Let's Get Oriented: Who's in the Room

• Which best describes the organization and role you're representing today? Options: Retailer — e‑commerce leader, Retailer — marketing/retail media leader, Retailer — CIO/engineering, Brand — shopper marketing director, Brand — media planner/buyer, Other (please specify)
• What is the legal/entity name of the company we should reference (and the best contact email)?
• Which business objective is the primary reason you're exploring a retail media platform right now? (select up to 2) Options: Monetize digital traffic and inventory, Standardize sponsored product management, Deliver closed‑loop purchase attribution, Improve cross‑retailer campaign consistency, Protect or improve shopper experience, Create a new revenue stream for stores
• How mature is your current sponsored‑product or retail media activity? Options: No program today, Ad‑hoc/manual sponsored products, Structured but manual (spreadsheets/POs), Partially automated with point tools, Fully operational retail media network
• Who will need to be involved from your side for pilot decisioning and technical validation? Options: E‑commerce/product team, Retail media sales/monetization, Marketing/brand partnerships, Data/analytics, Engineering/IT, Legal/privacy, Finance, Other (please list)

Why Now — What Would Happen If You Didn't Act?

• If you stayed with the status quo for 12 months, how would your business outcomes change—what would you stand to lose?
• Which internal or external pressures made this a priority now? Options: Brands demanding purchase-level attribution, Revenue targets not being met, Competitors launching media networks, Operational chaos from manual processes, New privacy/regulatory constraints, Other (please describe)
• How much estimated annual media revenue or advertiser spend is at stake if you don't move to a scalable platform? Options: <$100k, $100k–$500k, $500k–$2M, $2M–$10M, >$10M, Unsure
• When these gaps surface in conversations with brands, what emotions or fears come up internally—embarrassment, lost credibility, missed targets, or something else?
• How long have you been tolerating the manual processes or measurement limitations that currently exist? Options: Less than 6 months, 6–12 months, 1–3 years, 3–5 years, 5+ years
• What have previous attempts to fix this looked like, and why didn't they stick?

What If Measurement Actually Matched Your Sales Targets?

• Imagine attribution that directly maps ad exposures to product purchases — what would that enable you to do differently this quarter?
• Which measurement attributes are non‑negotiable for your brand or retail partners? (pick all that apply) Options: SKU‑level purchase attribution, Basket/incremental sales, Time‑to‑purchase window control, Cross‑channel deduplication, Holdout/incrementality testing, Third‑party auditability
• What performance metrics will you use to say a pilot moved the business needle? (select up to 3) Options: Incremental sales ($), ROAS/return on ad spend, Conversion lift (%), Cost per incremental purchase, Average order value uplift, Reach of targeted audiences, Brand satisfaction/renewal intent
• Who on your team will feel most rewarded if these metrics are achieved, and who will judge the pilot harshly if they aren't?
• How quickly would you expect to see measurable outcomes from a short pilot (timeframe)? Options: 2–4 weeks, 1–2 months, 2–3 months, 3–6 months, Longer/unsure

What's Getting in the Way — Let's Call the Real Barriers Out

• What single constraint do you believe will block a successful integration most—data, engineering bandwidth, legal, brand buy‑in, or shopper UX concerns? Options: Data readiness/quality, Engineering capacity, Legal/privacy controls, Brand participation, Shopper experience risk, Commercial terms
• Which legacy systems or formats could slow catalog ingestion or targeting (pick all that apply)? Options: Custom SKU IDs/no GTIN, Proprietary catalog API, Flat CSV exports only, No image assets tied to SKUs, Multiple inconsistent naming conventions
• Describe your data governance posture for shopper and transaction data—what can be shared, what must remain hashed/pseudonymized, and what requires contracts?
• How many dedicated engineering or data resources can you realistically commit to an integration sprint? Options: None (requires full vendor support), 1–2 part-time, 1 full-time, 2–3 full-time, 4+ full-time
• When you think about shopper experience, what would feel like an unacceptable tradeoff to the e‑commerce/product team? Options: Slower page loads, Cluttered UX, Irrelevant placements, Loss of organic merchandising control, Other (please specify)

Design a Pilot That Brands Can't Say No To

• If a brand had one hesitation about participating in a pilot, what would it be—and why would that matter to you?
• Which pilot placements are most likely to attract anchor brands for a credible test? (select up to 3) Options: Search/sponsored products, Category pages, Homepage showcase, Cart/checkout ads, Email/native promotions, In‑store digital screens
• What minimum audience size or sample of purchase events do brands expect before committing media spend in a pilot? Options: <5k weekly users, 5k–25k weekly users, 25k–100k weekly users, 100k+ weekly users, Brands will decide case-by-case
• Which commercial pilot structure would be most acceptable to you and your brand partners? Options: Platform fee as % of media spend, Flat technology fee for pilot, Revenue share on incremental sales, Discounted pilot pricing for proof, No upfront fees, measured success gateway
• What clear acceptance criteria would you set so both you and participating brands can confidently say the pilot succeeded?

Integration Reality Check — Truths on the Ground

• If integration took longer than expected, what would be the true cost to your organization beyond dollars—team morale, brand relationships, or go‑to‑market windows?
• Which shopper datasets can you connect to the platform within 30 days? (select all that apply) Options: Online transaction feed (orders), Loyalty transaction history, CRM/email hashed emails, In‑store point‑of‑sale, Device or cookie IDs, None readily available
• Which identity signals do you currently rely on for matching (pick primary and secondary)? Options: Hashed email/loyalty id, Device IDs, Third‑party graph, No stable identity available, Other (please describe)
• What tagging/pixel or SDK work will be required on your site/app to enable ad serving and conversion reporting? Options: Fully implemented already, Minor additions (events/parameters), Substantive dev work required, Requires platform to host measurement, Unsure—need audit
• What are realistic timelines for: catalog ingestion, identity mapping, and pilot launch? (please list or give ranges)
• Who will be the named owner(s) for integrations, and what authority do they have to make technical decisions?

Commitment & Next Moves — Who's Betting On This?

• If you had to set a go/no‑go decision date today, how soon could your leadership realistically decide to proceed to pilot? Options: Immediately (this week), Within 2 weeks, Within 1 month, 1–2 months, More than 2 months
• What contractual or policy red lines would block a pilot from happening (select all that apply)? Options: No sharing of raw PII, Only pseudonymized hashed matches, Strict SLA uptime requirements, Audit rights for attribution, Fixed maximum tech fee, Other (please specify)
• Which internal stakeholders must sign off on commercial terms, and what is their typical timeline for approvals?
• What deliverable from us would make you most comfortable greenlighting a pilot? (choose up to 2) Options: Detailed measurement plan, Integration runbook and data map, Pilot commercial term sheet, A reference case from similar retailer/brand, A demo dashboard with sample data
• On a scale from 1–10, how ready do you feel to move from discovery to a scoped pilot? Please explain the number briefly. Options: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10
• Who should we schedule a 30‑minute technical scoping session with next (name, role, email)?

• Solution Experience Kickoff — Context & Consequence
• Pilot Scenario Design Workshop
• Data, Catalog & Attribution Readiness
• Campaign Configuration & Measurement Demo (Proof)
• Pilot Acceptance & Launch Readout (Decision)

• Deliver the pilot dashboard template and sample reports that map impressions to purchase outcomes.
• Deliver a sample match‑rate report (impressions -> purchases) for the selected pilot scope within agreed timeframe.
• Customer to provide API keys/FTP credentials and sample catalog feed for ingestion testing.
• Remediate any missing identifiers or mapping mismatches identified in the sandbox run.
• Document and approve the data handling and retention plan with the customer's privacy/legal team.
• Campaign Setup Walkthrough
• Demonstrate a working end‑to‑end attribution proof using customer context that validates the future state.
• Ensure the customer can trace every measured outcome back to a specific step in the campaign flow.
• Obtain customer's validation on campaign parameters, reporting templates, and any needed adjustments.
• Produce an operational playbook for campaign execution and monitoring during the pilot.
• Introductions & Meeting Objectives
• Export and share sample impression-to-purchase log files used in the demo for auditability.
• Refine targeting/pacing parameters based on validation feedback and finalize campaign config.
• Create the campaign ops playbook with monitoring runbook and escalation paths.
• Executive Summary of Pilot & Proof
• Obtain mutual sign‑off to proceed with the pilot based on the defined acceptance criteria.
• Confirm commercial terms and any billing/fee responsibilities for the pilot.
• Assign integration and operational owners with clear responsibilities and timelines.
• Schedule the pilot launch date and monitoring cadence with agreed reporting templates.
• Circulate the signed pilot brief and SOW (or PO) capturing scope, KPIs, acceptance criteria, and commercial terms.
• Customer and platform teams to provision production credentials, tags/pixels, and confirm integration owners.
• Set up the monitoring cadence (daily/weekly dashboard) and assign reporting recipients.
• Create a rollback/mitigation plan in case initial validation gates are not met during the pilot.
• Document a crystal‑clear one‑sentence current state agreed by all parties.
• Quantify the business consequence of the current state with at least one numeric KPI or dollar estimate.
• Agree a concise future‑state success statement that the pilot must prove.
• Produce a concrete prework checklist (data, access, stakeholders) with owners and due dates.
• Capture and circulate the agreed one‑sentence current state and future‑state success statement.
• Customer to provide baseline metrics (sales, conversion, AOV) and any current sponsored-product performance within 5 business days.
• List and assign owners for required datasets and provide sample catalog and shopper data endpoints.
• Schedule the Pilot Design Workshop and share preparatory materials.
• Recap Context & Constraints
• Finalize the pilot objective and measurable success signals (KPIs, windows, thresholds).
• Agree the pilot scope (SKU list, placements, audience definitions, geography).
• Commit to a measurement methodology and acceptance criteria for closed‑loop attribution.
• Establish timeline, milestone owners, and validation checkpoints.
• Author and circulate a one‑page pilot brief capturing objectives, KPIs, scope, and measurement approach.
• Customer to provide definitive SKU list and placement inventory for the pilot.
• Map measurement events to concrete data fields and provide sample schemas.
• Schedule the Data & Measurement Readiness session with technical owners.
• Data Inventory & Access Review
• Confirm availability and access methods for all data required to run pilot measurement.
• Validate that catalog ingestion mapping is complete and that SKU identifiers align with purchase events.
• Establish that match rates meet the pre‑agreed threshold (or capture remediation steps if they do not).
• Agree data governance controls and necessary privacy approvals before any production data is processed.
• Ad Serving & Delivery Logs
• Acceptance Criteria & Measurement Gates
• Catalog Ingestion Requirements & Schema Mapping
• Define Pilot Objective and Success Signals
• Current State — One‑Sentence Diagnosis
• Commercial Terms & Technology Fee Overview
• Attribution Mapping & Identifier Match Rates
• Consequence Quantification
• Scope: SKUs, Placements, Audiences, Geography
• Attribution Demo: Impression -> Purchase Link
• Sandbox Proof / Sample Matching Report
• Dashboard Walkthrough & Reporting Template
• Operational Readiness & Responsibilities
• Measurement Methodology & Attribution Model
• Future State — Success Statement

• Import and Normalize Product Catalogs (SKU mapping)
• Connect First-Party Shopper Data Feeds
• Configure Web and Mobile Ad Placements
• Integrate In-Store Digital Screen Inventory
• Create and Activate Audience Segments
• Upload and Manage Creative Assets
• Set Targeting, Frequency, and Pacing Rules
• Enable Real-Time Ad Serving and Auctions
• Tag and Log Impressions, Clicks, Conversions
• Integrate Transaction and POS Data
• Generate Closed-Loop Purchase Attribution Reports
• Enable Cross-Retailer Campaign Management
• Train Retail Sales Team on Platform Use

Import and Normalize Product Catalogs (SKU mapping)

• Do you currently have a master product catalog to ingest? Options: Yes, No
• What format(s) is your catalog available in? Options: CSV/Excel export, PIM (Product Information Management), API/Feed, XML/JSON, Other
• Approximately how many SKUs (including variants) are in scope for the pilot? Options: Less than 1,000, 1,000–10,000, 10,000–100,000, More than 100,000
• Which identifiers are available on your SKUs (select all that apply)? Options: SKU, UPC/GTIN, Manufacturer Part Number, Retailer Internal ID, No standardized identifier
• Do you require attribute normalization (e.g., unit sizes, category mapping, brand harmonization)? Options: Yes, No
• Are there known catalog quality issues we should plan for (missing images, mismatched categories, duplicate SKUs)? Please describe.

Connect First-Party Shopper Data Feeds

• Which first-party shopper data sources will be connected? Options: CRM, CDP, Order/Transaction DB, Web/mobile analytics, Loyalty system, Other
• Will data be provided via API, SFTP, streaming, or batch exports? Options: API (real-time), SFTP (scheduled files), Streaming (Kafka/webhooks), Database replication, Other
• Do the feeds contain any PII that requires special handling or encryption? Options: Yes, No, Unsure - need to audit
• What matching keys are available to join shopper records to platform IDs (e.g., email hash, loyalty ID, device ID)?
• What is the expected freshness requirement for shopper data (e.g., hourly, daily, weekly)? Options: Near real-time (minutes), Hourly, Daily, Weekly
• Who will own the data feed integration on the retailer side (role or team)? Options: E‑commerce/Tech, Data Engineering, Marketing/Media Ops, Third-party vendor, Other

Configure Web and Mobile Ad Placements

• Which placement types do you want to configure for the pilot? Options: Search results, Category/listing pages, Product detail pages, Homepage/carousels, Mobile app native slots, Other
• Are placements primarily native (in-feed) or standard banner/slot units? Options: Native (in-feed), Banner/slot, Hybrid/mixed
• Do you have existing ad size/spec guidelines and creative constraints for each placement? Options: Yes - provide spec sheets, No - need specs defined
• Will placement rules include editorial guardrails or business rules (e.g., not on competitor pages, no ads on checkout)? Options: Yes, No, Need to define
• Do you require A/B or multivariate testing for placements during the pilot? Options: Yes, No
• Which teams approve placement UX changes (e.g., e‑commerce product, UX/design, legal)?

Integrate In-Store Digital Screen Inventory

• Do you operate digital screens in stores that should be part of media inventory? Options: Yes, No
• How many screens and store locations are tentatively in scope for the pilot? Options: 1–50, 51–250, 251–1,000, 1,000+
• What CMS or playback hardware/software manages the screens (vendor name or custom)?
• Do screens support programmatic triggers or real‑time signals (e.g., queue from POS, sensors)? Options: Yes - real-time triggers, No - scheduled playlists only, Limited capability
• Are there scheduling or regional restrictions (e.g., dayparting per store, regional campaigns)? Options: Yes, No
• Who is the operational owner for in-store content and compliance (store ops, merchandising, marketing)? Options: Store Operations, Merchandising, Marketing, Third-party vendor, Other

Create and Activate Audience Segments

• What types of audience segments do you plan to activate in the pilot? Options: Purchase history, Loyalty tiers, Behavioral (browsing), Demographic, Lookalike / modeled, Custom
• Do segment definitions need to be created from scratch or do you have existing segment definitions? Options: Create new, Use existing, Hybrid
• Should segments be built and evaluated in real-time or on a scheduled batch basis? Options: Real-time (streaming), Near real-time (hourly), Daily batch, Weekly batch
• What minimum audience size thresholds do you require for activation (per segment)? Options: No minimum, 1k+, 5k+, 10k+
• Are there data privacy or consent constraints that restrict use of certain segment types? Options: Yes, No, Unsure - need review
• Who will own segment governance, naming, and lifecycle (e.g., marketing ops, data team)? Options: Marketing Ops, Data Team, Media Sales, Third-party agency, Other

Upload and Manage Creative Assets

• What creative formats will you upload for the pilot? Options: Static images (JPG/PNG), HTML5 banners, Video (MP4), Dynamic product templates, Other
• Do you require dynamic creative (e.g., SKU-level substitution, price overlays)? Options: Yes, No
• What approval workflow is required for creatives (e.g., brand review, legal, retailer QoS)? Options: Single approver, Multi-stage approval, Automated with manual override, No formal workflow
• Are there file size or hosting constraints we should plan for? Options: Yes - provide limits, No
• Do creatives need localization (language/region) or store-specific variants? Options: Yes, No, Some regions only
• Who will be responsible for ongoing creative updates during the pilot (brand agency, retailer, in-house)? Options: Brand/Agency, Retailer, In-house Platform Team, Other

Set Targeting, Frequency, and Pacing Rules

• At what targeting granularity do you intend to run campaigns? Options: SKU-level, Category-level, Audience-level, Store/region-level, Custom
• What frequency cap policy should apply (impressions per user per day/week)? Options: 1–2/day, 3–5/day, No cap, Custom (specify)
• Which pacing strategy do you prefer for pilot budgets? Options: Even daily pacing, Front-loaded (early delivery), Performance-based (adaptive), End-of-period (burst)
• Do you require blacklists/whitelists for placements, brands, or SKUs? Options: Yes - blacklists, Yes - whitelists, Both, No
• Are there regulatory or brand-safety rules to enforce in targeting? Options: Yes - provide rules, No
• Who will own policy changes to targeting and pacing during the pilot (retailer, brand, platform)? Options: Retailer, Brand, Platform/Service Team, Joint

Enable Real-Time Ad Serving and Auctions

• Do you require real-time ad serving (sub-100ms) and programmatic auctions? Options: Yes, No, Partial (some placements only)
• Which auction or pricing model should be supported? Options: First-price auction, Second-price auction, Fixed CPM/Flat rate, Hybrid
• Will you integrate third-party demand partners or use platform-only buyers? Options: Platform-only, Third-party buyers, Both
• Are there latency or SLA requirements for ad decisioning and serving? Options: Yes - specify SLA, No
• Do mobile app placements require an SDK integration or MRAID support? Options: SDK required, MRAID supported, Webview only, Other
• Who will monitor auction health and troubleshoot delivery issues? Options: Retailer Ops, Platform Support, Brand/Agency, Third-party

Tag and Log Impressions, Clicks, Conversions

• Which tagging method do you prefer for web impressions and clicks? Options: Client-side JS pixel, Server-side tagging, Server-to-server events, Hybrid
• What event schema and naming conventions are required for logs?
• What retention period is required for raw logs and analytics data? Options: 30 days, 90 days, 1 year, Custom
• Do you require secure transmission/encryption and SOC/compliance controls on logs? Options: Yes, No, Unsure
• Will click/impression logs be used for real-time bidding decisions or only for post-hoc measurement? Options: Real-time bidding, Post-hoc measurement, Both
• Who will own tag deployment and QA (engineering, analytics, platform)? Options: Engineering, Analytics, Platform/Ad Ops, Third-party

Integrate Transaction and POS Data

• Which POS or transaction systems will be sources for the pilot?
• Will transaction data be provided in real-time, near-real-time, or batch? Options: Real-time, Near-real-time (hourly), Daily batch, Weekly batch
• Do you need line-item level detail (SKU-level) in transactions for attribution? Options: Yes, No, Partial (some channels)
• Are there data anonymization or aggregation requirements for POS data before sharing? Options: Yes, No, Need to define
• What fields are essential in the transaction feed (e.g., transaction ID, timestamp, SKU, price, store ID)?
• Who will be responsible for extracting and delivering transaction feeds? Options: Retailer Data Team, POS Vendor, Third-party ETL, Platform

• Commercial Term Sheet
• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Technology Fee & Pricing Schedule
• Billing & Payment Terms
• Service Level Agreement (SLA)
• Data Processing Agreement (DPA)
• Data Sharing & Governance Addendum
• Security & Compliance Addendum
• Measurement & Attribution Methodology Appendix
• Pilot Acceptance Criteria & Go/No‑Go Gates
• Implementation & Integration Plan
• Access Authorization & System Credentials
• Change Order / Scope Amendment Procedure
• Termination & Exit Plan
• Renewal & Expansion Agreement

• Success Review Workshop (Retailer + Brand)
• Attribution & Measurement Deep Dive
• Operational Root Cause & Learnings Session
• Backlog Prioritization & Roadmap Planning
• Executive Readout & Scaling Decision

• Publish a 90-day roadmap and share with retailer and brand stakeholders.
• Document measurement methodology and attach sample queries to the shared knowledge base.
• Add automated alerts for future match-rate regressions to monitoring dashboard.
• Incident Timeline & Facts
• Identify the primary root causes with supporting evidence for each operational issue.
• Agree on immediate remediation actions and permanent fixes with owners and SLAs.
• Update operational runbooks and monitoring to prevent recurrence.
• Implement hotfixes or configuration changes required to remediate production issues.
• Create/update runbook entries and post-incident report summarizing root cause and mitigations.
• Deploy monitoring/alerting for the specific failure modes discovered.
• Schedule a follow-up verification run to confirm fixes addressed the impact.
• Backlog Overview
• Produce a prioritized backlog with value/effort scores and owners for the top 8–12 items.
• Agree on a near-term roadmap and release windows for critical fixes and strategic enhancements.
• Define a communications cadence and format for customers regarding roadmap progress.
• Create prioritized tickets in the tracking system with clear acceptance criteria and owners.
• Introductions & Meeting Objectives
• Schedule regular backlog grooming cadence (weekly or biweekly) with stakeholders.
• Prepare customer-facing release notes for the upcoming release cycle.
• One‑Sentence Current State
• Obtain clear executive decision to scale, iterate, or pause with documented rationale.
• Secure commitment to any additional commercial or operational investments required for scaling.
• Align senior stakeholders on top risks and designate executive owners for mitigation.
• Capture executive sign-off in a decision memo and circulate to all stakeholders.
• If scaling: schedule a formal scaling kickoff with resourcing and milestones.
• If iterating: finalize iteration scope, timeline, and budget and communicate to customers.
• Update commercial agreement or SOW to reflect any newly agreed terms.
• Determine whether the pilot meets pilot acceptance criteria and reach a joint decision on scale/iterate/stop.
• Ensure business consequence is explicit and quantified for executive alignment.
• Capture top learnings and immediate remediation items to feed the shared backlog.
• Assign clear owners and timelines for next steps tied to the decision.
• Produce a one‑page joint decision memo summarizing outcome, consequence, and chosen path.
• Create/update backlog entries for all identified issues and enhancements with owners and priorities.
• Schedule follow-up checkpoint(s) based on decision (scale kickoff or iteration plan).
• Share finalized performance dataset and dashboards with stakeholders for auditability.
• Pre-work Validation Summary
• Confirm attribution accuracy or clearly define the gap and plan to remediate.
• Agree on a reproducible validation test suite and acceptance thresholds.
• Assign technical owners for reconciliation tasks and timeline to close gaps.
• Run agreed reconciliation scripts across full pilot window and deliver results.
• Implement agreed attribution rule adjustments and reprocess affected windows.
• Impact Assessment
• One‑Sentence Current State
• Business Consequence Headline
• Attribution Methodology Recap
• Value & Effort Scoring Exercise
• Prioritization & Tradeoffs
• Root Cause Brainstorm (5 Whys / Fishbone)
• Review Success Signals & Acceptance Criteria
• Data Quality & Edge Cases
• Key Metrics & ROI Summary
• Recommended Executive Decision
• Performance Snapshot (KPIs & Baseline Comparison)
• Remediation Plan & SLA Updates
• Roadmap Commitments & Resource Allocation
• Discrepancy Analysis
• Commercial & Contract Implications
• Customer Communications & SLAs
• Preventive Controls & Monitoring
• Consequence: Business Impact & Financials