Evolving an AI-powered contract manager

Transforming a file repository into an intelligent contract management tool

Image of desktop mockups showing contract manager project

The original contract manager was little more than a file repository—scattered, unstructured, and lacking contract intelligence. I led the UX redesign, transforming it into a structured, AI-powered contract management system. The new design introduced intelligent file grouping, surfaced key insights, and significantly improved usability. Additionally, new features like a chatbot and an Outlook plugin streamlined workflows, driving higher engagement and increasing contract uploads.

Type

Redesign

Timing

March – September 2024

Tools

Figma

Team

1 UX designer
1 product manager
1 engineering lead, 6 engineers

Problem

The original system was initially built as a simple file repository, intended to evolve into a contract management tool over time. Developed in an iterative fashion due to time and resource constraints, the system lacked structured design involvement.

While AI learning was happening as files were gathered, the data team was also labeling the files to help the system better understand contracts, gradually improving its training. However, without a proper design process, the system faced usability and functionality issues, making it difficult for users to derive meaningful value from the loose contract files.

Lack of actual contracts: The system stored individual files with no way to group or manage them as structured contracts.

Poor usability: Inconsistent UI, broken components, unclear hierarchy, and rushed styling caused major usability issues and frustrating navigation.

Confusing terminology: “Contracts" and "files" were inconsistently defined in both the UI and back-end, leading to user confusion and technical issues.

Annotated screenshots of existing product showing areas of improvement

Goals

1. Automatically group related files into structured contracts for better organization.

2. Improve usability to create an intuitive and effortless user experience, addressing key pain points.

3. Standardize terminology between "contracts" and "files" to eliminate confusion and ensure consistency.

4. Introduce a chatbot for contract insights and a plugin for easy file integration.

Role

As the lead UX designer, I drove the end-to-end redesign, defining strategy, leading design execution, and ensuring cross-functional alignment. Collaborating closely with product and engineering leads, I transformed user needs and business goals into a streamlined, AI-powered contract management experience. I guided technical feasibility discussions and advocated for scalable, user-centric solutions. I designed both the front-end UI and optimized back-end tools used by the operations team for "human in the loop" governance of AI-generated, mission-critical information.

Additionally, I partnered with another product manager and engineering team on features like a Microsoft Office plugin for importing contract files from Outlook and a chatbot for contract-related questions. This chatbot represents the first unsupervised AI assistant in the public parent company's product suite. I designed all key screens, including the main landing page, side drawers for detailed file and contract views, and dialogs for uploading contracts.

Key Responsibilities: Heuristic Evaluation, Stakeholder Interviews, Brainstorming, Wireframes, Mockups and Prototypes, Design Handoff

Process

A structured, iterative design process focused on usability improvements, AI enhancements, and aligning the product with user needs. Defining the relationship between contracts and files was challenging due to the original product’s development.

By stepping back and evaluating the structure from all angles, we were able to identify the best approach.

Visual showing the project process broken into phase 1, “understand the problem” (kickoff, heuristic evaluation, stakeholder interviews, and brainstorming) and phase 2, “explore solutions” (wireframes, design and feedback and iterations)

Research

I began with a heuristic evaluation of the existing product to identify usability issues and uncover any additional bugs or concerns. The research mainly came from discussions with stakeholders and feedback from customer success meetings with clients.

This helped pinpoint pain points and uncover opportunities for improvement. Since direct access to users was limited in this industry, we relied on customer success as the voice of the customer, gathering insights from their ongoing interactions.

Key Insights

Contracts often contain multiple files with conflicting expiration dates, making it unclear which date takes precedence.

Users struggled to track contract changes, particularly identifying term modifications from amendments or addendums.

Contract data overlapped with spend data, highlighting the need for a platform-wide strategy.

Ideation

The product team had previously created wireframes to explore how contracts could be displayed in the UI. However, we took a step back and ideated from scratch to define the hierarchy of contract sets and files, ensuring a clear structure. I collaborated with product and engineering leads to brainstorm how contracts and files should be organized, including the technical considerations for how they are defined in the code.

Visual of diagram and whiteboard going back to the basics. Reevaluating the fundamental difference between a contract and a file helped us establish a clear hierarchy from the ground up.

Design

I explored various ways to structure the relationship between contracts and files, using wireframes to visualize potential solutions. Initially, I considered restructuring the product to center entirely on contracts, but after evaluating feasibility, I realized this approach wouldn’t work. Using stakeholder feedback, I refined the designs to support both a contract view and a file view, ensuring users had the flexibility they needed.

To align early on feasibility, I developed wireframes for all critical screens and shared them with the engineering team for input. This proactive collaboration helped surface potential challenges early, allowing me to refine the concept before moving into high-fidelity designs.

Design Considerations

Core Sections

Solution

The redesigned contract manager tackled key challenges by enhancing organization and delivering intelligent insights. It replaced scattered files with structured agreements and introduced dual views for contracts and files, transforming contract management. These changes enabled easier navigation between the two views, displaying relevant information for each and providing clearer context.

A consistent structure across the interface ensured critical details were always accessible, reducing the need for excessive searching and improving usability. The Outlook plugin streamlined the file import process, while the chatbot gave users an intuitive way to access key contract insights.

Overall, the streamlined UI resolved previous inconsistencies, making the system more user-friendly. Moving forward, these enhancements set the foundation for a more cohesive and scalable tool, with future iterations continuing to refine the experience.

Design mockups. Structured agreements with dual views for contracts and files: Contracts shifted from scattered files to structured agreements, while dual views made it easier to navigate, compare, and manage contract data. Resolves the issue of the lack of actual contracts and accomplishes the goal of automatically grouping related files into structured contracts.

Design mockups. Improved usability for a streamlined and intuitive UX: The streamlined UI and consistent structure resolved issues like broken components and unclear hierarchy, improving usability and efficiency. Resolves the issue of poor usability and accomplishes the goal of improving usability.

Design mockups. Standardized terminology between contracts and files: By distinguishing contracts from files and aligning terminology, the UI became more intuitive, reducing confusion and improving user comprehension. Resolves the issue of confusing terminology and accomplishes the goal of standard terminology between “contracts” and “files”.

Design mockups. Chatbot for contract insights and Outlook plugin for file integration: The Outlook plugin simplifies file imports, while the chatbot provides quick access to contract insights, enhancing contract management and UX. Contributes towards the lack of actual contracts and accomplishes the goal of introducing a chatbot and plugin.

Results

+60% product adoption rate among existing customers, demonstrating improved contract workflows and user engagement.

Revenue-generating in 8 months: Processing thousands of healthcare contracts and driving business growth.

Expanded AI-driven features: Including a chatbot for instant contract insights and an Outlook plugin for seamless file imports.

Lessons Learned

Cross-team alignment is key: Early collaboration with engineering helped cut miscommunication, inefficiencies, and delays.

Strong UX advocacy drives impact: Challenging previous poor design choices was essential to creating a usable, scalable solution.

Standard terminology ensures clarity: Defining precise language upfront saves time and avoids redesign headaches down the road.

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