Email Marketing

Email deliverability, list management, sequences, segmentation, and campaign optimization.

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Install skill "Email Marketing" with this command: npx skills add kirkraman/toby-email-marketing

Deliverability Foundations

  • Authenticate all sending domains: SPF, DKIM, and DMARC — missing any one tanks deliverability
  • Warm up new domains/IPs: start with 50-100 emails/day, increase 20% daily over 2-4 weeks
  • Never buy email lists — purchased lists destroy sender reputation permanently
  • Clean list regularly: remove bounces immediately, unengaged after 90 days
  • Monitor blacklists: MXToolbox, Google Postmaster Tools — problems compound if not caught early

List Health Metrics

MetricHealthyWarningCritical
Open rate>20%10-20%<10%
Click rate>2%1-2%<1%
Bounce rate<2%2-5%>5%
Unsubscribe<0.5%0.5-1%>1%
Spam complaints<0.1%0.1-0.3%>0.3%
  • One spam complaint per 1000 emails is the danger zone — above this, inbox placement drops sharply

Subject Lines

  • 40-50 characters optimal — truncates on mobile after 35-40
  • Personalization works: name or company in subject increases opens 10-20%
  • Curiosity beats clarity for opens, but clarity wins for clicks — balance based on goal
  • Avoid spam triggers: ALL CAPS, excessive punctuation!!!, "free", "act now"
  • Test emoji: works for some audiences, hurts others — A/B test before committing
  • Preview text is second subject line — don't waste it with "View in browser"

Email Sequences

Welcome sequence (5-7 emails over 2 weeks):

  1. Immediate: Deliver promised value + set expectations
  2. Day 1: Best content or quick win
  3. Day 3: Story/origin + values
  4. Day 5: Social proof + case study
  5. Day 7: Soft offer or deeper engagement
  6. Day 10: Address common objection
  7. Day 14: Clear CTA
  • First email in sequence has highest open rate — make it count
  • Space emails 1-3 days apart — daily is too aggressive for most audiences

Segmentation

  • Segment by behavior, not just demographics — what they clicked matters more than job title
  • Minimum viable segments: new subscribers, engaged (opened in 30 days), unengaged, customers
  • Tag on every click — builds behavioral profile automatically
  • Sunset unengaged subscribers after 90 days — send re-engagement, then remove
  • VIP segment for highest engagement — reward them with early access, exclusives

Timing and Frequency

  • Tuesday-Thursday mid-morning performs best on average — but test your audience
  • B2B: business hours. B2C: evenings and weekends can work
  • Frequency depends on value: daily works if valuable, weekly fails if boring
  • Let subscribers choose frequency — reduces unsubscribes significantly
  • Send time optimization: most ESPs offer this, use it

Campaign Types

  • Newsletter: regular value, builds relationship, low direct conversion
  • Promotional: clear offer, urgency, direct conversion focus
  • Transactional: receipts, confirmations — highest open rates, add value here
  • Re-engagement: "We miss you" + incentive + easy unsubscribe
  • Announcement: product launches, major updates — segment to interested only

Writing for Email

  • One goal per email — multiple CTAs dilute response
  • Write for skimmers: bold key phrases, short paragraphs, bullet points
  • P.S. lines get read — put secondary CTA or key point there
  • Plain text often outperforms HTML for personal-style emails
  • Mobile-first: 60%+ open on mobile — single column, large tap targets

Automation Triggers

  • Sign up → Welcome sequence
  • Purchase → Onboarding + cross-sell sequence
  • Abandoned cart → 3-email recovery (1h, 24h, 72h)
  • No open in 30 days → Re-engagement sequence
  • Link click → Tag and trigger relevant follow-up
  • Date-based → Birthday, renewal reminder, anniversary

A/B Testing

  • Test one variable at a time: subject, send time, CTA, from name
  • Need 1000+ recipients per variant for statistical significance
  • Subject line tests: 20% of list first, winner to remaining 80%
  • Measure what matters: opens for subject, clicks for content, conversions for offers
  • Document every test — institutional learning prevents repeat experiments

Common Mistakes

  • Sending to entire list always — segment or face declining engagement
  • No double opt-in — leads to fake emails and spam traps
  • Ignoring mobile preview — broken layouts kill credibility
  • Same email to all segments — personalization is expected now
  • Hard selling too early — value first, offer later
  • Ignoring unsubscribe feedback — they tell you what's wrong

Compliance

  • Include physical address in every email — required by CAN-SPAM, GDPR
  • Unsubscribe must work within 10 days — one-click preferred
  • Honor opt-outs immediately — delayed removal is illegal in many jurisdictions
  • GDPR: explicit consent required, document it, allow data deletion
  • Separate consent for different email types — marketing vs transactional

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