Getting Oriented: Who You Are and Why You're Here

• In one sentence, how would you describe your brand and its current DTC presence?
• Which best describes your current annual DTC revenue? Options: <$1M, $1M–$5M, $5M–$20M, $20M–$50M, >$50M
• Who is filling out this form and what is their role in the decision (title + day-to-day responsibility)? Options: Founder/CEO, VP/Head of E‑commerce, Head of Digital/Marketing, Operations/Head of Fulfillment, Other
• Which channels currently generate revenue for the brand? Options: Direct-to-consumer website, Retail/wholesale partners, Marketplaces (Amazon, etc.), Subscriptions, Pop-ups/Events, Other
• What triggered taking a close look at a new platform or partner right now? Options: Outgrowing current platform capabilities, Investor/board request for visibility, Launching a DTC channel from wholesale-only, High subscription churn, Fulfillment failures, Cost/fee pressure, Other
• If you had to name the single most important outcome you're looking for from a new platform, what would it be?

If We Do Nothing, What Breaks First?

• If nothing changes in the next 12 months, what specific failure or missed opportunity worries you most?
• How often do existing platform limitations affect your weekly operations or marketing launches? Options: Daily, Weekly, Monthly, Rarely, Never
• Tell us about a recent moment where the current setup cost you revenue, time, or customer trust—what happened and what was the impact?
• Which of these consequences feel most likely if migration goes poorly? Options: Revenue drop during cutover, Loss of subscription data, Order fulfillment errors, Channel conflict with wholesale partners, Investor reporting gaps, Customer experience degradation
• How urgent is a change on a scale from 'explore casually' to 'must act within 3 months'? Options: Exploratory (6+ months), Prepare to move (3–6 months), Ready to act (within 3 months), Immediate (within 30 days)

Who Really Decides—and What Keeps Them Up at Night?

• If one stakeholder could veto the project, who is it and why would they say no?
• Which roles will require regular reporting or visibility from the platform? Options: Founders/CEO, Investors/Board, VP E‑commerce, Head of Finance, COO/Operations, Retail/Wholesale leadership
• What level of investor reporting do you need (data points and cadence)? Options: Monthly unit economics dashboard, Quarterly financial summaries, Real‑time revenue & LTV dashboards, Ad hoc investor packs, None/Not sure
• How would you describe your wholesale partners' sensitivity to a DTC channel (will they resist, tolerate, or support)? Options: Highly sensitive — may push back, Cautious but manageable, Neutral, Supportive
• For each stakeholder group you listed, what would 'success' look like from their perspective? (brief bullet points by role)

Where Your Revenue and Operations Live Today

• Which commerce platform(s) or systems currently host your storefront, subscriptions, payments, and customer data? Options: Shopify, BigCommerce, Custom platform, Magento, Subscription specialist (ReCharge, etc.), ERP/Order management system, Other
• Which fulfillment partners or models do you use today? Options: In‑house fulfillment, 3PL (single), Multiple 3PLs, Marketplace fulfillment (FBA, etc.), Dropship partners, Other
• Which revenue streams would be most fragile during migration (pick up to three)? Options: One‑time product sales, Active subscriptions, Wholesale orders, Marketplace orders, Gift cards/credits, Preorders
• Do you face any legal, contractual, or technical constraints on moving customer, subscription, or order data between systems? Options: Yes—contracts limit data moving, Yes—PCI or privacy constraints, No major constraints, Unsure, need to check
• Describe the single most fragile technical dependency or integration we should know about (payments, inventory sync, single sign‑on, etc.).

If We Only Measured One Thing, What Should It Be?

• Which primary metrics will determine whether this project is a success for you? Options: Gross margin per order, Customer lifetime value (LTV), Customer acquisition cost (CAC), Subscription retention/churn, Uptime/availability, Order accuracy/on‑time fulfillment
• For the top metric you picked, what is the target or threshold that would make you say 'this worked'?
• Besides metrics, what operational guarantees must be in place at launch (examples: 99.9% uptime, <1% order error, next‑day fulfillment for X% of orders)? Options: Uptime SLA (select below), Order accuracy target, Fulfillment SLA, Support response times, Data export/ownership guarantees
• Choose a desired uptime/availability target for your storefront Options: 99.9%, 99.5%, 99.0%, We need guidance

Migration Reality Check — What Would You Tolerate?

• If a migration caused a temporary revenue dip, what maximum % drop would be acceptable for you (short term) before pausing the project? Options: 0–5%, 6–10%, 11–20%, >20%, Not acceptable
• How long of a planned cutover window is realistic for your operations (hours/days)? Options: A few hours (night/weekend), 24–48 hours, 2–5 days, Longer with staged migration
• What rollback or no‑go triggers would force you to stop a launch and revert? Options: Payment processing failures, Subscription data loss, Fulfillment outage, Significant customer complaints, Other
• Who on your team will be the primary owners during migration and who is the escalation contact (name + role)?
• How do you prefer to run pilots—full funnel single SKU, geography-limited, beta customer cohort, or another approach? Options: Single SKU pilot, Geography-limited pilot, Invite-only beta cohort, Parallel run with current site, Other

Channel Sensitivities and Governance — Keeping Everyone Aligned

• If your wholesale partners saw a sudden uplift or price difference from your DTC launch, what is their most likely reaction? Options: Push for policy changes, Threaten order reduction, Accept with negotiated terms, Unknown/Depends on partner
• Do you have existing channel agreements or MAP policies that constrain pricing, promotions, or customer targeting? Options: Yes—strict MAP/policy, Yes—some constraints, No formal agreements, Unsure
• What specific governance or rules would make wholesale partners comfortable with a stronger DTC presence?
• How would you like to visualize and enforce channel rules post‑launch (examples: differentiated SKUs, geo restrictions, wholesale inventory pools)? Options: SKU-level controls, Geo/segment restrictions, Wholesale inventory pools, Pricing policies in platform, Manual governance
• Who should be part of the governance forum (internal + partner roles) and how often should it meet? Options: Founders + Sales + Ops (monthly), Monthly executive review with partners, Quarterly governance only, Ad hoc as issues arise

What Would a Perfect Launch Headline Look Like?

• Imagine six months after launch you’re writing an investor update—what’s the headline and three supporting bullets?
• Which analytics or dashboards do you need immediately after launch to feel confident (select top 3)? Options: Real‑time revenue & LTV, Cohort retention charts, Subscription health (dials), Fulfillment KPIs, CAC by channel, Customer support/ticket KPIs
• Which service model makes you most comfortable post‑launch? Options: Managed services + platform, Platform + internal team, Hybrid: transition from managed to internal, Consulting only
• What minimum customer experience guarantees should be visible to the team at launch (e.g., support SLA, dispute handling, returns flow)?
• Which early success signals (other than revenue) would make you say 'we nailed this'? Options: Subscription retention > target, Fulfillment error rate below target, Advertising ROAS meets plan, Positive NPS/CSAT feedback, Stable data pipelines and visibility

Deciding and Moving Forward — What Would Make You Sign?

• What would make you comfortable signing a pilot agreement within two weeks? Options: Clear migration plan, Defined pilot scope and acceptance criteria, Limited financial commitment, References from similar brands, Guaranteed rollback plan
• What commercial constraints matter most (budget limits, payment terms, milestone billing, pilot pricing)?
• What elements must be included in a pilot scope to say 'yes' (select up to 4)? Options: Subscription migration, Payments cutover, 1–2 SKUs storefront build, Fulfillment integration, Analytics dashboard setup, Customer support flow
• Do you have any hard dates we should avoid or target (peak selling windows, funding events, wholesale commitments)?
• What's the best next step you want from us right now? Options: Technical discovery call, Commercial proposal for pilot, Reference calls with similar brands, High-level timeline & scope, Other

Start Here: Snapshot of Your Current DTC Engine

• Briefly describe your current e‑commerce setup—platforms in use, primary partners, and who owns day‑to‑day operations.
• Which storefront, subscription, payment, and analytics products are currently live for you? Options: Shopify / Shopify Plus, Magento / Adobe Commerce, BigCommerce, WooCommerce, Custom / Headless, Recharge/Bold (subscriptions), Stripe, PayPal, Adyen, Klaviyo, GA4 / Looker / Segment, Other
• How would you rate your current platform’s ability to support roughly 2x revenue without a major rework? Options: Fully capable, Mostly capable with minor engineering, Needs moderate engineering effort, Unsustainable without platform change
• Who is the technical and business owner for migrations and integrations (name, role), and how much bandwidth can they realistically commit?
• Which recurring operational tasks consume the most engineering or operations time each month (list top three)?

If Your Platform Went Quiet, What Would Break First?

• If your storefront, payments, or subscription engine stopped working for 24 hours, what immediate customer and financial impacts would you expect?
• Which single failure keeps leadership awake at night—checkout errors, subscription billing failures, fulfillment disconnects, analytics blackout, or something else? Options: Checkout errors, Subscription billing failures, Fulfillment disconnects, Analytics / reporting blackout, Payment processor outages, Other
• How often do you currently see order failures, payment retries, or fulfillment misses (choose closest)? Options: Daily, Weekly, Monthly, Rarely/Never
• When incidents occur, what are your mean time to detect (MTTD) and mean time to resolve (MTTR)? Give examples with timings if possible.
• Who is on the escalation chain during an outage and what decision authority do they have (pause campaigns, divert orders, issue refunds)?

Where Is Revenue Living, and How Does It Flow?

• Which channels drive your revenue today and approximately what percent each? Options: DTC web, Subscriptions (direct), Marketplaces (Amazon etc.), Wholesale / B2B, Retail partners, Pop‑ups / Events, Other
• What portion of monthly revenue is recurring subscription versus one‑time purchases (approximate %)?
• How are refunds, chargebacks, and discounts reconciled across channels—central ledger, ERP, channel reports, or spreadsheets? Options: Central ledger / ERP, Accounting system (QuickBooks/NetSuite), Channel‑specific reporting, Manual spreadsheets, Other
• Which payment gateways are live and do you maintain a multi‑processor fallback strategy? Options: Stripe, PayPal, Adyen, Braintree, Authorize.net, Other
• Do settlement timing, reserves, or hold rules from processors or retail partners create cash‑flow stress? Options: Yes—regularly, Occasionally, Rarely, No / not aware

Who Delivers Your Product—and Where Do Bottlenecks Hide?

• List your fulfillment approach by geography: in‑house, primary 3PL(s), hybrid—include which services each partner runs (picking, kitting, returns, subscription inserts).
• What SLAs do you expect from each fulfillment partner (pick/pack time, same‑day ship, returns turnaround) and are they consistently met? Options: Always met, Mostly met with exceptions, Frequently missed, Not tracked / unknown
• How is inventory synchronized between storefront and fulfillment (real‑time API, hourly, daily, manual upload)? Options: Real‑time API, Near‑real‑time (minutes), Hourly sync, Daily sync, Manual CSV/SFTP
• How often do you experience oversells, mis‑shipments or missing SKUs and what is the customer/brand impact when they occur?
• If your primary fulfillment partner became unavailable, what fallback exists and how quickly could you route orders elsewhere? Options: Hot standby 3PL ready, Can onboard a partner within days, Needs weeks to onboard, No contingency

What Data Do You Truly Own—and What’s Locked Behind Vendor Walls?

• Can you export complete order, customer, subscription, and product datasets in raw format (CSV/JSON) on demand via API or UI? Options: Yes—full exports via API, Partial exports with limits, Manual exports only (UI), No / unknown
• Which systems contain customer PII and what are your data retention and compliance policies for that information?
• How detailed is your unit‑economics reporting today (LTV by cohort, CAC by channel, gross margin per order) and where are the biggest blind spots?
• Do any partners or marketplaces limit your right to export or use customer or subscription data? Name the partner and restriction if applicable.
• How confident are you that you can migrate historical subscription billing history, invoices, and payment tokens without disrupting recurring revenue? Options: Very confident, Some concerns, Uncertain, Not possible

How Entangled Are Your Integrations (and Who's Holding the Spaghetti Together)?

• List your mission‑critical integrations (ERP, WMS, OMS, CRM, marketing, tax engines) and whether they're native integrations, middleware, or custom connectors.
• Do any integrations rely on legacy patterns (SFTP drops, screen‑scrapes, single‑developer middleware) that pose replacement risk? Options: Yes—single‑person knowledge, Yes—but documented and supported, Some legacy pieces but manageable, No legacy risk
• What authentication and access methods are used for integrations (API keys, OAuth, SSO, VPN, SFTP) and are secrets centrally managed? Options: API keys, OAuth, SSO/SAML, VPN / IP allowlist, SFTP credentials, Other
• How often do schema changes or API versioning break flows, and what is your detection and remediation process?
• Which single integration would cause the most disruption if it failed during migration and why?

If We Moved Platforms, What Could Go Very Wrong?

• Describe the worst migration outcome you fear (lost subscription revenue, orphaned customer records, prolonged outages, partner fallout) and why that would be catastrophic.
• What maximum revenue decline (percent) is acceptable during migration and over what timeframe? Options: 0–2% (acceptable for <1 day), 3–5% (acceptable for up to a week), 6–15% (acceptable for up to a month), Greater than 15% is unacceptable
• Are there contractual obligations (retail/wholesale agreements, investor covenants) that restrict migration timing or require notification/approval? Options: Yes—wholesale/retail terms, Yes—investor reporting constraints, No contractual limits, Unsure, need to check
• What rollback criteria would require you to stop a migration (e.g., X% failed payments, >Y minutes of outage, critical 3PL SLA misses)?
• Which stakeholders must sign off at each migration milestone and what is their typical decision turnaround time?

Timing, People, and Governance — Real Constraints We Can't Ignore

• What is your target launch window and what immovable deadlines (marketing campaigns, investor reporting, seasonal peaks) drive that date?
• Who are the internal and external owners for migration tasks across engineering, marketing, finance, and fulfillment, and how many hours/week can each commit?
• What governance and audit requirements must we honor—data retention, investor reporting cadence, SOC/GDPR/PCI controls, channel conflict policies? Options: PCI scope requirements, GDPR/CCPA retention rules, Investor reporting cadence, Channel conflict / wholesale carve‑outs, Other
• How should day‑to‑day decisions be triaged during migration—weekly steering committee, daily ops standups, executive approvals only, or another model? Options: Weekly steering + daily ops, Weekly only, Daily standups, Ad‑hoc executive approvals, Other
• If launch slips, what downstream commercial or operational penalties should we expect (lost media spend, vendor fees, customer experience impact)?

Quick Intro — Help Us See You

• Who are you and what role will you own in this initiative? Options: Founder / CEO, VP of E‑commerce, Head of Digital, Marketing Director, Operations / Fulfillment Lead, Other (please specify)
• What is your brand’s current annual DTC revenue band? Options: <$1M, $1M–$5M, $5M–$15M, $15M–$50M, >$50M
• Which channels currently drive most of your revenue? Options: Own DTC site, Wholesale / Retail, Marketplaces (Amazon, etc.), Subscriptions, Direct-to-retailer partnerships, Other
• Briefly, what prompted you to explore a new platform now?
• If there's one thing you want us to understand about your business before we dive deeper, what is it?

Why Keep Accepting Friction?

• When you think about your current DTC tech and operations, what’s the one limitation you find yourself tolerating because changing feels too risky?
• How often does that limitation cost you measurable revenue or time? Options: Daily, Weekly, Monthly, Quarterly, Rarely
• Walk me through the last time that limitation caused a real problem—what happened and who felt the impact most?
• Have you tried specific workarounds or tools to bridge this gap? Which ones worked or failed, and why?
• If nothing changed for the next 12 months, how would that limitation likely affect growth, customer experience, or investor conversations?

What’s Eating Your Margins Right Now?

• Are your unit economics (LTV, CAC, gross margin) tracked to a level that lets you identify quick wins? Options: Yes, in detail, Partially — some metrics, No, we’re flying blind
• Which of these most threatens your ability to reach profitable CAC:LTV: subscriptions, fees, fulfillment, returns, or analytics gaps? Options: Subscriptions, Payment/transaction fees, Fulfillment costs, Returns & chargebacks, Insufficient analytics, Other
• What is your target CAC and target LTV for your core product or cohort?
• Which metrics would convince your investors or leadership that the new platform is paying off? Options: CAC, LTV by cohort, Repeat purchase rate, Subscription retention (MRR churn), Fulfillment error rate, Gross margin
• Share a recent example where lack of metric clarity delayed or distorted a business decision.

What’s Actually Broken Under the Hood?

• If you had to name the single technical risk that would make you pause a migration, what would it be? Options: Data loss/portability, Checkout/payment downtime, Subscription migration complexity, Fulfillment integration failure, Analytics discrepancy, Other
• List the core systems and vendors you currently rely on (platform, OMS/WMS, subscription engine, payments, analytics, 3PLs).
• Which integrations are non‑negotiable for launch (must exist before go‑live)? Options: Payments, Subscription engine, ERP/Inventory, 3PL/fulfillment, CRM/email, Analytics/BI
• How clean and accessible is your customer and order data for export and reconciliation? Options: Fully exportable and clean, Mostly usable with cleanup, Fragmented and messy, We don’t know
• Technically, what’s been hardest in past migrations or integrations—and how long has that been a recurring issue?

Will Your Customers Even Notice (and Will They Care)?

• Which customer experience element worries you most during migration—checkout stability, subscription continuity, fulfillment SLAs, or data visibility? Options: Checkout stability, Subscription continuity, Fulfillment SLAs, Order tracking & notifications, Customer service handoffs, Other
• Have you mapped customer journeys where the DTC experience is the brand’s core promise (unboxing, subscription cadence, personalization)? Which paths are highest risk?
• How would you measure whether customers experienced a smooth transition versus a disrupted experience? Options: Conversion rate, Payment decline rate, Subscription churn, CS ticket volume, NPS/CSAT, Other
• Do you have segments or cohorts (VIPs, subscribers, wholesale customers) that must be handled differently during cutover? Explain briefly.
• If a pilot caused a small outage for a non‑core cohort, would that be acceptable to prove migration safety? Options: Yes, for non-core cohorts, Only with explicit customer consent, No, zero tolerance

Who Can Stop This — and Who Must Be Reassured?

• Who are the internal and external stakeholders that must sign off on migration decisions (investors, ops, retail partners, legal)?
• Which stakeholders are most likely to resist a DTC platform change and why—channel conflict, reporting, or risk aversion? Options: Retail/wholesale partners, Investors/board, Internal ops team, Customer support team, External vendors
• How have you managed channel conflict historically, and what governance or reporting would make stakeholders comfortable now?
• Who will be the migration owner(s) on your side, and how many hours per week can they realistically dedicate during launch? Options: 0–5 hrs/week, 5–10 hrs/week, 10–20 hrs/week, 20+ hrs/week
• If investors asked for a 30‑day snapshot of unit economics post‑launch, what data would you need to deliver confidently?

Imagine It Worked — What Changes First?

• If the new platform delivered the outcome you hoped for in 90 days, what would look different in daily operations and revenue?
• Which KPI improvement would make this project a clear win (pick top two)? Options: CAC reduction, Higher LTV, Lower fulfillment cost, Lower churn, Faster release velocity, Better reporting
• What customer signals would show you the experience improved (qualitative or quantitative)? Options: Improved NPS/CSAT, Reduced support tickets, Higher on-site conversion, Longer subscription lifetime, Better repeat purchase rate
• How important is owning customer data and the first‑party relationship to your long‑term plan? Options: Critical — must own, Important but negotiable, Neutral, Prefer vendor-managed
• Describe the ideal state of your operational team 6 months after launch.

What’s the Smallest Thing That Proves this Will Work?

• Would you prefer a pilot that validates technical migration, unit economics, or customer experience first? Options: Technical migration (data & integrations), Unit economics (cohort LTV/CAC), Customer experience (checkout & fulfillment), Integrated pilot covering multiple areas
• Which SKU, campaign, or customer cohort would be the best low‑risk pilot to prove value?
• What success criteria would you set for a 30‑day pilot (be specific: % conversion change, churn delta, error rate)?
• What rollback triggers would force a stop to the pilot (payment failures, >X% revenue loss, customer complaints)? Options: Payment failures, Order fulfillment failures, >5% revenue drop, >10% support volume increase, Significant brand reputation issues, Other
• How quickly do you expect decisions after a pilot—immediate, after analysis, or after stakeholder review? Options: Immediate (real‑time), Within 1 week, 2–4 weeks, Require board/investor review

What Would Make You Say Yes — Right Now?

• What are the non‑negotiables we must include in a commercial or operational commitment to get a firm ‘go’? Options: Clear SLAs, Data ownership guarantee, Rollback plan, Transparent fees, Pilot acceptance criteria, Other
• What timeline feels realistic for you from agreement to pilot start? Options: 2–4 weeks, 1–2 months, 2–3 months, 3+ months
• How do you prefer to be updated during the project—daily standups, weekly summaries, or milestone check‑ins? Options: Daily standups, Weekly summaries, Milestone check‑ins, Ad hoc as needed
• If we could guarantee one thing to reduce your perceived migration risk, what should it be (technical, financial, or operational)? Options: Technical (no data loss), Financial (performance guarantee), Operational (white‑glove support), Governance/reporting assurances
• What would you like our next step to be after this discovery conversation? Options: Technical assessment, Pilot proposal, Commercial terms draft, Stakeholder workshop, Other

Why this moment? The trigger that matters

• What's prompted you to explore a new DTC platform or rethink your launch right now? Options: Revenue growth beyond current platform, Investor request for better reporting, Wholesale-to-DTC launch, High integration overhead, Fulfillment issues, Other
• How long have you felt limitations from your current setup—weeks, months, or years? Options: Less than 3 months, 3–6 months, 6–12 months, Over a year
• Who on your team will live with this platform day-to-day (roles and primary responsibilities)?
• If you could summarize one recent incident that made this a priority, what happened and what were the consequences?
• Which of the following outcomes would make this initiative feel worth it in the first 6 months? Options: Improved unit economics (LTV/CAC), Reduced platform downtime, Seamless subscription management, Faster fulfillment, Clear investor reporting, Other

Who's holding the reins—and who will judge success?

• If an investor or board member looked at your DTC channel today, what would they say is the single biggest vulnerability? Options: Unclear unit economics, Data/reporting gaps, Fulfillment reliability, Channel conflict risk, High transaction fees, Other
• List the decision-makers and their definition of 'good' for this project (e.g., CTO = no downtime; CFO = clean margin reporting).
• How sensitive are your wholesale partners to changes in pricing or product availability on DTC? Options: Highly sensitive, Moderately sensitive, Low sensitivity, No wholesale partners
• What reporting cadence and packet do investors demand today (monthly revenue, cohort LTV, churn, other)? Options: Monthly revenue & growth, Cohort LTV, CAC & marketing ROI, Inventory & fulfillment KPIs, Custom investor packet, None
• Who must sign off on migration windows, SLAs, and go/no-go decisions? Options: Founder/CEO, VP of E‑commerce, CFO, Head of Ops/Fulfillment, External investor representative, Other

Revenue Reality Check — the numbers people avoid

• What one metric do you think is masking deeper problems in your DTC economics? Options: High top-line revenue hiding poor margins, Average order value hiding low repeat rate, Low churn masking high CAC, Marketing ROI reported incorrectly, Other
• Please provide your most recent values for these metrics (if available): monthly DTC revenue, average CAC, LTV (12 months), churn rate.
• How confident are you in the accuracy of those numbers today? Options: Very confident, Somewhat confident, Low confidence, We don’t have reliable reports
• Which channels drive most new customers today? Options: Paid social, Paid search, Organic search/SEO, Email/CRM, Retail/Wholesale referrals, Affiliates/partners, Other
• Describe one recent marketing decision you made that would have been different with clearer cohort LTV or subscription visibility.

Migration Fear Factor — the risk we keep replaying

• If we had to name the single most catastrophic migration risk for your business, what would it be? Options: Checkout downtime, Lost customer data, Payment reconciliation failures, Fulfillment cutover errors, SKU and subscription mapping mistakes, Other
• What is your current tolerance for migration downtime in dollars per hour or % of average daily revenue? Options: Less than $500/hr, $500–$2,000/hr, $2,000–$10,000/hr, No downtime acceptable
• Describe the systems and formats where customer, order, and subscription data currently live (platforms, CSV exports, APIs).
• Which of these migration components are already documented and ready to export? Options: Product catalog & SKUs, Customer records, Active subscriptions, Payment tokens, Order history, None
• Have you completed any full or partial test migrations before? If yes, what broke and how was it resolved? Options: No test migrations yet, Yes — major issues, Yes — minor issues, Yes — went smoothly

Subscriptions & Loyalty — are we keeping customers or just processing orders?

• If you could guarantee one subscription behavior (e.g., low churn, easy swaps), which would move the needle most for your business? Options: Higher retention/churn reduction, Easy plan/variant swaps, Flexible billing & proration, Automatic recovery of failed payments, Clear subscription analytics
• What percentage of orders are recurring vs one-time today, and how has that trended over the last 12 months? Options: Mostly one-time, ~25% recurring, ~50% recurring, Majority recurring, Don't know
• How do you handle failed subscription payments, and what’s your current recovery success rate? Options: Manual outreach, Automated dunning & retry, Third‑party recovery service, We don’t recover reliably, Other
• Tell us about one subscription use-case you cannot support today but must have on day one after migration.
• Which customer communications are automated for subscribers (billing receipts, failed payments, renewals, churn prevention)? Options: All automated, Most automated, Some automated, None

Fulfillment & Reputation — small mistakes, big impacts

• What fulfillment failure would cause the most brand damage in a launch window? Options: High order error rate, Late deliveries, Lost packages, Incorrect customs/documentation, Poor packaging/unboxing, Other
• Who are your current fulfillment partners and what do they manage today (pick all that apply)? Options: In‑house fulfillment, 3PL (domestic), 3PL (international), Dropship partners, Marketplace fulfillment, None
• What SLAs matter most to you for fulfillment (pick top 3)? Options: Same-day pick/pack, Delivery within X days, Order accuracy %, Return processing time, Inventory accuracy, Custom packaging options
• Have you experienced a fulfillment incident that increased returns or negative reviews? Describe the impact and follow‑up.
• Which fulfillment integrations are required at launch (WMS, carrier APIs, customs, return portal)? Options: WMS integration, Carrier APIs, International customs, Returns portal, None required at launch

Analytics That Actually Guide Decisions — are you flying blind?

• How often have you made a pricing, promo, or acquisition decision in the last 6 months without cohort-level LTV visibility? Options: Frequently, Occasionally, Rarely, Never
• Which analytics or dashboards do you currently need but don't have? Options: Cohort LTV over time, CAC by campaign & cohort, Subscription health & churn alerts, Fulfillment cost per order, Profitability by SKU, Other
• Who on your team owns analytics and reporting, and how long does it take them to produce a monthly packet? Options: Head of Growth / Marketing, Finance / FP&A, Head of Ops, External analyst, No dedicated owner
• What external data sources must feed analytics (ad platforms, payment gateways, 3PL, marketplaces)?
• Describe an insight you wish you had this month that would materially change your go-to-market activity.

What would success feel like — your lead indicators and the human signals

• If we were to check in 90 days after launch, what single signal would make you say 'this was the right move'? Options: Subscription growth target met, CAC below target, No critical fulfillment incidents, Investor reporting automated, Positive customer NPS trend, Other
• What are the top three acceptance criteria you need met before you’d call the pilot a win? Options: Uptime & stability, Accurate billing & subscriptions, Fulfillment SLA met, Data integrity validated, Analytics match finance numbers, Other
• Beyond metrics, what emotional or reputational outcome matters—how should customers feel after purchase and during support interactions?
• What would a successful handoff to your internal team look like after the pilot—what documentation, training, or governance is required? Options: Comprehensive runbook, Recorded training sessions, SLA & escalation matrix, Monthly governance meetings, Other
• Which no-go or rollback triggers must be explicitly defined before migration begins? Options: X% payment failures, Y% order error rate, Downtime over Z minutes, Critical analytics mismatch, Other

Next steps & real commitments — who’s ready and what’s required

• What single internal barrier is most likely to stop this project between proposal and contract? Options: Budget approval, Team bandwidth, Wholesale partner objections, Technical debt in legacy systems, Investor pushback, Other
• What timeline feels realistic for pilot → migration → full launch for you? Options: 4–6 weeks (fast), 2–3 months, 3–6 months, 6+ months
• Which product line or campaign would you select for a pilot and why?
• Who is the budget owner and final signatory for this initiative? Options: Founder/CEO, CFO, VP of E‑commerce, Board/Investor approval required, Other
• What would make you comfortable committing to a pilot today (deliverables, SLA, trial pricing, references)? Options: Clear SLAs, Pilot pricing, Customer references, Technical migration plan, Other