Visibility & Planning - Pilot Program
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Due to a Non-Disclosure Agreements, the information on this project is limited. The “Automatic Offer Withdrawal” project was part of Upwork’s broader Project Harmony initiative, aimed at optimizing the hiring flow for both clients and freelancers. This project focused on simplifying the decision-making process for clients, particularly in preventing unintended offer withdrawals when they closed a job post. The goal was to create a more informed and seamless hiring experience, improving visibility and clarity during the contract and offer acceptance stages. By introducing a NEW “Hire/No Hire” interface, we ensured clients could make clearer, more intentional hiring decisions, which ultimately benefitted both enterprises and small businesses using the platform.
The core challenge of this project stemmed from the ambiguity in the offer withdrawal process. Hiring managers were often unaware that closing a job post would automatically trigger the withdrawal of all pending offers. This lack of visibility caused unintended cancellations, leading to delays and confusion in the hiring process. Additionally, the absence of a clear guide on the hiring page meant that clients were frequently making incomplete hiring decisions, which impacted the efficiency of the hiring flow.
Core Areas Addressed:
Scenario 1: No Pending Offers
When clients viewed the “Hire/No Hire” page and there were no other pending offers, the interface was designed to streamline the decision, ensuring the process was clear and concise.
Scenario 2: Pending Offers Present
When clients saw the “Hire/No Hire” page with other pending offers, we introduced clearer communication and options to prevent unintentional offer withdrawals, allowing clients to make a more informed decision without disrupting the hiring process.
Creating a dedicated “Hire/No Hire” decision point with contextual information at the end of the hiring journey will reduce unintended offer withdrawals, improve user experience, and lead to higher offer acceptance rates.
Led the design and alignment of new contract and hiring flows within the Payments Business Unit, ensuring integration with product vision and user needs.
Drove ideation, stakeholder alignment, and cross-functional collaboration, overseeing design reviews and coordinating efforts across engineering, product, and research teams.
Key contributors included product managers, senior product designers, principal product designer, senior researcher, senior data analytics partner, UX Director, lead engineer, senior director of engineering, and GM of Product for Payments.
Approvers and decision-makers within the DACI framework included the product director, senior director of engineering, and other senior leadership team members.
The project followed Upwork’s Amazon-inspired PDLC, with key stages including Define (identifying user pain points and solutions), Plan (collaborating on requirements and wireframes), Build (design implementation with engineering), and Launch (supporting readiness reviews and user acceptance testing).
Each stage ensured effective planning, collaboration, and execution for a seamless product launch.
Skills: Product design, user research, UX strategy, and stakeholder management.
Tools: Figma, JIRA, Slack, Confluence
Upwork’s UX organization was extensive, especially within my Payments BU, where I supported essential client-freelancer products.
Leading the design team, I drove alignment with product leadership to balance user needs with business goals, delivering intuitive, user-centered solutions across a broad scope.
As the Product Design Manager in the Payments Business Unit, I fostered collaboration between Product Design, Product Management, and Engineering through a triad model that unified diverse perspectives. By grounding decisions in user research, data, and market trends, I ensured our solutions addressed user pain points while aligning with business objectives.
This integrated approach streamlined workflows, empowered data-driven decisions, and enabled the delivery of innovative designs that enhanced the client-freelancer experience and supported Upwork’s strategic goals.
Guided the design team to align user-focused solutions with business goals in a fast-paced environment.
Worked with cross-functional teams to deliver data-driven, user-centered designs informed by market trends.
Early CL
decision making
Lack of
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CL/FL
match decline
In this phase of the project, I drove alignment with product leaders to address critical issues impacting both clients and freelancers in the hiring process. The focus was on improving decision-making, matching clarity, and providing clear information to avoid unnecessary actions and confusion. Below are the key areas identified:
Early client decision making – Hiring managers must decide if they’re done hiring without knowing if the freelancer will accept the offer.
The collaboration with the larger triad teams was essential here. The Payments and Marketplace Growth teams brought invaluable insights into the business objectives, while our UX research team provided critical user feedback. Working closely with product leadership, I helped ensure that our design decisions remained in alignment with forecast metrics and strategic goals, always keeping the user at the center.
To address the decline in the 28-day Contract Start Rate, we took a targeted approach to uncover and resolve friction points in the work management experience.
By aligning design and product solutions with long-term business objectives, we crafted a strategic roadmap to improve contract start rates, reduce offer expiry churn, and deliver measurable impact.
The UX Capacity Tracker was instrumental in this effort, enabling us to streamline resources for Harmony initiatives. By identifying bottlenecks and managing workloads transparently, we ensured a focused approach to high-impact areas while fostering clear communication across cross-functional teams and aligning with overarching goals.
Trusting the process was fundamental to the success of the project. Coming off a team architecture discussion, we reaffirmed our commitment to the Amazon-inspired PDLC framework, which prioritized working backwards from the customer’s needs. By defining the problem first, we ensured that our solutions would be laser-focused on user pain points.
From a leadership standpoint, I co-wrote the Product Requirements Document (PRD) with product management and the core team, ensuring that every design decision was backed by user insights and business goals. This was critical in maintaining clarity and focus throughout the design phase, as we were constantly iterating and adjusting based on new findings.
Image: Offer Decline Flow
Our approach to brainstorming sessions and user journey mapping went beyond discussions, incorporating detailed visual aids like user flow diagrams and acceptance metrics. For example, the Offer Decline Flow diagram was instrumental in pinpointing critical moments where users disengaged, allowing the team to focus on high-impact areas for improvement. Additionally, tracking the 7-day offer acceptance rate provided a clear metric to measure progress and align our efforts with measurable outcomes. These metrics acted as guideposts, ensuring every decision we made was grounded in tangible, results-oriented data.
To further refine our understanding, we facilitated workshops that encouraged cross-functional teams to collaborate on solving user pain points. This cross-pollination of ideas from product management, engineering, and research ensured that our solutions were both innovative and feasible within technical and business constraints.
By iteratively testing and refining these solutions, we were able to identify specific interventions, such as clearer offer status visibility and streamlined communication flows. These efforts were bolstered by ongoing validation through user research, ensuring that each enhancement directly addressed the needs of clients and freelancers. As a result, the project not only improved acceptance rates but also strengthened overall platform trust and usability.
Image: 7 day offer acceptance rate
Weekly rituals focused on creativity and discovery helped integrate research insights into design sprints.
We embraced innovation, leveraging AI and automation to streamline user interactions across devices. Alongside these efforts, I prioritized upskilling the team through workshops and collaboration, fostering growth and cross-functional expertise.
Through this research, we identified critical pain points, including inefficiencies in the offer acceptance process and a lack of transparency in offer statuses. These insights informed the creation of impactful features and streamlined processes that aligned with both user expectations and business objectives. By fostering collaboration and providing clarity to stakeholders, the research plan became a cornerstone for driving product enhancements and improving overall user satisfaction.
By analyzing the user experience, we identified the root causes of these challenges, such as unnecessary invitations and disjointed transitions from closed contracts to rescinded offers. Collaborating with product managers, we prioritized addressing the most impactful pain points, focusing on reducing inefficiencies and enhancing the overall workflow. This approach ensured our solutions were targeted, actionable, and delivered measurable improvements to the user experience.
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A pivotal moment in the project was defining the new product direction. We focused on three main areas: the Message Room, the “New” Hire/No Hire Page, and Notifications (SMF & Emails). These areas were critical in shaping the user experience and needed to be thoroughly mapped out in Miro to visualize the new flows.
Create better automation to streamline conversations by redesigning the Message Room as a centralized hub for contract-related actions and discussions.
Change the location and layout of the page to provide clear, actionable insights that help clients confidently make hiring decisions.
Create timely, relevant, and personalized notifications to keep users informed, engaged, and empowered seamlessly across channels.
Working closely with Engineering and Architecture teams, we collaborated to establish a new foundational user flow. This effort involved rethinking the system architecture to support these enhanced experiences while aligning with long-term platform goals. Weekly rituals in Miro allowed us to iterate quickly, ensuring all cross-functional insights were captured and integrated into the evolving designs.
We also incorporated recommendations from the UX Research team, ensuring that our plans were data-driven and user-focused. These inputs informed our approach to refining the flows, making them intuitive and accessible for both clients and freelancers. This process included exploring innovative solutions for improving key pain points identified in user feedback.
Image: A streamlined architectural map of the new user journey flow.
By breaking down each of these areas, we ensured that the user journey was not only seamless but also deeply aligned with user needs. The ultimate goal was to refine and iterate on these critical components, providing clarity, enhancing communication, and significantly improving the overall platform experience.
As we transitioned into the Build phase, it became clear that iteration and testing were key to refining the design. We held regular design and interaction reviews, using feedback loops to refine and adjust the experience.
Empowering the team to lead these reviews and clearly communicate the changes helped us improve the product in real time. The focus during this phase was on closing communication gaps and reducing friction, especially during the proposal and offer acceptance stages.
Hie/No Hire Page
Message Room
SMF's
Image: The new design showcases a streamlined flow for managing offer statuses within the platform: Expose, Elaborate, Educate, and Expand.
Display a clear indicator that provides an overview of all pending offers, allowing clients to quickly assess and take action on any outstanding offers with a seamless user experience.
An intuitive section that ensures clients can confidently confirm that all hiring decisions have been made, providing clarity and reducing any uncertainty about the status of the hiring process.
Clear communication will be provided to both parties, ensuring they are notified when an offer or opportunity is withdrawn, enhancing clarity and preventing misunderstandings.
Throughout the Build phase, we engaged with leadership to review non-happy paths in the user journey. These reviews were essential in refining features and ensuring we were addressing edge cases that could impact the overall experience.
In collaboration with the engineering team, we introduced enhanced logic, endpoints, and filters to streamline the user experience, ensuring a seamless and intuitive flow—especially for the automatic offer withdrawal feature as part of the Harmony Phase initiative rollout.
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Our initial focus was to refine the architecture and improve the location of the Hire/No-Hire page, ensuring a seamless decision-making process for clients. This meant rethinking how and when this page was presented in the user journey to better support informed hiring decisions.
By optimizing its placement and enhancing its clarity, we aimed to eliminate confusion and streamline the decision-making process. This refinement also included improving communication strategies between clients and freelancers, ensuring offer statuses were transparently conveyed.
Image: Original user flow, highlighting the initial focus on refining the Hire/No-Hire page’s placement to support seamless decision-making and improve communication between clients and freelancers.
Image: Revised location of the Hire/No-Hire page, highlighting how we expanded on customer feedback to Educate, Expose, Elaborate, and Expand the experience.
As we progressed through the product development cycle, each round of feedback from approvers and our broader UX team informed the new direction. We meticulously iterated on the Hire/No-Hire experience, focusing on creating a more natural flow.
This iterative approach allowed us to integrate feedback into every detail, ensuring that each refinement aligned with user needs and operational goals.
For example, we removed the Hire/No-Hire page at the “Red Dot” point in the journey, enabling a smoother transition from freelancer acceptance to client decision-making. By improving communication touch points across SMF, Email, and the Message Room, we ensured that all stakeholders remained informed at every step.
Image: The final design embodies a user-centered, intuitive solution achieved through strategic alignment, cross-functional collaboration, and iterative refinement.
As the product evolved, my leadership was pivotal in driving strategic alignment, guiding cross-functional teams, and ensuring the refinement process adhered to user-centric principles. Through collaboration with product leaders, engineers, and architects, I championed a clear vision that balanced innovation with operational feasibility. The final design reflected a culmination of this leadership, delivering a cohesive and intuitive experience that addressed the pain points identified early on.
Before diving into the metrics and wins, it’s worth noting that this journey exemplified the power of iterative design and collaborative leadership in achieving meaningful improvements.
This project reinforced the importance of detailed documentation and organization throughout the PDLC. From planning and defining to building and launching, I ensured that key documents like Architecture Design Docs, UX Brief Decks, and Resource Capacity trackers were well-organized and easily accessible.
I am deeply thankful for the team’s dedication to owning their destiny, playing to win as a cohesive unit, and sweating the details to get every aspect right. By fostering collaboration, empowering ownership, and embracing iteration, we turned a critical problem into a remarkable success. The improvements in contract start rates and user satisfaction highlighted the power of user-centered design to drive meaningful business outcomes.
