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Automating Your Emails for Convenient Customer Journeys


Manually sending one-off emails fails to nurture modern audiences expecting personalized, automated experiences tailored just for them.

By leveraging email automation tools, you can deliver individualized lifecycle journeys that build relationships, provide value, and drive conversions without burdensome constant manual efforts.

In this comprehensive guide, we’ll explore strategies for:

Identifying customer journey touchpoints

Map out what automated emails customers need and when. We’ll look at common triggering points.

Tagging leads for segmentation

Tags enable personalized journeys by segmenting your lists. We’ll examine effective tagging workflows.

Building tailored sequences

Personalized sequences resonate best. We’ll detail developing relevant auto-series tailored to customer groups.

Optimizing triggers and timing

The right triggers send emails when most relevant. We’ll review strategies for timely automated delivery.

A/B testing messages

Test email content for optimization just like web pages. We’ll discuss easy split testing approaches for continual refinement.

Analyzing performance metrics

Data illuminates opportunity. We’ll explore metrics revealing optimization areas.

Let’s dive into orchestrating automated email journeys that make each subscriber feel uniquely understood and supported.

Identify Customer Journey Touchpoints

The first step is mapping subscribers’ journeys to determine relevant automated email opportunities. Consider touchpoints like:

Welcome and Onboarding

Early emails introducing your brand, products, and community help subscribers know what to expect.

Education and Training

Provide a seamless progression of learning when subscribers access courses, tools, trials etc. through nurturing education.

Engagement and Community

Encourage return visits, referrals, and discussion by emails focused solely on enhancing their experience with your brand.

Milestones and Achievements

Acknowledge important milestones subscribers reach like anniversaries, completed projects, and retention rates. Celebrate progress.

Challenges and Support

Craft messages focused on specific struggles and objections offering help like technical issues, common confusions, stalled progress etc. Aid past pain points.

Cross-sells and Upsells

Send promotional series showcasing complementary or higher-tier products and services when subscribers show interest in offerings.

Map subscriber journey pain points, milestones, and needs so you can be helpful during each with relevant automated touchpoints.

Tag Leads for Segmented Journeys

Tagging subscribers allows sending tailored series based on interests and behaviors vs. one-size-fits-all blasts. Useful segmentation strategies include:

Tag by Purchases

Track products, services, and resources each subscriber buys or downloads to target associated upsells, training etc. accordingly.

Tag by Interests

Note topics subscribers explicitly state interest in like commenting, sharing content, or requesting information to align messaging.

Tag by Demographics

Capture demographic data like job titles, company sizes, locations etc. during signup to personalize outreach. Respect opt-in data policies.

Tag Based on Links Clicked

Use click tracking to automatically tag subscribers who click specific content types like webinars, events, or ebook downloads then customize follow-ups based on those leanings.

Tag by Engagement Level

Automatically tag highly engaged subscribers who frequently open, click, share, or post to provide them VIP bonuses and early access.

Tag by Channel Source

Denote subscribers who originated from specific channels like organic search, paid ads, referrals etc. Consider tailored messaging speaking to their source.

Tag Through Polls and Surveys

Prompt subscribers to self-identify categories, preferences, and use cases through quick surveys. First-party data aids personalization.

Sophisticated segmentation through subscriber tags enables hyper-relevant automated journeys.

Build Tailored Sequences

Armed with subscriber tags, you can develop fully personalized automated series catering to specific groups. Helpful sequence strategies include:

Welcome Series

Onboard new subscribers by introducing your brand values, popular content, and community. Set the stage for an aligned relationship.

Education Tracks

Move subscribers through multi-part training guides on using your product or implementing teachings over time based on their level.

Event Follow-Up Series

After event signups, send preparatory tips, recaps, continued learning prompts and event-specific offers.

Winback Campaigns

Reach out to inactive subscribers with special incentives and content re-engaging their interest after periods of inactivity.

Cross-sell Series

Send promotional series of emails focused on relevant upsell offers like higher-tier plans or complementary products to segment.

Customer-Type Journeys

Craft targeted series speaking to common questions, objections, and needs specific segments like young parents, retirees, freelancers etc. face based on demographics.

Milestone Series

Activate timed sequences when subscribers hit milestones like anniversaries, referrals sent, or retention duration reminding them of progress.

Personalized auto-series aligned to subscriber needs and characteristics boost engagement and delight.

Optimize Triggers and Timing

Automated sequences need the right triggers and send frequency for relevancy. Useful timing strategies include:

Base Triggers on Actions

Activate sequences using triggers like signups, purchases, content downloads, event registrations etc. based on target actions rather than just dates. Context-aware.

Set Frequency Based on Urgency

Send more urgent series like post-purchase onboarding daily while lower-priority newsletters can stick to lower weekly, monthly, or quarterly frequencies.

Test Days and Times

Try sending on different days and times based on open rate data to determine when particular segments are most responsive. Personalize delivery windows.

Make Re-Engagement Timely

Schedule winback and reactivation sequences to deploy after periods of inactivity like 2 weeks for email nurturing, 1 month for webinars etc. while interest still lingers.

Limit Overwhelm

Respect subscribers’ inboxes. Allow opting out or capping sequence frequency. Avoid hitting the same group with too many parallel sequences.

Offer Sequence Control

Provide visibility into series schedules and let subscribers control pauses if periods are too busy. Empowers user-centric delivery.

Dial-in triggers aligned to each audience’s preferred engagement pace for the right message at the right time automated.

A/B Test Email Content

Test email content and styles by segment to optimize performance. Valuable tests include:

Subject Lines

Subject lines drive opens. Test multiple subject options against your control against each audience to determine which resonate best.


Measure open and clickthrough rates for long paragraphs versus bullet points, personal notes versus formal announcements, and other format styles.

Calls to Action

Try different signup, checkout, and learn more button verbiage like “Subscribe”, “Join Now”, “Get Started” to see what converts each group best.

Content Topics

For sequences focused on recommendations, compare product suggestions, informational topics, special promotions etc. to hone in on ideal suggestions by segment.


Try discount codes, free shipping, extended trials, loyalty rewards, or complementary products to determine which offers excite each subscriber group.

Delivery Parameters

Test factors like email length, personalization tags used, number of images, time sent etc. to pinpoint the combinations that perform by segment.

Styles and Branding

Try A/B testing email templates, color schemes, imagery, and content tones aligned to different brand personalities.

Seek incremental optimization by continually testing how relatively minor content variations impact each target group’s engagement over time.

Analyze Performance Metrics

Crunch email data to identify bright and blind spots in your automated sequences. Key metrics to monitor include:

Open and Clickthrough Rates

High open and clickthrough rates indicate well-targeted, resonating messages while low response signals content missing the mark.

Unsubscribe and Complaint Rates

Spikes may indicate overwhelming send frequency, irrelevant messaging, deliverability issues, or outdated contacts data in specific segments. Troubleshoot causes.

List Growth Trends

Slow or declining list growth points to lackluster top-of-funnel efforts. Review lead capture forms, popups, and gating.

Engagement Across Sequences

Compare open rates, clicks per email, and completion rates across sequences. Shows which journeys resonate or need reassessment.

Email-Specific Revenue

For ecommerce brands, track sales attributed to automated campaigns like cart and browse abandonment flows. Optimizes funnels.

Demographic Open Rate Data

Review open rate averages across demographic groups like geography, age, department, job title etc. Allows further personalization.

Sequence Start and Finish Rates

Monitor the percent that start vs. complete sequences. High drop-off may indicate overly long or irrelevant paths.

Performance indicators spotlight successes to expand while revealing areas needing improvement. Monitor metrics continually.


Automating tailored subscriber journeys makes communicating convenient for you while providing recipients highly relevant, personalized experiences.

Map subscriber touchpoints, leverage segmentation, develop sequences aligned to needs, optimize timing, continually test, and analyze data. Doing so keeps your message resonating without constant heavy lifting.

Ready to scale delightful subscriber relationships? Automation tools empower consistent, individualized messaging and progress chasing. Now go engage audiences.


By Dani Davis

Dani Davis is the pen name of the writer of this blog with more 15 years of constant experience in Content marketing and informatics product, e-commerce niche.

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