Start Here — Tell Us About Your Team

• How many people are on your payroll today (headcount)? Options: 2-9, 10-24, 25-49, 50-99, 100-200
• Which of these best describes your current benefits setup? Options: No group benefits today, Medical only, Medical + Dental, Medical + Dental + Vision, HRA or stipend model, Other
• How are you currently sourcing benefits and support? Options: Independent broker, Broker through platform/marketplace, Direct with carrier, In-house HR, No one — exploring options
• How comfortable are you personally with how group health insurance works (levels of familiarity)? Options: Very comfortable, Somewhat familiar, A little confused, Overwhelmed
• What is the single most important thing you want a benefits solution to deliver for your business?

Is Premium Cost the Only Thing Guiding Your Choices?

• Tell us about the last time premium changes forced a business decision — did you change plans, shift contributions, or accept the cost? Options: Changed plans, Shifted employer contribution, Absorbed the cost, Reduced headcount or hiring, Haven't experienced this
• How do you currently budget for monthly premium expense? Options: Fixed monthly reserve, Pay as billed, Estimate with buffer, No formal budget
• What's your target for employer contribution (per employee) or contribution strategy right now? Options: Fixed dollar per employee, Percentage of premium (e.g., 50%), Composite rate, No set strategy yet
• If lowering premiums meant a narrower network, how willing would you be to consider that tradeoff? Options: Very willing, Somewhat willing, Only with guaranteed provider checks, Not willing
• Describe a scenario where a premium surprise (invoice spike, audit, mid-year assessment) affected your team or plans.

Who Will Actually Run This — And How Much Time Do They Have?

• Who will be the primary owner for benefit administration in your organization? Options: Business owner/CEO, Office manager, Part-time HR generalist, Payroll provider, Broker handles most tasks
• How many hours per week can that person realistically dedicate to benefits administration? Options: <1 hour, 1-3 hours, 4-6 hours, 7-10 hours, 10+ hours
• Which administrative tasks feel like the biggest drain today? Options: Enrollment paperwork, Eligibility tracking, Payroll deductions, Employee support/questions, ACA reporting, Carrier reconciliation
• Do you have systems that should integrate with enrollment (payroll, HRIS, timekeeping)? If yes, which? Options: QuickBooks/Payroll, ADP, Gusto, Paychex, BambooHR/HRIS, None / manual
• Tell me about a recent administrative headache and roughly how long it took to resolve.

Do Your People Keep Their Doctors — Or Is That an Acceptable Risk?

• How important is it that employees keep access to their current providers? Options: Critical — we risk losing staff, Important but negotiable, Somewhat important, Not a priority
• Do you have a list of high-priority providers or facilities we should check against networks? Options: Yes — we will provide a list, No list but can collect names, No, not necessary
• Would you like us to perform a roster-based provider coverage check during modeling? Options: Yes — please check coverage, Maybe — tell me more, No thanks
• How would losing access to a preferred provider likely affect an employee's decision to stay? Options: High risk of departure, May cause dissatisfaction, Unlikely to affect retention, Unsure
• If employees are geographically dispersed, which regions or states matter most for provider access?

Short-Term Fixes vs Long-Term Predictability — Which Side Are You On?

• When you picture a sustainable benefits program for your company, what matters most month-to-month? Options: Lowest possible premium today, Stable predictable premium, Simple administration, Broad provider access, Compliance certainty
• How much premium volatility (percentage change) have you seen year-over-year? Options: <5%, 5-10%, 11-20%, >20%, Not sure
• If we offered options that lock pricing for a period vs ones that reprice frequently, which would you prefer? Options: Lock pricing (predictable), Reprice for lower starting premium, Open to hybrid options
• What billing cadence and method would make payroll and cash flow easiest for you? Options: Monthly carrier-direct billing, Employer-billed consolidated invoice, Pay as you go, Other
• Describe your ideal experience when an invoice arrives—what should happen, who touches it, and how quickly should it be reconciled?

What Happens If the Timeline Slips?

• What is your target effective date or the date you need coverage in place? Options: ASAP / Within 30 days, 30–60 days, 2–3 months, 3–6 months, Six months or longer
• Who in your organization must approve this decision before you can bind coverage? Options: Owner/Founder, Finance lead/CFO, Board or investors, Office manager/HR, Other
• Which internal steps typically slow approvals (budget sign-off, legal review, payroll changes, employee communication)? Options: Budget sign-off, Legal/contract review, Payroll setup, Employee communication plan, Other
• If we need to accelerate timelines, what would help remove obstacles most quickly? Options: Simplified contract, Pre-filled enrollment, Dedicated implementation rep, Clear pricing guarantees
• If your ideal effective date shifts back by a month, what is the real-world impact? Options: No impact, Some disruption, Significant financial or staffing impact, We cannot shift

How Confident Are You About ACA and Compliance Requirements?

• Do you believe your business is an Applicable Large Employer (50+ FTE) for ACA purposes? Options: Yes, No, Unsure — need help determining
• How do you currently track full-time equivalents and variable hour employees? Options: Payroll reports, Manual spreadsheets, HRIS automation, We don't track reliably
• Have you ever received an ACA-related notice or assessment? Options: Yes — resolved, Yes — unresolved, No
• Would ACA compliance tools or a compliance review be valuable to you as part of our proposal? Options: Yes — very valuable, Somewhat valuable, Probably not necessary
• Tell us about any specific legal or regulatory worries you currently have around benefits.

What Would Make You Confident Enough to Say Yes?

• Which of the following would be non-negotiable for you to move forward? Options: Target premium threshold, Provider access for key doctors, Simple administration, Guaranteed effective date, Clear billing method, ACA compliance support
• What is the single biggest deal-breaker we should be aware of?
• How will you evaluate competing proposals — what's the top criterion? Options: Price/premium, Provider network, Administrative ease, Speed to enroll, Broker/carrier reputation
• Who else (roles or people) should be involved in our next conversation to move this forward?
• If we can meet your must-haves, how soon would you be prepared to commit? Options: Immediately, Within 30 days, 60–90 days, Longer than 90 days, Undecided

Open Flags — Anything We Haven't Asked That Keeps You Up At Night?

• Is there a recent employee or hiring situation that makes benefits especially urgent right now? Options: Yes — key hire/retention risk, Somewhat — upcoming hires, No urgent situation
• Are there legacy contracts, broker agreements, or union concerns we should know about? Options: Yes — details to share, No, Not sure
• What else worries you about switching carriers or plan designs that we haven't covered?
• Would you like us to run a roster-based model using your employee list and contribution targets? Options: Yes — please run modeling, Maybe — want to learn more first, No thanks
• Preferred next step and contact method (phone, email, portal) for scheduling the modeling or follow-up? Options: Phone, Email, Platform/portal message, Any of the above

• Pre-Modeling Data Confirmation
• Modeling Workshop: Premiums & Employee Cost Impact
• Provider Coverage & Critical-Provider Validation
• Administrative Effort Preview & Decision Alignment

• Carrier/broker to prepare contract modules and a single-page implementation checklist for employer approval.
• Broker to prepare initial model skeleton and bring assumptions log to the workshop.
• Employer to provide final roster CSV and payroll confirmation by the agreed deadline.
• Introductions & Meeting Objectives
• Confirm which scenarios meet the employer budget threshold and retention objectives.
• Force validation from the employer that model outputs match expectations and constraints.
• Create and share PDF/CSV exports of all modeled scenarios with line-item employer and employee impacts.
• Broker to annotate recommended contribution strategies and indicate which scenarios meet the employer's budget and retention targets.
• Assign owner to escalate any regulatory/ACA edge cases identified during modeling for legal review.
• One-sentence Current State for Provider Access
• Validate provider access for all critical employees with concrete evidence.
• Quantify cost and operational tradeoffs required to restore access where gaps exist.
• Get employer confirmation on acceptable tradeoffs and communication approach for impacted employees.
• Produce a provider coverage report listing status for each critical provider and suggested remedies.
• If required, run targeted alternative-network models and provide incremental premium deltas.
• Draft employee-facing communication templates for any access changes or waivers.
• One-sentence Future State Confirmation
• Agree on an implementation plan with owners and milestone dates that proves the future operational state.
• Confirm ACA compliance and the administrative burden expected during implementation and ongoing.
• Obtain explicit employer sign-off on the selected scenario or list required changes to achieve sign-off.
• Finalize effective date, billing method, and employer contribution schedule and circulate for signatures.
• Schedule enrollment kickoff with communications owner and set deadline for employee census confirmation.
• Employer to deliver sample premium invoices and current plan documents.
• Achieve a single, agreed one-sentence current state that will drive all models.
• Surface and quantify the primary cost, coverage, and administrative consequences of the current state.
• Confirm a complete, usable roster and required artifacts before the modeling session.
• Recap Current State and Future State Objective
• Produce proven, roster-based scenarios that demonstrate employer monthly premium and employee out-of-pocket impacts.
• Crystal-clear Current State Statement
• Live Provider Lookup for Critical Employees
• Baseline Model: Current Plan (Diagnosis)
• Implementation Milestones & Owners
• Administrative Effort & Automation Demo
• Alternative Plan Scenarios (Proof)
• Surface Consequences
• Impact Analysis for Access Gaps
• ACA Compliance & Risk Check
• Tradeoff Options: Network Tier vs Cost
• Net Take-home Impact & Affordability Analysis
• Validate Roster & Eligibility Rules
• Data Completeness Checklist & Prework
• Billing, Contribution & Premium Predictability
• Tie Results Back to Consequence
• Validation & Employee Communication Implications
• Validation Checkpoints & Live Adjustments
• Decision & Sign-off Criteria
• Next Steps & Decision Criteria

• Generate broker-ready small-group quote
• Bind group policy and issue master contract
• Provision employer and employee self-service portals
• Process employee online enrollments and eligibility
• Import employer roster and set premium billing
• Set up carrier-direct monthly billing
• Issue member ID cards and digital cards
• Activate HSA accounts and employer contributions
• Administer mid-year QLE enrollment changes
• Manage COBRA and continuation coverage administration
• Prepare and file ACA 1094/1095 employer forms
• Provide narrow-network provider directory integration
• Deliver new-hire benefits welcome kits

Generate broker-ready small-group quote

• Do you need a new broker-ready quote generated for this employer? Options: Yes, No
• Which coverages should be included in the quote package? Options: Medical, Dental, Vision, All (medical + dental + vision)
• Which plan designs should be priced in the quote (select all to include multiple options)? Options: High-deductible (HSA), Copay-based (traditional), HMO / narrow network, PPO / broad network, Custom employer contribution models
• What network tiers should be modeled in the quote? Options: Narrow, Mid-tier, Broad
• What employer contribution strategies should we model (choose primary options)? Options: Flat dollar employer contribution, Percentage of employee premium, Tiered by employee class (EE/EE+Spouse/Family), Composite rates
• What deliverable format do you require for the broker-ready quote? Options: PDF proposal, Excel rate worksheet, Online quote link, All of the above
• What is the required turnaround time for the quote? Options: Same business day, 24 hours, 48-72 hours, Standard (3-5 business days)
• Are optional quote assumptions required (e.g., expected participation, tobacco rates)? If yes, list specifics. Options: Yes, No

Bind group policy and issue master contract

• Will you require the carrier to issue a bound group policy and master contract? Options: Yes, No
• What is the proposed effective date for binding coverage?
• Which contract modules should be included (e.g., medical only, medical + ancillary, broker compensation addendum)? Options: Medical only, Medical + dental, Medical + dental + vision, Broker compensation addendum, Custom addenda
• Who will sign the master contract on the employer's behalf? Options: Owner/CEO, Office Manager/HR, Broker (with signed employer authorization), Other
• Are there specific acceptance criteria required before binding (e.g., minimum participation, verified census)? Options: Yes, No
• Does the employer require a paper contract, e-signature, or both? Options: E-signature, Paper (wet) signature, Both
• Is a rate guarantee or provisional premium hold needed prior to final underwriting? Options: Yes, No
• List any special underwriting requirements or eligibility conditions that must be reflected in the contract.

Provision employer and employee self-service portals

• Do you want employer and employee self-service portals provisioned for this group? Options: Yes - both, Employer only, Employee only, No
• Which features must be enabled in the employer portal? Options: Census upload, Billing view/pay, Access to invoices, ACA reporting tools, User/role management
• Which employee portal features are required? Options: Online ID cards, Benefit details & EOBs, Change of address, Dependent management, Download forms
• What SSO or authentication method should be used for portal access? Options: Email/password, SSO (SAML/OAuth), Carrier-managed credentials, Other
• Are branded portals and employer-specific messaging required? Options: Yes - branded, Yes - basic logo only, No - standard carrier portal
• Who will be the designated portal administrator(s) at the employer? Options: Owner/CEO, Office Manager, HR Generalist, Broker
• Are any data retention or audit logging policies required for portal activity? Options: Yes, No

Process employee online enrollments and eligibility

• Will employee enrollments be processed online through the carrier portal? Options: Yes - carrier portal, Yes - third-party enrollment platform, Paper enrollments only, Mixed (both digital and paper)
• What verification checks must be performed during enrollment? Options: SSN validation, Dependent documentation, Eligibility rules (hours/waiting period), Tobacco status verification
• What enrollment types should be supported at launch? Options: New hire, Open enrollment, Qualifying life events (QLE), COBRA/continuation
• What are the enrollment deadlines and effective dates to enforce (e.g., 30 days from hire)?
• Who is responsible for certifying eligibility and approving enrollments (employer or broker)? Options: Employer, Broker, Carrier, Third-party admin
• Do you require automated confirmations and welcome emails to employees upon enrollment? Options: Yes, No
• Are bulk enrollment uploads required for any groups (e.g., initial census enrollments)? Options: Yes, No

Import employer roster and set premium billing

• Will you provide an employer roster for import into the carrier system? Options: Yes - formatted census, Yes - raw spreadsheet, No - manual entry
• What file format will the roster be delivered in? Options: CSV/Excel, HRIS export, Payroll extract, Other
• What payroll/billing frequency should premium billing be set to? Options: Monthly, Semi-monthly, Bi-weekly, Other
• Which premium allocation method should be applied (per-employee, composite, tiered)? Options: Per-employee (by tier), Composite, Flat dollar employer-paid portions, Custom
• Who will be the billing contact and what billing delivery method is preferred? Options: Employer via email, Employer via portal, Broker copy, Carrier mail
• Do you require reconciliation or premium audit support during the first 90 days? Options: Yes, No
• Are there any payroll deduction codes or employee classes that must be preserved on import? Options: Yes - list required, No

Set up carrier-direct monthly billing

• Should billing be carrier-direct for monthly premiums? Options: Yes - carrier-direct, No - broker/TPA invoicing, Employer wants carrier-direct with broker copy
• Which billing method is preferred for payment? Options: EFT/ACH, Credit card, Check, Auto-debit
• Do you require electronic invoice delivery or physical invoice copies? Options: Electronic only, Physical only, Both
• Who is authorized to make billing changes or stop payments? Options: Employer admin, Broker, Authorized signer(s)
• Do you need premium financing or billing grace period exceptions configured? Options: Yes, No
• Are broker commission remittance preferences required to be reflected on invoices? Options: Yes - itemized, Yes - summary only, No
• Will billing require multiple bill-to entities or split billing across departments? Options: Yes, No

Issue member ID cards and digital cards

• Do you require physical member ID cards, digital ID cards, or both? Options: Physical cards, Digital cards, Both
• What card design elements should be included (logo, employer name, plan contact)? Options: Carrier standard, Employer logo & plan name, Custom messaging for employees
• When should ID cards be issued relative to effective date? Options: Prior to effective date, On effective date, Within 7 business days after effective date
• Do you require expedited card printing for any members? Options: Yes, No
• Should ID cards include broker contact information for member questions? Options: Yes, No
• Are any special member populations (COBRA, retirees) excluded from physical card issuance? Options: Yes - list, No

Activate HSA accounts and employer contributions

• Are HSA-eligible plans being offered that require HSA account activation? Options: Yes, No
• Will the carrier or a third-party custodian open HSA accounts for employees? Options: Carrier-managed, Third-party custodian, Employer already has custodian
• What employer HSA contribution cadence and amount should be configured? Options: One-time setup amount, Monthly contribution, Per-payroll contribution, Flexible (employer decides)
• Should employer contributions be set up for eligible employees only or for all enrolled in HSA plan? Options: Eligible employees only, All HSA-enrolled employees, Custom rules by employee class
• Who will provide employee bank account or transfer details for initial funding? Options: Employer payroll, Employee bank details, Custodian transfer
• Is payroll integration required to automate employer HSA contributions? Options: Yes, No

Administer mid-year QLE enrollment changes

• Do you want carrier-handled administration for mid-year QLE changes? Options: Yes - carrier manages, No - employer/broker manages, Hybrid
• Which QLE types should be supported and pre-configured? Options: Marriage, Birth/Adoption, Loss of other coverage, Change in employment status, Other
• What documentation requirements should be enforced for QLE approvals? Options: Proof required (upload), Attestation only, Case-by-case
• What is the allowed enrollment window for QLEs (e.g., 30 days from event)? Options: 15 days, 30 days, 60 days, Custom

• Group Master Application / Policy
• Statement of Work (SOW)
• Rate Confirmation & Pricing Addendum
• Effective Date & Enrollment Cutover
• Billing & Payment Authorization (EFT/ACH)
• Employer Contribution Schedule
• Broker Commission & Compensation Agreement
• Plan Documents & Summary of Benefits (SBC)
• Data Sharing & Systems Integration Addendum
• ACA Compliance & Large-Employer Attestation
• Mutual Obligations & Escalation Protocol
• Acceptance Checklist / Go-No-Go Authorization
• Amendment & Termination Terms
• Signature & Execution

• Enrollment Completion Review
• Premium Predictability & Billing Review
• Provider Access Validation Session (Roster-Based)
• ACA Compliance & Employer Obligations Check
• Success & Continuous Improvement Kickoff

• Assign a compliance owner to collect monthly census snapshots and escalate threshold risks.
• Produce a triaged exception list showing affected employees, proposed remediation, and expected costs.
• If provider exceptions are chosen, submit exception requests and track carrier responses.
• Prepare employee-facing communications for any changes or workaround instructions for impacted members.
• Schedule a follow-up validation after remediation actions to confirm employee access.
• Current State Summary (FTE Snapshot)
• Confirm whether the employer is an ALE and document the basis for that determination.
• Agree on owners for ACA reporting, data collection cadence, and filing timelines.
• Create an action plan to remediate any identified compliance gaps before filing deadlines.
• Deliver a signed ACA determination memo (ALE yes/no) with supporting FTE calculations.
• Introductions & Objectives
• Prepare documentation and template data extracts for 1094/1095 filings and schedule filing responsibility handoff.
• Schedule quarterly compliance checkpoints for the plan year.
• Recap of Confirmations
• Create and activate a single shared channel for post-launch communication with clear access and owners.
• Agree on SLAs and escalation paths so issues are handled predictably and quickly.
• Establish an enhancement backlog and a regular cadence to prioritize and implement improvements.
• Create the shared channel, invite stakeholders, and publish channel rules and owners.
• Publish the SLA document with severity definitions, response times, and escalation contacts.
• Log initial enhancement requests into the backlog with preliminary impact/effort estimates.
• Schedule recurring monthly success reviews and the first quarterly roadmap meeting.
• All active employees are reconciled between employer roster and carrier records, or have an assigned exception owner.
• Agree on timing and owners to resolve outstanding exceptions before coverage becomes active.
• Confirm communications plan for employees with pending or corrected enrollments.
• Owner to resolve each listed enrollment exception and update the shared roster by a specified date.
• Carrier liaison to provide final enrollment confirmations and policy numbers for reconciled members.
• HR/employer to notify impacted employees of confirmed coverage or next steps.
• Update master roster and upload finalized enrollment receipts to the shared channel.
• Opening & Billing Context
• Employer understands the composition of the current premium and any one-time line items.
• Identify primary drivers of future premium variance and quantify likely range under modeled scenarios.
• Agree on an early-warning process and owner to surface deviations before billing cycles.
• Deliver a premium-variance dashboard showing baseline and modeled scenarios to the employer weekly or monthly.
• Assign an owner to review and escalate any census or billing anomalies within 5 business days.
• If applicable, submit any disputed invoice items to the carrier for investigation and track until resolution.
• Define and document the employer contribution change process and freeze period to avoid mid-cycle surprises.
• One-sentence Current State
• Prove which providers on the roster are in-network and which are not using live lookups.
• Surface the operational and retention consequences of unresolved access gaps with concrete examples.
• Obtain employer decisions on remediation for each exception and assign implementation owners.
• Review Current Billing Statement(s)
• Define Shared Channel & Roles
• Consequence & Risk Assessment
• Consequence Statement
• Current Enrollment State & Reconciliation
• Live Provider Lookup on Sample Roster
• Identify Predictability Risks & Drivers
• Documentation & Filings Review
• Issue Triage, Prioritization & SLA Framework
• Outstanding Exceptions & Business Impact
• Remediation Options & Tradeoffs
• Carrier Confirmations & Effective Dates
• Enhancement Backlog & Prioritization Process
• Scenario Modeling Using Employer Census
• Operational Controls & Ongoing Tracking
• Monitoring, Early-Warning & Next Steps
• Cadence, Metrics & Close
• Resolution Plan, Owners & Timelines
• Validation & Employer Decision Points
• Remediation & Next Steps