Top Benefits
About the role
Company Description SimplePin revolutionizes financial operations for the insurance industry through its platform, designed to simplify complex workflows.
What you'll do You'll lead a team of about six engineers while staying hands-on with the codebase - roughly 60% building, 40% leading. This isn't a "meetings all day" role. You'll write code, review code, and ship code, but you'll also be the person your team looks to for direction, growth, and unblocking.
On the technical side: Design and build backend services in Java and Spring Boot. Own the architecture of our microservices — we started as a monolith and have been decomposing it where it makes sense. You'll help decide where the next boundaries go. Build and maintain REST APIs and integrations with internal and external systems. Work with transactions, concurrency, caching, and performance optimization. Drive engineering quality through testing, code reviews, and refactoring. TDD experience is a strong plus. Participate in AWS infrastructure decisions alongside our solutions architect, including contributing to our Infrastructure as Code practices. On the leadership side: Lead, mentor, and grow a team of ~6 engineers. You've done this before — you know what good 1:1s look like and how to give feedback that actually helps people improve. Sit in product design sessions with our Product Manager and CTO. We don't just want you to say "yes, that's feasible." We want you to have opinions about what we should build and push back when something doesn't make sense. Own delivery for your team. You'll set technical direction, help with estimation, remove blockers, and make sure the work gets done well. Drive technical decisions and establish best practices across the team. Requirements 8+ years of professional software development experience, with strong depth in Java (8/11/17+). Proven experience leading an engineering team — hiring, running 1:1s, managing delivery, growing people. Not just "senior person on a team," but actual team leadership. Deep knowledge of Spring / Spring Boot (DI, bean lifecycle, configuration, scopes). Solid understanding of JVM internals, OOP, SOLID principles, and common design patterns. Hands-on experience with microservices architecture — decomposition strategies, service boundaries, inter-service communication, and the tradeoffs involved. Strong testing habits: JUnit, Mockito (or equivalent), writing code that's actually testable. Experience with relational databases: SQL, transactions, JPA/Hibernate. Comfortable with Git, code review culture, and CI/CD pipelines. Hands-on AWS experience (EC2, ECS/EKS, RDS, SQS/SNS, S3, IAM, CloudWatch) with the ability to make infrastructure and architectural decisions. Comfortable participating in product discussions — you can translate between business needs and technical reality. Nice to have Infrastructure as Code experience, particularly Terraform. Caching strategies with Redis (TTL, invalidation patterns). Observability: structured logging, metrics, distributed tracing. Deep understanding of Spring AOP/Aspects and proxy behavior. AWS certifications (Solutions Architect Associate or Professional). Experience with Angular and TypeScript. What we offer Competitive compensation. Remote-friendly culture. Paid vacation. Strong engineering culture: quality, automation, and ownership.
Salary Range: ~$170,000 - $210,000 CAD (based on experience)
About SimplePin
Insurance is Complex. Financial Operations Doesn't Have to Be.
SimplePin automates the full financial operations lifecycle for agencies, MGAs, and carriers, from bill and bind through to direct bill reconciliation and GL posting.
Direct bill has shifted the reconciliation burden onto agencies. Manually tracking commissions, chasing statements, and reconciling by hand is costly and error-prone. SimplePin eliminates that entirely. We capture, match, and reconcile direct bill commissions and all incoming transactions automatically, posting back to your AMS without manual intervention.
Built for brokerages and MGAs that have outgrown manual processes, from ambitious mid-size operations to the most complex enterprise environments, with pre-built connectors to the industry's leading management systems.
One platform. Every financial touchpoint:
- Invoicing & Digital Payments
- eCommerce Payments
- Check & Statement Capture
- Direct Bill Commission Reconciliation
- AR Posting & GL Reconciliation
Similar Jobs
Top Benefits
About the role
Company Description SimplePin revolutionizes financial operations for the insurance industry through its platform, designed to simplify complex workflows.
What you'll do You'll lead a team of about six engineers while staying hands-on with the codebase - roughly 60% building, 40% leading. This isn't a "meetings all day" role. You'll write code, review code, and ship code, but you'll also be the person your team looks to for direction, growth, and unblocking.
On the technical side: Design and build backend services in Java and Spring Boot. Own the architecture of our microservices — we started as a monolith and have been decomposing it where it makes sense. You'll help decide where the next boundaries go. Build and maintain REST APIs and integrations with internal and external systems. Work with transactions, concurrency, caching, and performance optimization. Drive engineering quality through testing, code reviews, and refactoring. TDD experience is a strong plus. Participate in AWS infrastructure decisions alongside our solutions architect, including contributing to our Infrastructure as Code practices. On the leadership side: Lead, mentor, and grow a team of ~6 engineers. You've done this before — you know what good 1:1s look like and how to give feedback that actually helps people improve. Sit in product design sessions with our Product Manager and CTO. We don't just want you to say "yes, that's feasible." We want you to have opinions about what we should build and push back when something doesn't make sense. Own delivery for your team. You'll set technical direction, help with estimation, remove blockers, and make sure the work gets done well. Drive technical decisions and establish best practices across the team. Requirements 8+ years of professional software development experience, with strong depth in Java (8/11/17+). Proven experience leading an engineering team — hiring, running 1:1s, managing delivery, growing people. Not just "senior person on a team," but actual team leadership. Deep knowledge of Spring / Spring Boot (DI, bean lifecycle, configuration, scopes). Solid understanding of JVM internals, OOP, SOLID principles, and common design patterns. Hands-on experience with microservices architecture — decomposition strategies, service boundaries, inter-service communication, and the tradeoffs involved. Strong testing habits: JUnit, Mockito (or equivalent), writing code that's actually testable. Experience with relational databases: SQL, transactions, JPA/Hibernate. Comfortable with Git, code review culture, and CI/CD pipelines. Hands-on AWS experience (EC2, ECS/EKS, RDS, SQS/SNS, S3, IAM, CloudWatch) with the ability to make infrastructure and architectural decisions. Comfortable participating in product discussions — you can translate between business needs and technical reality. Nice to have Infrastructure as Code experience, particularly Terraform. Caching strategies with Redis (TTL, invalidation patterns). Observability: structured logging, metrics, distributed tracing. Deep understanding of Spring AOP/Aspects and proxy behavior. AWS certifications (Solutions Architect Associate or Professional). Experience with Angular and TypeScript. What we offer Competitive compensation. Remote-friendly culture. Paid vacation. Strong engineering culture: quality, automation, and ownership.
Salary Range: ~$170,000 - $210,000 CAD (based on experience)
About SimplePin
Insurance is Complex. Financial Operations Doesn't Have to Be.
SimplePin automates the full financial operations lifecycle for agencies, MGAs, and carriers, from bill and bind through to direct bill reconciliation and GL posting.
Direct bill has shifted the reconciliation burden onto agencies. Manually tracking commissions, chasing statements, and reconciling by hand is costly and error-prone. SimplePin eliminates that entirely. We capture, match, and reconcile direct bill commissions and all incoming transactions automatically, posting back to your AMS without manual intervention.
Built for brokerages and MGAs that have outgrown manual processes, from ambitious mid-size operations to the most complex enterprise environments, with pre-built connectors to the industry's leading management systems.
One platform. Every financial touchpoint:
- Invoicing & Digital Payments
- eCommerce Payments
- Check & Statement Capture
- Direct Bill Commission Reconciliation
- AR Posting & GL Reconciliation