Staff Software Engineer (GTM & AI Strategy)

• Toast is looking for a hands-on Staff Software Engineer to join the GTM & AI Strategy Engineering team
• In this role, you will be a primary builder of 0-to-1 tools designed to revolutionize how our sales teams operate
• This isn’t about maintaining legacy systems; it’s about writing the code and building the intelligence models that eliminate friction across the Go-To-Market stack
• As a technical lead, you will be responsible for building and productionizing agentic workflows and RAG pipelines to automate sales processes
• You will integrate AI services into the tech stack while maintaining rigorous standards for observability and performance monitoring
• 0-to-1 Development: Build and prototype new internal products from scratch that leverage LLMs and Agentic AI to automate account research, lead prioritization, and complex quoting logic
• Infrastructure Integration: Develop the backend connective tissue between our custom quoting engine, Salesforce, and internal data lakes to ensure a seamless, low-latency end-to-end experience
• Technical Problem Solving: Act as a key executor to solve complex synchronization and architectural challenges across the GTM stack, ensuring systems are scalable and resilient
• Build Great Products: Deliver significant core capabilities that have broad impact; take high-level goals and turn them into sequenced, production-ready code
• Problem Solve: Anticipate shifts in product needs and build flexible, decoupled backend systems that can evolve with our AI strategy
• Deliver Quality: Ensure the reliability of GTM tools by building deep observability into every service you ship

Benefits

• Peer and company recognition programs
• Unlimited Vacation
• Sabbatical opportunity after five years
• Professional Development Reimbursement Program
• Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
• Various peer and company recognition programs
• 401(k) and matching
• Medical, Dental, & Vision Coverage
• Mental Health Benefits
• Subsidized backup childcare

• Systems Architecture: Ability to implement event-driven architectures and manage data flow across disparate systems with high integrity
• Education: Bachelor’s or Master’s degree in Computer Science, or a related technical Field
• Applied AI/ML Skills: Practical, hands-on experience building LLM agents in a production environment
• Deep Backend Expertise: Extensive experience in backend languages (Java, Go, Python) with a track record of building complex, distributed systems
• Experience building internal “Sales Tech” or “Fintech” tools that directly impact revenue
• Familiarity with AWS data services (SageMaker, Lambda, SQS)
• A passion for removing “human-in-the-loop” friction through intelligent automation