Overview

Legal Checklist is a task management tool designed to optimize the closing process for our legal team during acquisitions. I led the end-to-end design, driving the overall strategy, design decisions, and cross-functional collaboration with a product manager, engineering lead, three engineers, and the legal team to deliver a solution that led to 100% adoption for every closing company and significantly improved their workflow.

The checklist system provides an intuitive, structured way for the legal team to track tasks and monitor progress at each stage of the closing process. By working closely with the product manager, I facilitated the breakdown of this feature into manageable milestones, incorporating feedback from the engineering lead to prioritize the MVP version and iterate based on early feedback.

Since its launch, the Legal Checklist has been fully adopted by the legal team (2 lawyers and 1 paralegal), leading to a more efficient and streamlined closing process. The implementation of this feature has resulted in a 70% reduction in manual updates and achieved a 5.0 user satisfaction score* based on survey results. By facilitating collaborative strategy sessions with cross-functional teams, I ensured that our design decisions were aligned with business objectives and user needs.

Problem Statement

As Teamshares expanded its portfolio of SMBs, the legal team faced challenges in managing tasks and tracking progress during the acquisition process. While team members were aware of their assigned leads, their individual task management approaches resulted in confusion and collaboration inefficiencies.

This lack of visibility caused delays, particularly during complex transactions, as manual updates to C-suite executives became necessary. The absence of a unified task management system led to bottlenecks, jeopardizing our goal of closing portfolio companies within 90 days. To enable a more scalable closing process, streamlining task management was critical for enhancing our EBITDA and steering Teamshares toward profitability.

Goals and Objectives

• Task Tracking: Create a checklist that lets the legal team easily track task progress, showing what's completed and what remains for the acquisition process.

• Unified Task Management: Standardize task management across the legal team to reduce confusion, improve collaboration, and increase efficiency.

• Visibility and Transparency: Provide task visibility for the legal team, while keeping C-suite executives and other relevant stakeholders informed on progress.

• Collaboration and Communication: Enable the legal team to leave comments and discuss tasks directly within the checklist, promoting collaboration and keeping a clear record for future use.

Design Process

Research and User Testing

To ensure the Legal Checklist met user needs, I collaborated with the product manager to conduct in-depth research, including interviews with the legal team and other stakeholders in the closing process. We gathered feedback throughout the design process, using it to refine the interface and improve functionality.

During our research, we found that some team members, including the paralegal, were using an existing task feature to track to-dos as deals progressed. However, this system didn’t fully address the legal team’s specific requirements. They needed a dedicated tool that supported their unique workflow, which the current feature lacked. This discovery informed the design of the Legal Checklist, tailoring it to the legal team’s needs.

Explorations and Iterations

I led the design for the Legal Checklist, integrating it within the closing dashboard to ensure it was easily accessible for the legal team. Collaborating with the product manager, we compiled a consistent set of checklist items that the legal team needed to complete for each closing, grouping them into pre-closing, post-closing, and miscellaneous tasks.

Throughout the design process, I conducted user feedback and testing sessions with the legal team to identify areas for improvement. Feedback included comments such as, “Having everything in one place makes it easier to track progress” and “The ability to leave comments keeps communication streamlined.” This information helped us refine the checklist's presentation, ensuring flexibility for users to add or modify tasks and incorporating the ability to leave comments and tag specific team members directly within the checklist.

Improvements

Based on user feedback and testing, I introduced several key enhancements:

• Fixed Checklist Placement: I ensured that completed items stayed in their respective sections (pre-closing, post-closing, or miscellaneous) for easy reference and tracking upon completion.

• Editable Line Items: The legal team are able to edit checklist item names to reflect any changes in the closing process, improving accuracy and flexibility.

• Introducing sub tasks: I collaborated with the lead engineer to design and implement subtasks within checklist items, ensuring the solution was optimized for our existing database infrastructure.

• Custom Checklist Items: Users could now add new checklist items and assign them to specific sections or parent tasks, providing flexibility for different stages of the closing process.

• Commenting and Collaboration: I created a drawer interface for checklist items that allows users to comment and tag other Buyout users, triggering Slack notifications for quicker follow-ups.

Challenges

One of the primary challenges was designing the Legal Checklist in the context of an existing task feature within Buyout. To expedite the design process, I chose to leverage familiar UI elements that users already understood while introducing functionalities tailored specifically to the legal team's needs.

As the design lead, I opted to align the Legal Checklist with the existing task feature, enhancing its usability for the legal team. This involved leading discussions with the product manager and engineers to advocate for the integration of subtasks, enabling precise tracking of legal tasks and ensuring all team members could monitor progress seamlessly through Slack.

This strategic decision was crucial for achieving 100% adoption of the Legal Checklist by our legal team and reducing manual updates by 70%, directly contributing to an increase in Teamshares' EBITDA and supporting the company's path to profitability.

Conclusion

The Legal Checklist significantly improved the efficiency and transparency of the closing process for Teamshares' legal team. By closely collaborating with cross-functional teams and keeping the users’ needs at the forefront, I delivered a solution that achieved 100% adoption, 70% reduction in manual updates, and a 5.0 user satisfaction score*. The enhancements I introduced, such as custom checklist items, subtasks, and Slack integration, not only streamlined the legal workflow but also ensured greater visibility for C-suite executives, ultimately contributing to Teamshares’ goal of improving profitability.

Personal Reflection

One of the biggest takeaways was working within the constraints of the existing infrastructure while introducing new functionality. This taught me the value of balancing innovation with practicality—sometimes, the best solutions come from building on what already works and refining it based on user needs.