Optimizing Freelancer
Plus Retention & Growth
Role: Lead Designer I Timeline: 3 months I Team: UX Design, Content, Product, Analytics
Freelancer Plus is one of the largest revenue-driving products within the Upwork ecosystem, creating a strong business focus on improving retention while increasing membership upgrades and reducing downgrades. To support this, I led a series of strategic UX enhancements that included designing a new membership hub, defining promotional placement logic, introducing social-proof driven value messaging, and creating more user-friendly downgrade barriers. The initiative tested positively and was scaled to 100% of traffic, resulting in a 3% increase in upgrades and a 1.9% reduction in downgrades.
Increased
Upgrades
↑ 3%
Reduced
Downgrades
↓ 1.9%
Context and the problem
The Freelancer Plus membership is a key revenue-driving program within the Upwork ecosystem, offering users access to strategic platform benefits and premium features. As Lead Designer, I partnered with product to identify critical gaps in the existing experience, including rising cancellations, declining retention, and low user awareness of membership benefits after upgrading.
To address this, we focused on improving promotional clarity, strengthening benefit communication, and creating more contextual touchpoints that reinforced the value of Freelancer Plus throughout the user journey.
Key issues
→ The experience lacked clear upgrade messaging.
→ Lack of contextual education around feature value.
→ No effective visibility into the benefits included within the membership.
Discovery &
Research
Because Freelancer Plus operates as a cross-functional product spanning multiple platform surfaces, I partnered closely with product, analytics, lifecycle, and growth teams to develop a holistic understanding of the membership experience and its performance challenges. I audited the end-to-end membership journey, identifying friction points across upgrade, retention, and cancellation flows using historical findings, behavioral data, and existing team insights. In partnership with analytics, I mapped the journeys of users who downgraded, cancelled, or abandoned the upgrade flow to uncover key behavioral patterns and motivations. It became necessary to reframe membership perception from cost-focused to value-driven
“Cost too much” → “It is worth it”
Cancellation flow insights
Research showed that the primary reason users cancelled their membership was: “Costs too much.” This reframed the core UX challenge from simply driving upgrades to reinforcing perceived value and helping users understand why the membership was worth the investment.
Upgrade Flow Insights
Analysis of the upgrade funnel revealed an 85% drop-off rate between the membership page and checkout flow, signaling significant friction within the conversion experience. Several key hypotheses emerged:
→ High cognitive load within the upgrade journey
→ Lack of contextual value communication tied to user goals
→ Disconnected upgrade flows when users entered from contextual promotional surfaces
As a strategic synthesis, I mapped user needs against business priorities to identify where alignment existed and where friction emerged:
Business Goals
→ Improve Freelancer Plus retention
→ Reduce downgrades and cancellations
→ Increase upgrades
User Goals
→ Continue receiving ongoing value from the membership
→ Feel that the membership benefits justify keeping the plan
→ Understand the benefits of Freelancer Plus and determine if it meets their needs
Competitor analysis
I evaluated a range of direct and indirect competitors to understand how mature membership ecosystems reinforce ongoing value and engagement. Two experiences stood out in particular: LinkedIn as a direct competitor, and Amazon as an indirect benchmark.
Both platforms make their memberships feel continuously valuable throughout the user journey—LinkedIn through personalized and actionable feature discovery, and Amazon through usage data of membership benefits. In both cases, premium value is reinforced contextually over time rather than concentrated only at the point of upgrade.
The existing Freelancer Plus experience lacked this ongoing reinforcement, revealing a key opportunity to redesign the upgrade flow and create a centralized membership hub that continuously surfaces benefits, encourages feature adoption, and strengthens perceived value.
Strategy &
UX Principles
Discovery revealed that the core challenge within the Freelancer Plus experience was not only driving upgrades, but reinforcing the ongoing value of the membership to improve retention and reduce cancellations.
Only page in all the experience for Freelancer plus
User Goals
The project goals focused on making benefits feel more actionable and directly valuable, strengthening upgrade motivation, and reinforcing membership value throughout cancellation flows through contextual messaging and targeted offers.
→ Reinforce the value of the membership to Freelancer Plus users to increase usage of them and therefore increase retention
→ Highlight benefits with actionable messaging and perceived direct benefit so users feel more connected and compelled to upgrade
→Remind users of the value of their membership and offer limited-time offers promotions in the cancellation flow to decrease cancellation rates
Design principles
To help shape these goals into UX enhancements I framed the following design principles.
1
Reinforce value through
contextual visibility
2
Drive action through clear and
outcome-oriented communication
3
Reduce churn by designing for
perceived continuity of value
Strategic mapping
The strategy then shaped into three different enhancements, which were then prioritized based on level of effort and roadmap blocking: 1. Freelancer hub, 2. Social proof messaging and 3. Streamline upgrade flow.
→ Freelancer Plus hub: a single destination for FAQs, benefit inventory, and more to increase subscriber activation and engagement and strengthen renewal intent.
→ Social proof messaging: Elevate the Freelancer subscription comparison experience by making the value of Plus tangible through quantified impact and social proof to improve conversion materially.
→ Streamline upgrade flow: Test a lightweight Freelancer Plus upgrade modal that surfaces plan benefits directly in the user’s flow instead of redirecting to a separate page, which reduces decision friction and helps prevent drop-off at a high-intent conversion moment.
Design Execution
The design exploration focused on surfacing membership value through contextual, actionable experiences across the user journey rather than limiting benefit communication to the membership plan page alone. The goal was to reinforce value for existing Freelancer Plus members while creating clearer upgrade motivation for users who would benefit from the membership. The enhancements delivered either positive or neutral improvements, which led the team to decide and release to 100% of users given the impact these enhancement have for Freelancer Plus member experiences coming in the roadmap
Freelancer Plus Hub
The primary objective was to communicate membership benefits in a clear, actionable way that directly reflected user value while maintaining consistency with the product’s brand experience. I structured and prioritized benefits based on actual usage patterns from active Freelancer Plus members, ensuring the hierarchy reflected real engagement rather than assumed value.
Test results: Neutral results (No harm)
Decision: Release to 100% users
Social proof messaging
To build trust and strengthen conversion confidence, I incorporated social proof through freelancer success metrics and testimonials. To manage cognitive load and avoid disrupting an already high-performing revenue surface, this content was added as a secondary layer beneath the existing page, reinforcing value without significantly altering the core experience.
Test results:
Upgrades increased by 3% ∣ Downgrades reduced by 1.9%
Decision: Release to 100% users
Streamline upgrade flow
I designed a modal-based upgrade experience instead of redirecting users to a separate page to preserve contextual continuity at the moment of intent. This approach aligned with user mental models by keeping them within their current flow while still providing access to supporting information. The experience prioritized high-impact conversion elements—key benefits and social proof—while maintaining optional pathways to deeper details from the original design.
Testing plan: Testing to be released in Q2 2026
Reflection
My role
As Lead Designer, I owned the UX strategy for the Freelancer Plus experience, shaping how membership value, upgrades, and cancellations were communicated across key surfaces. My role focused on translating business goals and user insights into a cohesive experience that improved retention, increased upgrades, and reduced churn while maintaining clarity and trust across the journey.
My responsibilities
→ Owned the end-to-end UX strategy for the Freelancer Plus experience, aligning it with business goals around retention, upgrades, and cancellations
→ Defined the structure of key surfaces, including the membership hub, upgrade flow, and cancellation experience
→ Translated user behavior and product data into clear UX decisions around hierarchy, messaging, and feature prioritization
→ Led interaction design decisions, including the use of modal vs. page patterns to preserve context and reduce friction
→ Integrated social proof and benefit communication to increase perceived value and trust
→ Aligned cross-functional teams around a unified experience vision while balancing conversion goals with usability and user trust
Learnings
In hindsight, I would have introduced a Freelancer Plus rebranding earlier in the release sequence to more clearly differentiate the membership and strengthen users’ emotional connection to its exclusive benefits. This would have helped elevate the perceived value and make the product’s advantages more immediately recognizable.
Given the limited timeline and constrained resources, I would also have leveraged more AI tools to improve execution efficiency, particularly for accelerating documentation and reducing operational overhead.