example full-time versus part-time Options: Yes, distinct tiers, No, single contribution, Partial with exceptions, Not sure
• How do you plan to fund year-over-year premium increases, for example by shifting costs to employees, changing plan designs, or absorbing them
• Estimate the percentage of payroll you are comfortable dedicating to employee benefits Options: Under 5%, 5-8%, 8-12%, Over 12%, Unsure
• If an HSA-compatible high-deductible option lowered premiums by about 15%, what would stop you from adopting it

ACA, compliance, and administrative triggers

• Are you within reach of the 50 full-time equivalent threshold that would trigger ACA employer responsibilities Options: No, well under 50, Approaching 50 (within 10), At or above 50, Unsure
• In the last 12 months, have you received any compliance notices, audits, or penalties related to benefits administration Options: Yes, with penalty, Yes, informational notice, No, Not sure
• Name the person who currently owns ACA tracking, reporting, and full-time equivalency calculations
• List the types of tools you use today to track hours, eligibility, and census data Options: Payroll provider, HRIS or HR platform, Timekeeping app, Manual spreadsheets, Broker-managed system, Other
• What single timeline constraint around reporting or open enrollment would make it impossible to switch carriers for the upcoming plan year

Alternatives you're weighing and why they might win

• Imagine the incumbent matched price and improved service, what would still push you to change
• Has anyone on your leadership team proposed solving benefits in-house rather than using an outside carrier or broker Options: Yes, this is in progress, Proposed but no plan, No one has proposed an internal solution, Not sure
• What would have to be true about your current plan for you to stay with it instead of changing
• Identify who would sign off on staying with the incumbent and state their main reason for doing so
• Explain any internal political or timing constraints that would prevent you from switching even if the numbers looked better

Operational readiness, systems, and data you can deliver

• Can your payroll or HR provider deliver a clean roster with employee identifiers and eligibility flags within four weeks Options: Yes, within 1 week, Yes, within 2-4 weeks, No, needs longer, Unknown
• Provide which system categories would need integration for enrollment and billing, for example payroll, HRIS, or benefits portal Options: Payroll, HRIS, Benefits portal, Broker platform, Timekeeping system, Other
• Are APIs or scheduled file feeds available from those systems, and who manages them Options: APIs available and managed internally, APIs available and vendor-managed, Only batch file feeds, No integrations available, Unsure
• Approximate the internal hours per month your team can commit to enrollment setup and ongoing reconciliation Options: Under 5 hours, 5-15 hours, 15-30 hours, Over 30 hours
• Can your team provide two weeks of IT or payroll support for carrier billing and integration within the proposed timeline Options: Yes, Maybe with vendor help, No, We would outsource

Decision drivers, timeline, and next steps

• Suppose the proposal meets price and provider needs, what could still stop you from signing within 14 days
• Identify the final budget approver and describe how they view benefits spend when making sign-off decisions
• Choose the single metric that would make you comfortable moving forward, total monthly cost, employee out-of-pocket exposure, or network coverage Options: Total monthly cost to employer, Average employee out-of-pocket per year, Network coverage for key providers, Predictability of monthly billing, Administrative simplicity
• Within what timeframe could you provide a current census and formal funding approval if we reached agreement today Options: Within 48 hours, 3-7 days, 1-2 weeks, Longer than 2 weeks, Not ready
• State any non-negotiable terms or deal breakers we should know about before drafting a proposal

• Solution Walkthrough Session

• Orientation: buying to go-live
• You confirm that the demonstrated employee scenarios reveal the true monthly premiums and expected out-of-pocket costs across plan options as described in Discovery.
• Deliver three tailored plan proposals with premiums, network maps, and employee-level cost summaries within two business days after receiving final census.
• Confirm the current state and its cost
• You identify at least one plan option that meets your target monthly budget and maintains access to required providers.
• Run the sample premium and out-of-pocket model for the provided census and deliver the comparison workbook before the follow-up session.
• Employee scenario walkthrough
• Provide final census including employee ages, ZIP codes, current providers, and current enrollment status within three business days.
• You agree on the remaining underwriting and census items required to produce final pricing and enrollment timelines.
• Confirm your preferred employer contribution strategy for the selected plan option so final pricing reflects the contribution approach.
• Network and provider tradeoffs
• Validate the future state
• Agreement on next steps and outstanding items

• Solution Walkthrough Session
• Solution Walkthrough Deck
• Plan Comparison Solution Brief

• meeting
• slides
• document

• Generate 24‑Hour Group Quote
• Provision Broker Portal and Quoting Access
• Configure Employer Contribution and Payroll Deductions
• Activate Employee Self‑Service Enrollment Portal
• Process Employee Eligibility Verification and Import
• Enroll Employees and Assign Coverage Effective Dates
• Verify Employee Provider Network Coverage
• Issue Member ID Cards and Welcome Packets
• Configure HSA‑Compatible Plan Settings
• Set Up Carrier‑Direct Billing and Invoicing
• Process Mid‑Year Qualifying Life Event Enrollments
• Produce ACA Compliance Reporting and Filings
• Deliver Annual Renewal Proposal and Rates
• Enable Dental and Vision Plan Add‑On Enrollment

Generate 24‑Hour Group Quote

• Provide the employee census file format you will supply for the 24‑hour quote (for example: CSV with first/last name, date of birth, ZIP code, hire date, employment status). Options: Spreadsheet (CSV/XLSX), Payroll export (CSV), Manual headcount only, Other
• Upload or confirm the effective date you want quoted for the group plan (the date coverage would begin for enrolled employees).
• Which network tier(s) should the quote include for comparison (for example: narrow network, mid‑tier, broad network)? Options: Narrow network, Mid‑tier network, Broad network, Compare all tiers
• How many full‑time equivalent employees are on your census for underwriting purposes? Options: 2-9, 10-49, 50-99, 100-200
• When do you need the formal proposal package (for example: within 24 hours, by EOD tomorrow)? Options: Within 24 hours, By end of next business day, Within 3 business days, Custom date
• Identify any recent claims or underwriting exceptions we should consider for the quote (for example: pending large claims, open specialty benefits, tobacco surcharge).

Provision Broker Portal and Quoting Access

• Who on your team should receive broker portal access and what email addresses should be provisioned?
• Specify the level of portal permissions needed for each user (for example: quote generation only, quote + enrollment upload, admin). Options: Quote only, Quote + enrollment, Admin (all permissions), Custom
• Are there IP restrictions or SSO (single sign on) requirements for your users to access the quoting portal? Options: Yes - IP or SSO required, No restrictions
• List any broker firm NPN or brokerage license numbers required to activate quoting access.
• Select preferred notification methods for new quotes and proposal updates from the portal. Options: Email alerts, Portal dashboard only, Webhook to your system, Both email and webhook
• Describe any approval workflow your brokerage requires before a quote is shared with the employer (for example: internal approval by senior broker).

Configure Employer Contribution and Payroll Deductions

• Specify your desired employer contribution strategy for employee premiums (for example: fixed dollar per tier, percent of employee cost, composite rate). Options: Fixed dollar per tier, Percent of employee cost, Composite employer contribution, Employer pays full premium
• Which employee tiers should be supported in payroll deductions (for example: employee only, employee + spouse, family)? Options: Employee only, Employee + spouse, Employee + child(ren), Family/all tiers
• Identify your payroll provider and the payroll cadence we must align deductions to (for example: biweekly, semimonthly, monthly). Options: Monthly, Biweekly, Semimonthly, Weekly, Other
• Indicate whether pre‑tax and/or post‑tax deductions are required for the offered plans. Options: Pre‑tax (IRC Section 125), Post‑tax only, Both pre‑tax and post‑tax options
• Do you require employer contribution tiers that vary by location or class of employee (for example: different rates for part‑time vs full‑time, or by state)? Options: Yes, by location/class, No, single employer contribution
• Specify any minimum employer contribution thresholds or affordability targets that must be met for ACA safe harbor (for example: contribution at or below X% of employee-only premium).

Activate Employee Self‑Service Enrollment Portal

• Who will be the portal administrator from your side to receive setup credentials and training?
• Specify the employee authentication method you prefer for the enrollment portal (for example: single sign on with your directory, email token, employee ID + DOB). Options: Email token, SSO with corporate directory, Employee ID + DOB, Other
• Indicate which employee-facing documents must be published in the portal at launch (for example: Summary Plan Description, plan SBCs, carrier ID PDFs). Options: SBCs (Summary of Benefits and Coverage), Summary Plan Description (SPD), Employee FAQs, All the above, Other
• Select languages required for the employee portal user interface and enrollment materials. Options: English, Spanish, Other
• Describe required open/close enrollment windows and whether you need self-serve COBRA continuation links exposed in the portal.
• Are you requesting automated reminders for employees who start but do not complete enrollment? Options: Yes, automated reminders, No, manual follow up only

Process Employee Eligibility Verification and Import

• Identify the canonical eligibility roster you will supply for import (for example: payroll export, HRIS report, spreadsheet) and its delivery method. Options: Payroll export, HRIS report, Spreadsheet upload, Manual entry
• Specify required eligibility rules to apply during import (for example: minimum hours per week, waiting period in days, hire date cutoffs).
• Indicate how you will document qualifying life events for mid‑year enrollments (for example: scanned certificate, carrier event form, HR attestation). Options: Scanned document, Carrier event form, HR attestation only, Other
• Provide the maximum acceptable error rate for imported eligibility matches (for example: no more than 1% unmatched records). Options: 0% unmatched, <=1% unmatched, <=5% unmatched, Custom
• Confirm the owner on your side who will approve the initial import and accept the verification report.
• What evidence will validate successful eligibility import and matching (for example: import reconciliation report with matched/unmatched counts and employee IDs)?

Enroll Employees and Assign Coverage Effective Dates

• Select the default rules for coverage effective dates after initial enrollment (for example: 1st of next month, date of hire + 30 days, fixed company effective date). Options: 1st of next month, Date of hire + X days, Fixed company effective date, Custom
• Specify whether you allow retroactive enrollments or backdated coverage for special cases and the approval process required. Options: Allow with approval, Do not allow retroactive, Allow up to X days
• Identify who will review and sign off on the final enrollment roster prior to submission to the carrier.
• Indicate whether employee dependents will be uploaded with the primary employee record or entered separately during enrollment. Options: Dependents included in upload, Entered during employee portal enrollment, Mixed
• Describe the notification method you prefer for enrolled employees to receive their coverage effective date confirmation. Options: Email confirmation, Portal notice only, Printed letter mailed, Both email and mail
• Specify any plan‑level auto‑assign rules (for example: all new hires auto‑assigned to default HDHP unless waived).

Verify Employee Provider Network Coverage

• Provide the primary provider directory source we should use to validate employee PCP and specialist coverage (for example: carrier provider directory export or portal lookup). Options: Carrier directory export, Portal provider search, Employee confirmation
• How many employees require a provider verification check against the selected network before plan selection? Options: All employees, A subset (list provided), Only those with ongoing care
• Identify the threshold for acceptable network coverage among employees (for example: 90% of employees have at least one in‑network PCP). Options: 100%, >=95%, >=90%, Custom
• List any critical out‑of‑network providers you must preserve access to when selecting a network tier (for example: named hospital or specialist).
• Indicate whether you want a written report mapping employees to in‑network providers and highlighting gaps prior to final plan selection. Options: Yes, provide report, No report needed
• Describe how provider mismatches should be handled (for example: broker outreach to employee, exception request to carrier).

Issue Member ID Cards and Welcome Packets

• Specify whether ID cards should be mailed to employee home addresses or delivered electronically via the portal. Options: Mailed to home address, Electronic portal delivery, Both
• Provide the welcome packet contents required at issuance (for example: ID card, SBC, plan contact card, pharmacy formulary). Options: ID card, SBC, Pharmacy formulary, Provider directory excerpt, All of the above
• Indicate the turnaround time expectation for printing and mailing physical ID cards after enrollment submission. Options: Within 5 business days, Within 10 business days, Custom
• List the return mailing address and any employer branding or logo required on the welcome packet.
• Choose whether temporary ID numbers should be issued immediately via the portal for urgent care before physical cards arrive. Options: Yes, temporary IDs via portal, No temporary IDs
• How will you verify successful delivery of member ID cards and welcome packets (for example: delivery confirmation report, employee attestation)?

Configure HSA‑Compatible Plan Settings

• Specify whether the HSA‑compatible plan needs automatic HSA trustee setup integration or if employees will enroll with an external HSA provider. Options: Carrier‑integrated HSA trustee, Employees choose external HSA provider, Both options
• Indicate the annual IRS family and individual contribution maximums you want communicated in enrollment materials (we will use current IRS limits unless you specify custom guidance). Options: Use current IRS limits, Provide custom contribution guidance
• Identify whether employer contributions to HSAs should be pro‑rated for mid‑year hires and how you want that calculated. Options: Pro‑rate by month, Do not pro‑rate, Custom calculation
• List any HSA eligibility exclusions to be enforced (for example: employees enrolled in other non‑HSA compatible coverage, Medicare enrolled).
• Select whether HSA payroll contributions should be pre‑tax through Section 125 cafeteria plan or post‑tax. Options: Pre‑tax (Section 125), Post‑tax, Employee choice
• Describe the employee communications you require about HSA bank account setup and employer seed contributions.

Set Up Carrier‑Direct Billing and Invoicing

• Identify the billing cadence you prefer from the carrier (for example: monthly, quarterly) and the invoice delivery method. Options: Monthly, Quarterly, Electronic invoice (EDI), Paper invoice
• Provide billing account and remittance details to be used for carrier‑direct invoicing setup.
• Specify whether billing should be consolidated across lines (medical, dental, vision) or billed separately per product. Options: Consolidated single invoice, Separate invoices per product
• Indicate required billing pay codes, PO numbers, or GL account mappings to appear on carrier invoices.
• Are you requesting electronic remittance advice or ACH debit authorization for automatic payment? Options: Yes - ACH debit, Yes - EDI remittance advice, No, manual payment
• Describe dispute resolution steps you expect for invoice discrepancies (for example: 30‑day review window, contact owner).

• Master Group Policy
• Employer Application & Underwriting Statement
• Rate Confirmation & Acceptance
• Billing & Premium Payment Schedule
• Enrollment Authorization & Eligibility Roster
• Contribution Strategy & Employer Notice
• Broker of Record / Commission Addendum
• Continuation Coverage (COBRA/State) Addendum
• ACA Reporting & Employer Mandate Addendum
• Data Privacy & Security Addendum (DPA / BAA)

• Go-live Health Check (weeks 1-4)
• First Measurement Review (weeks 4-10)
• Quarterly Coverage Success Review (ongoing)

• Close or reassign long-running support tickets and implement a plan to reduce average resolution time.
• Determine whether enrollment completion rate meets the deal target or requires remediation.
• Identify root causes for eligibility verification failures and agree on a remediation plan to raise the eligibility verification pass rate.
• Agree on a prioritized list of billing exceptions to resolve and a timeline to reduce carrier billing exception rate to acceptable levels.
• Provide a corrected enrollment roster and run a second eligibility verification pass by the agreed date.
• Reconcile and clear the prioritized list of carrier billing exceptions and submit adjustments to carrier billing where required.
• Implement identified process or configuration fixes that caused enrollment or verification gaps and report completion.
• Trend review for premium variance and ACA reporting
• Confirm monthly premium variance is within acceptable tolerance or document corrective financial actions required.
• Ensure ACA reporting completion rate is on schedule for the next filing window and any gaps are assigned owners and dates.
• Reduce open support ticket backlog and improve average ticket resolution time for the upcoming quarter.
• Reconcile premium variances for the quarter and submit any carrier billing adjustments required.
• Complete outstanding ACA reporting tasks and circulate a status summary ahead of the filing deadline.
• Re-confirm success criteria and owners
• Confirm deployment and enrollment flows completed and no critical defects remain at go-live.
• Top open issues enumerated, each assigned an owner and an expected resolution date.
• Incumbent plan wind-down status validated and next steps for any remaining actions recorded.
• Publish the deployment health summary and issue log for async review.
• Resolve top 3 critical enrollment defects and report completion before the first measurement meeting.
• Confirm incumbent contract termination or retention-read-only and archive legacy data as required.
• Present first outcome data
• Deployment and enrollment validation
• Mid-year events and enrollment changes
• Root-cause diagnosis for gaps
• Early adoption signals and usage patterns
• Support ticket volume and resolution performance
• Billing exceptions and premium variance review
• Incumbent wind-down confirmation
• Incumbent wind-down final check
• Persistent issues and backlog burn-down
• Blockers and open issues with owners
• Agree next-quarter operational actions
• Agree corrective action plan with dates
• Agree immediate remediation actions