Rubrik sells data security as a multi-product platform — backup, ransomware recovery, plus protection modules for SaaS apps like Microsoft 365, Salesforce, and Azure. Most existing customers used only one of those products, but the only way to evaluate the others was to schedule a sales call. Pre-IPO, the company needed cross-sell expansion (revenue from existing customers, not just new logos). I led a 9-team effort to design a gamified in-product trial that proven users could start themselves — and a modular framework other Rubrik product teams could plug into without redesigning their own onboarding.

Most of my work lives behind NDAs and embargoes. The walkthrough that matters — the why, the things I cut, the calls I'd make differently — happens in conversation, not on a page.
Rubrik's customer base had a structural growth problem: most customers were on one product (typically backup), but the platform now spanned protection modules for SaaS apps (Microsoft 365, Salesforce, Azure) that those same customers were heavy users of — so the cross-sell potential was real.
The barrier was process: evaluating a second Rubrik product meant talking to sales, and sales motion stalls in a pre-IPO quarter where the bar is expansion revenue, not new logos.
How do we let proven customers try, evaluate, and self-justify a purchase of a second Rubrik product — without a sales handhold, and in a way other product teams can plug into without rebuilding the trial UX every time?
Generated over two years from 57 Microsoft 365 contracts secured, including 16 large enterprise customers. Three additional Rubrik features were integrated into the trial framework after launch.
Across 15 customer interviews and five behavioral archetypes — Busy, Inquisitive, Skeptical, Price Sensitive, Novice — the trial framework's branching logic emerged. Each archetype enters with a different motivation, a different time investment, and a different need for communication, so the trial couldn't optimize for one path: it had to give every archetype a way through that felt natural to their motivation.
The Skeptical archetype became the framework's pressure-test. They're the customer most likely to evaluate value rationally; if the trial couldn't get a Skeptical user to a clear "yes" or "no" position by end of trial, it didn't deserve to be a sales motion. That archetype is what justified the auto-generated trial performance report — the artifact a Skeptical user would actually share with their manager to make the buying call.

I designed the trial as four phases — Discovery & Opt-in (offer + opt-out survey that captures objections for the sales team) → Onboarding & Multi-user (guided tutorial + multi-admin invitation built in from day one + cross-platform resume) → Hands-on Try Outs (structured task list, not open-ended exploration; each task builds domain confidence and generates evidence for purchase) → Persuasive Conversion (auto-generated trial performance report shareable internally — designed to answer "was this worth it?" for the buyer's manager).
The 6 design principles — Real Data Integration (live data from day 1, not demo content), Guided Experience, Role Management, Post-Trial Communication (trial report as internal sales tool), Effortless Accessibility, Phased Exploration — anchored 30+ reusable components, so adopting Rubrik product teams plugged in instead of redesigning their own onboarding.

End-to-end flow across the four phases — Targeted Trial Offer, Onboarding & Multi-user Support, Hands-on Product Feature Try-Outs, Persuasive Conversion — with branching for opt-out and the auto-generated trial performance report at the conversion step. Scroll horizontally to walk the whole journey.







What I'd port forward: making the trial output a buyer-internal sales artifact (the auto-generated performance report), not a vendor-marketing one. The user becomes their own buying advocate, which is the core PLG insight — let the customer answer "was it worth it?" to their own manager, not yours.
What I'd push harder on next time: the opt-out survey design. The "Not interested" exit was surfacing the most useful sales-team intel of the entire framework, but the survey itself was thin. Even a friction-free single-question prompt at that exit would have multiplied the value the sales motion got from the trial.