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Matt - Principal Product Designer & Leader

uxmatthew@gmail.com

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06·Private Investment Platform·Shipped

How do you turn a 40-page complex contract into something anyone can complete?

Private fund subscriptions require a complex legal document filled with conditional regulatory language. I reorganized it from scratch, and collaborated with the team to design and deliver.

Role: Product DesignerDuration: 1 quarterTeam: PM, Product Designer, 2 Front-end Engineers

Advisor feedback

"Best contract ever"

Subscription document overview screen showing eight labeled sections with status indicators, a Generate DocuSign Docs button, and a heads-up panel with guidance.

Problem

Private fund subscriptions require completing a 40+ page legal document filled with conditional regulatory language, repeated questions, and dense legal references. The users were advisors in small practices managing the process for their clients with no prior experience completing such documents. The task was to turn it into something lightweight and clear.

The constraint

Every question in the original document exists for a legal reason. The challenge was not to simplify the contract itself, but to find a better structure beneath it: one that matched how users think rather than how regulators write.

Thumbnail grid of all 40+ pages of the original subscription document, showing the sheer volume of content advisors were expected to navigate.

I started by printing the entire contract and physically cutting it apart. Every question became a separate slip of paper. I then used affinity diagramming to group related questions by topic, clipping them together and organizing them into folders by logical section.

Two things became clear immediately. First, the document's structure was driven by regulatory organization, not user logic; the same information was requested multiple times in different formats across different sections. Second, the investor's entity type (individual vs. business, trust, or IRA) determined roughly half the questions. An individual investor would never need to answer most of what the entity path required.

Physical analysis

Cutting the contract apart by hand made patterns visible that would have been easy to miss in a PDF. Redundant questions clustered together; topic groups emerged naturally. The physical process turned a 40-page problem into a manageable information architecture.

Physical affinity diagramming session with highlighted and cut-out contract questions spread across a table, grouped by topic with paper clips and sticky notes.
Pathway diagram showing two tracks branching by entity type, with shared sections at the start and end and distinct middle sections for Entity and Individual investors.

Two paths, one framework

Identifying entity type upfront let us eliminate roughly half the questions for individual investors before they had answered a single thing. Both paths shared the same section names and structure; only the content inside differed. This kept the experience consistent while dramatically reducing scope for the most common case.

Consolidating questions

The document asked for the same information multiple times in slightly different forms for legal reasons. Where possible, we consolidated these into a single question with smart conditional follow-ups: answer once, and the form only showed the next question if the answer made it relevant. This reduced the perceived length without removing any required information.

Conditional logic in practice

Each answer triggered only the follow-ups it warranted. A question that previously appeared three times in different sections became one question with two possible follow-ups, shown only when needed. The form felt responsive rather than exhaustive.

Form screen asking for the entity name with conditional follow-up fields revealed inline based on Yes and No answers about tax return names and business name distinctions.
Investment Documents step showing Investor Profile with four sub-tabs for Purchaser Status, Client Status, Accredited Status, and Advisor Status, each presenting accreditation options as clear selectable cards.

Organizing complex accreditation

Accreditation status was one of the most legally dense sections. Rather than presenting every option as a wall of text, we organized them into four distinct sub-steps with clear selectable cards. Dense regulatory language was preserved but given structure, making it scannable without obscuring what mattered legally.

question we faced

Should progress be shown as a persistent bar or an overview screen?

Options we considered

  • Persistent progress bar

    Familiar pattern, but hard to render accurately across branching entity paths, and it offers no way to jump between sections.

  • Overview screen

    Shows all sections at once, allows non-linear navigation, and was more feasible to build for the MVP timeline.

What we chose and why

An engineer suggested the overview screen, and we ran with it. Advisors could see the full scope upfront, jump to any section, and resume where they left off. It solved the progress and navigation problems in one move.

What we learned

Good ideas come from anywhere. The engineer's suggestion resolved a design problem I had been circling, and produced a better result than a progress bar would have.

The overview screen

The final overview showed all eight sections with numbered status indicators, a two-column layout for quick scanning, and a persistent heads-up panel explaining what to expect. Advisors could start anywhere and return to any section. When all sections were complete, the Generate DocuSign Docs button became active.

Final overview screen titled 'Time to generate the official documents' showing eight numbered sections in a two-column grid with status indicators and a Generate DocuSign Docs button.
Section review screen showing a green checkmark, a 'This section is complete' confirmation, and a full summary of entered data with inline edit links.

Section review

At the end of each section, advisors saw a full summary of their answers with inline edit links before moving on. This gave them confidence in their input and made corrections easy, without requiring them to navigate back through the questions.

What shipped

A complete 0→1 subscription document experience that enabled the company's first live investment transactions with minimal manual work. Expert partners well-versed in competitors gave unsolicited feedback: 'This is by far the best version of this I've ever seen.' The product positioned the company as the technology-forward option in a space where competitors were still sending PDFs.

Outcomes

Advisor feedback

"Best ever"

Async transactions

Enabled

Company perception

UX-Forward

Partner reaction

Celebration

Reflection

  • Taking the contract apart and sorting questions was the right approach. Strictly digitizing the standard flow would have made it painful.
  • Identifying entity type upfront was the single highest-leverage decision in the project; it eliminated roughly half the questions.
  • Collaborating with engineers during scoping, not just at handoff, led to the overview screen approach and a stronger product.

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