1. Trial User Context Analysis

1. Ask the user about their trial structure—length (7/14/30 days), what features are included vs. paywalled, and trial-to-paid conversion goal.
   • Example: "How long is your trial, what features can trial users access, and what's your current or target trial-to-paid conversion rate?"
2. Ask the user to describe the activation milestones that indicate a user is getting value—account setup, first use case completed, key feature used.
   • Example: "What actions indicate a trial user is activated and likely to convert—completing onboarding, using core features, inviting team members, achieving a result?"
3. Ask the user about common drop-off points or objections that prevent trial users from converting to paid.
   • Example: "Why do trial users typically not convert—don't understand the value, don't complete setup, price concerns, missing features, or they went silent?"
4. Ask the user what pricing or incentives they can offer to encourage conversion—launch discounts, annual plan deals, extended trials, or bonus features.
   • Example: "Can you offer conversion incentives—percentage off first year, discounted annual plans, extra month free, or upgraded plan access?"

2. Email Sequence Strategy

Design an email sequence that guides trial users through activation, education, and conversion:

Day 0 (Welcome Email):

• Purpose: Set expectations, provide quick start guide
• Content: Welcome message, here's what to do first (clear activation steps)
• CTA: Complete setup, book onboarding call, or access training resources
• Tone: Excited, supportive, here-to-help

Day 1-3 (Activation Emails):

• Purpose: Drive key actions that correlate with conversion
• Content: Feature spotlights, use case tutorials, "Here's how customers like you succeed"
• CTA: Try this feature, complete this workflow, see example
• Trigger-based: If user hasn't completed key action, send targeted nudge

Day 4-7 (Value Demonstration):

• Purpose: Show ROI and outcomes achievable
• Content: Customer success stories, results achieved, time/money saved calculations
• CTA: See your progress, invite team member, explore advanced features
• Social proof: Testimonials from similar customers

Day 8-10 (Objection Handling):

• Purpose: Address common concerns before they become blockers
• Content: FAQ, comparison to alternatives, pricing justification (ROI calculator)
• CTA: Talk to support, book demo with team, compare plans
• Offer help: "Questions? Our team is here"

Day 11+ (Conversion Push):

• Purpose: Create urgency and clear conversion path
• Content: Trial ending reminder, limited-time upgrade incentive, what you'll lose access to
• CTA: Upgrade now (with discount code), extend trial (if needed), schedule account review
• Progressive urgency: Friendly reminder → stronger FOMO → final notice

Post-Trial (Didn't Convert):

• Day after expiry: "Miss us already?" win-back email with strong offer
• 7 days post-expiry: Case study or new feature announcement
• 30 days post-expiry: Final reach-out or alternative offer (downgraded plan)

3. Personalization & Segmentation

Segment email content based on user behavior:

• Activated users (completed key actions): Focus on advanced features, team collaboration, scaling use cases
• Low engagement (haven't completed setup): Send simplified activation guides, offer onboarding help, remove friction
• Feature-specific interest (used certain features): Highlight related capabilities, show power-user workflows
• Team vs. individual: Different messaging for solo users vs. those who invited teammates

Dynamic content blocks:

• Insert user's name, company name, trial days remaining
• Show progress: "You've completed 3 of 5 key setup steps"
• Personalized ROI: "Based on your usage, you could save X hours per week"

4. Conversion Optimization Tactics

• In-app messaging: Coordinate email with in-app nudges for consistent guidance
• Upgrade CTAs: Make it one-click easy—pre-fill billing info, show plan comparison
• Social proof: Sprinkle customer logos, testimonials, and usage stats throughout sequence
• Guarantee/Risk reversal: Offer money-back guarantee or easy cancellation to reduce hesitation
• Limited-time incentives: Trial-exclusive discounts that expire with trial
• Human touch: Offer personal onboarding call, account review, or direct founder access for high-value trials

5. Sequence Delivery & Testing Framework

• Present complete email sequence with subject lines, body copy, CTAs, and sending schedule
• Format each email with clear sections: Subject | Preview Text | Body | CTA | Notes
• Include behavioral triggers: "If user does X, send email Y / Skip email Z"
• Provide A/B testing recommendations: subject lines, CTA copy, incentive timing, social proof placement
• Define success metrics: email open rates, CTA click rates, activation completion, conversion rate by email
• Invite feedback on sequencing, tone, incentive structure, or personalization depth before automation setup