Wealthsimple Technologies

Senior Software Developer - STAR

Wealthsimple TechnologiesYesterday
Location

Toronto Headquarters

Type

Full Time

Salary

CAD 151,200 – 189,000

Level

Senior

Role

Senior Backend Engineer

Posted

Jul 24, 2026

Full TimeSenior

The role

Summary

Senior Software Developer at Wealthsimple Technologies' STAR team will design and operate mission-critical financial systems processing 20M+ monthly statements, tax filings, and revenue calculations for 4M+ Canadian clients. This role combines backend engineering expertise with data architecture mastery, requiring 7+ years building scalable production systems with full ownership from technical design through regulatory compliance. You'll mentor a 7-person team, set architectural direction for Ruby services and Python/PySpark pipelines, and ensure financial correctness at scale across North America's regulated fintech landscape.

What you'll do

Design and Operate Critical Financial Systems: Design, build, and operate production pipelines and backend services generating millions of client statements, fee calculations, interest payouts, and tax slip filings across North American tax authorities. Ensure 100% accuracy and compliance with regulatory requirements while handling massive monthly volumes.
Set Architectural Direction and Make System Design Decisions: Propose and guide architectural decisions across the STAR domain, making sound technical trade-offs, communicating design rationale clearly, and ensuring consistent architectural choices across distributed Ruby services, Python data pipelines, and Airflow orchestration workflows.
Own End-to-End Technical Delivery: Take full ownership of significant features from technical design through production deployment and operational support. Own reliability during peak processing windows and regulatory deadlines, standing behind your work with accountability and incident response expertise.
Evolve Data Architecture for Scale and Consistency: Improve data architecture to enhance accuracy, reduce latency, and ensure consistency across all client-facing outputs. Drive evolution toward a unified source of truth, leveraging distributed computing and structured data modeling approaches to serve bulk data reliably at scale.
Raise Quality Standards Through Technical Leadership: Elevate team quality through rigorous code review, design conversations that catch issues before production, comprehensive testing frameworks, and architectural guidance. Establish standards for AI-assisted development tooling while maintaining the same quality rigor applied to hand-written code.
Mentor and Develop Team Members: Foster team growth through pair programming sessions, constructive code reviews, and real-time feedback. Share knowledge generously, invest in developer growth, and help the 7-person STAR team raise their collective technical capabilities.

What we look for

Technical

Backend Language MasteryProduction expertise in Ruby and/or Python with ability to reason about performance, memory management, concurrency, and operational reliability. Depth in one language with proven ability to ramp quickly on others.
Data Pipeline and SQL ExpertiseStrong PostgreSQL experience including schema design, query optimization, and indexing strategies. Proven ability designing efficient schemas and queries that serve bulk data reliably to end users at scale.
Distributed Computing and Data EngineeringHands-on experience with Apache Spark, PySpark, or comparable distributed compute frameworks for ETL and analytics. Understanding of MapReduce paradigms, partitioning strategies, and performance optimization in distributed systems.
Workflow Orchestration SystemsProduction experience with Apache Airflow or equivalent DAG-based workflow orchestration platforms. Understanding of scheduling, dependency management, failure handling, and monitoring for complex data pipelines.
System Design and Architectural ThinkingProven ability to hold mental models of complex distributed systems, make trade-off decisions between consistency/availability/partition tolerance, and design systems that remain maintainable and correct as they scale.
Production Operations and ReliabilityExperience operating systems in production with responsibility for uptime, performance monitoring, incident response, and post-mortems. Familiarity with observability tooling, logging, metrics, and alerting strategies.
Code Quality and TestingDeep understanding of testing strategies including unit, integration, and contract testing. Ability to design systems that are testable and to establish testing frameworks that catch issues before production deployment.

Education

Computer Science or Engineering BackgroundBachelor's degree in Computer Science, Software Engineering, Mathematics, or equivalent practical experience demonstrating mastery of algorithmic thinking and system design principles.

Experience

7+ Years Backend EngineeringDemonstrated 7 or more years building and operating scalable production systems at significant scale. Required track record of accountability during peak load scenarios, high-consequence deadlines, and production incident response.
Distributed Data Systems at ScaleHands-on experience designing and operating data engineering systems at scale, including distributed compute frameworks (Apache Spark or comparable), data pipeline orchestration, and experience serving bulk data reliably to users in production.
Financial or Regulated Domain (Preferred)Background in fintech, banking, brokerage, cryptocurrency, or other regulated industries. Experience with tax reporting, statement generation, ledger systems, or financial-correctness systems is highly valued but not required.
Regulatory and Compliance Context (Preferred)Exposure to government or regulatory body interactions, tax compliance workflows, or working in domains where correctness and regulatory adherence are non-negotiable business requirements.

Skills

Required skills

Ruby Backend DevelopmentProduction-grade Ruby expertise building scalable web services and business logic. Understanding of Ruby's ecosystem, frameworks, performance characteristics, and operational deployment patterns.
Python Data EngineeringStrong Python proficiency for data pipeline development, ETL workflows, and data transformation logic. Comfort with Python's data science ecosystem and ability to write maintainable, performant data processing code.
SQL and Relational DatabasesExpert-level PostgreSQL and SQL skills including complex query writing, schema design for performance, transaction handling, and optimization techniques. Ability to diagnose query performance issues and design schemas that scale.
Distributed Systems DesignStrong systems design ability with proven track record designing scalable architectures. Familiarity with concepts like eventual consistency, idempotency, sharding, replication, and failure modes in distributed systems.
Data Pipeline ArchitectureExperience building robust, maintainable data pipelines with clear data lineage, error handling, and monitoring. Understanding of data quality verification, schema evolution, and ensuring correctness in data transformations.
Mentorship and Technical LeadershipDemonstrated ability to elevate team capabilities through code review, design guidance, and knowledge sharing. Proven experience growing junior engineers and establishing technical standards.

Nice to have

Apache Spark and PySparkHands-on experience with Apache Spark for distributed data processing. Understanding of RDD operations, DataFrame APIs, partitioning strategies, and performance tuning in large-scale data jobs.
Apache Airflow OrchestrationProduction experience managing complex Airflow DAGs, handling scheduling, dependency management, and dynamic pipeline generation. Familiarity with best practices for reliable, maintainable workflow definitions.
Fintech and Financial SystemsDomain expertise in fintech, wealth management, or financial systems. Understanding of investment accounting, tax compliance, regulatory reporting, and financial reconciliation processes.
Tax Reporting and ComplianceKnowledge of tax reporting requirements across North American jurisdictions (US, Canada, potentially Mexico). Familiarity with tax slip generation, RRSP/TFSA accounting rules, or cryptocurrency tax implications.
AI-Assisted Development ToolsHands-on experience with modern AI code generation tools (GitHub Copilot, Claude, etc.) with strong critical thinking about code quality and correctness. Ability to review AI-generated code with the same rigor as human-written code.
dbt and Data ModelingExperience with dbt (data build tool) or similar structured data modeling frameworks. Understanding of medallion architecture, semantic layers, and version-controlled data transformations.
Observability and MonitoringExperience designing monitoring strategies, building dashboards, and implementing alerting systems for production data pipelines. Familiarity with tools like Datadog, New Relic, or similar platforms.

Compensation & benefits

Salary

CAD 151,200 – 189,000 (annual)

Stock options

Available

Benefits

Top-Tier Health and Life Insurance

Comprehensive health coverage including medical, dental, vision, and coverage for mental health services. Life insurance provided as part of employee benefits package.

Long-Term Group Savings with Employer Match

Long-term retirement savings program through Wealthsimple for Business with employer matching contributions. Aligns with company's financial expertise and commitment to employee financial wellness.

Generous Vacation and Wellness Time

20 paid vacation days annually, 4 designated wellness days, and unlimited sick and mental health days per year. Demonstrates strong commitment to employee work-life balance and wellbeing.

Extended Remote Work Flexibility

Ability to work outside Canada for up to 90 days per year. Supports distributed work arrangements and flexibility for travel or temporary relocation while maintaining employment.

Employee Resource Groups and Inclusion Programs

Active employee communities including Rainbow (2SLGBTQ+), Women of WS, and Black at WS. Demonstrates commitment to diversity, equity, and inclusive workplace culture.

Hybrid Work Environment

Flexible hybrid work model with over 1,500 employees across North America. Access to collaboration with talented teams while maintaining location flexibility and autonomy.

Equity Compensation

Stock options providing ownership stake in Wealthsimple Technologies. Aligns employee success with long-term company growth and value creation in a well-funded fintech company.

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Wealthsimple Technologies

Wealthsimple Technologies

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Wealthsimple Technologies is a Canadian financial technology company that provides automated investing and personal finance management solutions to consumers. The company offers a range of digital wealth management products, including robo-advisor investment accounts, tax-free savings accounts, and financial planning tools designed to make investing accessible and affordable for everyday people. Wealthsimple operates in the fintech and wealth management industry, serving millions of users across multiple countries with a mission to democratize access to financial services.

Toronto, CanadaFounded 2014wealthsimple.com/en-ca

Tech Stack

Languages
RubyPythonSQL
Frameworks
Apache Spark / PySparkApache Airflow
Databases
PostgreSQL
Tools
Git / Version ControlDocker / Container OrchestrationObservability and MonitoringCI/CD Pipelines
Other
Financial Systems ArchitectureRegulatory and Compliance SystemsData Quality and Testing Frameworks
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