Rejigg2025 – Present
Designing an AI-guided marketplace for buying and selling small businesses
I lead product design for Rejigg, an AI-powered marketplace that helps first-time entrepreneurs discover, evaluate, and acquire small businesses. I established the product's experience model, design system, and AI interaction patterns, creating a scalable foundation for a complex, high-trust transaction.
Role
Founding Product Designer
Timeline
12 months
Scope
Marketplace and deal-management platform
Target
Make small-business acquisition understandable and accessible for first-time buyers, while simplifying the sale process for business owners
The Challenge
Buying or selling a business is a lot like dating. Both sides need to understand what they want, where they align, and where friction may emerge.
Rejigg uses responses from buyer and seller onboarding questionnaires to score compatibility across six weighted pillars, including timing, industry experience, financing structure, and cultural fit. The resulting profile highlights motivation alignment, potential negotiation points, and areas of strongest agreement, giving both parties greater clarity before beginning a conversation.
The compatibility categories and their weighting were informed by recurring themes identified in onboarding conversations between sellers and Rejigg's inside sales representatives.
The Opportunity
Traditional marketplaces can identify businesses that match a buyer's preferred industry, location, size, or price. But completing a successful acquisition also depends on whether the buyer's capabilities, financing, timing, and plans align with the seller's expectations.
Rejigg needed to move beyond listing search and help both parties understand whether they were prepared to pursue a deal together.
OUTCOME
A scalable marketplace and deal-assistance foundation
Established the design system, compatibility model, AI-guided discovery, and interaction patterns connecting business search, evaluation, and deal coordination.
Traditional E-Commerce Meets AI
Rejigg retains the familiar structure of an e-commerce marketplace while adding AI-guided discovery. Buyers begin by describing their ideal business in natural language. Rejigg interprets that description and automatically converts it into relevant search terms and filters, turning a broad acquisition goal into a focused set of opportunities.
Establishing Compatibility
Buying or selling a business is a lot like dating. Both sides need to understand what they want, where they align, and where friction may emerge.
Rejigg uses responses from buyer and seller onboarding questionnaires to score compatibility across six weighted pillars, including timing, industry experience, financing structure, and cultural fit. The resulting profile highlights motivation alignment, potential negotiation points, and areas of strongest agreement, giving both parties greater clarity before beginning a conversation.
The compatibility categories and their weighting were informed by recurring themes identified in onboarding conversations between sellers and Rejigg's inside sales representatives.
Rejigg Deal Assistant
Rejigg is designed to replace the traditional broker's role by providing the guidance and coordination needed to move a deal forward. The Deal Assistant identifies next steps, surfaces missing information, summarizes activity, and recommends actions while keeping buyers and sellers in control.
It presents action cards in response to partner activity, newly identified deal information, and key milestones. Signals can come from messages, uploaded documents, emails with Rejigg representatives, and video meetings conducted through the platform.
Interaction Model
The Deal Assistant is available from both Messaging and the global navigation. When it suggests an action, the interface considers the action's complexity. Whenever possible, the action opens in a right-hand drawer, allowing the user to complete it without leaving the Deal Assistant.
The long-term product goal is to enable buyers and sellers to complete every deal-related task directly from the Deal Assistant.
Establishing Trust in AI
When the Deal Assistant identifies new information in a conversation, it presents a review card summarizing the finding. Users can accept it, correct or ignore it, or select View source to display the supporting information in the right-hand panel.
This gives users control over what is added to their profile and deal record, which is especially important when that information may inform legally binding documents.
Making Diligence Manageable
Having bought and sold a business, I understood how endless the diligence process can feel from both perspectives. Buyers, sellers, and even brokers can seem as though they are navigating the process for the first time.
To create a clearer path forward, I worked with an M&A specialist to identify the core documents common to most transactions.
We organized them around three milestones:
- Completing the Business Profile
- Building the Confidential Information Memorandum, which Rejigg calls the Confidential Deal Overview
- Completing due diligence
The interface presents these milestones as three columns, creating a document roadmap through the transaction. Each column tracks what is required and provides a call to action for viewing the document or deliverable being assembled.
The Confidential Deal Overview and Diligence Report serve two important purposes:
First, AI analyzes information from uploaded files and organizes it into a structured document that is easier to review and reference.
Second, each artifact can be downloaded and printed, supporting sellers who prefer to review, share, or retain important deal materials outside the platform.
Reflection
Designing Rejigg reinforced that AI is most valuable when it reduces uncertainty without removing human judgment. Buyers and sellers need help understanding what matters, what comes next, and why the product is making a recommendation.
The challenge was not simply digitizing an acquisition process. It was creating a product model that made a high-stakes, unfamiliar transaction feel structured, transparent, and manageable while preserving the agency of everyone involved.
