From Blank Slate to
AI-Powered Onboarding
How Touchstay solved the “empty CMS” problem with AI content generation, lifting trial-to-paid conversion from 35% to 49% and cutting time-to-activation by 66%.
• AI Product Strategy
• UX Reframing
• Lifecycle Email
The Challenge
When Sivan Kadosh joined Touchstay as Fractional CPO, the platform faced a common but costly issue. New users were landing in an empty CMS and immediately stalling at the first step: creating content. With no examples or drafts to guide them, the experience felt overwhelming.
The digital guidebook platform served vacation rental hosts who needed to populate listings with local recommendations, check-in instructions, and house rules. Without pre-built content to start from, users faced a blank page and most never made it past that first hurdle.
The Core Problem:
Only 35% of trial users converted to paid plans, and just over half completed the onboarding process. Time-to-activation averaged 3.5 days, well beyond the window where most users lose interest. The “empty CMS” was bleeding revenue every day.
Touchstay needed a way to show value immediately, not after days of manual content creation.
My Role
As Fractional CPO at Touchstay, Sivan Kadosh owned the product strategy for activation and conversion. The engagement spanned six months with an 8-person product and engineering squad. Responsibilities included diagnosing the onboarding funnel, defining the AI integration roadmap, coordinating design and engineering on the “review” flow, establishing success metrics, and running the re-engagement email sequences.
Sivan Kadosh reported directly to the Touchstay executive team, providing weekly progress reports and strategic recommendations throughout the engagement.
The Strategy
The initiative combined AI integration, UX reframing, and lifecycle email to systematically eliminate onboarding friction.
AI Content Generation
Integrated AI directly into the Touchstay CMS to auto-draft listings and descriptions as soon as users signed up, eliminating the blank-page problem from day one.
“Review” vs “Create”
Redesigned onboarding around a Review checklist, shifting the user mindset from “start from scratch” to “refine what’s already there” for faster activation.
One-Click Validation
Added a one-click “Approve or Improve” flow so users could validate AI-drafted content fast, keeping humans in control while removing the burden of first-draft creation.
Re-engagement Loop
Implemented email sequences deep-linking users back to their “Review Generated Content” step, closing the loop for anyone who dropped off before completing onboarding.
The Impact
By reframing onboarding around AI-generated content, Touchstay saw measurable improvements across conversion, engagement, and support load.
Engagement Details
“We did not add complexity. We removed friction so value appears in minutes, not days. The AI does not replace the host — it gives them a running start.”
Why It Worked
The initiative succeeded because it tackled the root cause of churn — cognitive load at first login — rather than adding features or discounts.
The “blank slate” was not a feature gap — it was a cognitive-load problem that AI could absorb. Sivan Kadosh identified that Touchstay users did not lack motivation; they lacked a starting point.
Changing “Create your guidebook” to “Review your guidebook” removed the intimidation of starting from zero. This single UX reframe transformed how new Touchstay users perceived the product.
AI-generated content meant users saw a populated CMS on first login, proving the platform’s value immediately. Time-to-activation at Touchstay dropped from 3.5 days to 1.2 days.
The “Approve or Improve” flow kept humans in control while removing the burden of first-draft creation. Vacation rental hosts trusted the output because they always had the final say.
Targeted emails brought back users who dropped off, deep-linking them straight to their AI-drafted content. The 28% CTR on these sequences nearly doubled the SaaS industry benchmark of approximately 15%.
Ready to remove onboarding friction in your product?
A fractional CPO can turn first-login drop-off into a conversion win.
Client references are published at /references/, and further references are available on request.