Senior/Staff Software Engineer, Care Experience

About the role

Toast is building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. The Care Experience team is responsible for the systems and tools that Toast's care agents use every day, forming the foundation behind every phone call, chat conversation, and support case. This work directly determines how quickly restaurants get back online when issues arise. As an engineer on this team, you will own the end-to-end delivery of the agent experience, driving the migration to a new omnichannel contact center platform while shaping the future of care tooling. You will build integrations, design workflows, and continuously improve the system based on real operational feedback from hundreds of agents supporting tens of thousands of restaurants. This role requires strong empathy for internal customers and the ability to operate within real-world constraints, navigating vendor limitations and system dependencies. If you are motivated by building for internal customers and want to see your work have a direct, measurable impact on how support scales, this is a role where your contributions will be seen and felt.

Key facts

What you'll do

Drive end-to-end development of care agent features, owning the full lifecycle from discovery through production and iterating based on agent feedback and operational metrics.

Build and evolve reliable integrations between the contact center platform and Toast's backend systems, enabling real-time access to customer data, account state, device information, and case history.

Own the reliability, performance, and scalability of business-critical agent tools to ensure they remain fast and available in a high-throughput, always-on support environment.

Partner closely with care operations to understand agent workflows, identify friction points, and translate operational needs into solutions that improve resolution speed and efficiency.

Make pragmatic technical decisions that balance vendor platform capabilities, integration complexity, system reliability, and delivery speed while operating within real-world constraints.

Contribute to technical design and architecture discussions, helping shape the foundation of Toast's care tooling as the platform evolves, scales, and supports new omnichannel capabilities.

Mentor and support other engineers through code reviews, pairing, and technical guidance, fostering a culture of ownership, quality, and continuous improvement across the team.

Evaluate and incorporate new technologies, frameworks, and best practices to improve developer experience, maintainability, and long-term system health.

Collaborate with product, design, and data teams to validate hypotheses, analyze usage patterns, and prioritize work that drives meaningful improvements in agent efficiency and restaurant outcomes.

Act as a systems thinker, anticipating edge cases, failure modes, and operational risks to build tools that are robust, debuggable, and resilient under pressure.

Serve as a technical leader in defining standards, patterns, and best practices for agent-facing features, ensuring consistency across the care platform.

Engage directly with support agents through testing, interviews, and feedback sessions to ensure solutions are intuitive, efficient, and aligned with real workflows.

Monitor and analyze key operational metrics to inform improvements, validate changes, and guide roadmap decisions for the care tooling portfolio.

Represent the Care Experience team in cross-functional discussions, communicating tradeoffs, timelines, and risks to stakeholders with clarity and transparency.

Requirements

5+ years of software engineering experience with a strong track record of building and operating production systems using Java, Kotlin, or other object-oriented languages.

Demonstrated ability to own complex systems or features end-to-end, from initial design and scoping through implementation, rollout, and ongoing iteration in production.

Experience integrating with third-party platforms or vendor systems, including working within external constraints, evolving APIs, and managing integration dependencies.

Proven capability to partner closely with operations, support, and internal stakeholders to understand workflows and translate them into effective technical solutions.

Strong focus on reliability and operational excellence, with an understanding of monitoring, observability, and incident response in high-availability systems.

Comfortable making technical decisions that involve tradeoffs between vendor capabilities, integration effort, system complexity, and delivery timelines.

Excellent written and verbal communication skills, with experience collaborating across distributed teams and aligning on technical direction.

Willingness to work within real constraints, balancing business needs, platform limitations, and technical debt while delivering sustainable solutions.

Nice to have

Experience with contact center platforms or omnichannel systems is preferred.

Background in high-throughput, always-on support environments is preferred.

Practical notes

This role is full-time based in Toronto, Ontario, Canada.

Employment eligibility to work in Canada is required.

The position may require occasional travel within the Toronto area for team collaboration or stakeholder meetings.