Customer Journeys Orchestrated with Resend + Segment

Journeys stopped being generic blasts and became useful conversations.

Context

Onboarding emails were manual, adoption reminders arrived late, and upsell plays lived in spreadsheets. I rebuilt customer journeys as modular flows powered by Segment, Resend, Notion, and n8n so every touchpoint is personalized, measurable, and easy to edit.

Architecture

1. Segment captures product events and traits, routes them to Snowflake + n8n.
2. Notion CMS stores copy blocks referenced by ID (title, CTA, experiment variants).
3. Resend + React Email render templates, inject data, and send via verified domains.
4. n8n automation layer orchestrates timers, branching logic, and multichannel triggers (email, Slack, in-app).
5. Supabase logs journey state, ensuring idempotency and GDPR compliance.
6. Metabase/PostHog track activation, feature adoption, ARR influenced.

State Management

| Table | Purpose | |-------|---------| | journey_state | Stores current step, next send, snooze flag per account/journey | | journey_events | Append-only log of triggers, emails, failures | | journey_feedback | CS/AE notes that influence future steps |

Keeping state outside Resend lets us pause/resume journeys safely and answer auditors quickly.

In-App Instrumentation

• PostHog feature flags gate tooltips, banners, and checklists by journey stage.
• Every in-app component logs journey_component_rendered with stage + variant so we correlate UI exposure with email performance.
• Flags default to “off” and only activate when Supabase confirms the customer is eligible, preventing mixed messaging.

Journey Stack Overview

| Stage | Trigger | Channels | KPI | |-------|---------|----------|-----| | Onboarding | workspace created, seat invited | Email, in-app walkthrough | Activation rate, time-to-value | | Adoption | feature flag enabled, usage drop | Email, Slack, in-app tips | Feature usage, retention | | Expansion | usage > 80%, billing tier mismatch | AE Slack alert, CSM playbook, in-app CTA | Expansion ARR | | Advocacy | NPS > 9, successful launch | Customer marketing, review asks | Reviews, referrals |

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Playbook

1. Map Stages & KPIs

• Workshops with CS, Product, Marketing to define desired outcomes and health metrics per stage.
• Documented in Notion as journey_stage objects with KPIs, triggers, owners.

2. Externalize Copy & Assets

• Notion database stores copy blocks with IDs (e.g., adoption_playbooks.billing_links.cta).
• Resend template fetches copy via API at send time, so marketers edit once without redeploying code.

3. Build Automation Engine

• n8n flows watch Segment events (via webhook) and Supabase state.
• Each journey is a YAML config listing trigger, eligibility filters, steps, fallback, and sunset conditions.

journey: onboarding_core
trigger: segment.event == "workspace_created"
filters:
  - seats_active == 1
steps:
  - wait: 5m
  - email: template onboarding_welcome
  - wait: 2d
  - branch:
      condition: feature_usage.automations >= 1
      true: email onboarding_pro_tip
      false: email onboarding_use_case
sunset: 14d

4. QA & Testing

• Mailosaur catches rendering issues across devices.
• Automated integration tests simulate events and assert Resend received the payload we expect.
• Beta program with 10 customers validated tone before full rollout.

5. Measurement & Iteration

• PostHog experiments compare variants (e.g., video vs. written tutorial) while Resend logs store deliverability + open/click data in Snowflake.
• Metabase dashboards show stage conversion, drop-offs, and ARR influenced per journey.
• Monthly “Journey Council” reviews performance, sunsets underperforming flows, and plans experiments.

6. Implementation Timeline

| Week | Milestone | |------|-----------| | 1 | Map lifecycle stages, define KPIs, gather copy | | 2 | Wire Segment destinations, Supabase state table, Notion CMS | | 3 | Code React Email templates, wire Resend + n8n flows | | 4 | QA via synthetic accounts, run beta, integrate Metabase dashboards | | 5 | Roll out globally, train CS/Marketing, set guard rotation |

Metrics & Telemetry

• Activation rate: +31% (workspace → first automation).
• Time-to-value: -42% (customers reach aha moment sooner).
• Quarterly upsell ARR: +18% attributable to expansion journeys.
• Average send latency: 18 seconds (Segment → Resend).
• Opt-out complaints: <0.2% thanks to preference center integration.
• Journey coverage: 92% of customers touch at least one journey every quarter.
• Reply-to-CSM ratio: 1 in 5 emails triggers two-way conversation, feeding qualitative insights.

Governance & Enablement

• Notion portal includes playbook cards (goal, copy preview, owner, performance).
• Marketers submit changes via form → Linear ticket → PR to Notion copy + YAML config.
• CS gets Slack digest summarizing which accounts are mid-journey so conversations stay aligned.
• Legal reviews any journey touching personal data; consent stored in Supabase ensures only opted-in contacts receive emails.
• Request SLA dashboard sits in Metabase so stakeholders see what’s shipping next.

Troubleshooting Runbook

1. Email didn’t send? Check Supabase state + Resend webhook logs; requeue via n8n if needed.
2. Customer opted out mid-journey? Snooze flag flips automatically; guard verifies in preference center.
3. Copy typo? Editor updates Notion block, runs preview command, merges PR—no code deploy.
4. Metrics look off? Compare Segment event freshness; rerun dbt job if late.

Communication & Ops

• Daily digest of triggered journeys + KPI deltas auto-posts in #cx-journeys.
• Weekly retro highlights experiments, customer quotes, and backlog items.
• Guard rotation monitors n8n failures; PagerDuty alerts if queue backlog exceeds thresholds.
• Monthly executive summary ties journey performance to ARR and churn to keep leadership invested.

Cost Snapshot

• Resend (two domains + 100k emails): ~$120/mo.
• Mailosaur testing: $39/mo.
• n8n on Fly.io + Supabase hosting: ~$30/mo combined.
• Segment + Notion already budgeted; incremental cost basically the QA tools.
• One expansion deal influenced by the journeys pays for the stack for months. Previously we spent entire sprints hand-emailing cohorts; now the stack runs itself for less than a team lunch.

Case Study: Churn Rescue Play

• Trigger: drop in weekly active users + support ticket flagged risk.
• Journey sent personalized email with product tips + CSM Slack ping with talk track.
• Result: 38% of accounts reactivated within two weeks; others escalated to Success early, preventing churn.
• Automation logged every step so finance could attribute saved ARR.
• Follow-up experiment paired the email with an in-app checklist; those customers adopted the feature twice as fast, so we now ship multichannel steps by default.

Lessons Learned

• Separate content from automation—Notion IDs + Resend templates empower marketers without touching code.
• Log everything. Supabase state table prevents double sends and fuels debugging.
• Tie journeys to business KPIs; we only keep flows that move activation, adoption, or ARR.
• Governance beats heroics: request forms, SLAs, and councils keep noise out of production.

FAQ

How do you handle localization? Each Notion copy block has locale variants. Journey config picks language based on customer profile; Resend selects correct version automatically.

What about user preferences? Preference center writes to Supabase. n8n checks consent before firing any step, ensuring GDPR compliance.

Can CS pause a journey? Yes—there’s a “snooze” button in the Slack digest that flips a Supabase flag, pausing further steps for that account.

How do you test? We run “journey drills” every month: synthetic accounts trigger each stage, QA screens emails/in-app prompts, and metrics dashboard must light up within minutes.

How do you stop overlap between marketing and CS emails? Supabase state table tracks last-touch per channel; n8n checks it before sending. If a CSM just emailed, the journey waits or swaps in-app nudges instead.

Can journeys trigger human tasks? Yes—n8n can open Linear tasks or Attio activities (e.g., “Call customer after milestone”) so humans stay in the loop.

What I'm building next

Journey simulator UI where PMMs can drag events and see which emails/in-app prompts would fire, plus AI-generated copy suggestions that still respect our tokenized components.

Want me to help you replicate this module? Drop me a note and we’ll build it together.