Director of Engineering - Canada

Your Role:

As the Founding Director of Engineering for Canada, you will demonstrate visionary leadership by shaping the overall direction of multiple divisions and establishing Alpaca's engineering presence in the Canadian market from the ground up. This is a unique opportunity to build a world-class engineering organization, architect critical financial infrastructure, and shape the technical strategy for one of North America's largest and most sophisticated financial markets.

You will serve as the strategic technical leader for Canada operations, balancing high-level strategic planning with the operational oversight necessary for execution. This role requires exceptional technical depth combined with strategic vision, capable of guiding transformational technical initiatives that span multiple divisions. You will serve as a key liaison between teams and executive leadership, facilitating communication and alignment while influencing the function's strategic direction and culture.

You will engage with senior leadership to ensure functional initiatives align with broader business objectives, and evaluate and oversee complex technical projects to ensure scalability, reliability, and alignment with industry best practices. You will balance a high-level technical overview with an understanding of day-to-day engineering challenges, ensuring that large-scale initiatives are executed with excellence and that responsibilities are clearly defined across the organization.

For this role, we are seeking an industry-recognized engineering leader who drives innovation at a strategic level and encourages teams to explore breakthrough ideas and technologies. You must understand and advocate for the needs of both the team and the end user, ensuring that technical decisions serve both engineering excellence and business outcomes. You will be responsible for building a talented engineering organization in Canada, establishing engineering culture and practices, and ensuring operational excellence in a highly regulated environment.

You will lead the rapid development of a comprehensive Canadian brokerage solution, including localized infrastructure, ledger systems, account creation & KYC, funding & foreign exchange, settlement, corporate actions, compliance, trading, and reporting capabilities. What you build here will become the foundation for launching in the Canadian market and scaling across Canada and other similar international markets.

Things You Get To Do:

Team Building and Leadership

• Build and lead a world-class engineering organization in Canada from the ground up, establishing hiring standards, engineering culture, and technical practices across multiple divisions
• Exhibit visionary leadership by shaping the overall direction of engineering teams, encouraging exploration of breakthrough ideas and technologies
• Understand and advocate for the needs of both the engineering team and end users, ensuring that technical decisions serve both engineering excellence and user outcomes
• Serve as the primary technical mentor and advisor, providing strategic guidance across teams and deeply engaging in long-term planning.
• Establish engineering best practices, code review standards, and technical decision-making frameworks tailored to the Canadian market context
• Foster Alpaca culture in the region while adapting practices to local market dynamics and regulatory requirements
• Lead regional recruitment initiatives, identifying top talent and building a diverse, high-performing engineering organization
  
• Ensure that responsibilities are clearly defined across the organization, establishing accountability frameworks for large-scale initiatives

Strategic Technical Leadership

• Drive innovation at a strategic level, encouraging teams to explore breakthrough ideas and technologies that transform our Canada operations
• Influence the strategic direction and culture of the engineering function, shaping not just projects but overall functional strategy
• Engage with senior leadership to ensure functional initiatives align with broader business objectives and market opportunities
• Evaluate and oversee complex technical projects across multiple divisions, ensuring scalability, reliability, and alignment with industry best practices
• Balance high-level strategic planning with operational oversight necessary for execution, ensuring large-scale initiatives are executed with excellence
• Act as a key liaison between engineering teams and executive leadership, facilitating communication and alignment on strategic technical decisions
• Possess deep technical expertise combined with strategic vision, capable of guiding transformational technical initiatives that span multiple divisions
• Balance a high-level technical overview with an understanding of day-to-day engineering challenges, ensuring architectural decisions are grounded in practical implementation experience
• Influence company-wide policies and contribute to industry best practices, establishing Alpaca as a technical leader in the Canadian fintech ecosystem

Business Stakeholder Engagement

• Collaborate directly with business stakeholders, including finance, operations, product, legal, and compliance teams, understanding and advocating for both team needs and end user requirements
• Translate complex business requirements into robust technical solutions, balancing innovation with regulatory compliance and operational constraints
• Engage with local regulators (CIRO), vendors, and partner operations teams to ensure the development of robust, scalable systems that comply with Canadian market regulations
• Work closely with partners to understand requirements, align on technical integration, and ensure a successful launch
• Communicate project statuses, technical challenges, and solutions effectively to both technical and non-technical stakeholders, including C-level executives and senior leadership
• Participate in strategic planning sessions, contributing technical insights that inform business strategy and market expansion decisions
• Act as a key liaison between engineering teams and executive leadership, facilitating communication and alignment on strategic initiatives
• Ensure that large-scale initiatives are executed with excellence, with clearly defined responsibilities across the organization

Technical Architecture and Implementation

• Design and architect mission-critical financial systems for the Canadian market, including Canadian Ledger, regulatory reporting, multi-currency transaction processing, and compliance systems
• Lead the design and implementation of backend solutions where reliability, scalability, and regulatory compliance are paramount
• Work closely with Alpaca's core teams to enhance and transform the core framework, enabling support for Canadian markets, currencies (CAD), and regulatory requirements
• Architect and implement key Canadian brokerage capabilities, including:

• • Localized Infrastructure and Ledger (Canadian Ledger instance)
  • Account Creation & KYC systems
  • Funding & Foreign Exchange (FX) processing
  • Settlement systems
  • Corporate Actions processing
  • Compliance and regulatory reporting
  • Trading infrastructure
  • Reporting systems
    
• Design systems with scalability in mind, ensuring the solution built for our partners can scale across multiple Canadian fintech partners
• Drive technical decisions around cloud infrastructure, data residency, security, and observability for Canada operations
• Establish infrastructure patterns and practices for Canadian deployments, ensuring compliance with CIRO regulations and data residency requirements

Operational Excellence

• Ensure operational reliability engineering and serve as incident commander during regional business hours, ensuring proactive 24x7 stability
• Establish monitoring, alerting, and incident response practices tailored to Canada operations and regulatory requirements
• Troubleshot critical incidents and reported bugs, leading resolution efforts with authority and technical depth
• Participate in on-call rotations and ensure timely response to engineering projects and production issues
• Establish disaster recovery and business continuity practices that meet CIRO regulatory requirements
• Manage vendor relationships for infrastructure and services, ensuring vendors meet operational and regulatory requirements
• Coordinate with vendors for infrastructure provisioning, maintenance, upgrades, and incident resolution
• Ensure systems are designed for high availability and can handle the scale required for multiple Canadian fintech partners

Cross-Functional Collaboration

• Collaborate with tech leads in other regions (APAC, Americas, EMEA) both synchronously and asynchronously, using Slack and occasional meetings outside of regular working hours to align with global teams
• Lead cross-functional projects that span multiple teams and regions, ensuring alignment and effective execution
• Influence architectural decisions across the organization, contributing to global platform capabilities while addressing Canada-specific requirements
• Establish clear ownership boundaries and async-first practices to reduce synchronous dependencies across time zones
• Work closely with product, compliance, and business teams to ensure technical solutions align with regulatory requirements and business objectives

Who You Are (Must-Haves):

Technical Excellence

• 12+ years of professional software engineering experience with a proven track record of architecting and building complex, large-scale financial systems in production
• Recognized as an industry authority with a strong record of solving high-impact technical challenges at scale
• Deep technical expertise combined with strategic vision, capable of guiding transformational technical initiatives across multiple divisions
• Experience evaluating and overseeing complex technical projects, ensuring scalability, reliability, and alignment with industry best practices
• Deep expertise in Go or similar backend languages, with exceptional ability to design robust, efficient, and scalable system architectures
• Proven experience in designing and developing complex financial systems, including double-entry accounting, ledger structures, and transaction reconciliation
• Strong understanding of accounting principles, financial transaction processing, and regulatory compliance requirements in financial markets
• Experience building scalable, high-availability financial applications that handle multi-currency transactions and complex regulatory reporting
• Exceptional system design skills with the ability to make architectural decisions and trade-offs that balance technical excellence with business objectives
• Proven experience designing and implementing event-driven architectures for large-scale distributed systems
• Experience with message queues, pub/sub systems, and asynchronous processing patterns for building scalable, decoupled systems
• Strong computer science fundamentals and proven software engineering architecture experience
• Ability to balance a high-level technical overview with an understanding of day-to-day engineering challenges

Leadership and Influence

• Proven experience exhibiting visionary leadership by shaping the overall direction of multiple divisions or engineering organizations
• Exceptional ability to balance high-level strategic planning with operational oversight necessary for execution
• Demonstrated experience acting as a key liaison between teams and executive leadership, facilitating communication and alignment
• Proven track record of influencing the strategic direction and culture of the engineering function
• Experience engaging with senior leadership to ensure functional initiatives align with broader business objectives
• Possesses deep technical expertise combined with strategic vision, capable of guiding transformational technical initiatives
• Experience evaluating and overseeing complex technical projects, ensuring scalability, reliability, and alignment with industry best practices
• Ability to balance a high-level technical overview with an understanding of day-to-day engineering challenges
• Proven experience building and leading engineering organizations from the ground up, establishing culture, practices, and technical standards across multiple teams
• Strong mentorship capabilities, with experience providing strategic mentorship across teams and contributing to long-term planning
• Demonstrated ability to drive innovation at a strategic level, encouraging teams to explore breakthrough ideas and technologies
• Proven experience understanding and advocating for the needs of both engineering teams and end users
• Track record of ensuring large-scale initiatives are executed with excellence, with clearly defined responsibilities across organizations

Business Acumen and Stakeholder Management

• Strategic thinking and the ability to translate technical concepts into business strategies and market opportunities
• Proven experience collaborating with business stakeholders, including finance, operations, product, legal, and compliance teams
• Strong communication skills to collaborate effectively with global teams, local regulators, vendors, and internal stakeholders at all levels, including senior leadership
• Ability to communicate complex technical concepts to non-technical audiences, including C-level executives, board members, and business leaders
• Experience engaging with regulators and ensuring technical solutions comply with regulatory requirements
• Proven ability to act as a key liaison between engineering teams and executive leadership, facilitating strategic alignment
• Experience engaging with senior leadership to ensure functional initiatives align with broader business objectives
• Demonstrated ability to understand and advocate for both team needs and end-user requirements in technical decision-making
• Experience working with partners and customers to understand requirements and deliver solutions that meet their needs

Problem-Solving and Execution

• Obsession with performant, defect-free, maintainable code and systems
• Strong problem-solving skills paired with a proactive mindset and the ability to foresee problems before they occur
• Ability to work independently and under pressure in a fast-paced, high-stakes environment
• A preference for simple and elegant solutions that balance technical excellence with practical constraints
• Ability to act as incident commander and lead troubleshooting efforts with authority and technical depth
• Proven experience in ensuring that large-scale initiatives are executed with excellence, with clearly defined responsibilities
• Track record of evaluating and overseeing complex technical projects, ensuring they meet scalability, reliability, and alignment requirements
• Ability to balance strategic oversight with operational execution, ensuring initiatives deliver measurable business outcomes
• Experience delivering complex projects on tight timelines while maintaining quality and compliance standards

Domain Expertise

• Experience working with financial APIs, market data integrations, and trade settlement processes
• Familiarity with regulatory compliance requirements in financial markets, preferably with experience in Canadian or North American financial regulations
• Experience with domain-driven design and event-driven design patterns
• Strong familiarity with the software development life cycle, including testing, deployment, and operational practices
• Understanding of brokerage operations, account management, KYC processes, and regulatory reporting
• Experience with foreign exchange (FX) processing and multi-currency transaction handling
• Knowledge of corporate actions processing and settlement workflows

Infrastructure Management

• Proven experience managing cloud infrastructure (GCP, AWS, Azure) in production environments
• Strong expertise in cloud-native architectures and infrastructure as code (Terraform, Ansible) and GitOps practices
• Deep understanding of Kubernetes orchestration and containerized application deployment
• Experience with infrastructure monitoring, observability, and incident management
• Strong knowledge of networking, storage, and compute infrastructure in cloud contexts
• Experience ensuring data residency compliance and regulatory requirements for financial services

Regional and Market Knowledge

• Understanding of the Canadian financial services market, regulatory landscape, and CIRO requirements (preferred) or ability to quickly acquire this knowledge
• Experience working in a startup or fast-growing technology company, preferably in fintech or financial services
• Ability to thrive in a global environment, effectively navigating regulatory requirements and building scalable solutions to support international growth
• Understanding of the Canadian fintech ecosystem and market dynamics

Who You Might Be (Nice-To-Haves):

• Experience in the Canadian financial services sector or CIRO-regulated environments
• Experience working with CIRO regulations or similar North American financial services regulatory frameworks
• Experience managing vendors, organizational budgeting, and resource allocation
• Experience working with global teams across multiple time zones
• Knowledge of emerging technologies and their application to financial services
• Experience or passion for financial markets, algorithmic trading, or brokerage operations
• Experience building teams in Canada or other North American markets
• Familiarity with the Canadian fintech ecosystem, market dynamics, and competitive landscape
• Experience with partner integrations and B2B2C financial services platforms
• Experience launching new markets or products in regulated financial environments
• Certifications in cloud platforms (GCP, AWS, Azure) or infrastructure management (Kubernetes, Terraform)