Redefining Onboarding Strategy

Moving from anecdotal inconsistency to a quantified, multi-product retention framework.

Role Staff Product Designer

Scope Cross-Platform Strategy

Output Lifecycle Framework

01 // The Diagnosis

Measuring the Invisible

I was initially asked to "look into onboarding" across Outside’s portfolio (Gaia GPS, Trailforks, MapMy). What began as a UX request quickly revealed a structural void.

My initial audit exposed that the organization lacked the basic infrastructure to support a cohesive experience:

No Ownership: No single team was responsible for the user's first 30 days.
No Definition: "Activation" was measured differently by every product lead.
Value Gap: While marketing promised an "Ecosystem," the products operated as silos.

FIG 01. THE DATA AUDIT. I quantified "Value Reach Rate" (users who actually experienced the core utility), revealing drop-offs as high as 58% in products like Trailforks.

02 // The Strategy

Reframing the Problem

The Insight

"The real onboarding problem wasn't the UI—it was the business definition. We needed to shift from Onboarding as a 'Doorway' (getting them in) to Onboarding as a 'System' (getting them to value)."

I developed a Two-Layer Framework to align the product teams. This separated the technical "setup" from the actual "value discovery."

FIG 02. THE FRAMEWORK. Distinct layers for "Out-of-Box Experience" (Setup) vs. "Ongoing Onboarding" (Value Drip).

Handling Complexity: The Scenario Matrix

A "one size fits all" flow was impossible given our diverse user base. I introduced a Multi-Scenario Model that dynamically adjusted the onboarding path based on two variables:

Subscription Status: (Free vs. Premium vs. Trial)
Entry Point: (Web vs. App Store vs. Referral)

This allowed us to serve a "Hard Sell" flow to App Store downloads, while serving a "Value Reinforcement" flow to users who had already purchased a subscription via the web.

03 // The Execution

From Abstract to Concrete

To prove the framework's viability, I translated the high-level strategy into a "Canonical Flow"—a single architectural diagram that defined the required steps for every product in the portfolio.

This allowed engineering to build a shared backend service while allowing individual brand designers to apply their specific visual language on top of the logic.

FIG 03. THE UNIFIED ARCHITECTURE. By defining a single "master flow", we ensured consistent data capture across the portfolio while preserving unique brand identities.

04 // The Impact

Organizational Shift

While resource constraints limited immediate full-stack implementation, this strategic work fundamentally altered how Outside approaches product growth:

The "North Star" Report: I authored the strategic white paper that became the reference point for the VP of Product and Engineering leadership.
Unified Metrics: We moved from vanity metrics (Account Creates) to value metrics (Reach Rate), now tracked on a shared cross-product dashboard.
Unblocking Brand Strategy: My work highlighted that our "House of Brands" confusion was hurting retention, directly influencing the executive decision to consolidate subscription tiers.