Designing an Estate Plan Drafting System for Solo Attorneys
Summary
I joined Keepsake pre-launch a designer/developer and later led product. After a B2B pivot and founder exit, I helped reconnect the product to attorney workflows.
I defined and designed a missing draft-generation system essential for adoption, while managing a five-person engineering team to deliver it.
Company
Keepsake
Role
Product Designer
Head of Product
Timeline
Nov 2024 - Feb 2025
Background
The Start
Keepsake began as a B2C estate planning app for elderly users and their families. While the concept resonated emotionally, the team struggled with monetization and user acquisition.
The Pivot
The company shifted to B2B, targeting solo estate planning attorneys. During this transition, the founding team stepped away, leaving product direction unclear.
My Role
I joined pre-launch to help rebuild the product around the B2B model. A critical “plan design” feature, turning intake data into usable legal drafts, was only partially defined, preventing beta attorneys from adopting the platform.
Problem
Attorneys weren’t onboarding.
The product was technically functional, and we had a waitlist of attorneys generated through months of cold outreach. The challenge wasn’t building more features — it was making the MVP adoptable.
Goal
How do we move from built to launch-ready?
- Identify the critical gaps preventing attorney adoption
- Align the product with real drafting processes
- Convert waitlist attorneys into our first paying users
The objective was proving attorneys could integrate Keepsake into their practice with confidence.
Constraints
- No dedicated PM
- Limited runway
- A backend-driven roadmap
- High domain complexity and no access to insider connections
Discovery
Process
- Conducted Zoom interviews with waitlisted attorney clients
- Analyzed clients’ PDF intake forms and drafting documents
- Audited competitor products and compiled analysis
With our findings, I mapped the end-to-end user flow of both attorneys and their clients without our app, and with our app included in their workflow.
Attorney Flow
Client Flow
Insight 1
Adoption hinged on draft generation
Attorneys didn’t want another intake form tool.
They wanted fewer meetings and faster draft turnaround.
Keepsake’s MVP handled client intake, but the workflow stopped there. Attorneys still had to manually turn intake responses into legal drafts.
Insight 2
Customization was not optional
Attorney workflows varied widely. Each practice:
- Had unique intake forms (including custom languages)
- Required different logic for post-intake drafting.
Some drafted collaboratively with clients, others handed forms to a drafter, and some didn’t use a formal design document at all.
A single standardized template would have increased friction rather than reduced it.
The Refined Problem
Keepsake aimed to bridge both the legal and personal sides of estate planning, but it emphasized intake mechanics without supporting the drafting workflows attorneys actually needed.
The platform wasn’t missing a feature. It was missing a complete branch of the workflow.
Solution
Designing flexible intake
Intake fields needed to translate into structured legal outputs, so sections on assets, beneficiaries, trustees, etc. required conditional logic
We manually recreated intake forms in the app for 3 beta customers, and structured them to test repeatable logic
The “plan design” feature
I defined requirements for the critical “plan design” system that enabled legal draft generation.
I additionally refined and expanded the Figma-based design system left by the founding designer, and managed engineering priorities and product direction using Linear.
I also contributed UI improvements directly in the codebase and contributed PR Reviews in github.
Forms in Keepsake
Conclusion
Impact
- Clarified product direction and defined requirements for the draft-generation system
- Re-established a direct user feedback loop with attorneys
- Identified architectural needs to support scalable customization
- Enabled two attorneys to adopt the platform and successfully onboard new clients using it
Learnings
- Early-stage product success requires a clear vision and leadership. Even strong teams can struggle to communicate value and gain adoption without it.
- Surface-level feedback isn’t enough. You must follow users through their actual workflows to understand how a product truly fits.
- Dedicated alpha testing with a small, controlled group is essential before engaging beta customers.
I joined Keepsake as the sole designer and assumed head-of-product responsibilities, guiding both design and development. Overall, this was a valuable opportunity to work with a very talented team. Thanks to Sabih, Yohance, Cade, and everyone for your passion and hard work:)
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