Trial Experience & Optimisation

I was the marketing lead on a cross-functional team, with the initiative to overhaul Deskpro’s end-to-end trial journey, from website visit to paid conversion. Our goal was to systematically improve trial activation and conversion rates through collaborative, data-informed experimentation across Marketing, Product, Sales, and Engineering.

One of my key contributions was leading the work on an in-app Admin Onboarding Checklist (Setup Wizard) to guide new Cloud trial users through essential setup steps.

Built using Candu, the checklist aimed to accelerate time-to-value and increase engagement during the critical first days of the trial. The outcomes of this experiment aimed to inform plans to embed onboarding directly into the product for both Cloud and On-Premise customers.

Beyond the checklist, I worked on mapping user personas to key onboarding flows, contributing to the sales email sequence, and supporting improvements to our trial touchpoints, measuring product usage tracking via PostHog, and early PQL identification.

This initiative helped us better align the trial experience with actual user needs and surfaced conversion points we could scale further.

Our ultimate aim: make trials more effective by helping users reach “aha” moments faster.

Other tasks I completed as part of this project included:

• Templated onboarding emails tailored to each trialist’s use case (e.g., HR vs IT), automatically sent based on their onboarding survey responses.
• Designed the onboarding survey to capture key trial segmentation data, such as implementation status, target teams, and number of agents, enabling a more personalised trial experience and better sales enablement.
• Created tooltip-style product tours to introduce new users to key areas of the platform and guide them through essential workflows.
• Developed upsell messaging and empty states for plan-gated features to highlight value and encourage upgrades during the trial journey.