Email Marketing 101: The Founder’s Automation Playbook

Why Email Marketing Matters for Founders

Email marketing is the single highest ROI marketing channel available to founders. Here’s the reality: welcome emails achieve open rates of 50-60%, and a well-designed welcome sequence can convert 2-4% of subscribers into customers.

Why? Because email reaches users where they’ve opted in. No algorithm. No feed. Just direct access to an interested audience.

The Numbers That Matter

• Welcome email open rates: 57.8% (vs. 21.5% for regular campaigns)
• Welcome email click-through rates: 14%+ (vs. 2-3% for regular emails)
• Welcome sequence conversion rate: 2-4% (vs. 0.5-1% for batch campaigns)
• Email ROI: For every $1 spent on email marketing, average return is $42
• Automation workflows: 54% increase in open rates when triggered by user behavior

These aren’t small numbers. For a founder with 10,000 email subscribers, a 2% conversion on a $500 product generates $100,000 in revenue. That’s why email is non-negotiable.

Platform Comparison: Mailchimp vs Substack vs Brevo

The email platform you choose determines your ability to automate, segment, and monetize. Here’s how the three major platforms compare:

Mailchimp Deep Dive: Pricing & Features (2025)

Mailchimp is the market leader for good reason. It’s used by 12+ million businesses. Here’s the complete 2025 pricing breakdown:

Mailchimp Pricing Tiers

Key Mailchimp Features by Plan

Free Plan ($0)

• Up to 500 contacts
• 1,000 emails per month (500 daily cap)
• Basic templates and reports
• Email support for first 30 days only
• NO automation (classic automation removed from free in 2024)
• NO A/B testing

Essentials Plan ($13/month)

• Up to 500 contacts starting point
• 5,000 monthly email sends
• Basic automation included
• 24/7 support (important upgrade from free)
• Segmentation and targeting
• Standard templates

Standard Plan ($20/month)

• 6,000+ monthly sends
• Dynamic content
• Send time optimization
• Predictive segmentation
• A/B testing (crucial for optimization)
• Advanced analytics

Premium Plan ($350/month)

• Unlimited sends
• Dedicated IP option
• Advanced segmentation
• Priority phone support
• API access
• Custom integrations

When Mailchimp Makes Sense

Use Mailchimp if you’re building a SaaS, ecommerce store, or product with a lead nurturing strategy. The automation workflows are powerful, and the pricing scales reasonably as you grow.

Substack Deep Dive: Pricing & Monetization (2025)

Substack is fundamentally different. There’s no monthly platform fee. Instead, Substack takes a revenue share only when you monetize.

How Substack Pricing Works

Publishing is always free. You can send unlimited emails to unlimited free subscribers with zero cost. The fees only kick in when someone pays for a subscription.

Substack Revenue Share Breakdown

Real Math Example

You have 1,000 paid subscribers at $5/month = $5,000 monthly revenue.

• Substack takes 10%: -$500
• Stripe processing (2.9% + $0.30): -$145 – $300 = -$445
• Billing fee (0.5%): -$25
• Your net: $5,000 – $970 = $4,030 (80.6% retained)

Substack Subscriber Pricing

You set your own prices. Common pricing models:

• Standard tier: $5-10/month
• Premium tier: $15-25/month
• Founding member tier: $100-500/year (limited spots, exclusive access)
• Annual discount: Typically 17% off (e.g., $50/year for $5/month)

When Substack Makes Sense

Use Substack if your primary goal is monetizing a newsletter and building community. The built-in payment processing means you don’t need to integrate third-party tools. The lack of automation isn’t a problem if you’re writing personal, relationship-driven content.

Brevo (Formerly Sendinblue): The Alternative

Brevo is the underrated alternative. It’s powerful for automation and significantly cheaper than Mailchimp at scale.

Brevo 2025 Pricing

Brevo Key Features

• Email automation: Powerful workflows included in all paid plans
• SMS marketing: Included (vs. add-on in Mailchimp)
• CRM: Built-in contact management
• Transactional emails: Separate pricing (good for SaaS)
• Landing pages: Included
• Compliance: GDPR compliant, strong IP reputation

Brevo vs Mailchimp: Cost Comparison at Scale

Real insight: Brevo wins at very low volumes (<20K/month) and very high volumes (100K+/month). Mailchimp’s Standard plan ($20/month) is competitive in the middle range but starts looking expensive at higher volumes.

Email Automation Workflows Explained

Automation is where email earns its reputation. A well-designed automation workflow can generate revenue 24/7 without human intervention.

What is Email Automation?

Email automation is a triggered email sequence that responds to specific user actions. Instead of sending one email to everyone, automation sends the right message to the right person at the right time based on their behavior.

Types of Automation Triggers

1. Behavioral Triggers

• User downloads a resource (trigger: welcome sequence)
• User visits pricing page (trigger: pricing objection email)
• User clicks a specific link (trigger: deeper nurture email)
• User abandons shopping cart (trigger: reminder + discount)

2. Lifecycle Stage Triggers

• New subscriber (trigger: welcome sequence)
• Free trial expiring (trigger: upgrade reminder)
• Customer made purchase (trigger: onboarding sequence)
• Dormant customer (trigger: re-engagement campaign)

3. Event-Based Triggers

• User misses meeting (trigger: reschedule prompt)
• Product purchase (trigger: thank you + upsell)
• Birthday/anniversary (trigger: personalized offer)

Automation Results: Real Data

• Open rate increase: 54% higher when emails are triggered vs. batch
• Click-through increase: 3% higher for triggered emails
• Conversion increase: Behavior-based emails convert 2-3x higher
• Revenue per email: Automated sequences often have 10x ROI vs. broadcast emails

Simple Automation Framework

Real Automation Example: Demo Request

Trigger: User books a demo call

Email 1 (Day 1): Thank you + one relevant case study

Logic: Wait 3 days

Email 2 (Day 4): Success story from similar customer

Logic: If they click the link → Create task for sales rep to follow up. If no click after 5 days → Send final email

Email 3 (Day 9): “One last thing before we talk” + exclusive resource

This simple 3-email sequence took 30 minutes to build, but it runs forever with zero human intervention.

The Perfect Welcome Sequence Framework

Your welcome sequence is your highest-ROI automation. Welcome emails have 57.8% open rates and 14%+ click rates. This is where you make your first impression.

The 3-Email Welcome Sequence (Proven Framework)

This framework is used by top performers and converts 2-4% of new subscribers into customers.

Email 1 (Immediate – Within 1 hour): Acknowledge

Purpose: Make a great first impression and build trust

What to include:

• Personalized greeting (use their name)
• Recognition of what they just did (“Thanks for downloading [resource]”)
• Clear expectation-setting (“Here’s what you’ll get from me”)
• One valuable insight or resource
• Soft CTA: “Reply and tell me your biggest challenge” (engagement, not selling)

Subject line example: “Your [Resource] is ready”

Why it works: Users expect you to acknowledge their action immediately. When you do, you stand out from 90% of competitors who ignore them.

Email 2 (Day 2): Include

Purpose: Provide value and build credibility

What to include:

• Reference to Email 1 (“Following up on what I mentioned…”)
• Customer success story or case study
• Specific result achieved (numbers matter)
• Actionable tip they can implement today
• CTA: “Want to see how others did this?”

Subject line example: “How [Customer Name] grew revenue 40%”

Why it works: Social proof + actionable insights = engagement. By day 2, they’re deciding if you’re credible. Prove it.

Email 3 (Day 5): Mobilize

Purpose: Drive action (conversation, trial, or purchase)

What to include:

• Clear problem statement (their pain point)
• Your solution (how you solve it)
• Specific CTA (book call, start trial, view pricing)
• Objection handling (“Not sure if it’s for you? Here’s [resource]”)

Subject line example: “Can we help with your [specific pain point]?”

Why it works: By email 3, they know you. Now it’s time to ask for the next step. Don’t hide what you want—be clear and direct.

What NOT to Do in Welcome Sequences

• Don’t: Send 5-10 emails in first week (overwhelm kills engagement)
• Don’t: Make first email all about your product (they don’t care yet)
• Don’t: Wait more than 1 hour to send first email (momentum dies)
• Don’t: Use generic, templated language (“Hey there”)
• Don’t: Forget to segment (one welcome sequence doesn’t fit all)

Welcome Sequence Performance Targets

If you’re below these targets: Test different subject lines, sending times, or copy. A/B test one element at a time.

Measuring Success: Key Email Metrics

You can’t improve what you don’t measure. Here are the metrics that actually matter.

The Big Three: Open Rate, CTR, Conversion Rate

1. Open Rate

Formula: (Unique opens / Sent emails) × 100

Benchmark: 15-25% for most industries; 50-60% for welcome emails

Improvement tactics:

• Personalize subject lines (include name + specific benefit)
• Send at optimal times (usually 9-11am or 6-7pm)
• Test subject lines with A/B testing
• Keep list clean (remove inactive subscribers)

2. Click-Through Rate (CTR)

Formula: (Unique clicks / Unique opens) × 100

Benchmark: 2-5% for most campaigns; 14%+ for welcome emails

Improvement tactics:

• Use clear, compelling CTAs
• Add multiple CTAs (different angles work)
• Test button text and colors
• Make emails mobile-friendly (50%+ opens are mobile)

3. Conversion Rate

Formula: (Conversions / Unique clicks) × 100

Benchmark: 2-4% for welcome sequences; varies by industry for others

Why it matters: This is revenue. Track it obsessively.

Secondary Metrics Worth Tracking

• Unsubscribe rate: If above 0.5%, your frequency is too high
• Bounce rate: Hard bounces (invalid email) should be near 0
• List growth rate: You should grow your list faster than people unsubscribe
• Spam complaint rate: Keep below 0.1% (indicates serious problems)

Email Automation Benchmarks (2025)

2025 Best Practices & Implementation

The Core Rules (Non-Negotiable)

Rule 1: Send First Email Within 1 Hour

Email frequency tolerance is highest in the first hour after signup. Welcome emails have 75% of their opens in the first 15 minutes. If you wait 24 hours, you’ve lost momentum.

Rule 2: Personalize Beyond First Name

Generic “[FirstName]” tokens don’t work anymore. Use behavior personalization:

• “I noticed you downloaded [specific resource]”
• “You visited our pricing page”
• “Your industry typically sees [X% result]”

Rule 3: Mobile-First Design

50-60% of email opens are on mobile. If your emails don’t look good on phone, you lose 50% of your audience. Test every email on mobile before sending.

Rule 4: One CTA Per Email (Or Clear Primary)

Multiple CTAs dilute action. If you need multiple, make one primary and others secondary. Clear hierarchy matters.

Rule 5: Segment Your List

Send different welcome sequences to different audience segments:

• First-time visitor welcome
• Customer comeback welcome
• Free trial signup welcome
• Referral signup welcome

Implementation Checklist: 30 Days to Functional Email Automation

Platform-Specific Implementation

If You Choose Mailchimp:

• Start free (500 contacts), upgrade to Essentials when hitting 500 subscribers
• Use “Automation” feature (found in left menu), not “Email” for workflows
• Set up welcome sequence in Automation tab (not main email builder)
• Test automation with test contact to verify timing and triggers

If You Choose Substack:

• Start with free publishing, focus on quality content
• Build to 500+ free subscribers before turning on paid
• Test pricing with Founding Member tier ($50-100/month) before regular subscriptions
• Use Substack Notes (short form content) to drive new subscribers

If You Choose Brevo:

• Start free (300/day), excellent for testing automation
• Build automation workflows in “Marketing Automation” tab
• Upgrade to Starter ($8.08/month) as soon as you hit consistent sending
• Take advantage of included SMS later when you need it