Overview

The Investment Memo project was designed to accelerate lead preparation for transaction associates and streamline acquisition decision-making for C-suite executives at Teamshares, enabling smarter acquisitions and scaling investment impact.

• Streamline Information Extraction: Automate data extraction to reduce manual labor, minimize errors, and increase efficiency.

• Capture Red Flags and Risks: Equip users to flag potential risks early and monitor key issues throughout the acquisition process.

• Enhance Decision-Making: Present critical insights in a structured, accessible format to facilitate faster, more informed decisions.

• Establish a Source of Truth: Create a centralized, authoritative document that serves as a reliable reference for all SMB acquisition decisions.

Problem Statement

Transaction associates spent too much time collecting scattered information, highlighting the need for a centralized solution that enables executives to efficiently review more leads during investment meetings and acquire high-performing businesses with reduced risk.

Design Process

Research and Brainstorming

To ensure the Investment Memo met user needs, I conducted 1:1 research with C-suite executives and transaction associates, integrating their feedback throughout the design process. Collaborating with the Product Manager and Lead Engineer, we focused on two key areas for AI-driven extraction: critical information from CIMs and insights from owner call notes, optimizing each for accuracy. We also identified essential data points for associates to emphasize in IC meetings, guiding the rapid design of the initial Investment Memo iteration and fostering alignment between teams.

Explorations and Iterations

I led rapid design ideation on compiling extracted data into the Investment Memo, ensuring transaction associates could edit and refine drafts before finalizing the document as the definitive source of truth. I conducted user feedback sessions with executives and associates to identify improvement areas, particularly in the presentation of extracted information, which guided refinements to enhance both user experience and accuracy.

Design Solution

I implemented key enhancements to improve the Investment Memo's functionality and usability:

• Data Comparison & Editing: Enabled associates to view, compare, and refine extracted data from CIMs and owner call notes, ensuring accuracy.

• Red Flag Management & Notifications: Enhanced the interface for flagging and tracking critical issues, with seamless Slack notifications to keep downstream teams promptly informed.

• Funnel Stages: Clearly defined each acquisition stage within the memo, improving transparency throughout the process.

Outcomes

The Investment Memo reduced lead preparation time by 33%, saving associates 3 hours daily and enabling C-suite leaders to review 10-15 leads per meeting. This efficiency supported a strategic shift in investment range from $2–$8 million to $10–$25 million, enabling larger, high-impact acquisitions and more informed, profitable decisions.

Personal Reflection

One of the primary design challenges I faced was aligning the team's priorities around data extraction accuracy while ensuring transaction associates retained the flexibility to manually adjust data as needed. After conducting user testing, I facilitated discussions with the product manager and engineers to find the right balance between automation and manual control. This approach was essential for maintaining the accuracy of the AI-driven data extraction while ensuring the tool remained user-friendly and accurate to their daily workflow.