Strategies for Re-engaging Non-Paying Users: Share Your Insights!

Jacob S. · 2025-09-09 10:54:52.334803+00

👋 Has anyone here built a Clay automation (or similar) to re-engage non-paying users? Context: At Passion.io (http://Passion.io), we’re testing a flow for a large pool of new non-paying customers who’ve 1) attended a webinar, 2) set up an app, but 3) haven’t converted to paid. From that pool we want to identify and target ICPs with automated but personalised outreach (Clay + email/social/Loom) and test gifts like a “free monetization audit” or early access to a new AI feature. I’d love to hear from anyone who’s: • Run a similar “inbound-led outbound” play to convert non-paying but engaged users • Used Clay (or other enrichment/prospecting tools) for semi-personalised nurture • Seen success with gifting, audits, or other hooks in this type of funnel Any wins, pitfalls, or tech-stack tips would be gold. If you’ve tried something like this, please share your experience in the thread so others can learn too.

Join the Community

Strategies for Re-engaging Non-Paying Users: Share Your Insights! | RevGenius

5 comments

Lara D.
·
·
Jacob S. Treat them as ‘warm outbound,’ not email list. Build 3 micro-cohorts by job to be done, then send Looms that reference their in-product behavior. Add a single friction-free offer like ‘monetization audit’ with 72-hour calendar windows. We bumped trial-to-paid by 14 points using that exact pattern. Hope it helps!
👍1
Vincent
·
·
HI Jacob S., just coming across this thread now as I've joined recently. You play sounds very much like a PLG approach and from past experience the conversion of user into paid users must be done via your product consumption functionalities (at least this where you'll drive the biggest conversion), of course layering additional intents like webinar or other content engagement is good too. You could use tools like mixpanel, common room or amplitude to track product signals. What's key is to design specific user engagement level where you know how good and dependant/interested in your product they become based on how much they advance with the feature/functionality usage. Then you could bake in specific rewards such as gift, point system, or product freebies to get them to stay in the product longer. Once you have the right data from the above tools, you use Clay to built your sequences end-to-end to run on auto-pilot. Does that make sense?
👍1
Josiah S.
·
·
Hey Jacob S. we run plays like this all the time with webinar attendees, website visitors, event attendees, badge scans... Gifts perform well, as does multi-channel outreach (email/LinkedIn). Rarely see "free audits" that perform well, I'd suggest finding a different way to phrase it. You could build the workflow and launch the play straight from something like Tapistro. Happy to share more info if you're open to it.
🙌1
Jacob S.
·
·
Thank you Vikas K.
🙌1
Vikas K.
·
·
In my previous role, I used to run free base monetization plus lead revitalization campaigns as a Head of Growth Analytics team. Tech stack is easy to figure out, and you can keep optimizing based on internal/external signals which work (product usage, recent growth/funding news/multiple signups from the same org). Fine tuning the model may take 2-4 weeks. Program managing is the tricky part, as you would need to internally sell this idea to sales/SDRs. They need to believe that this segment of lead is worth their time. Easier to sell to SDRs than to AEs, as AEs prefer warm/hot leads. In my experience you can add 2-5% to new revenue using such initiatives, and you cna train new joiner in the sales team using this initiative. It'll be a win-win. Let me know if you would like to know further on the tech stack. Wrote a white-paper on this topic. Can DM if you are interested.
❤️1

Loading comments

Lara D.
·
·
Jacob S. Treat them as ‘warm outbound,’ not email list. Build 3 micro-cohorts by job to be done, then send Looms that reference their in-product behavior. Add a single friction-free offer like ‘monetization audit’ with 72-hour calendar windows. We bumped trial-to-paid by 14 points using that exact pattern. Hope it helps!
👍1
Vincent
·
·
HI Jacob S., just coming across this thread now as I've joined recently. You play sounds very much like a PLG approach and from past experience the conversion of user into paid users must be done via your product consumption functionalities (at least this where you'll drive the biggest conversion), of course layering additional intents like webinar or other content engagement is good too. You could use tools like mixpanel, common room or amplitude to track product signals. What's key is to design specific user engagement level where you know how good and dependant/interested in your product they become based on how much they advance with the feature/functionality usage. Then you could bake in specific rewards such as gift, point system, or product freebies to get them to stay in the product longer. Once you have the right data from the above tools, you use Clay to built your sequences end-to-end to run on auto-pilot. Does that make sense?
👍1
Josiah S.
·
·
Hey Jacob S. we run plays like this all the time with webinar attendees, website visitors, event attendees, badge scans... Gifts perform well, as does multi-channel outreach (email/LinkedIn). Rarely see "free audits" that perform well, I'd suggest finding a different way to phrase it. You could build the workflow and launch the play straight from something like Tapistro. Happy to share more info if you're open to it.
🙌1
Jacob S.
·
·
Thank you Vikas K.
🙌1
Vikas K.
·
·
In my previous role, I used to run free base monetization plus lead revitalization campaigns as a Head of Growth Analytics team. Tech stack is easy to figure out, and you can keep optimizing based on internal/external signals which work (product usage, recent growth/funding news/multiple signups from the same org). Fine tuning the model may take 2-4 weeks. Program managing is the tricky part, as you would need to internally sell this idea to sales/SDRs. They need to believe that this segment of lead is worth their time. Easier to sell to SDRs than to AEs, as AEs prefer warm/hot leads. In my experience you can add 2-5% to new revenue using such initiatives, and you cna train new joiner in the sales team using this initiative. It'll be a win-win. Let me know if you would like to know further on the tech stack. Wrote a white-paper on this topic. Can DM if you are interested.
❤️1