Case study · TravelTech SaaS · 2025
"TouchStay" is a TravelTech SaaS whose guest guide setup lost close to half of new accounts before they finished. I owned onboarding strategy and led the team that rebuilt it around AI-assisted setup. Over two quarters completion moved from 52% to 81% and trial to paid from 35% to 49%. The method transfers to any setup-heavy product.
30 minutes. No pitch, no deck.
Three numbers moved, all of them tracked by "TouchStay" before I arrived. Each tile states the metric, the reading before and after, and what was being measured over which period.
Onboarding completion
52% to 81%
+29 points +29 pts
"TouchStay", TravelTech SaaS. New accounts finishing guest guide setup, measured over two quarters in 2025.
Trial to paid
35% to 49%
+14 points +14 pts
Same cohort window. Free trials converting to a paid subscription, no change to pricing or trial length during the period.
Time to activation
3.5d to 1.2d
2.3 days faster 2.3d faster
Median elapsed time from sign-up to an activated account, same two quarters.
Figures from the client's own analytics, 2025. Before readings are the trailing quarter prior to the rebuild. Nothing is modeled, estimated or rounded.
Three facts, so you can decide in five seconds whether this is your company.
Product
The digital guidebook platform served vacation rental hosts who needed to populate listings with local recommendations, check-in instructions, and house rules.
Team
The engagement spanned six months with an 8-person product and engineering squad.
The bottleneck
New users were landing in an empty CMS and immediately stalling at the first step: creating content.
01
Only 35% of trial users converted to paid plans, and onboarding completion sat at 52%. Time to activation averaged 3.5 days, well beyond the window where most users lose interest.
When I 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 empty CMS was bleeding revenue every day. "TouchStay" needed a way to show value immediately, not after days of manual content creation.
02
As Fractional CPO at "TouchStay", I owned the product strategy for activation and conversion. The engagement spanned six months with an 8-person product and engineering squad.
Decisions I owned
I reported directly to the "TouchStay" executive team, providing weekly progress reports and strategic recommendations throughout the engagement.
03
The initiative combined AI integration, UX reframing, and lifecycle email to systematically eliminate onboarding friction.
Move one
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.
Move two
Redesigned onboarding around a Review checklist, shifting the user mindset from "start from scratch" to "refine what's already there" for faster activation.
Move three
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.
Move four
Implemented email sequences deep-linking users back to their "Review Generated Content" step, closing the loop for anyone who dropped off before completing onboarding.
04
Onboarding completion moved from 52% to 81% and trial to paid from 35% to 49% over the six-month engagement. Median time to activation fell from 3.5 days to 1.2 days.
By reframing onboarding around AI-generated content, "TouchStay" saw measurable improvements across conversion, engagement, and support load. First-session engagement rose 40%, with users engaging with the AI-generated content.
Onboarding support tickets fell 35%, which were mostly the "How do I start?" queries. Re-engagement email click-through reached 28%, above the SaaS benchmark of approximately 15%.
The full figures are in the results card above and come from TouchStay's own analytics.
Three principles from this engagement that hold outside TravelTech software. They are the part worth stealing whether or not your product looks anything like "TouchStay".
01
Onboarding completion rises when you remove work, not when you explain it better, because every field a new account has to think about is a place the setup stops.
02
AI earns its place in a product when it delivers a first draft the customer edits, rather than a suggestion the customer has to evaluate.
03
Measure activation at the point value is delivered rather than at account creation, because the second number can climb while the first one falls.
If new accounts are stalling before they reach value, the fix is usually a decision about what the product does for them, not another email in the sequence. Bring me your funnel and I will tell you where it breaks.
30 minutes. No pitch, no deck.
Thirty minutes with Sivan Kadosh. Bring the number that is not moving and I will tell you what I would do about it, whether or not you hire me.
Book a Product Strategy SessionClient references are published at /references/, and further references are available on request.
