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[Remote] Senior Software Engineer, Support AI

Work from home Full-time role Hiring

Note: The job is a remote job and is open to candidates in USA. Toast is a company focused on building a restaurant platform that enhances operational efficiency. They are seeking a Senior Software Engineer for the Support AI team to develop voice and chat systems that improve customer support for restaurants, ensuring quick resolution of issues before they escalate.

Responsibilities

  • Drive end-to-end development of voice and chat AI systems—from concept through production—owning the full lifecycle and iterating based on real customer and operational outcomes
  • Build and evolve integrations with third-party AI platforms and internal Toast systems, making pragmatic decisions that balance speed, reliability, and long-term scalability
  • Design and implement observability, monitoring, and outcome tracking for AI-powered support experiences—using production data to understand system performance and continuously improve customer outcomes
  • Make technical decisions grounded in production data, customer feedback, and operational constraints—navigating ambiguity while building systems that scale
  • Partner closely with product, support operations, and AI/ML engineering teams to translate ambiguous problems and workflows into robust, maintainable systems that drive measurable impact
  • Contribute to technical design and architecture discussions, helping shape system design, tradeoffs, and engineering standards
  • Mentor and support other engineers through code reviews, pairing, and technical guidance, fostering a culture of ownership, quality, and continuous improvement

Skills

  • 5+ years of experience in software engineering, with a strong background building and maintaining production systems using Java, Kotlin, or other object-oriented languages
  • Proven ability to own complex features or projects end-to-end, from design through production and iteration
  • Experience building integrations with third-party APIs or platforms, especially in domains where reliability, latency, and vendor constraints matter
  • Comfortable working in ambiguity and making pragmatic tradeoffs between shipping quickly and building for scale
  • Strong collaborator who can work effectively across product, operations, and technical teams to deliver customer and business outcomes
  • Proficient with AI tooling such as Cursor, Claude, and MCP servers
  • Self-starter who takes ownership of problems, unblocks themselves, and drives work forward without waiting for perfect conditions

Benefits

  • Cash compensation (overtime, bonus/commissions if eligible)
  • Equity
  • Benefits
  • Hybrid work model that fosters in-person collaboration while valuing individual needs
  • Reasonable accommodations for persons with disabilities to enable them to access the hiring process

Company Overview

  • Toast is a point-of-sale and restaurant management platform designed for businesses in the food service and hospitality industry. It was founded in 2011, and is headquartered in Boston, Massachusetts, USA, with a workforce of 1001-5000 employees. Its website is https://pos.toasttab.com.
  • Company H1B Sponsorship

  • Toast has a track record of offering H1B sponsorships, with 14 in 2026, 26 in 2025, 32 in 2024, 39 in 2023, 66 in 2022, 29 in 2021, 17 in 2020. Please note that this does not guarantee sponsorship for this specific role.
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