Increasing Ring subscription conversion by double digits through relentless iteration
Owned the end-to-end redesign of the Ring Protect checkout flow across mobile and web, addressing critical drop-off points in a fragmented ecosystem.
The starting point
Back in 2023, the Ring Subscriptions organization was officially assigned to me. The platform had launched to great success, maintaining an above-average conversion and sign-up rate. As a result, the ecosystem had remained largely unchanged for years, receiving mostly ad-hoc content updates and cosmetic changes. Why fix what is already working?
Although the initial assignment was mostly nominal, designating me as the design support for future content updates, I took it upon myself to look deeper. I initiated a comprehensive strategic and tactical diagnosis, actively searching for hidden friction and underlying signals.
When a major corporate shift in plan strategy was announced in 2024, I knew it was the perfect catalyst. Instead of executing a superficial content update, I leveraged my findings to pitch a complete overhaul, re-architecting the cross-platform monetization ecosystem between our native mobile app and the web.
Signals & strategic diagnosis
Choose your own adventure: does “Continue” select a plan or just show more details? Without a side-by-side view, users were forced to play a guessing game just to compare value.
My early research had already delivered some critical leads. To move the needle, I just had to synthesize the signals:
The 30-day cohort dilemma (loss aversion)
Our trial automatically ends 30 days after a device is activated, triggering a massive spike in sign-ups on that exact day. Users can tolerate losing premium features, but losing their recorded video history triggers immense loss aversion. While this captured the Day 30 cohort effectively, it exposed a glaring gap: we were completely failing to capture intent early or drive preventative upgrades during the trial.
The cross-platform chasm (the app-to-web gap)
Behavioral data showed that close to 100K users on average discovered subscription value within the native iOS/Android app. However, due to App Store fee policies, the transaction had to occur on the web. Because we lacked a seamless native bridge, users hitting the rigid “trial is ending” gates were forced to abandon their mobile context, completely cooling down purchase intent during the handoff.
The feature comprehension deficit
UXR unraveled a critical commercial bottleneck: users were subscribing solely to keep their videos. They were fundamentally unaware of any other benefit provided by our tiers. This explained a stagnating ecosystem, if users only perceive value in basic video storage, there is zero incentive to buy a higher tier or bother upgrading.
The pogo-sticking loop (mobile friction)
Mobile behavioral data on Heap revealed massive drop-offs during plan exploration. Because 80% of our traffic is mobile, forcing users to jump back and forth between separate plan selection and deep-detail screens triggered heavy decision fatigue, forcing them to rely on short-term memory to compare value.
The laundry list fallacy
Expert audits proved the legacy checkout flow was heavily over-indexing on technical jargon and endless feature grids instead of articulating core user value at a glance.
The post-purchase void (activation & TTFV bleed)
Our ecosystem was severely fragmented and disconnected post-checkout, with success pages that completely failed to prompt users to configure or activate their new services. By treating the checkout success page as a dead end rather than a launchpad, we were actively damaging our activation rates and inflating our Time-to-First-Value (TTFV) metrics.
Left: a trial expiration screen that functioned as a dead end rather than a conversion opportunity. Right: a success page that offered zero guidance on activating newly purchased services. Both exemplify the fragmented ecosystem we set out to fix.
Enter Live Oak
Project Live Oak's structural disruption of the legacy 2020 monetization model: a 25% price increase on the most populated plan, feature unbundling, and a deliberate push toward higher-value tiers.
As you can see above, this was a deep structural disruption of our legacy 2020 monetization model. We were changing plan names and deprecating legacy plans (people will freak out the moment they see a name they don’t recognize on their bill), increasing prices by 25% on a majority of our users, and pushing everyone toward more expensive plans. What’s not to love?
The baseline shift
We instituted a 25% price increase on our most heavily populated plan (the Basic tier).
Feature unbundling
We detached Alarm Pro Monitoring from the core premium tier, rebuilding it alongside Virtual Security Guard as a standalone, specialized add-on.
The scorecard
To measure the health of this transition, Product and I aligned on a clear metric matrix. North Star: Sign-up Rate (maximizing the percentage of our total active user base that subscribes). Truth Metrics: ARPU and Plan mix, to understand if the plan mix was actively shifting toward higher-value tiers. Guardrail: Gross churn and Customer support tickets, using design clarity as a shield to hold the line against a spike in cancellations.
The strategic trade-off
We also tracked Funnel Ingress CTR and overall volume. Because we had historically high-intent traffic, we made a conscious trade-off: we chose to prioritize top-of-funnel volume over local checkout efficiency. We were completely willing to open the floodgates and bring a massive wave of new users into the experience, accepting that our net checkout conversion percentage might take a temporary hit, as long as it maximized absolute expansion revenue.
Platform tenets & architecture
Rather than jumping straight into wireframes, I used our initial data signals and early usability testing to establish a set of core platform design principles. These tenets served as our north star to navigate a highly fragmented device ecosystem and diverse user cohorts:
Ecosystem over interface (the connected journey)
I refused to design the checkout as an isolated transaction page. Graceful cross-platform transition was the name of the game. The goal was to bridge the native mobile app experience seamlessly to the web checkout, and then launch the user directly into a post-purchase activation flow, systematically cutting down our Time-to-First-Value (TTFV).
Mobile-first (for real this time)
Behavioral data showed that 80% of our traffic enters the monetization funnel on mobile. If the design didn’t work flawlessly on a small screen under real-world constraints, it didn’t work at all. Full stop.
Proactive discoverability
Users shouldn’t have to guess what they are paying for. The legacy app completely hid feature gates and funnel ingresses for unsubscribed users, if you didn’t pay, the premium features literally didn’t exist in the UI. We shifted to a proactive discovery model: if users don’t know what the platform can do for them, there is zero incentive to buy or upgrade.
Comprehension over speed
We validated through unmoderated testing that some early design iterations performed worse on time-on-task, but drastically better on overall comprehension. We made a conscious decision: we were explicitly willing to slow down the funnel speed and add deliberate friction if it guaranteed absolute cognitive clarity. A better-informed customer means higher lifetime value, cleaner activation metrics, and zero room for buyer’s remorse.
From strategy to execution
The output of our working session: opportunity mapping against the signals we had identified, converging on three concrete workstreams to pursue.
With our signals synthesized and tenets defined, we needed to align on execution priorities. Rather than a fully fledged design sprint, we ran a focused 4-hour working session with Product, Engineering leads, and Legal. The objective was clear: map the most effective solutions against the opportunities we had uncovered, including increasing funnel volume, capturing earlier intent, reducing mobile fatigue, and eliminating cross-platform friction.
The session produced a concrete set of initiatives to pursue: a new bundle activation flow, a redesigned account onboarding that incorporated subscriptions from the start, and proactive feature gates across every premium capability for unsubscribed users.
Proactive discoverability in action
Each screen represents a newly surfaced ingress point within the native app, replacing invisible feature gates with proactive discovery moments that drive subscription intent.
We mapped every possible ingress point within the native app where users interact with locked premium features. Previously, these gates simply didn't exist in the UI for unsubscribed users. By surfacing them proactively, we created organic discovery moments that drive intent before the user ever reaches the checkout.
Columns and simplification
Columns Tiles The two final candidates after 27 rounds of validation. Left: the structured Column approach (industry standard validated against Figma, Dropbox, Slack, Heap, and Netflix). Right: the modern Tiles approach forcing extreme content frugality to avoid false-floor issues on mobile.
Over several weeks, I designed multiple variations of the core purchase experience, strictly tied to our platform tenets. I killed the pogo-sticking loop by bringing all plans into a single, cohesive view using a responsive, column-based layout optimized for mobile-to-desktop transitions. To combat the laundry list fallacy, my product partner, UXR, and I ruthlessly limited the volume of text, selecting only the core features that qualitative user research proved actually drove purchase intent.
Because we were ahead of schedule vis-à-vis engineering, we had the luxury to extensively pressure-test our work. We ran 27 unmoderated and moderated tests in total, ranging from core flow validations and trial screen designs to feature retention mechanics and specific lines of copy.
Eventually, our testing whittled the execution down to two final candidates:
Comprehension over speed, validated
Our testing data clearly favored the traditional Column approach. Unmoderated sessions showed that while users spent more time evaluating the column cards, they could accurately explain the plan benefits afterward, perfectly aligning with our tenet of Comprehension over Speed.
The psychology of intent
During these tests, we discovered a critical psychological trigger regarding copy: a generic "Continue" button felt passive and caused friction, whereas a specific action like "Subscribe to Home Premium" felt like an intentional commitment. It transformed a thoughtless click into a conscious choice, making users feel in control rather than just funneled.
Disagree and commit
However, leadership had already caught a glimpse of the modern Tiles approach early on and was completely sold on its aesthetic. By that point, our timeline leeway with engineering had expired, and it was time to ship. I took a mature Disagree and Commit route. I knew the Tiles design would perform reasonably well out of the gate, and as a platform piece, we could always leverage production data to run a clean A/B test later. We locked the design and prepared for launch.
Scaling the solution across device categories
Visible logic and copy have been intentionally obfuscated/blurred to respect NDA and confidentiality agreements.
Strategy is nothing without execution. After 27 rounds of validation, it was time to scale. Ring’s user base is highly fragmented, so partnering with Product, we segmented users into cohorts defined by two axes: device type (cameras, doorbells, alarm systems) and device density (single-device owners vs. multi-device households).
Each cohort required its own recommendation logic, plan hierarchy, and content strategy. I designed 11 distinct variations of the core flow, each tailored to surface the most relevant value proposition for that specific segment. The strategic priority was clear: secure the base conversion first, then drive add-on revenue (Alarm Pro, Virtual Security Guard) as a dedicated post-purchase step rather than cluttering the initial decision.
This separation was deliberate. By decoupling add-ons from the primary checkout, we reduced cognitive load at the moment of highest intent and created a clean secondary conversion opportunity once the user had already committed.
Moving the needle: conversion lift, tradeoffs and lessons
The redesigned ecosystem: A seamless end-to-end journey across Mobile and Desktop.
Post-launch data confirmed our hypothesis. We didn’t just see a significant conversion lift; users naturally gravitated toward higher-tier plans, boosting our ARPU and positioning me for my next career milestone.
Is it perfect? No. But iteration is the heartbeat of design. I had to pick my battles, balancing GTM’s copy needs and Legal’s guardrails on recommendation logic. We’ve been gathering a steady stream of data since shipping, and I already have the next set of hypotheses ready. We found our ██████ improvement, and I’m confident we’ll find the next one soon.
Cross-org influence
This redesign did not stay within Ring. The Blink team used my strategy and design as the cornerstone for their own transition from in-app purchases to a web subscription flow. I worked closely with their design team to help them adapt and implement a version of the system for their product context. Talk about cross-team impact; how about cross-org impact.