E-commerce Director of Retention

Snapshot

  • Role: Director of Retention
  • Company type: DTC e-commerce brand with repeat purchase model
  • Company size: 20 to 120 employees
  • Revenue stage: $5M to $40M annual revenue
  • Buying authority: Owns CRM, lifecycle, and retention tooling budget with founder or CFO sign-off
  • Why this segment is interesting: Retention leaders feel daily pressure from CAC increases and margin erosion.

Core Pain Points

  • Email and SMS flows are running but repeat purchase rate is flat.
  • Promotions lift short-term sales but train customers to wait for discounts.
  • Attribution confusion causes internal fights between paid media and CRM teams.
  • Inventory decisions are made without clear cohort behavior data.
  • The retention lead feels blamed for revenue dips they cannot fully control.

What They’ve Already Tried

  • Copied benchmark lifecycle flows from agencies without adapting to product behavior.
  • Increased send frequency, causing unsubscribe spikes and lower engagement quality.
  • Tested loyalty programs with low enrollment and low repeat order impact.
  • Hired a freelancer for segmentation cleanup without changing execution habits.

Hypotheses

  • Retention failure is often segmentation and offer-timing failure, not channel failure.
  • They reply when outreach references concrete retention metrics, not creative ideas.
  • Urgency spikes after board review or after two weak months of repeat revenue.
  • We must validate whether they can implement changes quickly or rely on overloaded teams.

DM Angles to Test

  1. Your repeat purchase rate may be flat because your post-purchase timing is too generic.
  2. Discount-led retention often hides weak product usage patterns until margin drops.
  3. If unsubscribe rate climbed after frequency increases, your lifecycle logic may need a reset.
  4. Most retention teams leak revenue in the second-order window, not at first checkout.
  5. Attribution debates usually block retention fixes more than tooling gaps do.
  6. Small cohort behavior changes can outperform big campaign launches.

Questions to Ask

  • Which retention metric has moved in the wrong direction over the last 90 days?
  • Where do customers drop out between first and second purchase?
  • How do you currently segment high-intent buyers versus discount-only buyers?
  • Who approves major lifecycle strategy changes when results are weak?
  • What has already failed that your team does not want to repeat?
  • What internal dependency slows down retention experiments the most?

Signals to Track

  • Positive signal: They share real retention metrics and time windows.
  • Positive signal: They explain current experiment cadence and blockers.
  • Neutral signal: They ask for more details but provide no operating context.
  • Neutral signal: They acknowledge issue but defer until next quarter planning.
  • Strong rejection: They state retention is outsourced and not internally owned.
  • Strong rejection: They report no current pressure on repeat revenue performance.
  • Patterns to log after 100 DMs: objection categories, angle reply rates, decision-maker response share, and time-to-first-meaningful call.

After 100 Conversations

Placeholder for validated findings, updated segment assumptions, and revised outreach angles.