The Emails That Make Money

Automated email flows are where the real revenue lives. Campaign sends are important, but automations generate 30 times more revenue per recipient than one-off campaigns. The reason is simple: they’re triggered by behaviour, which means they arrive when someone is already engaged.

Chase Dimond (co-founder of Structured Agency, responsible for over $200M in email revenue) has noted that most brands he audits are missing 3-4 of the core flows entirely, and the ones they have are often only 1-2 emails deep when they should be 3-5. Setting up all core flows, even basic versions, before worrying about campaign strategy is the highest-ROI use of your time.

Chase Dimond’s revenue attribution framework for ecommerce is useful here: roughly 30% of total ecommerce revenue should come from email. Within that, the split should be approximately even between automated flows and campaigns. Brands that rely too heavily on campaigns (blasting the full list) leave money on the table because flows convert at dramatically higher rates per recipient.

Here’s the performance difference between automations and campaigns, to give you a sense of scale:

Metric	Automations	Campaigns
Revenue per recipient	30x higher	Baseline
Open rate	Typically 40-55%	Typically 15-25%
Click rate	Typically 5-10%	Typically 2-3%
Relevance	Behaviour-triggered	Calendar-triggered

Here are the flows every brand needs, in order of priority.

Welcome Series

Welcome emails have an average open rate of 51-55% and generate 320% more revenue per email than other promotional emails. Subscribers are 50% more likely to open a welcome email than any other type. This is the highest-engagement moment you’ll ever have with a subscriber.

The data says the most effective welcome series includes 4-6 emails spread over 1-2 weeks. Send the first email immediately after signup. Not in an hour. Not the next day. Immediately. Multiple practitioners have reported that welcome emails sent within 5 minutes of signup get 2x the open rate of those sent within 1 hour. The subscriber is still on your site, still thinking about your brand. Every minute of delay degrades engagement.

Email 1 (Immediate): Welcome + deliver the promise. Whatever you offered to get the signup (discount code, lead magnet, free resource), deliver it now. Introduce your brand briefly. And critically: ask for a reply. Something simple like “Hit reply and tell me what you’re working on” or “Reply with a quick hello so I know you’re real.” This isn’t just friendly. Replies are one of the strongest engagement signals you can send to Gmail and other inbox providers. A reply tells Gmail that this is a sender the subscriber wants to hear from, which improves inbox placement for every subsequent email. This is a genuine deliverability hack.

Also in Email 1: ask one segmentation question. Brennan Dunn’s technique: include a simple survey or a few links that let subscribers self-identify. “Which best describes you?” with two or three options. Their click tells you how to tag them, which powers all future personalisation.

Email 2 (Day 2): Your story. Who you are, what you stand for, why you exist. DFS Furniture personalised their welcome series based on customer interests and saw a 4% revenue increase. Starbucks uses their welcome series to teach new rewards members how their programme works, reducing support tickets and increasing programme engagement.

Email 3 (Day 4): Social proof. Testimonials, reviews, case studies. Show that other people trust you. This email reassures new subscribers that they made the right decision signing up.

Email 4 (Day 7): Your best content or product. What do new subscribers need to see? Your bestsellers? Your most-read article? Guide them to what matters. If you collected segmentation data in Email 1, use it here to show different content to different segments.

Email 5 (Day 10): Soft sell. If they haven’t converted, now’s the time for a limited-time offer. Most people make a purchase within 10 days of subscribing to a mailing list. Samar Owais (Email Conversion Strategist at Emails Done Right, who has worked with HubSpot and Pinterest) advocates for making this offer feel like a natural next step rather than a hard pivot to selling.

Email 6 (Day 14): Set expectations. What will they hear from you going forward? How often? What kind of content? This reduces future unsubscribes by aligning expectations. Include a link to your preference centre so they can customise what they receive from day one.

The welcome series is where you set the tone for the entire relationship. Get it right and you have a subscriber who trusts you, understands what you offer, and has demonstrated engagement that strengthens your sender reputation. Get it wrong (or skip it entirely) and you’ve wasted your highest-attention moment.

Companies using automated welcome series see conversion rates up to 2.5 times higher than those sending a single welcome email. Sending multiple welcome emails drives 51% more revenue than a single one. Ban.do’s welcome series achieves a combined 38.6% open rate, with the first email hitting 51.7%.

A common mistake with welcome series: making them too sales-heavy from the start. The first 2-3 emails should build relationship, trust, and value. The selling comes later. People who just gave you their email address need to feel good about that decision before you ask for their money. If they unsubscribe during your welcome series, your welcome series has a problem.

Another mistake: not stopping the welcome series when someone converts. If a subscriber makes a purchase after Email 2, they shouldn’t receive the promotional nudge in Email 5. Suppress them from the welcome flow and move them into the post-purchase flow instead. Most ESPs handle this with exit conditions on automation flows, but you have to set them up.

One more thing worth noting: the welcome series is your natural IP and domain warming mechanism. New subscribers are engaged, so they open and click, which sends positive signals to inbox providers. If you’re warming up a new sending domain or IP, your welcome flow does part of the heavy lifting automatically.

Abandoned Cart and Browse Abandonment

Seventy percent of ecommerce shopping carts are abandoned. That’s not a problem. That’s an opportunity.

Abandoned cart emails have an average open rate of nearly 50% and a conversion rate of 17.12%. The top 10% of senders generate $3.07 revenue per recipient from cart flows. The key is speed and restraint.

Email 1 (1-4 hours): Simple reminder. “You left something behind.” Show the product with an image and a direct link back to their cart. No discount yet. Critically, don’t frame this as a guilt trip. The reframe that works better: “Having trouble checking out?” assumes friction rather than guilt, and one practitioner reported a 30% conversion increase from this change alone. This first email recovers more revenue than emails 2 and 3 combined. Speed is the most important variable. Brands sending their first reminder within 1 hour consistently outperform those waiting 4 or more hours. The purchase intent is still warm. Every hour of delay lets it cool.

Email 2 (24 hours): Address objections. Add reviews, free shipping info, money-back guarantee. Create a small sense of urgency if genuine (low stock, ending sale). This is where you build the case for why they should complete the purchase.

Email 3 (48 hours, optional): Incentive. A small discount or free shipping, only if margins allow it. And here’s the important nuance: don’t offer a discount in email 1. Ever. It trains customers to abandon carts deliberately. If you do discount in email 3, use a unique code that expires in 24-48 hours, and consider only offering it to first-time abandoners. Repeat customers who abandon carts are usually price-shopping or waiting, and a discount devalues the product for them.

One frequently cited experiment showed that an abandoned cart series without discounts had 82% of the recovery rate of one with discounts. The 18% gap in recoveries was more than offset by protecting margins on the other 82%.

Smart discount segmentation: first-time visitors get the discount. Returning customers don’t (they’re more likely to convert without it). This is a small thing to set up but it protects your margins where it matters most.

Browse abandonment is the lighter version: someone looked at a product page but didn’t add to cart. These emails perform slightly lower than cart abandonment individually, but they catch people much earlier in the funnel. The audience for browse abandonment is 5-10x larger than cart abandonment, so the total revenue can rival or exceed cart recovery.

Send one email 24 hours after browsing. Show what they looked at plus similar items. Keep it lighter in tone than a cart email, more “thought you might like these” than “you forgot something.”

Chase Dimond advocates for testing urgency-based subject lines against benefit-based ones in cart emails. The winner varies by brand, but he’s noted that for automated flows where the context is already established (they know they abandoned a cart), benefit-driven subject lines tend to outperform curiosity-driven ones. The reverse is often true for campaign emails.

Cart abandonment for low-AOV products

Store owners selling $10-30 products sometimes wonder if cart emails are worth the effort. They are, but adjust the strategy. Don’t offer percentage discounts on low-AOV items (10% off a $15 product is $1.50, which isn’t motivating). Instead, offer free shipping (the number one reason for cart abandonment at any price point), suggest bundles that increase the order value, or use ‘complete the look’ cross-sells. Keep the sequence to 1-2 emails maximum for low-AOV. The margin doesn’t justify three emails.

For very low AOV (under $10), consider browse abandonment combined with product bundles instead of individual cart recovery. Show them the item they viewed plus complementary items that bring the total to a more meaningful basket.

Post-Purchase and Review Requests

The sale is where the relationship begins, not where it ends.

Order confirmation. This is the most-read email you send. Transactional emails get 6x more revenue than promotional emails and 8x more opens and clicks. Users spend about 8 seconds reading them, which is an eternity in email.

Use this attention. Add product recommendations in the first 300 pixels (below the transaction details but above the fold). Include care instructions, usage tips, or links to educational content. Keep the transaction info front and centre, customers expect receipts within 5 minutes, but don’t waste the remaining attention.

Shipping updates. Every shipping notification is an opportunity to delight. Include tracking info, expected delivery, and what to do if there’s an issue. Some brands add personality here: “Your order just left our warehouse and it’s very excited to meet you.” It’s a small touch that builds brand affinity.

Review requests (7-14 days after delivery). Give them time to use the product. Don’t ask for a review the day it arrives. Keep it simple. One CTA. Make the review process as frictionless as possible, ideally letting them leave a star rating directly from the email without navigating to another page.

Cross-sell and upsell. Based on what they bought, what else might they need? Upselling can increase revenue by 10-30%. But timing matters. Too soon feels pushy. Wait until they’ve had a chance to enjoy their purchase, typically 14-30 days after delivery depending on the product category.

Replenishment emails. For consumable products (supplements, skincare, coffee, pet food), send a reminder based on expected usage cycles. If a 30-day supply of vitamins was purchased 25 days ago, email them with an easy reorder link. Amazon’s model works because the timing is based on actual usage data, not arbitrary calendars. If you sell consumables, this flow is one of the highest-converting automations you can build.

The post-purchase sequence matters more than most brands realise. This is where you build the repeat purchase habit that drives lifetime value. A customer who makes a second purchase is far more likely to make a third, fourth, and fifth. Increasing customer retention by just 5% increases profits by 25-95%. Your post-purchase flow is the mechanism that turns one-time buyers into repeat customers.

Here’s a sample post-purchase timeline:

Timing	Email	Purpose
Immediately	Order confirmation	Receipt + product recs
Day 2-3	Shipping confirmation	Tracking + anticipation building
Day 7-10	Delivery follow-up	Check satisfaction, offer help
Day 14	Review request	Social proof collection
Day 21-30	Cross-sell	Complementary products
Day 25-30 (consumables)	Replenishment	Easy reorder

Each email in this sequence should have an exit condition: if the customer makes another purchase at any point, restart the relevant flows for that new purchase.

Win-Back and Re-engagement

Nearly 80% of new leads never make a purchase. But re-engagement campaigns can bring some of them back.

Target subscribers who haven’t engaged in 60-90 days. The typical re-engagement sequence is 2-4 emails:

Email 1: “We miss you.” Show them what’s new. Highlight what they’re missing. New products, new content, recent wins. Make it about them, not about you.

Email 2: Value offer. Offer an incentive. A discount, free resource, or exclusive access to something. Don’t start with discounts in Email 1. Start with content, then escalate to offers.

Email 3: The breakup email. “Should I remove you from the list?” This email generates the highest reply rate in the sequence because of loss aversion. People respond when they think the opportunity to respond is ending. Expect a 10-15% re-engagement rate from this email specifically. Some subscribers will reply just to say “no, keep me!” and that reply itself improves your deliverability with their inbox provider.

Email 4 (optional): Confirmation. “You’ve been unsubscribed” with an easy re-subscribe link. Clean and respectful.

After the sequence, anyone who hasn’t engaged gets moved to suppression. Reduce their frequency first (sunset flow), then suppress entirely. Keep the data for analytics, but stop mailing them.

An important distinction: suppression is not deletion. Suppression means you stop emailing them but retain their data. They might re-engage through another channel (website visit, social media, in-store purchase), and if they do, you can reactivate them. Deletion is permanent and usually unnecessary.

Nurtured leads spend up to 47% more than non-nurtured leads, and lead nurturing can reduce conversion costs by 33%. The maths works even if your win-back rate is modest. A 5% re-engagement rate from a sunset flow sounds low, but when those 5% go on to make purchases at a 47% higher average order value, the economics are compelling.

Nurture Sequences

Nurture sequences are the slow game. They’re designed for leads who aren’t ready to buy but might be in three, six, or twelve months.

The data suggests 4-10 emails spaced 4 days to 2 weeks apart. Sixty-three percent of leads convert within 3 months when nurtured properly. The sweet spot is providing value that positions you as the obvious choice when they’re ready.

Brennan Dunn framework works well for structuring these: deliver the asset (whatever they opted in for), share a quick win (something actionable they can do today), add social proof (case study or testimonial), then invite the next step. Each email should provide standalone value, not just tease a sale. The biggest mistake in nurture sequences is making every email a setup for the eventual pitch. If someone can’t get value from email 3 without having read emails 1 and 2, the sequence is too dependent on sequential consumption. Most subscribers won’t read every email in order.

Andre Chaperon’s Soap Opera Sequence is another effective structure. Five emails that tell a story:

1. Set the stage. Introduce a character (usually you or a customer) and a situation the reader can relate to.
2. Backstory. How did this person get here? What was the struggle? Build empathy and connection.
3. Turning point. The moment things changed. What was the insight, discovery, or decision?
4. Hidden benefit. Something unexpected that came from the turning point. An outcome they wouldn’t have predicted.
5. Urgency + CTA. Close the loop. Make the connection between the story and what you’re offering. Give them a reason to act now.

the power of this structure is that each email ends with an open loop that makes the reader want to see what happens next. It’s the same mechanism that keeps people watching Netflix, applied to email. The Soap Opera Sequence works particularly well for course creators, coaches, and service providers where the buying decision is emotional as much as logical.

Alex Hormozi’s proof-stacking approach also works well: use the sequence to systematically address every objection a prospect might have, one per email. Email 1: social proof (testimonials). Email 2: logical proof (case study with numbers). Email 3: risk reversal (guarantee explanation). Email 4: urgency (limited availability, if genuine).

B2B nurture is different from B2C. B2B companies should aim for greater than 20% open rate and 12% click-to-open rate. Case studies are particularly effective for B2B prospects because they show specific use cases, budgets, and results. The sales cycle is longer, so patience is more important.

For B2C, behavioural triggers based on browsing and purchase history work better than time-based sequences. The browsing data tells you what someone is interested in right now, which is more valuable than where they are in an arbitrary email sequence.

Val Geisler (founder of Fix My Churn) makes an important distinction here: onboarding emails should be triggered by what the user does (or doesn’t do), not by when they signed up. A user who activates the core feature on day 1 should get a different email than a user who hasn’t logged in since signup. Time-based sequences treat all users identically, which wastes the most engaged users’ attention and fails to rescue the disengaged ones.

Her ‘Dinner Party’ framework for SaaS onboarding illustrates this well. Email 1: the invitation (welcome, set expectations). Email 2: the introduction (introduce yourself, share your story). Email 3: the meal (deliver the core value, guide them to their ‘aha moment’). Email 4: the dessert (surprise and delight). Email 5: the follow-up (check in, gather feedback). Each email maps to a user milestone rather than a calendar date. The right metric for measuring onboarding email success isn’t open rate or click rate. The right metric is: did the user reach their activation milestone?

Drip emails (another name for nurture sequences) generate up to 80% higher open rates and 3x more clicks than standard one-time sends. The copy matters, but so does the context in which it arrives. An email that arrives because you did something specific feels relevant. An email that arrives because it’s Tuesday feels arbitrary.

Promotional Campaigns

These are your regular campaign sends. New products, sales, seasonal events, content roundups. They’re the bread and butter of email marketing.

The key difference between promotional campaigns that work and ones that don’t is segmentation. Sending the same promotional email to your entire list is the lowest-performing approach. Segmented promotional campaigns can generate 780% more revenue.

The 3:1 ratio. For every promotional email you send, send three value emails first. Educational content, useful tips, entertaining stories, curated resources. This ratio keeps your audience engaged between asks. Chase Dimond has shared that brands sending exclusively promotional content see unsubscribe rates 3-4x higher than those mixing in genuine value.

Seasonal campaigns. These work when they create genuine urgency. Limited-time offers drive action when the scarcity is real. When every email is “LAST CHANCE,” nothing feels urgent. Save urgency for when it’s genuine. Plan your seasonal campaigns at least 30 days in advance. The brands that scramble to put together a Black Friday email on the Wednesday before are always outperformed by the brands that planned their full holiday email calendar in October.

New product launches. Build anticipation before the launch (teaser emails to your most engaged segment), send the announcement to your full list, then follow up with social proof (reviews, press coverage, user photos) in the days after. Stagger the launch emails so your VIP customers get early access before the general list. This creates genuine exclusivity and rewards loyalty.

The shipping deadline email. For ecommerce, this is consistently the highest-converting email of the holiday season. “Order by [date] to get it by Christmas” converts at extraordinary rates because the deadline is real, immovable, and universally understood. If you send one email during the holidays, make it this one.

Resending to non-openers. Some marketers report significant additional revenue from resending a campaign to non-openers with a different subject line 24-48 hours later. This can generate 15-20% extra opens. Jay Schwedelson’s position: it works in moderation but shouldn’t become standard practice for every send because it can accelerate list fatigue. Reserve this tactic for your most important campaigns. Don’t make it routine.

Campaign planning. Chase Dimond plans email campaigns 30 days in advance. His framework: content emails (value, education, entertainment) should outnumber promotional emails by at least 2:1. Having a plan prevents the common pattern of scrambling for email ideas the morning of a send. A testing calendar (as Gavin Laugenie, Head of Strategy at Dotdigital, advocates) takes this further: plan not just what you’ll send but what you’ll test in each send.

Transactional Emails (The Hidden Revenue Channel)

Transactional emails, your order confirmations, password resets, account notifications, and shipping updates, are the most underrated revenue opportunity in email marketing. They get 3-8x higher open rates than marketing emails. Users spend about 8 seconds reading them. And they’re expected and wanted, which means engagement is nearly universal.

Separate your sending infrastructure. Send transactional emails from a different subdomain and IP than marketing emails. If your marketing sends get spam complaints, your order confirmations shouldn’t suffer. SaaS founders on Reddit report losing password reset delivery because they sent marketing campaigns from the same domain and got flagged. One post described losing paying customers because signup confirmation emails were delayed by hours after a marketing blast.

Speed requirements. Users waiting for password resets give up after 60 seconds. Two-factor authentication codes expire in 5-10 minutes. For these high-urgency transactional emails, speed is everything. Target delivery within seconds, not minutes. Your infrastructure needs to handle spikes too. A flash sale or security breach can cause instant volume surges. Lauren Meyer (CMO of SocketLabs and author of the Send It Right newsletter) emphasises that transactional email infrastructure needs to handle these spikes reliably. Target a 99%+ delivery success rate.

Don’t use no-reply addresses. They frustrate customers and inbox providers flag them as impersonal. Use a monitored reply-to address. Replies are a positive engagement signal, and some of your most valuable customer feedback will come from replies to transactional emails.

Add value without breaking the rules. You can include product recommendations (16% of consumers want to learn about product features through transactional emails) and cross-sell suggestions. But keep the transaction content in the first 300 pixels. The primary purpose must remain transactional, or you risk compliance issues and deliverability problems. CAN-SPAM treats primarily transactional emails differently from primarily commercial ones. If the marketing content overwhelms the transactional content, the email gets reclassified as commercial and all commercial email rules apply.

Authenticate everything. SPF, DKIM, DMARC for your transactional sending domain too, separate from your marketing domain. Set token expiration for password resets within an hour. Use secure, single-use tokens for every action link. Transactional email is not just a revenue opportunity. It’s a trust signal. When order confirmations arrive promptly, password resets work instantly, and shipping updates are accurate, customers trust your brand. When they don’t, customers leave.

Customer Service Emails

Ninety percent of customers rate an immediate response as important or very important. Fifty-four percent use email as their primary support channel.

Speed matters more than perfection. Sending a short acknowledgment email within an hour is usually better than waiting to send one perfect reply. Let them know you received their message and when to expect a full response. First response time is the most critical metric for customer service email.

Templates save everyone’s time. Customer service email templates save time and boost consistency. Use them for high-volume scenarios: shipping updates, refunds, complaints, technical issues. But personalise them. Use customer names, order information, and your brand voice. A template that sounds like a template damages trust.

Monitor the right metrics. Track first response time, resolution time, and reopen rates. High reopen rates signal that agents are closing cases prematurely or providing unclear responses. A single agent can manage several email threads in parallel, making email one of the most cost-effective support channels. But only if the responses are clear, concise, and actually solve the problem.

Proactive customer service emails. Don’t wait for customers to report problems. If you know there’s a shipping delay, email affected customers before they ask. If a product has a known issue, send care instructions proactively. Proactive communication builds trust and reduces inbound support volume. The best customer service email is the one that prevents a support ticket from being filed in the first place.

No-reply is especially destructive here. When someone replies to a customer service email and gets an automated bounce, you’ve created a frustrated customer out of someone who was simply trying to communicate. Use a monitored reply-to address for every customer-facing email.

The Priority Order for Flow Setup

If you’re starting from scratch, build your flows in this order. Each one builds on the previous, and the list is ranked by revenue impact per hour of setup time.

1. Welcome series (highest volume, reaches every new subscriber)
2. Abandoned cart (highest RPR, $3.07 for top performers)
3. Browse abandonment (catches the larger funnel above cart abandonment)
4. Post-purchase follow-up (builds repeat purchase behaviour)
5. Win-back / re-engagement (recovers lapsed subscribers)
6. Cross-sell / upsell (increases customer lifetime value)
7. VIP / loyalty flows (rewards your best customers)
8. Sunset flow (protects deliverability by managing unengaged subscribers)
9. Birthday / anniversary emails (if you collect birth dates, these get 25% more opens and 40% more clicks)
10. Replenishment emails (for consumable products, timed to reorder cycles)
11. Back-in-stock notifications (captures demand you would otherwise lose)
12. Price drop alerts (converts price-sensitive browsers)

Don’t try to build all twelve at once. Build the first two or three, optimise them, then add the next. Most brands Chase Dimond audits are missing 3-4 of the core flows entirely. Just filling those gaps can add 15-25% to email revenue.

One final thought on this chapter. Consistency and optimisation are complementary, not competing forces. Consistency builds habit and brand recognition — same day, same time, same format. Subscribers develop expectations around your email. Breaking the pattern, even for a ‘better’ approach, causes engagement drops. Optimisation builds growth within that consistent framework. Find a format that works, a voice that feels natural, and a frequency your audience responds to. Then stick with it while testing incremental improvements. The fancy stuff matters less than showing up reliably.