Trial Onboarding Email Sequence
Trigger: User starts a free trial Length: 7 emails over 14 days Goal: Drive setup completion, feature adoption, and trial-to-paid conversion
Email 1: Welcome to Your Trial
Send: Immediately (Day 0) Subject Line: "Welcome to WithinEHR -- let's get you set up" Preview Text: "3 steps to get your group practice running in under 30 minutes"
Body:
Hi [First Name],
Welcome to WithinEHR! Your 14-day free trial is active, and I want to make sure you get the most out of it.
Here's your quick-start checklist (under 30 minutes):
Step 1: Set up your practice profile (5 min) Add your practice name, locations, and basic settings. [→ Set Up Your Practice]
Step 2: Add your first provider (5 min) Invite a provider or create a test account to explore clinical workflows. [→ Add a Provider]
Step 3: Try your first AI-generated note (5 min) Create a sample session and let the AI draft a progress note. This is usually the "aha moment." [→ Try AI Notes]
That's it for today. Tomorrow, I'll walk you through the billing setup.
If you need help at any point, just reply to this email or use the chat widget in the app.
Let's do this, [Founder Name]
CTA: Three action buttons for each setup step Design notes: Numbered steps create clear action. Keep it focused -- don't overwhelm on day 1.
Email 2: Provider Setup Walkthrough
Send: Day 1 Subject Line: "Set up your first provider in 5 minutes" Preview Text: "Step-by-step walkthrough (with video)"
Body:
Hi [First Name],
Day 2 of your trial -- let's get a provider set up so you can see how WithinEHR handles multi-provider workflows.
[Watch: Setting Up Providers in WithinEHR (3 min video) →]
What you'll set up:
- Provider profile (name, credentials, NPI)
- Schedule template (availability, session types, durations)
- Clinical preferences (note templates, treatment plan defaults)
- Access permissions (what they can see and do)
The group practice advantage: Unlike solo EHRs, WithinEHR lets you:
- See all providers' schedules side-by-side
- Standardize note templates while allowing provider customization
- Set practice-wide billing rules that apply to every provider
- Manage permissions by role (admin, clinician, billing staff)
[Set Up Your First Provider →]
Already done? Great -- tomorrow we'll cover the feature everyone talks about: AI documentation.
Best, [Founder Name]
Email 3: AI Documentation Tutorial
Send: Day 3 Subject Line: "Try AI notes -- the feature everyone loves" Preview Text: "See how AI drafts a progress note in under 60 seconds"
Body:
Hi [First Name],
This is the feature that makes most practice owners say "wait, seriously?"
WithinEHR's AI documentation drafts progress notes, treatment plans, and session summaries based on your session data. You review, edit, and approve -- cutting documentation time by 60% or more.
Here's how to try it:
- Go to any provider's schedule
- Create a sample appointment (use test data)
- After the "session," click "Generate AI Note"
- Watch the AI draft a clinically appropriate progress note in seconds
- Review, make any edits, and sign
[Watch: AI Documentation in Action (2 min video) →]
What makes this different from templates:
- The AI considers session context, not just fill-in-the-blank fields
- Notes use proper clinical language and format
- Each note is unique -- no copy-paste detection risk
- Clinicians maintain full control: the AI drafts, you approve
[Try AI Notes Now →]
Trust me -- once your clinicians see this, they won't want to go back.
Best, [Founder Name]
Email 4: Billing Setup
Send: Day 5 Subject Line: "Connect your insurance billing" Preview Text: "Eligibility checks, claims, and tracking -- all in one screen"
Body:
Hi [First Name],
Let's tackle billing. This is where group practices typically lose the most time (and money).
WithinEHR's billing system includes:
- Real-time eligibility verification: Check insurance coverage before the first session
- One-click claims submission: Submit claims directly from the session note
- Automated claim tracking: See the status of every claim in real time
- Denial management: Get alerts on denials with suggested next steps
- ERA/EOB processing: Automatically match payments to claims
To set up billing:
- Go to Settings → Billing
- Add your practice's tax ID, NPI, and billing address
- Add your payer list (common insurance companies)
- Run your first eligibility check on a test patient
[Watch: Billing Setup Walkthrough (4 min video) →]
[Set Up Billing Now →]
Fun fact: Practices that use automated eligibility checks reduce claim denials by up to 40%. That's real money.
Best, [Founder Name]
Email 5: Check-In
Send: Day 7 Subject Line: "How's it going? Quick check-in" Preview Text: "I'm here to help -- just reply to this email"
Body:
Hi [First Name],
You're halfway through your trial. How's it going?
Quick status check:
- Practice profile set up?
- At least one provider added?
- Tried AI documentation?
- Billing configured?
If you're stuck on anything, just reply to this email. I personally read every response and will get back to you within a few hours.
If you haven't had a chance to explore yet, no worries. Here are the two things I'd prioritize with your remaining trial time:
- AI documentation -- this is the biggest time-saver and the feature that usually seals the deal
- Unified dashboard -- see how all your providers, schedules, and billing look in one view
[Log In to WithinEHR →]
Want a guided walkthrough? I'm happy to do a quick 15-minute screen share to show you around.
[Book a Quick Walkthrough →]
Best, [Founder Name]
P.S. If you've already decided WithinEHR isn't the right fit, I'd genuinely appreciate knowing why. Your feedback makes the product better. Just reply and let me know.
Design notes: This email should feel personal and genuine. No hard sell. The goal is to re-engage and identify potential blockers.
Email 6: Feature Highlights + Urgency
Send: Day 10 Subject Line: "3 things to try before your trial ends" Preview Text: "You have 4 days left -- don't miss these features"
Body:
Hi [First Name],
You have 4 days left on your free trial. Here are three features you should try before it ends -- they're the ones that make the biggest difference for group practices:
1. Multi-Provider Dashboard See every provider's schedule, notes, and billing status in one view. This is the "group practice brain" that solo EHRs don't have. [→ Try the Dashboard]
2. Telehealth Integration Start a video session directly from the scheduling screen. No Zoom link juggling, no separate app. It's built in. [→ Try Telehealth]
3. Reporting & Analytics Run a revenue report, see provider productivity, check claim denial rates. These insights are usually trapped across 3 different tools. [→ Try Reporting]
What you'll lose when your trial ends:
- Access to AI documentation
- Your practice setup and configurations
- Any test data and notes you've created
What you keep:
- Everything -- if you subscribe before your trial ends, all your setup transfers seamlessly. No re-doing work.
[Subscribe Now and Keep Everything →]
Questions? Reply anytime.
Best, [Founder Name]
Email 7: Final Day -- Last Chance
Send: Day 14 (or day 13 if trial ends at midnight) Subject Line: "Your trial ends tomorrow -- here's what you'll lose" Preview Text: "Everything you've set up will be preserved if you subscribe today"
Body:
Hi [First Name],
Your WithinEHR trial ends tomorrow.
Here's a quick recap of what WithinEHR gives your group practice:
| What You Get | The Impact |
|---|---|
| AI documentation | Save 2+ hours per provider per day |
| Automated insurance billing | Fewer denials, faster payments |
| Unified dashboard | See every provider in one place |
| Built-in telehealth | No more Zoom link juggling |
| Multi-tenant architecture | Designed for groups, not retrofitted |
If you subscribe today:
- All your trial setup (providers, templates, billing config) transfers automatically
- No downtime, no re-configuration
- Full access continues immediately
[Subscribe Now →]
Not ready yet? I understand. Here are your options:
- Need more time? Reply to this email and I'll extend your trial by 7 days.
- Need to discuss with your team? [Book a quick call] and I'll help answer their questions.
- Not a fit? No hard feelings. I'd appreciate a quick reply about what didn't work -- it helps me build a better product.
Thank you for trying WithinEHR. Whatever you decide, I hope the trial was valuable.
Best, [Founder Name] Founder, WithinEHR
Design notes: Urgency is real but respectful. Always provide an extension option -- converting a trial user next week is better than losing them forever. The tone should be helpful, not pushy.