Note: The job is a remote job and is open to candidates in USA. Toast is a technology company that helps restaurants and local businesses succeed in a digital world. They are seeking a Senior Manager, GTM Sales Engineer & AI solutions to lead the deployment of AI applications to improve productivity and automation in Retail sales. The role involves architecting solutions, collaborating with various teams, and ensuring the integration of AI into core systems.
Responsibilities
- Stand up the Retail AI GTM Pod to surface, qualify, and scale AI applications across the Retail field
- Serve as the production engine for ideas surfacing through the pod and field
- Evaluate what is worth scaling, determine the right build, buy, or borrow path, and take the strongest ideas from experiment to production tool—launching with Enablement to non-technical end-users and maintaining active ownership through adoption tracking, feedback, and iteration
- Lead technical discovery to determine the most efficient path for problem statements, assessing whether to build a custom agentic solution, stitch existing APIs, or coordinate with vendors to purchase a scalable product
- Translate decisions into a sprint-based roadmap, prioritizing developments based strictly on their potential to drive vertical PPR and eliminate administrative friction
- Maintain and execute against a technical scrum board, operating on defined sprint cycles to continuously ship, test, and iterate on AI-powered features
- Take successful, unscaled local experiments (e.g., territory expansion scoring, contact discovery pipelines, multi-intent category parsers) and harden them with error handling, version control, scalable code, and secure coding practices like input validation, secrets management, and mitigation of LLM risks (e.g., prompt injection)
- Coordinate integration efforts to map vertical AI outputs into core GTM platforms (Salesforce, Snowflake, Taskray), ensuring local applications enhance rather than disrupt foundational enterprise pipelines
- Build & monitor data validation frameworks ensuring model inputs are pristine and outputs are entirely auditable and trusted by the field
- Design & enforce security controls for Retail AI applications, including authentication/authorization frameworks, secrets management, access controls on model outputs, and mitigations for LLM risks (prompt injection, data exfiltration)
- Contribute to cross-functional AI coordination cadences connecting Revenue Operations, Marketing AI, and Business Technology teams across Toast
- Align on company-wide AI investments, advocate for Retail use cases and merchant requirements in shared roadmaps, and identify where central efforts can be leveraged, adapted, or extended
- Serve as Retail's active voice in sequencing these shared initiatives while staying coordinated
- Monitor central enterprise tool developments (e.g., prospecting or enablement agent suites) to identify opportunities to clone, customize, or extend for Retail merchant types
- Establish a pipeline for sharing locally developed code, architecture patterns, and prompt structures with central teams, ensuring Retail's breakthroughs help elevate Toast's engineering ecosystem
- Design and execute vertical-wide enablement tracks to build a baseline of confident, independent AI tool usage across sales reps, onboarding consultants, and managers
- Build & monitor adoption tracking mechanisms for deployed AI solutions, ensuring training translates into consistent field usage and measurable reductions in level of effort (LOE)
Skills
- Applied AI Deployment: 4+ years of experience in a technical, analytical, or GTM operations role, with a track record of owning the full deployment lifecycle of applied AI applications, RAG pipelines, or agentic workflows, including post-launch monitoring, alerting, rollback procedures, and model version management
- Modern AI Toolchain Literacy: Advanced, hands-on proficiency with developer-focused AI tools, specifically the Gemini Suite, Claude Cowork, and Claude Code
- Modern Deployment Stack: Experience deploying and operating AI backend systems in production (API services, model inference pipelines, orchestration layers), with demonstrated ownership through reliability, observability, and incident response
- Application Security Awareness: Familiarity with security best practices for AI-native systems, including authentication/authorization, secrets management, access controls on outputs, and awareness of LLM attack surfaces (prompt injection, data exfiltration)
- Agile Operational Fluency: Experience operating within an agile engineering model, including managing technical product backlogs, running sprint cycles, and maintaining scrum boards
- Strategic Diplomacy: Exceptional communication skills with a proven ability to enter central enterprise forums, align stakeholders, advocate for vertical needs, and collaborate across business units
- Software engineering or computer science background with the ability to write functional code (Python, JavaScript, or equivalent) and construct robust API integrations from scratch
- Direct domain familiarity with B2B SaaS and Retail tech spanning grocery, convenience, or wholesale commerce environments
- Experience building or scaling an AI program for non-technical end-users, including driving literacy, prompt engineering, or tool enablement
- Degree in Computer Science, Engineering, a related technical discipline, or equivalent practical experience as a technical founder or builder
Benefits
- Competitive compensation and benefits programs
- 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
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