The overengineered welcome sequence I'm building...

Hey Party People!

Just caught our AI writing passive-aggressive emails to users who haven't logged in for a week. While I was teaching it about boundaries, it got me thinking about how we could make Penfriend's onboarding more fun (and less threatening)...

Why This Matters 👀 I've been tinkering with ideas for Penfriend's email onboarding. We had a butt tonne of people sign up after Black Friday and I wanna say hi to everyone.

The goal? Making it feel less like another SaaS signup and more like finding an easter egg in your favorite video game.

And I realised I have an old Zapier account with unlimited triggers and I’m abusing it until they ask me upgrade….

🤿 Going Scuba Mode: Zapier Onboarding Flow

This is what I’m thinking so far. It’s all here for you to follow along.
(Scuba mode is what I heard the kids call a deep dive, idk, could be the new term).

1️⃣ SIGNUP MAGIC

• Connect Zapier to your CRM/database with "New Row" trigger

• Use custom fields to track signup details

• Pro tip: Use webhooks if you have a custom API Tool stack: Zapier + CRM (HubSpot/Pipedrive/Sheets)

2️⃣ PERSONALIZED WELCOME

• Set up immediate email trigger after signup. (We use Klaviyo for this, but I’m not the biggest fan tbh.)

• Use dynamic fields for name + interests

• Add P.S. with dashboard Easter egg Tool stack: Zapier + Email Platform (Mailchimp/ConvertKit)

3️⃣ ENGAGEMENT TRACKING

• Track first in-app actions

• Split automation for active/dormant users:

  • Active: Bonus feature unlocks

  • Dormant: "Still there?" nudges Tool stack: Zapier + GA4/Segment + Email Platform

4️⃣ GAME ON

• Create milestone tracking in Coda.io

• Set up triggers for completion steps

• Add progress trackers to emails Tool stack: Zapier + Coda.io + Email Platform

5️⃣ AI SMARTS

• Connect OpenAI/Claude via Zapier plugin

• Generate tailored recommendations

• Create custom content ideas Tool stack: Zapier + OpenAI + Email Platform

6️⃣ HIDDEN TREATS

• Track Easter egg discoveries in Google Sheets

• Set up Slack notifications for team

• Trigger bonus feature emails Tool stack: Zapier + Sheets + Slack + Email

7️⃣ FEEDBACK LOOP

• Create Typeform/Google Forms survey

• Set up conditional emails based on scores

• Trigger team notifications for low scores Tool stack: Zapier + Forms + Email + Slack

8️⃣ WEEK ONE SURPRISE

• Set up time-based trigger (7 days)

• Create Google folder with bonus content

• Automate access email Tool stack: Zapier + Dropbox + Email

9️⃣ GENTLE NUDGES

• Connect SMS service (like Twilio)

• Set up 3-day dormant triggers

• Create team alerts for VIP users Tool stack: Zapier + Twilio + Slack

  • So I can say thanks and book calls with the biggest users.

🎯 BONUS IDEA

• Monitor social mentions

• Auto-curate user content for marketing emails…

• Create social proof emails Tool stack: Zapier + Social Monitoring + OpenAI

This is all experimental stuff I'm playing with - would love to hear your thoughts on what feels engaging vs what feels like too much.

⚙️ Today’s quick tip

Take any blog post that ranks on page 2-3 of Google (positions 11-30). Add 5-10 relevant internal links TO that page from your other content. Wait 2-3 weeks.

It's simple, but it works because you're:

• Strengthening the page's topical relevance

• Helping Google understand the context better

• Using your site's existing authority to boost the page

Takes 15 minutes. Costs nothing. And it often bumps you up several positions.

We just dropped this feature as an automatic thing in Penfriend.ai. It’s in clusters.

🛠️ TOOL DISCOVERY:

Riverside dot EFF EMM. Riverside.fm. I love it. We’ve got a bunch of video content coming out. Magic clip is dope. Honestly wondering what I could have done with all this I’m saving. Knowing me, make another business.

Have a great weekend

Tim
CCO @Penfriend

P.S. Totally re-doing the newsletter. I wanna do this short, simple, daily tips around content marketing. I’ve been doing this ish for 10 years now and I have a lot in this gnoggin’ and I want to share the things I’ve learnt over the years.

Each day is different. I’ve a bunch of ideas about this, but I’m excited to write again.
Would love to know either way what you think. Good, bad, it’s all helpful :D