Grayson Rosato
Montessori Billing Platform
A flexible, fully-featured billing platform designed to meet the unique financial needs of Montessori schools. From tuition plans and activity fees to split payments and audit trails, the system supports the entire billing workflow—combining the power of tools like QuickBooks with a user-friendly interface built specifically for school admins. It brings clarity, automation, and confidence to daily operations, while laying the groundwork for scalable, future-ready financial systems.
The Challenge
Montessori schools have uniquely complex billing needs. Most were managing with spreadsheets, QuickBooks, and a lot of manual effort. I interviewed administrators and accountants across schools and quickly saw that no off-the-shelf solution could handle the combination of custom schedules, parent splits, variable discounts, and education-specific charges.
My challenge was to design a billing platform powerful enough to handle all of that complexity—but clean and intuitive enough for daily use by overextended school staff.
My Role
I was the sole product designer on this project. I led everything from research and information architecture to visual design, prototyping, user testing, and async engineering collaboration. I worked closely with our Head of Product, engineering team, and CEO to shape the feature and make sure it fit within a larger product rollout.
Research & Discovery
Deep Discovery
I started by interviewing admins, accountants, and heads of school from multiple Montessori programs. I mapped out their workflows and identified major friction points—especially around invoicing flexibility, multi-child families, and handling parents with split payment responsibilities.
The beginnings of lesson cards were born! I knew I needed to distill all the avalible information to the
The beginnings of lesson cards were born! I knew I needed to distill all the avalible information to the
Defining the Catalog
This became the foundation for all logic in the system.
Design Process
Ground-Up Architcture
I broke down the design into modular workflows—catalog setup, invoice generation, parent splits, payment tracking—so features could be shipped independently and scale over time. I created wireflows and prototypes for each scenario and collaborated closely with product and engineering to validate feasibility.
The beginnings of lesson cards were born! I knew I needed to distill all the avalible information to the
Ground-Up Architcture
I created a fully clickable prototype and validated it with the new head of school at Montessori ONE Academy. Her feedback helped fine-tune invoice views, fee application, and payment plan flexibility.
Collaboration & Implementation
Ground-Up Architcture
Because our engineering team was remote and asynchronous, I used detailed annotations, structured Figma flows, and granular design tickets to keep communication clear. I adjusted my workflow to break designs into atomic units, allowing for smoother development and faster iteration.
Outcome & Impact
Designing the billing experience for parents was a unique challenge. I needed to create a clean, streamlined view that combined all student accounts and invoices in one place. This allowed parents to make a single consolidated payment or explore the details of each individual bill.
The billing platform is now live and in use at Montessori ONE Academy. Early feedback has been strong:
The platform is already replacing multiple third-party tools and spreadsheets—and it’s ready to scale.
What I Learned
back
Grayson Rosato
Montessori Billing Platform
A flexible, fully-featured billing platform designed to meet the unique financial needs of Montessori schools. From tuition plans and activity fees to split payments and audit trails, the system supports the entire billing workflow—combining the power of tools like QuickBooks with a user-friendly interface built specifically for school admins. It brings clarity, automation, and confidence to daily operations, while laying the groundwork for scalable, future-ready financial systems.
The Challenge
Montessori schools have uniquely complex billing needs. Most were managing with spreadsheets, QuickBooks, and a lot of manual effort. I interviewed administrators and accountants across schools and quickly saw that no off-the-shelf solution could handle the combination of custom schedules, parent splits, variable discounts, and education-specific charges.
My challenge was to design a billing platform powerful enough to handle all of that complexity—but clean and intuitive enough for daily use by overextended school staff.
My Role
I was the sole product designer on this project. I led everything from research and information architecture to visual design, prototyping, user testing, and async engineering collaboration. I worked closely with our Head of Product, engineering team, and CEO to shape the feature and make sure it fit within a larger product rollout.
Research & Discovery
Deep Discovery
I started by interviewing admins, accountants, and heads of school from multiple Montessori programs. I mapped out their workflows and identified major friction points—especially around invoicing flexibility, multi-child families, and handling parents with split payment responsibilities.
Dividing catalog items into categories helped reframe a typical invoice into a mix of automated recurring payments and one-time charges—making the system more flexible and easier to manage.
Providing examples for each category helped stakeholders and research participants better conceptualize the new system. It also sparked excitement and built early buy-in.
Defining the Catalog
This became the foundation for all logic in the system.
Design Process
Modular Architecture
I broke down the design into modular workflows—catalog setup, invoice generation, parent splits, payment tracking—so features could be shipped independently and scale over time. I created wireflows and prototypes for each scenario and collaborated closely with product and engineering to validate feasibility.
Because the product was designed iPad-first, every interaction had to be both touch- and mouse-friendly. I also avoided patterns that couldn’t be completed within a standard viewport to ensure accessibility and ease of use across devices.
Prototyping & Testing
I created a fully clickable prototype and validated it with the new head of school at Montessori ONE Academy. Her feedback helped fine-tune invoice views, fee application, and payment plan flexibility.
Collaboration & Implementation
Async Dev Collaboration
Because our engineering team was remote and asynchronous, I used detailed annotations, structured Figma flows, and granular design tickets to keep communication clear. I adjusted my workflow to break designs into atomic units, allowing for smoother development and faster iteration.
Outcome & Impact
Designing the billing experience for parents was a unique challenge. I needed to create a clean, streamlined view that combined all student accounts and invoices in one place. This allowed parents to make a single consolidated payment or explore the details of each individual bill.
The billing platform is now live and in use at Montessori ONE Academy. Early feedback has been strong:
The platform is already replacing multiple third-party tools and spreadsheets—and it’s ready to scale.
What I Learned
back