PROBLEM AREA
Legacy System Constraints Limiting Educational Impact
Seesaw's administrators were trapped by an inflexible folder system that couldn't support the complex organizational needs of modern curriculum management. This wasn't just a usability issue—it was limiting the educational impact of the platform and threatening admin retention.
Core Administrative Challenges:
Limited organization tools: No nested folders or reordering capabilities for lesson materials
Inefficient workflows: Manual, one-by-one updates required for bulk content management
Insufficient permissions: Lack of granular teacher access controls limiting effective collaboration
Approval bottlenecks: No review process for shared materials entering the library
Technical Reality: The legacy tech stack created significant constraints on what organizational features could be implemented, requiring creative solutions that worked within existing architecture limitations.
Business Stakes:
Administrator frustration leading to reduced platform engagement
Inefficient workflows limiting curriculum distribution effectiveness
Competitive disadvantage in the EdTech market where organizational flexibility is increasingly expected
Risk of admin churn in a relationship-dependent education market
Legacy school & district library
01
Limited browsing capabilities - no sorting or grouping functionality available
02
No permissions structure or admin controls to easily distribute lessons to teachers
03
No organizational structure to the lessons and activities making it hard to find a curriculum
04
No metadata on the type of lesson or activity, usage rates, or otherwise
DESIGN DECISION 01
Systematic Problem Prioritization Through Cross-Functional Analysis
Working collaboratively with curriculum specialists, engineering, and product teams, I led a comprehensive mapping and ranking exercise to prioritize which problems to solve first. This systematic approach ensured we addressed user needs within technical constraints and business timelines.
Prioritization Methodology:
User impact assessment based on admin feedback and workflow analysis
Technical feasibility evaluation with engineering team input on legacy system constraints
Business value analysis with product team to align with strategic goals
Implementation complexity mapping to optimize development resources
Resulting Priority Framework:
Nested Folders for Organization - High user impact, moderate technical complexity
Bulk Actions - Critical workflow efficiency, manageable within existing architecture
Permissions - Important for collaboration, but more complex implementation
Approval Queue - Valuable feature, scheduled for future iteration due to scope
Cross-Functional Impact: This prioritization framework became a template for future feature development across the curriculum team, improving overall product planning efficiency.
Strategic Outcome: By focusing on nested folders and bulk actions first, we could deliver immediate value while building toward more complex features in later phases.
Problem
Description
Examples
Distribution and Organization
Admins needed subfolders to categorize resources more effectively.
Teachers struggled to find specific lessons within large, disorganized folders.
Bulk Actions
Admins requested the ability to manage multiple activities at once (e.g., moving, editing, or deleting).
Adding lessons one by one was time-consuming and inefficient.
Permissions
Admins wanted to set role-based permissions to control access to folders (e.g., viewer, editor).
Only specific teachers should have editing rights for shared resources.
Approving Activities
Admins needed a review process to ensure the quality of shared materials.
Teachers frequently shared incomplete lessons, which disrupted the library’s integrity.
DESIGN DECISION 02
Component-Based Solutions Within Technical Constraints
Working closely with the engineering team, I designed solutions that maximized user value while respecting legacy system limitations. My engineering background helped identify which approaches would be technically feasible and how to create flexible components that could evolve with future platform updates.
Technical Collaboration Process:
Early feasibility discussions with developers for each proposed component
Iterative design reviews to ensure buildability within existing architecture
Component documentation that considered both user needs and technical implementation
Cross-functional validation with curriculum team to ensure educational effectiveness
Implementation Strategy: Each component was designed to be independently deployable, allowing for phased rollout and reducing technical risk while delivering incremental user value.
Reorganized Library Homepage
Restructured navigation by subject and grade to improve resource discoverability without requiring backend architecture changes.
Bulk Actions System
Created efficient workflows for multiple activity management, designed to work within existing data relationships and permissions.
Hierarchical Folder Structure
Enabled nested organization while respecting current database constraints and user permission models.
Enhanced Activity Cards
Redesigned information display to help teachers make faster decisions, using existing metadata more effectively.
DESIGN DECISION 03
Strategic Effort-Level Analysis for Optimal Resource Allocation
Drawing on my engineering background and product strategy experience, I conducted a comprehensive analysis of three implementation approaches to find the optimal balance between user value and development complexity. This systematic evaluation involved close collaboration with engineering and product teams to assess both technical feasibility and business impact.
Evaluation Framework:
User experience assessment through prototype testing and feedback
Technical complexity analysis with engineering team input on implementation requirements
Business value calculation considering development time vs. user impact
Risk assessment for each approach's potential complications
Decision Methodology: Selected the medium-effort approach because it delivered significant user value improvements while remaining within reasonable development timelines. This decision balanced immediate user needs with long-term platform scalability.
Cross-Functional Impact: This effort-level analysis framework was adopted by other product teams at Seesaw for future feature planning, improving overall resource allocation efficiency.
PROS
Required minimal development effort, ensuring a faster release.
Leveraged existing design patterns, reducing complexity.
CONS
Provided the least guidance, potentially confusing users unfamiliar with the process.
Relied heavily on users to figure out the next steps, which could lead to errors or frustration.
PROS
Balanced usability and development effort.
Allowed users to start organizing collections quickly while maintaining flexibility.
CONS
Lacked the seamless experience of the high-effort design.
Required users to take additional steps to add activities, which could cause minor friction.
PROS
Provided the most intuitive and user-friendly experience.
Reduced cognitive load by walking users through each step.
CONS
Large development and implementation effort
Longest process for the user
DESIGN DECISION 04
Implementation Strategy and Cross-Functional Validation
Based on the effort-level analysis, I implemented the medium-effort approach for admin controls, working closely with the engineering team to ensure the solution balanced user needs with technical constraints. This collaborative implementation process became a model for future feature development.
Implementation Approach:
Phased rollout strategy to minimize risk and gather user feedback iteratively
Component-based design system integration to ensure consistency and future scalability
Cross-functional testing with curriculum team to validate educational workflow effectiveness
Performance monitoring setup to track user adoption and workflow efficiency
Technical Collaboration: The engineering team appreciated the systematic approach to balancing user needs with development complexity, leading to smoother implementation and fewer mid-development changes.
User Validation: Admin testing confirmed the medium-effort approach provided the right balance of functionality and simplicity, achieving high task completion rates without overwhelming users.
RETROSPECTIVE
Cross-Functional Collaboration and Strategic Decision-Making
This project reinforced the value of systematic analysis when balancing user needs with technical constraints. By treating implementation complexity as a design parameter rather than an afterthought, we delivered a solution that satisfied users while respecting development realities.
Key Learnings
Effort-level analysis prevents scope creep: The systematic evaluation of low/medium/high effort approaches kept the project focused and deliverable within timeline constraints
Cross-functional collaboration amplifies impact: Working closely with curriculum specialists, engineering, and product teams led to solutions none of us could have achieved independently
Legacy constraints drive innovation: The old tech stack limitations forced creative component-based solutions that actually improved the user experience
Methodological Insights
The most successful aspect was treating technical feasibility as an equal partner to user needs in the design process. This approach prevented costly late-stage changes and built stronger relationships with the engineering team.
Strategic Impact
The effort-level analysis framework and collaborative implementation approach were adopted by other teams at Seesaw, improving overall product development efficiency across the organization.
15%
Increase in daily active usage
50%
Increase in user satisfaction
“Jordan was an integral part of the Content and Instruction team […]”
Kristen Thayer
Engineering Manager
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