Job Description

What is Caseware Cloud?

Caseware Cloud

is the foundation of Caseware's cloud-based solutions, designed to streamline

practice management and client collaboration

for accounting firms and professional services. It provides

secure, scalable, and integrated tools

that help firms manage engagements, collaborate with clients, and maintain compliance with industry standards.

Cloud Collaborate Platform

Caseware Cloud Collaborate

is a core component of

Caseware Cloud

, specifically focused on

client collaboration and document exchange

. It enables firms to securely communicate with clients, request and share documents, track progress, and ensure efficient workflows.

Key aspects of

Cloud Collaborate

include:

Secure Client Portals

- A centralized, encrypted space for firms and their clients to share documents, messages, and updates.

Workflow Automation

- Automates document requests, approvals, and follow-ups to improve efficiency.

Integration with Caseware Cloud Apps

- Seamlessly connects with other Caseware solutions, ensuring a unified experience.

Scalability & Performance

- Designed for global firms, handling large-scale data exchanges with robust

AWS-backed infrastructure

.


As Caseware

modernizes its platform

, Cloud Collaborate plays a key role in evolving from

a .NET monolith to a microservices-based architecture

. This transformation aims to enhance

performance, security, and future scalability

, making it more flexible and efficient for firms of all sizes.

About the Role:

We are looking for a

Principal Software Developer

to lead the architectural evolution of

Caseware's Cloud Platform

, which powers our core Caseware Cloud product--a mission-critical suite for practice management and client collaboration.

In this role, you will

design and implement microservices in Java

,

migrate functionality from a .NET monolith

, and ensure our cloud platform is

scalable, secure, and maintainable

. While

.NET expertise is not required

, you must be comfortable

reading .NET code

to understand the existing architecture and successfully guide the transition to a

Java-based microservices ecosystem

.

This role is a

blend of technical leadership, hands-on coding, and mentorship

, ensuring our engineering teams adopt best practices in cloud architecture, security, and quality engineering.

If you're a

Java architect with hands-on coding experience

, expertise in

AWS and microservices

, and a passion for

mentorship and cloud transformation

, we'd love to hear from you.

Location:

Hybrid (3 days WFO in GTA), Toronto, ON

Contact:

Chengeer Lee - Principal Talent Acquisition Partner & Coach
###

What You Will Do:

Lead the migration from a .NET monolith to

Java microservices

, designing

scalable and secure

cloud-native solutions. Build

authorization and authentication microservices

as part of a

tech enablement

strategy. Drive

API-first development

for seamless integration across Caseware's platform. Design scalable solutions that support

AWS Elastic Kubernetes Service (EKS)

. Write

production-quality Java code

and develop

proof of concepts (POCs)

to validate new technology decisions. Debug and

troubleshoot complex production issues

, ensuring platform reliability. Collaborate on

AWS infrastructure configurations, CI/CD pipelines, and observability improvements

.

Mentor senior developers and tech leads

on microservices, cloud architecture, and security best practices. Provide

guidance to teams

struggling with debugging, performance tuning, and architectural decision-making. Work closely with

distributed teams across Canada, the Netherlands, and Romania

to drive architectural excellence.

Optimize SQL Server performance

as we migrate to a microservices-based architecture. Work closely with

DevOps

to ensure scalable and secure

cloud-native deployments on AWS

. Influence

CI/CD and cloud security best practices

. Partner with

engineering leaders and product teams

to align

technical decisions with business objectives

. Support

future tech acquisitions

, evaluating integration strategies for acquired products. Contribute to

sunsetting legacy applications

through a

phased API migration approach

.
###

What you bring:

10+ years

of software development experience, with deep expertise in

Java

and cloud-native architectures. Experience with

microservices design, distributed systems, and API-first development

.

Comfortable reading .NET code

to understand legacy architecture while driving Java microservices adoption.

Strong AWS experience

, particularly with

EKS, Cognito, IAM, Lambda, and API Gateway

.

SQL expertise

, particularly with SQL Server and experience migrating databases from monolithic to microservices.

Identity and access management (IAM) expertise

, with experience in

Auth0, Keycloak, or AWS Cognito

. Experience

mentoring teams, improving code quality, and enforcing architectural best practices

. Deep understanding of

DevOps, CI/CD, and automated testing methodologies

. Exceptional

problem-solving and debugging skills

, with the ability to

lead technical initiatives

across teams.
###

Key Success Factors (First 6-12 Months)

Microservices Architecture:

Successfully

design, prototype, and build

new Java-based services.

Scalability & Security:

Implement solutions that scale securely

on AWS

, ensuring high availability.

Tech Mentorship:

Establish yourself as the

go-to expert

for Java microservices and security best practices.

Sunsetting Legacy Systems:

Develop an API strategy to

gradually phase out legacy products

.

Quality Engineering Leadership:

Drive

best practices for test automation and developer-led quality efforts

.
###

What's in it for you:

Architectural Ownership:

Drive the

transformation of a mission-critical platform

.

Hands-On Leadership:

Get the balance of

high-level decision-making and hands-on coding

.

Strategic Influence:

Play a key role in

shaping Caseware's technology direction

.

Hybrid Work Model:

Work from home with

3 days in-office in Toronto

. *

Strong Team & Vision:

Collaborate with

engineering leaders and a strong CTO

to drive innovation.