Start Here — Tell Us About Your Account

• Which best describes you for this conversation? Options: Employee benefits broker, HR Director / Benefits leader (employer), Benefits administrator, Payroll/HRIS owner, Other
• Company or brokerage name (or enter 'confidential')
• How many employees or covered lives does this account represent? Options: 500–999, 1,000–2,499, 2,500–4,999, 5,000–9,999, 10,000–20,000, Other / prefer not to say
• When is your next open enrollment or major benefits event? Options: Within 1 month, 1–3 months, 3–6 months, 6–12 months, Not on calendar yet
• Which voluntary products are currently offered to this population? Options: Accident, Critical illness, Hospital indemnity, Supplemental life, Disability, Legal/identity theft, No voluntary products, Other
• Name the single most important goal you want this voluntary benefits program to achieve (e.g., improve employee financial security, increase broker retention, simplify payroll).

Are You Quietly Losing Credibility?

• How often do employees or clients escalate issues tied to slow claim payouts or billing mistakes? Options: Weekly, Monthly, Quarterly, Rarely, Never
• Tell us about a recent escalation—what happened, how long did it take to resolve, and who was most impacted?
• Approximately how many client-facing complaints related to claims or billing do you handle per month? Options: 0, 1–5, 6–15, 16–50, 50+
• And how long has this complaint pattern persisted? Options: Under 3 months, 3–12 months, 1–2 years, Over 2 years
• What outcome from a carrier would restore confidence quickly—faster claim payments, error-free billing, transparent reports, or something else? Options: Faster claims payout, Zero billing reconciliation issues, Detailed monthly reports, Better employee communications, Other

What's Broken Today in Enrollment and Billing?

• If your enrollment and billing were a customer experience, what single complaint would customers most likely leave in a review?
• Which HRIS/payroll/benefits platforms must integrate for this account? Options: Workday, ADP (Workforce Now/Run), UKG/Ultimate Kronos, Paylocity, Ceridian, Bswift / Ease / PlanSource, Custom/Proprietary, Other
• How do premiums flow to carriers today? Options: Automated ACH/remittance, Electronic billing files (EFT/EDI), Manual check/invoicing, Payroll provider remits, Mixed / manual exceptions
• Describe the single most common payroll deduction or carrier-billing error and the manual steps you use to correct it.
• How many hours per month does your team spend reconciling voluntary benefits premium and fixing exceptions? Options: 0–5 hours, 6–20 hours, 21–50 hours, 51–100 hours, 100+ hours
• Which recurring failure modes do you see (select all that apply)? Options: Missing payroll deductions, Duplicate deductions, Carrier invoicing mismatches, Incorrect effective dates, Employee mis-allocations, Late carrier payments, Other

How Do You Measure Success — and What Keeps You Up at Night?

• What enrollment penetration or participation rate would make this program a clear success for you? Options: <5%, 5–10%, 11–20%, 21–35%, 36%+
• What claims adjudication speed would you require to feel comfortable recommending a carrier on renewal? Options: Under 24 hours, 24–48 hours, 2–3 business days, 4–7 business days, Longer acceptable
• Which outcomes beyond participation matter most (select up to three)? Options: Employee satisfaction/NPS, Fewer HR support tickets, Broker renewal retention, Reduced payroll time, Lower error rate in billing, Measurable reduction in employee financial hardship
• How do you currently track and report these KPIs—and who reviews them monthly or quarterly?
• Which metric, if it missed target, would cause you to pause or walk away from a carrier? Options: Participation rate, Claims speed, Billing accuracy, Customer satisfaction, Portability terms, Other

What's Your Appetite for Risk and Rules?

• Are current eligibility and underwriting rules quietly shrinking participation or protecting you from adverse selection? Options: Rules are shrinking participation, Rules are protecting against adverse selection, Balanced correctly today, Unsure
• What guaranteed-issue (GI) thresholds are required or preferred for your groups? Options: GI at 200+ lives, GI at 100+ lives, GI at any size, EOI required for most groups, Case-by-case
• Which product rules or limits are mandatory (select all that apply)? Options: Age-banded rates, Coverage tier limits, Salary/hourly eligibility caps, Open enrollment only, Guaranteed-issue for core tiers, Other
• How do you currently detect or respond to adverse selection spikes? Give an example if you've experienced one.
• What portability or termination terms would you require in the contract for employee satisfaction and compliance? Options: Portable coverage for terminated employees, COBRA-like continuation, No portability, Partial portability options, Other

Imagine a Seamless Enrollment Experience — What Changes?

• If employees could understand cost, coverage, and claims expectations in under two minutes, how would that change engagement?
• Which decision-support tools would move the needle most for your population? Options: Side-by-side product comparisons, Take-home cost-of-care calculators, Peer-penetration benchmarks, Personalized benefit recommendations, Quick video explainers
• What communication channels and formats have historically driven the best enrollment outcomes for your employees? Options: Email, SMS/text, Live webinars, On-site meetings, In-platform nudges, Printed mailers
• Describe the ideal end-to-end enrollment flow from the employee's first touch to payroll deduction appearing on pay stub.
• What accessibility, language, or demographic accommodations must be included for your population? Options: Multi-language support, Mobile-first experience, Low-literacy UI, ADA-compliant features, No special accommodations

Operational Reality Check — Who Does What and When?

• If a deployment delay cost you a renewal, who would be held accountable—and who has the authority to unblock the work?
• Which stakeholders will be actively involved in delivery and sign-off (select all that apply)? Options: Broker lead/AE, Regional sales director, HR Director / Benefits lead, Payroll/HRIS owner, IT/Integration lead, Carrier operations rep, Third‑party enrollment vendor
• Please list the names and emails (or roles) of the primary decision-makers and operational owners for this project.
• What is your target timeline from selection to pilot start and to full rollout? Options: Pilot within 2–4 weeks, Pilot in 1–2 months, Pilot in 3+ months, Timeline flexible / not yet decided
• Which approvals typically create the longest delay (legal, finance, payroll, IT, executive)? How long do they usually take?

Next Steps That Would Make This an Easy Yes

• What is the smallest, least-risky pilot we could run that would prove value to you?
• Which sample files or test artifacts do you need to validate claims speed, billing accuracy, and enrollment UX? Options: Sample claims adjudication logs, Demo group enrollment data, Payroll remittance file sample, API/Sandbox access, SFTP transfer sample files
• What objective acceptance criteria would you require to move from pilot to full rollout?
• Which technical connectivity tests must pass before build work begins? Options: Payroll mapping verification, Benefits admin API calls, Carrier billing EDI/CSV exchange, User SSO and provisioning, Data encryption/transfer validation
• Identify the top three blockers (internal or external) that would prevent you from signing a Statement of Work in the next 30 days.
• How do you prefer to receive pilot results and make decisions—dashboard, written report, live review call, or a mix? Options: Interactive dashboard, Executive summary report, Live review meeting, Email with attachments, Combination

Starting Point: A Rapid Snapshot of How You Enroll Today

• Which systems or methods do you currently use to enroll employees and manage voluntary benefits? Options: In-person/paper forms, Carrier portals only, Benefits platform (BAM/ACA vendors), HRIS with benefits module (e.g., Workday, ADP, BambooHR), Payroll system handles elections (e.g., ADP, Paychex), Custom spreadsheets / manual reconciliation, Enrollment vendor / third-party firm, Other
• How long is your typical open enrollment window (or qualifying life event window) from communication to close? Options: Less than 1 week, 1–2 weeks, 3–4 weeks, More than 4 weeks, Rolling / ongoing enrollment
• Who leads and owns enrollment execution for voluntary products at your organization? (role or team name) Options: HR Director / Benefits Lead, Payroll Manager, Broker / Benefits Consultant, Third-party enrollment firm, HRIS/IT owner, No single owner / shared responsibility, Other
• What are your current penetration / participation benchmarks for voluntary lines (accident, critical illness, hospital indemnity, supplemental life)? Give ranges per product if available. Options: <5%, 5–10%, 10–20%, 20–35%, 35–50%, >50%
• Briefly describe one recent enrollment (last 12 months) that went well and one that didn’t—what happened?

Are We Comfortable With ‘This Is How We’ve Always Done It’?

• What compromises are you tolerating in your current enrollment process because changing it feels too risky or expensive?
• Which manual tasks consume the most time or cause the most errors during enrollment? Options: Paper data entry, Manual payroll deduction setup, Carrier invoice reconciliation, Correcting elections post-close, Dependent verification, Other
• How often do manual errors (deduction mistakes, incorrect elections, missed enrollments) occur during an enrollment cycle? Options: Multiple times per week, Weekly, Monthly, Rarely, Almost never
• When those issues happen, what internal emotions or reputational impacts do they create for HR and the broker (e.g., distrust, extra escalations, churn)?
• What workarounds have you accepted that you wish you could eliminate (even if they feel entrenched)?

Where Payroll and Carrier Billing Keep Colliding — And Why It Hurts

• How frequently do payroll deduction files and carrier billing statements fail to reconcile cleanly? Options: Every cycle, Most cycles, Occasionally, Rarely, Never
• Which payroll system(s) do you use and how are deductions currently mapped to voluntary products? Options: ADP Workforce Now, ADP Vantage, Paychex, UKG/Ultimate Kronos, Workday Payroll, Ceridian, Other
• Describe your current reconciliation process: who runs it, what tools are used, and how long it typically takes each pay period?
• How do you handle retroactive changes, chargebacks, or payroll corrections when a carrier billing error occurs? Options: Manual adjustments in payroll, Carrier issues credit/memo, We run separate reconciliation projects, Pass-through to broker/vendor, Other
• How many hours per month or full-time-equivalent (FTE) are dedicated to premium reconciliation and billing exceptions? Options: <5 hours, 5–20 hours, 20–40 hours, >40 hours, Not measured

When Claims Break, Who Gets Blamed?

• Have you experienced claims delays or errors that led to employee complaints or broker escalation in the last 12 months? Options: Yes — multiple times, Yes — once, No — but close calls, No
• If yes, please describe the most damaging claim incident and its consequences (employee impact, communications, retention, broker relationship).
• What is your acceptable SLA for claims adjudication and payment from a carrier (hours/days)? Options: <24 hours, 24–72 hours, 3–5 business days, 5–7 business days, >7 business days
• How do employees typically discover whether a claim was paid—direct deposit, portal notice, HR email, or broker outreach? Options: Direct deposit notification, Carrier portal message, HR communicates, Broker contacts employee, Employee calls HR/broker, Other
• What channels or language have you used to calm employees when a claim was delayed, and which worked best?

Where Data Flows Leak — Mapping the Arrows You Don’t See

• If you drew a map of every data handoff (HRIS → Payroll → Benefits platform → Carrier), where do you believe data most often gets lost or corrupted?
• Which integration methods do you currently rely on for enrollment and billing feeds? Options: Real-time API, Batch SFTP/flat files, 834/EDI feeds, Manual CSV uploads, Direct carrier portal entry, None / manual process
• How often are integration failures identified proactively vs. discovered through employee complaints? Options: Proactively caught, Even mix, Mostly discovered through complaints, Unknown
• Do you maintain a test/sandbox environment for integrations and payroll mapping before each enrollment? If so, how complete is it? Options: Full sandbox with test employees, Partial testing, Ad-hoc testing only, No sandbox/testing
• Are there compliance, security, or vendor access constraints (e.g., restricted file sharing, vendor NDA) that typically delay integrations? Options: Yes — major constraints, Yes — minor constraints, No constraints, Not sure

Enrollment Through an Employee’s Eyes: Where Confusion Starts

• When employees enroll, which step causes the most confusion or drop-off (finding plans, understanding benefits, payment setup, dependent verification)? Options: Finding plans, Understanding coverage vs. employer benefits, Setting up payroll deduction, Dependent/beneficiary entry, Submitting evidence/forms, Other
• Which channels do employees use most to enroll or ask help (mobile app, desktop portal, call center, HR in-person)? Options: Mobile app, Desktop/portal, Call center, Email, In-person HR assistance, Broker/advisor help
• What decision-support (comparison matrices, calculators, scenario examples) do you currently provide to employees, and how often do they use it? Options: Robust calculators and comparisons, Basic plan descriptions, Broker-led webinars, None provided, Other
• How long does an average employee take to complete voluntary elections from start to finish? Options: <5 minutes, 5–15 minutes, 15–30 minutes, >30 minutes, We don't track
• Share one verbatim example of a question or frustration an employee raised during enrollment recently (exact wording if possible).

Risk Hotspots: The Small Failures That Scale Into Big Problems

• If one failure mode persisted unchecked, which would most likely lead to broker churn, HR burnout, or compliance exposure? Options: Chronic payroll/billing mismatches, Slow or inaccurate claims payments, Major enrollment data loss, Adverse selection concentration, Portability disputes, Other
• Which of the following failure modes have you experienced in the past two years? Options: Duplicate deductions, Missed enrollments, Late carrier invoices, Incorrect employee coverage levels, Claims denied for enrollment errors, All of the above, None
• When failures occur, how is root cause identified and how long does remediation typically take? Options: Immediate root-cause analysis & <1 week fix, Takes weeks to months, Requires external vendor assistance, Often unresolved, Not tracked
• Have any of these issues triggered contractual penalties, carrier repricing, or changes to guaranteed-issue rules? Options: Yes — penalties/repricing, Yes — tightened GI rules, No, not yet, Not sure
• What monitoring or alerting would make you feel confident these hotspots were under control? Options: Automated reconciliation alerts, Real-time claims SLA dashboard, Payroll/carrier exception reports, Dedicated escalation owner, Other

Quick Wins and Non-Negotiables: What Would Make Change Safe?

• What are the non-negotiables we must guarantee before you’d accept a new enrollment and carrier integration? Options: Payroll accuracy, Claims speed & transparency, Portability for separated employees, No manual carrier invoice work, Data security/compliance, Broker approval process, Other
• What pilot scope (number of employees, lines of coverage, timeline) would you consider sufficient to validate a new flow? Options: Small cohort <100 employees, Mid-size 100–500, Large 500–2,000, Full population >2,000, Unsure — discuss
• What SLA or measurable acceptance criteria would make you comfortable signing off after pilot (e.g., reconciliation accuracy %, claim pay time)?
• Who are the decision-makers and operational owners that must be satisfied before full rollout (names, roles, approval thresholds)?
• If you had one small change we could implement in the next 30 days to reduce your biggest pain, what would it be?

Getting Oriented: Who Are We Helping Today?

• Tell us the employer group we're discussing (company name), current employee count, and the primary HR and broker contacts we should know.
• Which person or team is driving the decision right now? Options: Benefits/HR Director, Employee Benefits Broker, CFO/Finance, People Ops, Payroll, Benefits Committee, Other
• What is your committed target timeline for selection and live enrollment? Options: Next 30 days, 30–60 days, 2–3 months, 3–6 months, 6+ months, Undecided
• Who must sign commercial terms and SLAs before work begins? List roles or titles. Options: HR Director, Broker/Agency Principal, CFO/Finance Lead, CEO/Founder, VP Total Rewards, Benefits Committee, Other
• What operational non-negotiables should we record now (examples: guaranteed-issue threshold, payroll freeze dates, specific portability terms)?
• Which stakeholders should be invited to the technical kickoff to avoid surprises later? Options: Benefits Admin/HRIS, Payroll, Broker/Producer, Carrier Ops, IT/Security, External Enrollment Vendor, Other

Are We Comfortable Betting Your Reputation on This?

• If a carrier pays claims slowly and employees complain, how likely is that to harm your broker relationship or employee trust? Options: Highly likely — relationship risk, Somewhat likely, Unlikely, Not sure
• What evidence would you need to feel confident making a recommendation (e.g., average claims-to-payment hours, peer employer references, enrollment penetration benchmarks)? Options: Claims speed data, Peer employer case study, Customer satisfaction scores, Enrollment penetration benchmarks, Integration test results, Other
• Tell us about a time a carrier’s operational failure reflected back on your organization—what happened and what were the consequences?
• How important is a measurable claims SLA (e.g., <24 hours) versus other attributes like price or product breadth? Options: Claims SLA is the top priority, Claims SLA is important but secondary, Price/product breadth matter more, Equal importance, Undecided
• How would quicker claims payments change your conversations with employees and renewal conversations with clients?
• What would make you remove a carrier from consideration during selection—what’s a hard stop? Options: Slow claims history, No guaranteed-issue terms, Poor payroll integration, Unclear billing reconciliation, Unwillingness to sign SLA, Other

Where the Process Breaks (and How It Feels)

• When enrollment or billing goes wrong, who hears about it first—and how does it usually surface? Options: Employees contact HR, Payroll notices discrepancy, Broker receives complaints, Carrier flags an issue, Other
• Describe the most common failure mode you've seen in voluntary benefits (examples: duplicate deductions, missed premiums, delayed claims). Which one hurts the most?
• How often do these issues occur today? Options: Daily, Weekly, Monthly, Quarterly, Rarely, Never
• When an issue occurs, how much HR or broker time is typically required to resolve it (estimate hours per month)? Options: <1 hour, 1–5 hours, 5–10 hours, 10–20 hours, 20+ hours
• How do those breakdowns affect employees emotionally or behaviorally (examples: lost trust, declined enrollment, calls to service line)?
• How are errors currently tracked and escalated? Can you share a brief example of your escalation path and timeline?

Reality Check: Systems, Flows, and Data

• Which payroll system(s) and HRIS/benefits admin platforms must this integrate with? Options: ADP Workforce Now, ADP Vantage, Paychex, UKG/UltiPro, Workday, BambooHR, Namely, Rippling, Other
• How is carrier billing handled today and what cadence is required (e.g., monthly employer-paid reconciliation, employee direct-bill)? Options: Carrier bills employer monthly, Carrier bills employer per pay period, Carrier bills employees directly, Carrier sends detailed remittance files, Manual invoice reconciliation, Other
• What file formats and delivery methods do you currently use or require for premium and enrollment feeds? Options: CSV/SFTP, API/JSON, EDI, Secure email, Carrier portal upload, Other
• Are there payroll constraints we must respect (payroll freeze windows, cut-off times, deduction rounding rules)? Please list timing and rules.
• Who will own operational access and user roles on the platform post-launch (HR admin, broker, payroll)? Options: HR admin, Broker/Admin user, Payroll, Benefits vendor, IT/Security, Other
• What data elements are non-negotiable in the enrollment feed (examples: employee ID mapping, hire date, payroll deduction code)?
• Have you run integration tests before with other carriers? If yes, what broke and how long did remediation take?

If It Went Perfectly, What Would Your Team Finally Stop Saying?

• What are the top 3 measurable outcomes that would make this project a clear success for HR and the broker (examples: penetration %, claims turnaround hours, payroll error rate)?
• Choose the metrics you will use to evaluate success post-pilot. Options: Enrollment penetration (%), Employee satisfaction/NPS, Average claims-to-payment time, Payroll reconciliation errors per pay period, Time HR spends on enrollments, Retention of broker-client relationship, Other
• What targets would you set for those metrics (e.g., penetration 10–20%, claims paid <24 hours, payroll errors <1% per pay period)?
• How soon after launch do you expect to see signal data that tells you whether it's working (e.g., within 30 days, first payroll cycle, end of pilot)? Options: Within 30 days, First payroll cycle, End of 90-day pilot, After full rollout, Unsure
• Which employee experience outcomes matter most to you emotionally—what would make you feel proud to have recommended this? Options: Fast claims payouts, Clear enrollment UX, Fewer admin tickets, High employee satisfaction, Seamless payroll deductions, Other
• If we achieve the targets, what would success enable next (examples: broader product shelf, multi-site rollout, preferred carrier status)?

Hidden Costs or Rules That Will Kill the Project

• Are there procurement, legal, union, or compliance rules that typically block carrier selection unless satisfied? If so, what are they?
• Are portability and termination terms a hard requirement? If yes, which of the following are non-negotiable? Options: Portability on voluntary plans, COBRA handling required, Guaranteed-issue for certain group sizes, Specific portability premiums, None of the above, Other
• What billing reconciliation tolerance will finance accept (examples: <$100/month variance, <$1% of premiums, manual reconciliation allowed)? Options: <$50/month, <$100/month, <1% of premiums, Manual reconciliation acceptable, No tolerance — must match exactly, Other
• Have past projects failed because of hidden integration costs or unexpected mapping work? Tell us one example and how long the remediation took.
• Which contractual protections or SLAs must be included for you to feel comfortable (select all that apply)? Options: Claims adjudication SLA, Billing cadence guarantees, Data security/PII clause, Portability clause, Service credits for missed SLAs, Other
• What internal approvals or budget cycles could delay signup even if technical readiness is confirmed? Options: Board approval, Quarterly procurement cycle, Finance budget window, Broker commission schedule, None, Other

Pilot or Launch — Which Path Seals the Deal?

• Would you prefer a pilot with a subset of employees or a full enrollment roll at go-live? Explain the experiences that make you lean one way. Options: Small pilot (department/site), Large pilot (percentage of population), Full launch, Unsure—need recommendations
• If running a pilot, what sample size and population mix would convince you (examples: 200 lives across multiple locations, 10% of population, specific demographics)? Options: <200 lives, 200–500 lives, 500–1,000 lives, 10% of population, Specific demographics only, Other
• Which pilot metrics will you watch most closely to greenlight a full rollout? Options: Claims turnaround, Enrollment penetration, Payroll reconciliation accuracy, Employee support volume, Satisfaction surveys, Other
• What training and enablement do frontline HR and brokers need before pilot starts (examples: platform demo, enrollment scripts, FAQs)? Options: Platform admin training, Enrollment walkthrough for employees, Broker sales kit, Payroll reconciliation SOPs, Employee FAQs, Other
• Who on your side will be the day-to-day owners during pilot and who signs off on acceptance criteria?
• Assuming a pilot reveals 1–3 issues, what remediation SLA would you expect before full rollout? Options: <48 hours for critical fixes, <1 week, <30 days, Depends on issue severity, No firm SLA

Decision Momentum — Next Steps & Risk Trade-offs

• What is the single biggest risk you’re worried we’ll learn during discovery that could stop this deal?
• If we had to prioritize three items to de-risk the project in the next 30 days, which would they be? Options: Integration test pass, Claims SLA confirmation, Signed commercial terms, Pilot plan agreed, Training scheduled, Other
• How much internal runway do you need to commit once integration readiness is validated (e.g., resources, payroll dates)? Options: Immediate (within 2 weeks), 2–4 weeks, 1–2 months, Longer than 2 months, Undecided
• What trade-offs would you accept to accelerate launch (examples: narrower product scope, manual interim reconciliation, limited pilot size)? Options: Narrower product set, Manual reconciliation for first cycle, Smaller pilot, Extended support hours, None — no trade-offs
• Who else should we align with this week to keep momentum (names, roles, and best contact method)?
• Finally, what's the easiest next step you want us to take after this discovery call to build confidence and keep things moving? Options: Send a tailored pilot plan, Provide claims speed proof and references, Schedule an integration discovery call, Draft commercial term highlights, Other

Quick Grounding: Who's in the Room?

• Which of these best describes your role in benefits decisions for this employer group? Options: Benefits Broker (regional/independent), HR Director / Head of Benefits, Payroll or HRIS Admin, Enrollment Vendor / TPA, Other (please specify)
• How many employees are in the employer group we're discussing? Options: 500–999, 1,000–2,499, 2,500–4,999, 5,000–19,999
• What is your target timeframe for a pilot and/or full launch? Options: Within 30 days, 30–90 days, 3–6 months, 6+ months, TBD
• Briefly describe your prior experience with voluntary products in this account—what has gone well and what has caused headaches?
• Who typically signs the contract and owns vendor selection for voluntary benefits at this employer? Options: Broker leads; employer signs, Employer HR leads, Joint decision (Broker + HR), Third-party consultant or benefits admin, Other (please specify)

Are You Comfortable Gambling on Claims Speed?

• If claims took a week instead of a day, how many broker relationships or renewals would be at real risk? Options: None, A few, Several, Many, Not sure
• Tell us about a specific time when claims speed or accuracy changed an employee's view of benefits or affected broker retention—what happened?
• What turnaround time for claims payment do you currently regard as acceptable for voluntary benefits? Options: Under 24 hours, 24–48 hours, 2–5 business days, 5+ business days, Varies by product
• Which performance metrics or artifacts do you ask carriers to provide when you evaluate their claims capability? Options: Average time to payment, Claims denial/appeal rate, Sample claim audit files, Employee satisfaction/NPS, Case studies from similar groups, Other
• How would consistently delivering an 18-hour average from submission to payment change your sales pitch, retention conversations, or employee satisfaction expectations?

Where Does Enrollment Break Down Today?

• Why do we keep accepting manual enrollment errors and reconciliation workarounds as 'the way it is'? Options: Lack of bandwidth to fix it, Legacy systems lock-in, Vendors are incompatible, Low perceived ROI to change, Other (please specify)
• Walk me through the employee enrollment journey today—from benefit education to final payroll deduction—who touches it and at what points?
• Which enrollment platforms or benefits administrators does this employer currently use (select all that apply)? Options: Benefitfocus, Workday Benefits, ADP WFN Benefits, iSolved, PeopleSoft, BambooHR, Other (please specify)
• How often do payroll deduction mismatches or carrier billing discrepancies occur during or after open enrollment? Please estimate frequency or give a recent example. Options: Rarely (<1%), Occasionally (1–3%), Often (3–10%), Regularly (>10%), Don't know
• Describe the most common failure mode you see (e.g., duplicate deductions, missed enrollments, wrong plan codes) and share a recent incident.
• What manual reconciliations or workarounds are used today to resolve enrollment or billing issues, and how many staff-hours do they typically consume each week?

Who Really Owns Payroll and Billing Headaches?

• If payroll errors mean someone has to work late, who usually bears the burden—HR, the broker, or the employee? Options: HR team, Broker, Affected employees, Carrier/customer service, Shared / varies
• Which payroll system is the employer using? Options: ADP, Paychex, Ceridian/Dayforce, UKG (Kronos/Ultimate), Workday Payroll, Other (please specify)
• What file formats, cadence, and delivery methods are available for carrier billing and payroll feeds (e.g., ACH, flat file, SFTP)? Please list what you currently exchange.
• How often have you needed to run off-cycle payroll corrections due to voluntary benefits, and what authorization process is used? Options: Never, Rarely, Occasionally, Frequently, Always
• Who will be the operational owner responsible for monthly carrier reconciliations and do they have the bandwidth to absorb this work post-launch? Options: HR/Benefits team, Payroll team, Broker operations, Third-party admin, Unassigned / TBD
• What tolerance for payroll variance (in dollars or number of impacted employees) is acceptable before a manual audit is triggered?

If Participation Could Be Higher, What Would That Mean?

• What if low penetration is not a people problem but a design problem—are you willing to rethink the enrollment experience itself to move participation? Options: Yes, fully willing, Maybe with clear evidence, Prefer incremental changes, Not open right now
• Today, what penetration rate do you consider successful for voluntary lines at this employer? Options: Under 5%, 5–10%, 10–20%, 20–40%, 40%+
• What penetration target (specific % or employee count) would make the broker comfortable recommending the program and the employer feel the ROI?
• Which communication channels and tactics have historically driven the most enrollments here? (Select all that apply.) Options: Email campaigns, Onsite benefits fairs / presentations, In-platform decision support, Manager communications, Payroll stub messages, Direct mail, Other (please specify)
• Describe any messaging, cost calculators, or side-by-side product comparisons you've tested and what impact they had on employee decision-making.
• Are guaranteed-issue thresholds, medical underwriting, or payroll deduction limits materially restricting participation? Please specify thresholds and concerns.

What Would a Claims Nightmare Look Like—and How Would You Recover?

• Imagine a wave of unpaid claims and angry employees—what single capability would most quickly defuse the situation: faster payments, proactive communications, or broker-led triage? Options: Faster payments, Proactive communications, Broker-led triage / case management, Financial remedy/service credits, Other (please specify)
• Have you experienced claim disputes that escalated to formal HR complaints or public issues? Please describe the event and how it was resolved.
• What contractual SLA for claims adjudication would you insist on (pick the closest)? Options: Same-day, Under 24 hours, 24–48 hours, Up to 5 business days, No strict SLA required
• How should employee support be staffed and routed to prevent escalations (e.g., carrier call center, dedicated case manager, broker hotline, digital chat)? Which of these would you prioritize? Options: Carrier call center, Dedicated case manager, Broker support hotline, Digital self-service + chat, Combination (please describe)
• If a carrier misses its SLA, what remedies would you expect to see in the contract or in practice? Options: Financial penalties, Service credits, Escalation & remediation plan, Termination rights, Informal remediation only

Integration & Portability: Are You Prepared for Employee Lifecycle?

• Do you assume that when an employee leaves the company, their coverage and billing will 'just work'—and what happens if it doesn't? Options: Assume it works, Expect some issues, Often problematic, Unsure / need to test
• Which HRIS and benefits admin systems must we integrate with for enrollment, terminations, and census updates? (Select all that apply.) Options: Workday, ADP (WFN/Run), Benefitfocus, BambooHR, iSolved, PeopleSoft, Other (please specify)
• How are offboarding, deduction stops, and portability/conversion currently handled—and how often do those flows fail?
• Which portability or continuation terms are non-negotiable for you or employees (select all that apply)? Options: Portability without underwriting on termination, Standard conversion rights, COBRA-like continuation options, Premium guarantees for a period, Other (please specify)
• What specific data fields and sync cadence do you require in feeds to avoid enrollment drift (e.g., employee ID, hire/term dates, benefit codes), and are any of these currently missing?
• Have you previously tested end-to-end termination and portability scenarios with carriers? If yes, what failed and what worked?

Pilot & Success Signals: What Would Make You Confident to Rollout?

• Is your typical pilot a rigorous stress test that proves the solution under pressure, or a checkbox meant to reassure stakeholders? Options: Rigorous stress test (crucible), Mix of both, Mostly a checkbox, We rarely run pilots
• What pilot size and duration would you require to feel comfortable moving to full rollout? Options: Small (25–100 employees), Medium (100–500 employees), Large (500+ employees), Percentage-based (5–20% of population)
• List the top three success signals you need from a pilot (e.g., penetration %, NPS, average time-to-payment, payroll reconciliation time).
• Which pilot activities must be performed live to qualify the program (select all that apply)? Options: Live enrollments through platform, Payroll reconciliation and test files, Claims test with sample payouts, Full employee support routing, Training and admin playbooks, Other (please specify)
• How should defects discovered during the pilot be documented, prioritized, and verified—what acceptance process satisfies both broker and employer?
• If the pilot meets its success signals, what gates must be closed before full rollout (select all that apply)? Options: SLA signoff, Integration / end-to-end test signoff, Pilot acceptance criteria met, Training & enablement complete, Contractual commercial terms finalized, Other (please specify)