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45+ Email Flows & Automation Playbook: Proven Strategies to Automate, Segment, and Drive Sales
Did you know?
Email marketing delivers an average ROI of 3,600% - 4,500%.
That means businesses earn $36 for every $1 spent and in some industries up to $46 for every $1 spent, according to Email Tool Tester. Whether you’re chasing B2B leads, winning over e-commerce shoppers, converting SaaS trial users, or re-engaging loyal customers, email marketing is severely undervalued–especially when you can set up flows for automation.
This evergreen playbook breaks it down with plug-and-play sequences and smart triggers that work for any audience.
From SaaS trials to abandoned carts, B2B demos to post-purchase wins, these strategies adapt to your business—big or small, B2B or B2C.
  • Part 1: How to segment your users (Free & Paid)
  • Part 2: 45+ Automated Email Flows With Events and Triggers
Part 1: User Segments
Free Users
  • Unactivated Users: Signed up but haven't used credits/features (0 usage).
  • Maxed-Out Users: Consistently hit free plan limits monthly.
  • Partial Users: Use some, but not all, free resources monthly.
  • Dormant Users: Inactive (no logins/usage) for 30+ days after prior activity.
Paid Users
Active Paid Users: Regular platform users.
  • High-Tier (Monthly | Yearly)
  • Middle-Tier (Monthly | Yearly)
  • Minimum-Tier (Monthly | Yearly)
Occasional Paid Users: Sporadic usage.
  • High-Tier (Monthly | Yearly)
  • Middle-Tier (Monthly | Yearly)
  • Minimum-Tier (Monthly | Yearly)
Dormant Paid Users: Inactive for 30+ days.
  • High-Tier (Monthly | Yearly)
  • Middle-Tier (Monthly | Yearly)
  • Minimum-Tier (Monthly | Yearly)
Loyal Paid Users: Long-term subscribers.
  • High-Tier (Monthly: 6+ months | Yearly: 1+ year)
  • Middle-Tier (Monthly: 6+ months | Yearly: 1+ year)
  • Minimum-Tier (Monthly: 6+ months | Yearly: 1+ year)
Canceled Users
  • Recently Canceled (Within 30 Days):
  • Active Before Cancellation (High/Middle/Minimum; Monthly/Yearly)
  • Inactive Before Cancellation (High/Middle/Minimum; Monthly/Yearly)
  • Long-Term Canceled (30+ Days Ago):
  • Active Before Cancellation (High/Middle/Minimum; Monthly/Yearly)
  • Inactive Before Cancellation (High/Middle/Minimum; Monthly/Yearly)
Prospects (B2B Lead Gen)
  • Website Visitors: Visited site but didn't sign up.
  • Content Downloaders: Accessed gated content (e.g., whitepapers, lead magnet).
  • Demo Requesters: Scheduled but haven't completed a demo.
  • Trial Users: Signed up for a free trial (SaaS-specific).
Part 2: Automated Email Flows & Triggers
Lead Generation & Nurturing
Grow your pipeline—perfect for B2B, SaaS, SMB's, and lead-driven E-commerce.
1. Website Visitor Follow-Up
  • Event: User visits key pages (e.g., homepage, pricing) but doesn't sign up.
  • Trigger: Send a "caught your interest?" email 24 hours later with a value prop and CTA (e.g., free trial or resource).
  • Sequence: Kick off with a recap of their visit to grab attention, follow with a trust-building benefit tease, then close with an irresistible nudge to act.
2. Content Downloader Welcome
  • Event: Prospect downloads gated content (e.g., lead magnet).
  • Trigger: Instant thank-you email with the asset and a soft pitch for next steps.
  • Sequence: Deliver the goods with a warm intro, share a juicy tip to keep them hooked, then wrap with a results-focused invite to connect.
3. Demo Request Nudge
  • Event: User requests a demo but doesn't attend.
  • Trigger: Make sure to send reminder 1 hour before, then a "missed you" email 24 hours post-no-show.
  • Sequence: Hype the demo with a prep nudge, re-offer it with a value hint after they miss, then seal it with a can’t-say-no perk.
4. Pricing Page Visit
  • Event: User views pricing but doesn’t buy.
  • Trigger: "Questions?" email 20 minutes later with a limited-time perk.
  • Sequence: Ease their doubts with a quick win, back it up with proof of worth, then push with a ticking-clock offer.
5. Event Registrants
  • Event: User signs up for webinar/workshop.
  • Trigger: Instant confirmation email with a value teaser.
  • Sequence: Confirm and excite them with what’s coming, remind them to show up with a prep tip, then follow up with a next-step push.
6. Social Media Engagers
  • Event: User interacts with your social post.
  • Trigger: "Hey, thanks!" email within 24 hours with a value-add.
  • Sequence: Thank them with a small gift, tie it to a bigger benefit, then invite them to dive deeper.
7. Lead Magnet Abandoners
  • Event: User starts but abandons lead magnet form.
  • Trigger: "Almost there!" email 1 hour later with a link.
  • Sequence: Gently pull them back with the asset, tease its value to spark curiosity, then nudge them over the finish line.
Onboarding & Activation
Turn sign-ups into active users—ideal for SaaS, B2C, and subscription businesses.
8. New User Welcome
  • Event: User signs up (free or paid).
  • Trigger: Instant email with greeting, onboarding video, and core feature CTA.
  • Sequence: Greet them warmly with a first-step guide, nudge them with a quick win, then encourage broader exploration.
9. Unactivated Reminder
  • Event: No usage after 3 days.
  • Trigger: Friendly nudge with a testimonial and bonus after 3 days.
  • Sequence: Reassure with proof it works, simplify their start with a perk, then make one last enticing push.
10. First Action Celebration
  • Event: User completes first meaningful action.
  • Trigger: "You’re on your way!" email right after action.
  • Sequence: Celebrate their win with a pat on the back, suggest a next move to keep momentum, then tease bigger possibilities.
11. Trial Sign-Up Welcome
  • Event: User starts a free trial.
  • Trigger: Welcome email with onboarding tips and guide link.
  • Sequence: Set them up with essentials, check in with a feature spotlight, then ramp up to a must-have upgrade pitch.
12. New Credits Added
  • Event: Free user’s credits refresh monthly.
  • Trigger: Notify with an industry-tied use case (e.g., "Boost Q1 campaigns").
  • Sequence: Alert them with a creative idea, inspire with a success hint, then nudge toward a paid boost.
13. Account Setup Staller
  • Event: User signs up but skips setup.
  • Trigger: "Finish up!" email 48 hours later with a guide.
  • Sequence: Prompt them with a setup lifeline, tease the payoff, then sweeten it with a completion reward.
14. Early Adopter Boost
  • Event: User joins during beta/launch.
  • Trigger: "You’re in early!" email with a perk right away.
  • Sequence: Hype their VIP status with a bonus, share an insider tip, then ask for feedback with a perk.
Engagement & Adoption
Deepen usage across SaaS, B2C, and loyalty-driven models.
15. Feature Exploration
  • Event: User tries a new/premium feature.
  • Trigger: "How-to" email within 24 hours with ROI tips.
  • Sequence: Show them the ropes with a benefit, deepen their use with a pro tip, then tease the premium upgrade.
16. Team Invite Prompt
  • Event: User adds a team member.
  • Trigger: Collaboration guide email right after addition.
  • Sequence: Guide them to teamwork wins, highlight scaling perks, then offer a deal for more seats.
17. Content Sharing
  • Event: User shares platform output.
  • Trigger: "Thanks!" email with a reward and referral link.
  • Sequence: Thank them with a small prize, encourage more sharing with a bonus hint, then push for broader reach.
18. Multi-Device Sync
  • Event: User logs in from multiple devices.
  • Trigger: "Sync tips" email after second login.
  • Sequence: Offer sync basics with a tease, showcase premium sync value, then pitch a seamless deal.
19. Milestone Celebration
  • Event: User hits a milestone (e.g., 10 projects).
  • Trigger: "Big win!" email with a perk right away.
  • Sequence: Cheer their progress with a reward, suggest a next level, then lock in loyalty with a perk.
20. Feature Abandonment
  • Event: User starts but ditches a feature.
  • Trigger: "Need help?" email 24 hours later.
  • Sequence: Help them finish with a tip, prove it’s worth it with a win, then nudge them back with a perk.
21. Seasonal Engagement
  • Event: Holiday/season nears.
  • Trigger: "Seasonal boost" email 7 days before.
  • Sequence: Spark ideas with a themed hook, sweeten it with a seasonal perk, then close with a timely push.
Conversion & Upsell
Boost revenue for E-commerce, SaaS, B2B, and beyond.
22. Abandoned Cart
  • Event: User adds to cart but bails.
  • Trigger: "Forgot something?" email 2 hours later with an incentive.
  • Sequence: Remind them what’s waiting with a perk, back it with a reason to buy, then push with urgency.
23. Credit Exhaustion (Free Users)
  • Event: Free user runs out of credits.
  • Trigger: "Out of credits?" email with a plan pitch right away.
  • Sequence: Pitch a plan with a bonus tease, remind them of the value, then close with an upgrade nudge.
24. Upsell Opportunity
  • Event: Loyal user hits milestone (e.g., 3 months).
  • Trigger: "Ready for more?" email with a tier offer.
  • Sequence: Tease a higher tier with a benefit, show why it’s a fit, then seal it with a deal.
25. Annual Plan Push
  • Event: Monthly user nears 6 months.
  • Trigger: Send a "Save big" email with savings calculator at 6-month mark.
  • Sequence: Pitch annual savings with a perk, highlight the upside, then lock it in with a deadline.
26. Loyalty Program Members
  • Event: User joins or earns points.
  • Trigger: "Welcome to the club!" email with details.
  • Sequence: Welcome them with perk details, nudge them to redeem, then gamify the next level.
27. Low Stock Alert
  • Event: Item user viewed is low stock.
  • Trigger: "Hurry, low stock!" email when threshold hit.
  • Sequence: Warn them with a grab-it-now hook, ramp up scarcity, then push for the last chance.
Retention & Loyalty
Build lasting bonds for B2C, E-commerce, SaaS, and SMBs.
28. Subscription Renewal Reminder
  • Event: Paid user's renewal approaches (7 days prior).
  • Trigger: Highlight their usage value (e.g., "You've saved X hours") and offer a renewal bonus (e.g., extra credits).
  • Sequence: Show their wins with a bonus, remind them of the value, then push to renew.
29. Inactivity Alert
  • Event: User inactive for 15 days.
  • Trigger: "Hey, you OK?" email with a teaser.
  • Sequence: Wake them with a tease, boost with a perk, then make a final re-engagement play.
30. Return After Inactivity
  • Event: Dormant user logs in after 30+ days.
  • Trigger: "Welcome back!" email with updates.
  • Sequence: Greet them with what’s new, nudge them to restart, then lock in with a perk.
31. Feedback Request
  • Event: User active for 30 days.
  • Trigger: Send a "What do you think?" email.
  • Sequence: Ask for input with a reward tease, remind them why it matters, then wrap with a final ask.
32. Referral Program Launch
  • Event: User shows high engagement (e.g., 5+ logins/month).
  • Trigger: Send an "Invite Friends" email with dual incentive(e.g., "You both get X credits").
  • Sequence: Pitch the referral win-win, nudge them to share, then boost with an extra reward.
33. Post-Purchase Follow-Up
  • Event: User completes purchase.
  • Trigger: Send a "Thanks!" email with receipt right away.
  • Sequence: Thank them with next steps, check in with a tip, then tease more value.
34. Anniversary Celebration
  • Event: 1-year sign-up anniversary.
  • Trigger: Send a "Happy anniversary!" email with gift on the date.
  • Sequence: Celebrate with a gift, deepen loyalty with a perk, then tease a next step.
35. VIP Tier Invite
  • Event: User meets VIP criteria.
  • Trigger: Send a "You’re a VIP!" email with perks.
  • Sequence: Invite them with VIP perks, tease exclusive value, then push to join.
Churn Prevention & Win-Back
Save and reclaim users across all industries.
36. Pre-Cancellation Warning
  • Event: Usage drops 50% over 2 weeks.
  • Trigger: Send a "What’s up?" email when drop detected.
  • Sequence: Check in with support and an offer, reinforce value, then make a save-the-day plea.
37. Cancellation Feedback
  • Event: User cancels.
  • Trigger: Send a "Sorry to see you go" email with survey immediately.
  • Sequence: Ask why with a soft win-back, tease a return perk, then make a final comeback offer.
38. Post-Cancellation Win-Back
  • Event: 7 days post-cancel.
  • Trigger: Send a "Miss us yet?" email with case study.
  • Sequence: Rekindle with proof and an offer, boost the perk, then push for one last shot.
39. Long-Term Canceled Re-Engagement
  • Event: 60+ days post-cancel.
  • Trigger: Send a "Big updates!" email with trial.
  • Sequence: Tease what’s new with a trial, highlight the upside, then close with a deal.
40. Risky Behavior Alert
  • Event: User deletes key data.
  • Trigger: Send a "Whoops!" email with recovery right away.
  • Sequence: Help them recover with support, check in with value, then secure them with a perk.
Customer Success & Advocacy
Turn fans into promoters for SaaS, B2C, and brand builders.
41. Community Join Welcome
  • Event: User joins community (e.g., forum).
  • Trigger: Send a "Welcome to the crew!" email with guide immediately.
  • Sequence: Welcome them with a guide, nudge them to connect, then tease a community perk.
42. User-Generated Content Praise
  • Event: User posts about you.
  • Trigger: Send a "You rock!" email within 24 hours.
  • Sequence: Thank them with a reward, encourage more with a tease, then push to amplify.
43. Advocate Program Invite
  • Event: Loyal user (6+ months, engaged).
  • Trigger: Send a "Be our advocate?" email with perks when criteria met.
  • Sequence: Pitch advocacy with perks, show why they’re a fit, then nudge them to join.
44. Account Review Invite
  • Event: Paid user active for 90 days.
  • Trigger: Send an "Optimize your account" email with a free review call offer.
  • Sequence: Offer a review to boost their results, highlight potential wins, then nudge them to book the call.
45. Case Study Request
  • Event: User hits success milestone.
  • Trigger: Send a "Tell your story?" email with perk when success detected.
  • Sequence: Pitch the story with a reward, ease them in with a step, then wrap with a final ask.
Let's Make It Happen
From working with SaaS, B2B, and Ecommerce brands, I’ve seen what actually moves the needle and these 45 flows are the backbone. They're proven frameworks, but the real impact comes when they're set up for automation and tailored to your audience and offer. If you're ready to turn your inbox into a consistent revenue channel (even while you sleep), let’s talk about what that could look like for your business.
Jake Cohn
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