Reimagining Onboarding for a Rapidly Evolving Product
Role / UX Manager | Responsibilities / leadership, growth design, vision
Shop was evolving quickly — from a utility used to track parcels into a broader shopping destination. But most new users still arrived expecting the original value proposition: ~70% downloaded Shop via a "track order" button on order confirmation pages. They expected a package tracker. They landed in a shopping app.
This mismatch showed up clearly: rising negative reviews, confusion in the first session, and a drop in early retention. Onboarding was no longer supporting the product's shift, nor bridging expectations for users who still came for tracking first.
This mismatch showed up clearly: rising negative reviews, confusion in the first session, and a drop in early retention. Onboarding was no longer supporting the product's shift, nor bridging expectations for users who still came for tracking first.
The problem
We had a three-part challenge:
- User expectation gap
Most users expected order tracking, not discovery or shopping. We needed to meet that expectation quickly, while gently expanding their understanding of Shop's broader value. - Product value-prop shift
Shop's mission was evolving faster than its first-time experience. Onboarding needed to support a shopping-led future without abandoning the core utility users relied on. - Organisational ambiguity
Growth was structured into three mission teams — Activation, Retention and Infrastructure — each operating with significant autonomy but lacking coordinated direction. Growth has no product lead, Activation had no senior PM and the team's roadmap had devolved into disconnected experiments. The team lacked strategic direction and momentum.
This was Shop's onboarding prior to this initiative. It focussed strongly on tracking yet users were sceptical on the idea of connecting their Gmail.
Strategy
I reframed the work as a vision-led, hypothesis-driven initiative that would give the team clarity while leaving room for experimentation. The strategy had three pillars:
- A North Star vision to clarify where onboarding needed to go
- Central hypotheses to guide experiments and learning
- Cross-functional alignment, ensuring onboarding evolved alongside broader product work
This gave the team a coherent direction and the flexibility to explore.
How I led the work
1. Creating clarity quickly: the design sprint
I led a cross-functional sprint to quickly build shared understanding around first-time behaviour and intent. It revealed the key friction points, established three principles to guide direction, and produced early prototypes that made the future feel concrete.
Our core principles would help serve as a key way for us to align around specific ideas about what onboarding should be. These principles were:
I led a cross-functional sprint to quickly build shared understanding around first-time behaviour and intent. It revealed the key friction points, established three principles to guide direction, and produced early prototypes that made the future feel concrete.
Our core principles would help serve as a key way for us to align around specific ideas about what onboarding should be. These principles were:
- Make it personal
Use personalisation to create early, meaningful relevance. - Highlight shopping
Reduce that 'bait & switch' feeling by priming shopping intent from the first moment - Connect the dots
Highlight the a-ha moments in the journey to reinforce the moments where users found value
This aligned the team around a shopping-centred future, but also highlighted unresolved questions — especially around the 70% of users expecting tracking first.
2. Broadening the vision: designing for all three buyer segments
In parallel to this work, Shop's lead researcher was conducting crucial work on segmentation. As this research matured, we had more clarity on three distinct user groups:
1. Tracking-first buyers (majority) — those coming from order confirmation pages
2. Organic explorers — people who discovered Shop organically
3. Shop Pay-familiar buyers — users who loved Shopify's checkout option, Shop Pay
This surfaced the core tension:
How do we honour the tracking-first value prop while expanding the story?
Just focussing on tracking-first buyers wouldn't be enough for us to keep up with the quick shift in value proposition. Yet ignoring them would be a set up for failure, given the majority of our users were acquired this way. I aligned with my peers in the Growth leadership team to expand the scope.
This broadened the scope from a shopping-focused onboarding vision for Activation to a holistic North Star for Growth, shaping how we welcomed each segment and how onboarding could adapt across them.
In parallel to this work, Shop's lead researcher was conducting crucial work on segmentation. As this research matured, we had more clarity on three distinct user groups:
1. Tracking-first buyers (majority) — those coming from order confirmation pages
2. Organic explorers — people who discovered Shop organically
3. Shop Pay-familiar buyers — users who loved Shopify's checkout option, Shop Pay
This surfaced the core tension:
How do we honour the tracking-first value prop while expanding the story?
Just focussing on tracking-first buyers wouldn't be enough for us to keep up with the quick shift in value proposition. Yet ignoring them would be a set up for failure, given the majority of our users were acquired this way. I aligned with my peers in the Growth leadership team to expand the scope.
This broadened the scope from a shopping-focused onboarding vision for Activation to a holistic North Star for Growth, shaping how we welcomed each segment and how onboarding could adapt across them.
3. Bringing narrative and research together
To help the team think beyond screens, I introduced a storytelling approach that combined: Behavioural data, research insights and upcoming strategic bets across the org.
Working closely with a Staff Designer in the Activation team, I guided us towards mapping future-state buyer journeys for each segment. These outcome focussed stories were rooted in research, and showed how onboarding could flex to meet different entry points while still advancing Shop's shopping-first vision.
To help the team think beyond screens, I introduced a storytelling approach that combined: Behavioural data, research insights and upcoming strategic bets across the org.
Working closely with a Staff Designer in the Activation team, I guided us towards mapping future-state buyer journeys for each segment. These outcome focussed stories were rooted in research, and showed how onboarding could flex to meet different entry points while still advancing Shop's shopping-first vision.
Through vision sessions, I acted as a sparring partner and coach toward developing the future-state journeys, connecting future product capabilities with the realities of the first session. This established a narrative spine the team could build from.
Above is an example of one of our segments, the Shop Pay user. This story weaved upcoming bets (like Shop Cash and Shop ID) with our onboarding principles, such as personalisation and highlighting shopping.
These journeys, combined with our three principles, became the North Star that guided experimentation.
Above is an example of one of our segments, the Shop Pay user. This story weaved upcoming bets (like Shop Cash and Shop ID) with our onboarding principles, such as personalisation and highlighting shopping.
These journeys, combined with our three principles, became the North Star that guided experimentation.
4. Turning vision into hypotheses and experiments
We translated the principles and journeys into central hypotheses, which then shaped a coherent experimentation roadmap. Here's how it worked:
We translated the principles and journeys into central hypotheses, which then shaped a coherent experimentation roadmap. Here's how it worked:
Vision principle 💡
Highlight shopping
↓
Central hypothesis 🔮
Help buyers quickly understand Shop's value proposition and remove barriers to starting
↓
Experiment 🧪
A one-screen onboarding flow that communicates shopping messaging more clearly
This framework replaced the unfocused roadmap with a structured pipeline of learning-driven experiments.
Beyond MVP experiments, we explored how key onboarding moments could evolve. Using prototypes to visualise how brand, motion and narrative could come together to create a more crafted experience.
Beyond MVP experiments, we explored how key onboarding moments could evolve. Using prototypes to visualise how brand, motion and narrative could come together to create a more crafted experience.
Simplified onboarding experiment aligning with the shopping-first vision.
5. Extending onboarding beyond the app
As onboarding emerged as a strategic priority, I advocated for a designer dedicated to bridging product and marketing. Resulting in a Marketing UX Designer joining Growth.
They partnered with Activation, content design, and lifecycle teams to:
As onboarding emerged as a strategic priority, I advocated for a designer dedicated to bridging product and marketing. Resulting in a Marketing UX Designer joining Growth.
They partnered with Activation, content design, and lifecycle teams to:
- Craft narrative-driven email onboarding aligned with Activation
- Extend the value story beyond in-app flows
- Create cohesive storytelling across channels
Outcomes & Impact
Aspirational North Star
Growth adopted the Onboarding North Star as a core part of its strategy, aligning the team around a clear, long-term direction.
Clearer direction and stronger collaboration
The strategic framework unlocked a coherent roadmap, improved cross-team collaboration, and strengthened the team’s ability to argue from principles rather than opinion.
Meaningful product impact
A series of experiments shipped, contributing to improvements in early funnel metrics.
+9% increase in email verification, a critical early trust signal. Connecting a Gmail account had high friction due to trust concerns, but once users verified, they typically had higher retention rates.
Organisational influence
The work strengthened alignment between Buyer, Merchant, and Shop Pay teams, as well as marketing. It also established a repeatable, narrative-driven approach to hypothesis-led vision work that continued to guide experimentation and cross-channel storytelling beyond the initial project.
Growth adopted the Onboarding North Star as a core part of its strategy, aligning the team around a clear, long-term direction.
Clearer direction and stronger collaboration
The strategic framework unlocked a coherent roadmap, improved cross-team collaboration, and strengthened the team’s ability to argue from principles rather than opinion.
Meaningful product impact
A series of experiments shipped, contributing to improvements in early funnel metrics.
+9% increase in email verification, a critical early trust signal. Connecting a Gmail account had high friction due to trust concerns, but once users verified, they typically had higher retention rates.
Organisational influence
The work strengthened alignment between Buyer, Merchant, and Shop Pay teams, as well as marketing. It also established a repeatable, narrative-driven approach to hypothesis-led vision work that continued to guide experimentation and cross-channel storytelling beyond the initial project.
Why this mattered
This work helped Shop navigate a pivotal moment: evolving its value proposition without breaking trust with users who still relied on tracking first.
It gave the organisation a clear, principle-led direction for onboarding and laid the foundations for experimentation, personalisation, and cohesive storytelling across the product experience.
It gave the organisation a clear, principle-led direction for onboarding and laid the foundations for experimentation, personalisation, and cohesive storytelling across the product experience.
