Email not working? 💌 Maybe you're just doing it wrong...
Now, I know it hurts to hear something is not working because you're not doing it the right way - I've been there.
For the longest time - email wasn't working for us. Our cold emails were giving us few responses other than "no" or "unsubscribe". And worst of all - we weren't doing *any* lifecycle marketing (read this brilliant post about launching your first lifecycle program by Jeanne Jennigns btw!)
Why was that?
Quite frankly - pushing the right behavioral triggers (e.g. a PQL doing something in their trial account, a customer getting stuck on a feature) to our email marketing tool was super-hard, and would require a lot of engineering resources 😬
But this is about to change - because Userpilot is soon launching AI-powered emails 💌 - designed especially for lifecycle marketing! ✨
If you think "AI emails" is a fad - think again. Imagine being able to send a bespoke email with "best tips how to improve [X]" based on your new users' trial activity so far - without having to go into their trial, watch session recordings, and try to make sense of what to write based on what they are doing, their role, company size, use case...for every single trial user.
Hardly any company is doing that right now because it's almost impossible to do it manually at scale.
But soon, with technology akin to OpenAI's Operator - and all the insights you aready have about the user, their comany, including all their interactions with your product and the recordings of their sessions - you will soon be able to do that effortlessly.
Book a discovery session to get a sneak peek of what's coming!
I had a "come to Jesus" moment this year when I realised the only emails I ever respond to from companies are the ones offering me some value for free.
And since we started doing that - e.g. offering fee feedback on Product Experience, Onboarding Setup, Product Analytics & Feedback usage - for all lifecycle stages - our positive response rate soared:
How can you offer more value at all stages of lifecycle marketing?
Here are a few ideas how you can offer value at different lifecycle stages, using email + AI:
PQL (Product-Qualified Lead)
3-point “quick win” audit of their trial workspace (screenshots + suggestions).
Interactive checklist to hit first value moment within 24 hours.
Short Loom video showing how a similar company activated key features.
“ROI Calculator” template that auto-fills with their own usage data.
SQL that didn’t convert
One-pager mapping your solution to the pains they raised on the sales call.
Comparative teardown vs. their incumbent tool highlighting gaps (no pitch).
Invite to an office-hours AMA with your product strategist.
Access to an exclusive mini-course on solving the problem you address.
New / Early Customer (first 30–60 days)
Personalized onboarding roadmap with milestone badges they can share internally.
Weekly “pro-tip in 90 seconds” GIF or micro-video tied to their actual usage.
Free health-check after day 21 with a scored report and next-step advice.
Peer story from another customer at the same maturity stage.
At-Risk Customer (usage or NPS drop)
“We noticed X dropped—here are two friction fixes” email with embedded how-to gifs.
Free 15-min rescue call booked directly from the email CTA.
Offer a success workshop for their team (one-pager agenda attached).
Share a new feature beta that directly tackles their pain point.
Advocate / Power User
Early access to roadmap features + feedback loop survey.
Co-marketing opportunity outline (blog, webinar, LinkedIn Live).
“Referral Kit” with swipe copy and a tracked link—plus a give-get reward.
Monthly advanced-tips newsletter curated from internal experts.
Churned Customer
“Since you left” value recap with new capabilities/videos relevant to their old use case.
Invite to a no-pitch product tour showcasing fixes to their original objections.
Limited-time reactivation code plus a migration concierge offer.
Industry benchmark report comparing their metrics before vs. market averages.
Read more about lifecycle email marketing
Call for Papers - will you be our next Product Drive speaker?
Who’s the hottest thought leader in AI product development right now, according to you?
Respond to this email with a list of people you’re following - and would like to do a live session with at our annual conference, Product Drive!
Yes, I’m doing a CALL FOR PAPERS!
PRODUCT DRIVE 25 is looking for speakers who want to share how AI has transformed their work in product management and UX design so far - especially in industries like FinTech, EdTech, MarTech or HealthTech.
Last year, our annual conference Product Drive has attracted over 6,200 signups from top Product, UX, and Customer Experience teams - and we want to hear from YOU, the practitioners, as well!
Hit me up if you have insights to share on the following topics:
Leading in the age of AI – how to leverage AI tools as a product leader
Building AI-powered products – lessons from launching AI features
Vision vs. velocity – how great leaders balance short- and long-term goals
From PM to CPO – how to scale your career into product leadership
The new skills every product leader needs in 2025
Driving innovation without chaos – frameworks for structured experimentation
Product strategy in uncertain times – how to prioritize and align
Building a culture of product thinking across teams
The rise of AI copilots – how LLMs are reshaping product teams
Measuring product leadership impact – which KPIs actually matter
Increasing in-app user engagement in EdTech, HR Tech, FinTech, or HealthTech companies
Using AI for product development in a Regulated Industries (HealthTech/ FinTech/EdTech) - how PMs navigate the privacy and security challenges, while not sleeping on the opportunities AI creates?
Product-Led Growth in a Regulated Industry - navigating complexity while creating simplicity
Building better EdTech / FinTech/ or HealthTech products with AI - challenges and opportunities
How AI disrupts products insights to inform roadmap in EdTech / FinTech/ or HealthTech products