Senior Engineering Manager leading OLO’s guest ordering, experimentation, and menu - quality systems. Owner’s AI platform helps local restaurants grow revenue and operate digitally.
About the role
- Head of Engineering leading Xero’s software teams and AI-first modernization for small-business accounting technology. Balancing product, technical, and commercial priorities while growing engineering leaders and reliable services in Vancouver.
Responsibilities
- Lead and grow multiple engineering teams within the product portfolio
- Deliver high-quality software improving the lives of small business customers globally
- Act as a technical anchor for system health and code quality
- Drive product delivery velocity and enterprise-wide progress
- Simplify complex cross-departmental challenges and act as a change agent
- Advocate for AI-first methodologies and high-impact outcomes
- Partner with Product and Design leaders to balance customer, business, and technical priorities
- Champion responsible AI architecture and AI-powered workflows
- Lead technical modernization from monoliths to decoupled services and API-first integration patterns
- Execute complex cross-team programs with accountability and proactive risk management
- Define hiring strategies and grow high-performing engineering talent
- Raise operational excellence through ownership of reliable, observable, high-quality production services and continuous improvement
- Build an inclusive, positive team culture and foster psychological safety and innovation
Requirements
- Deep understanding of software architecture, design trade-offs, and managing technical debt at scale
- Proven track record managing and growing high-performing leaders and engineering teams
- Ability to navigate conflict in an open, positive, and proactive way
- Strong strategic acumen for simplifying complex cross-functional challenges in fast-scaling environments
- Ability to foster a growth mindset and culture of accountability across multiple teams
- Bias for action and ability to make sound decisions quickly
- High emotional intelligence, including self-awareness, self-regulation, motivation, empathy, and interpersonal skills
- Experience or capability advocating for responsible AI architecture, AI-powered workflows, technical modernization, API-first integration, operational excellence, reliability, and observability
- Ability to work in or relocate to the role’s Canada-based location and meet applicable Canadian working-rights requirements
Benefits
- Annual bonus eligibility for permanent employees
- Equity (RSU) program eligibility for permanent employees
- Performance-based cash or equity incentives depending on role level and company performance
- World-class health, wellness, and retirement programs
- Wellbeing days
- Generous leave
- Dedicated professional development budgets
- Hybrid working environment with remote flexibility
- Modern office spaces and boost days for team connection, alignment, and creativity
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