Quick Warm‑Up: What Brought You Here Today?

• What prompted you to start exploring telematics now—what incident or insight moved this from a 'nice to consider' to 'we need to act'?
• Which of these best describes the primary sponsor or business case for this initiative? Options: Loss ratio improvement, Customer retention / churn reduction, New product / pay-per-mile, Market differentiation / competitive response, Regulatory compliance / reporting, Other
• Who is formally sponsoring or funding the project today? (select all that apply) Options: Chief Actuary, Head of Personal Auto/Product, CUO, CIO / CTO, Head of Legal / Privacy, Head of Marketing / Growth, Other
• Where would you place the program on an internal maturity scale today? Options: We are curious / exploratory, Proof of concept planned, Pilot approved and funded, Deployment ready (org & ops in place), We already have a partial program, Unsure
• What timeline do you have in mind to launch a pilot (not full rollout)? Options: 0–3 months, 3–6 months, 6–12 months, 12+ months, No set timeline

If You Waited a Year, Would You Regret It?

• If a competitor rolled out a high-performing telematics product in the next 6–12 months, how would that change your market position or retention risk? Options: Significant risk of losing low‑risk drivers, Moderate competitive pressure, Little immediate impact, Would accelerate our plans but not critical, Unsure
• How much of your loss ratio gap do you believe is addressable by behavior‑based pricing vs other levers (e.g., underwriting rules, rate changes)? Options: >50%, 25–50%, 10–25%, <10%, Don't know yet
• What keeps you awake at night about waiting—regulatory change, market share, rising claims, or internal momentum? Options: Competitive product launch, Regulatory openings or constraints, Loss ratio deterioration, Talent / org politics, Vendor lock‑in concerns, Other
• Describe a worst‑case scenario that would make you wish you'd acted sooner (brief example of market or financial consequence).
• How does your leadership team view the tradeoff between being a first mover vs. a fast follower on telematics? Options: Prefer first mover, Prefer fast follower, Depends by line/geography, No consensus yet

What’s Really Broken in Your Current Rating?

• Which current rating variables feel most like blunt instruments—pulling good and bad drivers together—rather than distinguishing true risk? Options: Age, Credit score, Territory, Vehicle type, Annual mileage, Other
• Can you share a concrete example where current factors led to mis‑priced risk or customer churn?
• How often do you see materially different loss patterns within segments that your current model treats as homogeneous? Options: Very often, Sometimes, Rarely, Never, Unsure
• Which operational pain points tie back to rating accuracy (claims leakage, fraud, underwriting backlog, customer disputes)? Options: Claims leakage, Fraud false positives/negatives, Underwriting complexity, Customer complaints / disputes, Loss of profitable renewals, Other
• When you think about fixing these issues, what feels most valuable: better segmentation, personalized pricing, or behavioral nudges to change driving? Options: Better segmentation, Personalized pricing, Behavioral coaching / engagement, All of the above, Other

Who Holds the Keys—and Who Keeps Saying 'Not Yet'?

• Who are the people or functions that must sign off for a pilot to proceed? List roles and their top concern in one sentence each.
• Which stakeholder typically has the most influence over pricing / rating changes in your organization? Options: Chief Actuary, CUO, Product Head, Legal / Compliance, CIO / Data Office, Executive Committee
• Which function is most likely to raise a veto or delay—what do they worry about most (e.g., legal: privacy, actuary: model stability)? Options: Legal / Privacy, Actuarial team, Regulatory affairs, IT/Integrations, Distribution / Agents, Other
• What evidence or artifact would convince the skeptical stakeholders (examples: actuarial lift analysis, consumer opt‑in data, legal memo, regulator pre‑brief)? Options: Actuarial case study, Regulatory memo / precedent, Privacy impact assessment, Pilot results from comparable carrier, Consumer engagement metrics, Other
• How have past initiatives been derailed—bureaucracy, procurement timelines, integration surprises, or results that didn’t meet expectations?

Can We Trust the Data You Have—and the Data You’ll Need?

• Which telematics source(s) are you most willing to adopt for a pilot (select all that apply)? Options: Smartphone app, OBD‑II device, Embedded OEM data, Third‑party fleet telematics, Combination / multi‑device
• How would you describe your current data maturity for telematics‑style inputs (collection, storage, labeling, QA)? Options: Ready for production, Prototype / partial, Data exists but needs work, No internal telematics data yet, Unsure
• Do you have existing integrations or vendors for mileage / trip data, and can you name them (or list 'none')?
• What data governance and privacy constraints should we plan around (select all that apply)? Options: State privacy laws (e.g., CCPA equivalents), GDPR or cross‑border transfer limits, Data retention limits, Anonymization or pseudonymization required, Explicit consent for secondary use, Other
• How sensitive is latency for you—do you need near‑real‑time scoring, daily batches, or is weekly acceptable for the pilot? Options: Near‑real‑time, Daily, Weekly, Monthly, Undecided
• Describe the ideal consent and opt‑in UX you imagine we present to policyholders (brief).

What Would Success Really Look Like—Beyond Buzzwords?

• What are the quantitative targets that would make this project 'a success' for you? Please list targeted opt‑in %, loss ratio lift (points or %), retention lift, or ROI horizon.
• Which of these KPI targets feels most critical to greenlight a broader rollout? Options: Loss ratio improvement, Policy retention / reduced churn, Sustained opt‑in rate, Customer NPS / satisfaction, Regulatory approval / no objections
• What acceptance thresholds would you set for pilot success (e.g., minimum opt‑in, loss ratio change, statistical confidence)? Options: Predefined numeric thresholds (we have them), We need your help to define thresholds, Flexible — we'll iterate, No thresholds yet
• How will you balance short‑term financial impact vs. long‑term strategic benefits when evaluating results? Options: Focus on short‑term P&L, Prioritize long‑term share & retention, Equal weight to both, Depends on board guidance
• Who will be the final owner of these KPIs post‑pilot (actuarial, product, ops, or a cross‑functional board)? Options: Actuarial, Product / Head of Personal Auto, CUO, Operations, Cross‑functional governance, Other

What Could Break the Pilot—and How Would You Recover?

• If opt‑in falls below expectations, what are acceptable remedial steps (pricing incentives, broader device set, UX changes, pausing rollout)? Options: Increase discounts/incentives, Change opt‑in messaging or UX, Add device options (OBD/app/OEM), Pause expansion and analyze, Cancel pilot
• How do you want to handle regulatory or consumer complaints during pilot—immediate pause, notify regulator, customer remediation, or escalate internally? Options: Immediate pause & notify regulator, Customer remediation plan, Internal incident review then decide, Continue with communication, Undecided
• What rollback or remediation criteria should be documented up front (e.g., scoring instability, adverse selection beyond X%, legal risk)?
• What SLAs or uptime / data quality targets are non‑negotiable for integrations during the pilot? Options: 99.9% availability, 99% availability, Daily data completeness >95%, Weekly reconciliation acceptable, Other
• Who should be on the incident response team and how quickly must they be reachable (hours)?

How Smooth Do You Need the Integration to Be?

• Which core systems must the telematics platform integrate with for the pilot (select all that apply)? Options: Rating engine, Policy administration system, Claims system, Billing system, Data warehouse / analytics, Mobile app / customer portal, Other
• Do you prefer a phased integration (start with analytics + side‑by‑side scoring) or end‑to‑end pricing integration for the pilot? Options: Phased (analytics first), End‑to‑end pricing, Hybrid approach, Undecided / need recommendation
• What internal resources and estimated FTEs can you commit to integrations, testing, and deployment during the pilot?
• Do you have sandbox/test environments available for safe end‑to‑end testing, and if so, how mature are they? Options: Full sandbox available, Partial test environments, Limited test data only, No sandbox available
• Are there hard change windows, release blackout periods, or regulatory filing windows we must avoid? Options: Yes—specific blackout windows, No strict windows, Not sure / need to check

What Will You Want to See Before You Sign?

• Which commercial models would you consider for a relationship with us? Options: Per‑policy subscription, Revenue share on savings, Fixed fee + success bonus, Pilot discount then standard pricing, Other
• What are your must‑have legal / commercial terms (data ownership, liability caps, exclusivity, audit rights)?
• How important is vendor transparency into models (full actuarial disclosure vs. high‑level performance reporting)? Options: Full disclosure required, High‑level performance reporting is fine, Prefer partial transparency, Undecided
• What procurement or contracting steps typically add the most time (insurance legal review, security review, executive approval)? Options: Insurance legal review, Security / IT due diligence, Procurement PO process, Executive sign‑off, Other
• How soon after a satisfactory pilot would you expect commercial close / enterprise rollout to begin? Options: Immediately, Within 3 months, 3–6 months, 6–12 months, Depends on board sign‑off

If This Works, How Will You Keep It That Way?

• What monitoring cadence do you expect for scoring and model performance post‑pilot (daily, weekly, monthly)? Options: Daily, Weekly, Monthly, Quarterly
• Who should own ongoing governance for telematics models once scaled (actuarial, model risk, product, or a new center of excellence)? Options: Actuarial, Model risk / validation team, Product / Pricing, Center of Excellence, Other
• How do you want model drift and recalibration decisions to be made—automated alerts, scheduled reviews, or event‑driven? Options: Automated alerts + review, Scheduled periodic recalibration, Event‑driven only, Combination
• Are you planning to expand telematics beyond personal auto (commercial, fleet, usage‑based other lines)? If so, which? Options: Personal auto only, Commercial auto, Fleet / usage billing, Other lines of business, Undecided
• What capabilities would you want us to own long‑term vs. what you'd prefer to keep in‑house (modeling, data ops, UX, regulatory filing)?

Where You Stand Today — a quick snapshot

• Briefly describe your current personal auto product portfolio and whether telematics is already part of any product.
• Which internal stakeholders are currently involved in pricing, data, and telematics decisions? Options: Chief Actuary, Head of Personal Auto/Product, CUO, CIO/Head of IT, Legal/Compliance, Marketing/Retention, Distribution/Agency, Other
• What primary rating variables are in your current base rate plan today? Options: Age, Gender, Credit score, Territory/zip, Vehicle year/make/model, Annual mileage (self-reported), Prior claims/loss history, Driving record (violations), Other
• When was your most recent rating plan update or major filing (month/year)? Options: Within the last 6 months, 6-12 months ago, 1-2 years ago, More than 2 years ago, We can't recall
• How do you currently measure pricing performance across products (list the specific metrics you look at and the cadence)?
• Which one outcome are you most hoping telematics will influence (pick one primary focus)? Options: Improve loss ratio, Increase retention, Attract low-risk drivers, Price more competitively, Reduce fraud, Support new product (PAYD/PPO), Other

Are We Still Pricing on Hunches?

• How confident are you that your current demographic and vehicle proxies truly separate safe drivers from risky ones? Options: Very confident, Somewhat confident, Doubtful, Not confident at all
• Which existing rating factors do you suspect are masking real driving risk rather than explaining it? Options: Age, Credit score, Territory, Vehicle value, Marital status, Prior claims, Other
• Tell us about a segment you believe is consistently mispriced today—who are they and what feels wrong?
• Have you run any retrospective analyses that estimate the incremental predictive value of telematics signals versus your current model? If yes, summarize key findings. Options: Yes — we have detailed results, Yes — high-level estimates only, No — but we plan to, No — not yet
• How does it feel internally when pricing misses occur—who gets the heat and what are the typical consequences?

Data Reality: What’s Actually in Your Hands?

• What critical driving signals do you not have today that, if you did, would most change your pricing or segmentation? Options: Trip-level mileage, Time-of-day driving, Hard braking/acceleration events, Speeding frequency, Phone distraction, Brake/turn/cornering patterns, OEM vehicle telematics, None—we have most signals, Other
• Which data sources are already available to feed modeling or BI (select all that apply)? Options: Policy administration system (PAS), Claims system, Telematics vendor feeds, OEM connected vehicle feed, Mobile app trip data, OBD-II device feeds, Third-party data (credit, DMV, socioeconomic), Data lake/warehouse, None of the above, Other
• Describe the size and recency of any telematics or driving-signal dataset you already own (e.g., N drivers, last collection date, sampling frequency).
• Do you currently store trip-level PII or only aggregated/hashed identifiers? If mixed, describe which datasets contain PII. Options: Trip-level PII retained, Only hashed/anonymous IDs, Aggregated metrics only, Varies by system — explain below
• What internal data quality checks or thresholds do you apply today (completeness, GPS accuracy, event thresholds)?
• Estimate what percent of your active policybase could be instrumented with telematics within 12 months (best estimate). Options: <10%, 10–25%, 25–50%, 50–75%, >75%, Unsure

Integration Nightmares or Smooth Sailing?

• If implementing telematics were likely to break a critical system, which single integration risk worries you most? Options: Rating engine changes, Policy admin sync, Billing/prorations, Claims linkage, Data pipeline throughput, Vendor security/compliance, Other
• Which systems must telematics outputs feed into to realize value (select all that apply)? Options: Rating engine, Policy administration system, Billing system, Claims handling system, CRM/retention tools, Underwriting workflow, Business intelligence/analytics, Mobile policyholder app, Other
• What integration methods do you prefer or require from vendors? Options: API (real-time), Batch SFTP exchanges, Message bus/Kafka, Direct DB writes, Pre-built connectors to our PAS, Other
• What are your minimum non-functional requirements for integrations (latency, uptime, throughput, encryption)? Please be specific if possible.
• Do you maintain an internal integration or middleware team, or do you rely on vendors/partners to handle end-to-end integration? Options: In-house integration team, Hybrid (in-house + vendor), Vendor-managed integrations, We would need assistance — no team
• Are there specific security/compliance certifications or contractual clauses vendors must satisfy (SOC 2, ISO 27001, data residency)? Options: SOC 2 Type II, ISO 27001, HIPAA (if applicable), GDPR/CCPA considerations, Data residency requirements, No formal certification required, Other

Regulators, Lawyers, and the Fine Print — candidly

• What is your biggest unspoken regulatory or legal fear about using behavior-based telematics scoring?
• Which states or jurisdictions in your footprint impose restrictions or have active scrutiny of telematics/use-based rating? Options: All states, Specific states — list below, No known restrictions, We are unsure
• If you answered 'Specific states,' list them and note any unique constraints (e.g., disclosure requirements, banned factors).
• Have you previously submitted rate filings or actuarial memos that reference telematics-derived factors? Options: Yes — approved, Yes — denied or modified, Filed and pending, No prior filings
• What documentation or evidentiary support will your regulators expect for telematics factors (validation studies, fairness tests, privacy notices)? Select all that apply. Options: Actuarial validation study, Fairness/non-discrimination analysis, Privacy/consent documentation, Model governance/monitoring plan, Pilot results, None specified, Other
• How comfortable is your legal/compliance team with vendor-held raw telematics data versus anonymized aggregated scores? Options: Prefer vendor holds raw data, Prefer anonymized/aggregated only, Comfortable with either if controls exist, Undecided — need guidance

Tech Readiness: Can Your Stack Take the Load?

• If we started sending daily trip-level records tomorrow, how quickly would your systems ingest, process, and make them available for pricing decisions? Options: Within 24 hours, 24–72 hours, Weekly batches, We cannot ingest such volumes today, Unsure — need to check
• Where is your core infrastructure hosted? Options: Cloud — AWS, Cloud — Azure, Cloud — GCP, Hybrid cloud/on-prem, Fully on-premises, Other
• Do you have an existing data schema or telematics ingestion pipeline (e.g., standard trip schema, event definitions)? Options: Yes — documented schema, Partial — ad hoc fields, No schema today, We use vendor-specific formats
• How mature is your team's capability to operationalize model scoring and monitor model drift (alerts, retraining, ownership)? Options: Established MLOps and monitoring, Some monitoring but manual, No formal model monitoring, We outsource model ops
• What SLAs or tolerance levels would you set for scoring latency, model uptime, and data completeness before pushing to production?
• Who would be the day-to-day technical owner(s) for telematics data pipelines and scoring in your organization (roles, not names)?

If Telematics Moved the Needle, Would You Recognize It?

• What single KPI would make executives say "this telematics program is a success" within the first 12 months? Options: Loss ratio improvement (absolute points), Retention uplift, Opt-in rate, New low-risk policy acquisition, ROI / payback period, Other
• Which metrics do you currently track at a cohort level and how often (select all that apply)? Options: Loss ratio — monthly, Loss ratio — quarterly, Retention/churn — monthly, Opt-in rates — weekly, Claims frequency/severity — monthly, Pricing error by segment — quarterly, We don't track cohort metrics regularly
• What acceptance thresholds would you set for a pilot to be considered for production (e.g., X% loss ratio lift, minimum opt-in, stable score distribution)? Please be specific.
• Who in your organization has final authority to approve moving from pilot to enterprise rollout? Options: Chief Actuary, CUO, Head of Personal Auto/Product, CIO/CTO, Legal/Compliance sign-off also required, Cross-functional steering committee
• If opt-in is low in early months, which corrective actions would you be willing to deploy (select all you’d consider)? Options: Increase marketing incentives, Use OBD device offers, Simplify consent flows, Provide driving rewards, Adjust targeting/segments, Pause and re-evaluate
• What reporting cadence and format would stakeholders find most actionable during a pilot (examples: weekly dashboard, executive snapshot, actuarial memo)? Options: Weekly operational dashboard, Bi-weekly executive summary, Monthly actuarial report with tables, Ad-hoc deep dives on demand, Other

Quick Snapshot: Who's in the Room and What You're Betting On

• Which title best describes your role in shaping telematics strategy here? Options: Head of Personal Auto, Chief Actuary, Chief Underwriting Officer (CUO), Chief Information Officer (CIO), Legal/Privacy Lead, Product Lead, Other
• How would you classify the scale of personal auto business this initiative would touch? Options: Pilot (under 10k policies), Small line (10k–50k), Mid (50k–250k), Large (250k–1M), Enterprise (1M+), Unsure
• Where are you in your telematics journey today? Options: No program / starting from scratch, Exploratory pilots only, Active pilot(s) with limited scale, Live program in select states, Production at scale, Sunsetting previous program
• Who are the core decision-makers who must sign off for a pilot and for a full-scale roll-out? Options: Chief Actuary, CUO/Head of Underwriting, Head of Personal Auto Product, CIO/CTO, Legal/Compliance, Distribution/Sales Lead, Other
• What is the primary business driver for exploring telematics right now? Options: Improve loss ratio, Protect/earn back profitable drivers, Grow retention, Regulatory differentiation, New product (PAYD/PPO), Digital engagement/experience, Other

What If Your Best Drivers Are Already Being Poached?

• When you look at recent lapses or new-business cohorts, do you see evidence that safer drivers are being captured by competitors? Options: Strong evidence, Some evidence, No clear signal, We haven't investigated
• Which customer segments do you suspect are most at risk of being mispriced today (and why)? Options: Low-mileage urban drivers, High-tech/connected-vehicle owners, Young safe drivers, Seniors with low mileage, Rural low-risk drivers, Other
• How do you currently detect when competitive products are winning your best drivers? Options: Churn analytics, Agent feedback, Market research, Price shopping tools, We don't have a reliable detection method
• If your top-performing drivers left at a 5–10% higher rate next year, what would that mean financially and culturally for the business?
• On an emotional level, what worries you most about being late to telematics adoption? Options: Losing market position, Regulatory scrutiny, Operational complexity, Brand erosion, Internal resistance, Other

Show Me Your Data — and Where It Breaks

• What rating variables and data sources do you rely on today to predict driving risk? Options: Age/Gender, Credit score, Territory/ZIP, Vehicle make/model/year, Annual mileage estimate, Claims history, Telematics (limited), Other
• Which systems hold that data (policy admin, rating engine, data lake, MDM)? Please list the primary platforms or vendors.
• How complete and timely is the data you need for pricing and segmentation (e.g., mileage, claims linkage, VIN)? Options: High completeness & near real-time, Moderate completeness with delays, Fragmented and slow, Significant gaps
• Which telematics capture options are you technically prepared to support for a pilot? Options: Smartphone app, OBD-II plug-in, OEM / embedded telematics, Third-party connected car feed, We are not prepared yet
• Do you have accessible historical trips or telematics-like samples (even small) we could use to validate models quickly? Options: Yes — large dataset, Yes — small sample, No, but can get data from partners, No and difficult to obtain

How Will You Know It Worked — Before We Build Anything?

• If telematics went live tomorrow, which one metric would make you declare the program a success after the first 12 months? Options: Loss ratio improvement (aggregate), Loss ratio improvement (cohort), Net retention uplift, Opt-in rate, Return on investment (ROI), Regulatory acceptance
• What minimum improvement/threshold would you need on that metric to move from pilot to scale? Please quantify if possible. Options: >10% relative improvement, 5–10% relative improvement, 1–5% relative improvement, Improvement is secondary to strategic value, Unsure / need guidance
• Which set of KPIs will be monitored during the pilot (choose all that apply)? Options: Opt-in conversion, Policy retention by score, Claim frequency/severity shifts, Score distribution stability, Customer NPS/engagement, Underwriting throughput
• Who within your organization will be the formal approver of pilot success (role, not name)? Options: Chief Actuary, CUO/Head of Underwriting, Head of Personal Auto Product, CIO, Legal/Compliance, Board/Executive Committee
• How long of an observation window do you consider credible for telematics-driven loss ratio signals? Options: 3 months, 6 months, 12 months, 18+ months, Depends on cohort size

If We Launched Tomorrow, What Would Fail First?

• What are the top three scenarios you fear could derail a pilot (technical, regulatory, behavioral, commercial)? Options: Regulatory pushback, Low opt-in rates, Data integration failures, Score instability / poor predictive lift, Customer privacy complaints, Distribution resistance
• Have you previously experienced regulatory objections to using behavior-based factors? If so, what happened? Options: Yes — formal objections/fines, Yes — informal pushback, No regulatory issues, Not sure / haven't engaged regulators
• How comfortable are you with anonymization and privacy controls that remove PII but preserve utility for modeling? Options: Very comfortable, Somewhat comfortable, Skeptical, Need education
• If a scoring model began to drift after deployment, what remediation or rollback process do you expect to be available? Options: Immediate rollback to benign score, Phased throttling, Manual hold-and-investigate, We don't have a defined process
• What would be a showstopper issue that would force you to pause the pilot? Options: Regulatory cease directive, Data breach, Severe adverse selection, Unacceptable customer complaints, Material system outage

The Policyholder Experience That Wins—and Keeps—People

• Which opt-in model do you believe would be most acceptable to your customers and regulators? Options: Opt-in with incentives (discounts/rewards), Automatic enrollment with opt-out option, Voluntary opt-in with education only, Mandatory in specific products
• What incentives have the best chance of driving enrollment in your book (and please list any you’ve tried)? Options: Upfront discount, Trial period discounts, Gamified rewards, Partner discounts, No incentives / rely on value proposition
• How important is real-time feedback (app coaching, weekly score) versus periodic summary statements for engagement? Options: Real-time is critical, Both real-time and periodic are valuable, Periodic only is fine, Unsure
• What communication channels resonate best with your customers for behavioral programs? Options: Mobile app + push, Email, SMS, Agent outreach, Customer portal, Direct mail
• From a brand perspective, what tone and messaging have to be avoided when discussing behavior-based pricing?

Integration Reality: How Deep and Fast Can We Go?

• If we asked your IT team to integrate a streaming pipeline and a batch feed, what would you expect the realistic timeline to be? Options: <4 weeks, 4–8 weeks, 8–16 weeks, 16+ weeks, Depends on approvals
• Which core systems must we integrate with for a pilot (select all that apply)? Options: Policy Admin System, Rating Engine, Claims System, Customer CRM, Data Lake/Warehouse, Identity/Access Management
• Do you have a sandbox or test environment we can use, and how close is it to production data schemas? Options: Production-like sandbox available, Sandbox but with limited data, No sandbox; only production, Unsure / need to confirm
• What security and compliance certifications or controls will we need to meet before ingesting telemetry? Options: SOC 2, ISO 27001, State-specific privacy standards, Vendor security assessment, Custom legal agreement
• How much ongoing operational support can your team provide for monitoring and incident response during a pilot? Options: Dedicated cross-functional team, Partial support (limited hours), Ad-hoc support only, Minimal to no capacity

Commitment & Next Steps: What Would Make You Say Yes?

• Which commercial model aligns best with how you want to buy this capability? Options: Per-policy SaaS fee, Pay-for-performance tied to loss improvement, Upfront platform fee + integration, Revenue share on savings, Pilot-friendly fixed-fee
• Would you be open to a limited pilot that ties some fee to early KPI performance? Options: Yes, Maybe — with guardrails, No
• What pilot population size would give you credible statistical signals while remaining operationally manageable? Options: 1k–5k drivers, 5k–25k drivers, 25k–100k drivers, 100k+ drivers, Unsure — need help sizing
• What are your expected legal/regulatory lead times before a pilot can launch in a given state? Options: <4 weeks, 4–8 weeks, 8–16 weeks, 16+ weeks, Varies significantly by state
• What would success look like for you at the end of the discovery phase (deliverables, approvals, or decisions needed)? Options: Signed pilot statement of work, Regulatory pre-clearance, Internal executive approval, Data sharing agreement signed, Technical integration plan approved
• Finally, what is the single biggest ask you need from a vendor during discovery to feel confident moving forward?

Where We Start: A quick check-in

• Briefly: how would you describe your organization’s current stance on telematics—exploring, piloting, scaling, or deployed at scale? Options: Exploring conceptually, Running pilots, Limited commercial deployments, Scaling across lines/products, Embedded program at scale
• Who on your team has been most vocal about pursuing telematics—and why does this matter to them?
• What’s one concrete thing you hope a telematics program will change for your business in the next 12 months?
• When you picture a successful pilot, what’s the single metric you’d show your executive committee first? Options: Loss ratio improvement, Opt-in rate, Retention lift, New business conversion, Customer satisfaction (NPS), Other

What's Getting Hidden by Your Current Pricing?

• If your current rating toolkit actually captured true driving risk, why are your best drivers still overpaying or leaving?
• How confident are you that your current variables (age, territory, credit) are identifying low-risk drivers accurately? Options: Very confident, Somewhat confident, Neutral, Somewhat doubtful, Not confident at all
• Tell us about a recent surprise in your book—an apparently ‘low-risk’ cohort that produced worse-than-expected losses. What pattern did you notice?
• What assumptions about policyholder behavior or selection do you suspect are wrong, and how long have you been tolerating them?
• Which competitor moves or market shifts make you feel urgency about changing your approach now? Options: Competitors launching telematics offers, New product entrants, Regulatory changes, Channel partners pushing telematics, Evolving consumer expectations, Other

If This Works, What Changes on Your P&L?

• Imagine telematics delivered measurable benefit—what does ‘benefit’ look like to you: margin expansion, retention, new segments, or something else? Options: Loss ratio improvement, Retention lift, New business growth, Reduced volatility, Operational efficiency, Other
• What minimum loss-ratio lift or ROI would make this program unambiguously worth scaling for you? Options: >5% lift, 3–5% lift, 1–3% lift, Break-even first year, Other
• How do you plan to trade off acquisition versus retention benefits when evaluating success? Options: Prioritize retention, Prioritize acquisition, Balance both equally, Depends on line/product, Undecided
• What time horizon do you require for a pilot to demonstrate success (months)? Options: <3 months, 3–6 months, 6–12 months, >12 months
• Which KPIs beyond loss ratio must move to satisfy the board (select all that apply)? Options: Opt-in rate, Retention/renewal rate, Customer lifetime value, Claim frequency/severity, Model calibration/stability, Regulatory acceptance

Who Carries the Risk—and Who Gets the Credit?

• If this initiative fails publicly, whose career would be most exposed—and what would that pressure look like?
• Which stakeholders must formally sign off at pilot go/no-go, and what is each person’s primary concern? Options: Chief Actuary, Head of Personal Auto/Product, CUO, CIO/CTO, General Counsel/Privacy, Regulatory Affairs, Distribution/Channels, Marketing
• How do you prefer decisions to be made—consensus across functions, executive-level decision, or delegated to a program owner? Options: Consensus across functions, Executive committee decision, Delegated to program owner, Hybrid
• Who will be the operational owner responsible for pilot execution (name + role) and who’s the backup?
• What approval or documentation does Legal/Privacy require before you allow live data collection from policyholders?

Your Data: The Good, The Messy, And The Missing

• Which of the following data sources are available today and ready to connect for a pilot? Options: Policy system (rating/eligibility), Claims history, Telematics via mobile app, OBD-II data, OEM/connected vehicle feed, Third-party exposure data, None of the above
• What proportion of your book is reachable for telematics through smartphone vs. device vs. OEM integrations? Options: Mostly smartphone, Mostly OBD/device, Mostly OEM, Even mix, Unknown
• Where are your most fragile integration points (e.g., policy system, billing, rating engines) that could slow delivery?
• How large a historically-labeled sample do you have to calibrate a driving score (number of policies or drivers)? Options: <5k, 5k–25k, 25k–100k, >100k, Unsure
• What anonymization, PII minimization, or data retention rules must we design for from day one?

How Will Policyholders React—And What Will Move Them?

• What would you do if opt-in rates are 20% lower than your forecast—double down on incentives, change UX, or pause? Options: Increase incentives, Redesign UX/communications, Target different segments, Pause and reassess, Other
• Which incentive levers have you considered or tested (select all that apply)? Options: Upfront discount, Guaranteed renewal benefit, Gamified rewards, Cashback/credits, Pay-per-mile savings, No incentives—behavioral nudges only
• Describe a customer segment you believe will enthusiastically opt in—and why you think they'll respond.
• How do your distribution partners (agents, direct channels) feel about telematics offers—supportive, neutral, or resistant? Options: Supportive, Neutral, Resistant, Not engaged
• What are your biggest fears about customer privacy backlash, and do you have recent examples of similar initiatives that went well or poorly?

Regulators, Filings, and The Things That Can Stop You Cold

• Which regulatory or state-specific issues could force you to change or stop a telematics program? Options: Rate filing rejection, Usage restrictions on data, Privacy law constraints, Anti-discrimination concerns, Mandatory opt-in rules, Other
• Do you have prior experience getting telematics-based factors accepted by regulators—if yes, where did you win or stumble?
• What documentation will regulators expect from you (e.g., actuarial support, consumer disclosures, validation studies)? Options: Actuarial validation, Consumer-facing disclosures, Privacy impact assessments, Third-party audits, Model performance monitoring
• How much lead time does your filing cycle allow between pilot results and a commercial rate change? Options: <3 months, 3–6 months, 6–12 months, >12 months, Varies by state
• Are there states or lines where we should not even test telematics due to legal or company rules? Please list.

Pilot to Production: What Would Make You Confident—or Hit the Brake?

• What single failure mode would cause you to stop a pilot immediately (e.g., model instability, regulatory pushback, low opt-in)?
• Define measurable 'go/no-go' criteria we should instrument from day one (select all that apply). Options: Model calibration metrics (PSI/KS), Opt-in rates, Retention delta vs. control, Claim frequency/severity change, Customer complaint volume, Operational SLA adherence
• How will you evaluate statistical significance vs. commercial significance—what lift is actionable even if marginally significant?
• What remediation or rollback playbook do you require (steps, owners, communication templates)?
• Who will monitor the pilot daily/weekly and who signs off on each threshold breach?

Integrations, Automation, and Operational Expectations

• Which systems must be updated in real time versus batched (rating engine, policy admin, claims, CRM)? Options: Real-time rating engine, Policy admin/billing (daily), Claims system (batch), CRM/engagement (real-time), Other
• What level of technical support and SLAs do you expect from a telematics vendor during pilot and post-launch? Options: 24/7 support with SLAs, Business hours support, Dedicated engineering support, Quarterly reviews only, Unsure
• Which internal teams will own ongoing model monitoring, recalibration, and feature stewardship? Options: Actuarial, Data Science, Pricing/Product, Analytics/BI, Operations, Vendor-managed
• How automated do you want scoring updates—manual approval, scheduled retrain, or continuous learning with guardrails? Options: Manual approval, Scheduled retrain (monthly/quarterly), Continuous learning with guardrails, Vendor-managed monitoring only
• What reporting cadence and dashboarding detail will your executives require (weekly snapshot, monthly deep-dive, KPI owners)? Options: Weekly snapshot + monthly deep-dive, Bi-weekly updates, Monthly only, Quarterly executive reviews

Commercial and Data-Sharing Boundaries

• If a vendor promises a guaranteed loss-ratio improvement, would you accept a performance-based commercial model, or prefer fixed fees? Options: Performance-based (shared savings), Fixed fees, Hybrid, Undecided
• What data-sharing constraints or proofs do you need before you allow an external partner to access raw telematics? Options: Anonymized data only, Data use agreements, On-premise processing, Third-party audit, Other
• How comfortable are you with vendor-hosted analytics versus running models in your environment? Options: Prefer vendor-hosted, Prefer in-house, Hybrid approach, No preference
• What contract terms (term length, audit rights, IP, liability) would be immediate blockers for you?

Closing the Loop: What Would Make Us Partners, Not Vendors

• If we delivered a pilot that hit your stated KPIs, what would a desirable next step look like to you? Options: Scale to full book, Phase-based rollout, Productize for specific segments, Renegotiate commercial terms, Other
• How do you want knowledge transferred—embedded resources, joint governance, or fully handed-off operations? Options: Embedded vendor resources, Joint governance, Full handoff to internal teams, Combination
• What would make you recommend our platform internally to peers or the board (one sentence)?
• Realistically, when would you like to run a pilot if all blockers are cleared? Options: Immediately, In 1–3 months, In 3–6 months, 6+ months