Senior Manager of GTM Sales Engineer & AI solutions, Toast

• 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
• Ability to travel to US as needed

Desirable

• The GTM Sales Engineer & AI solutions is the core functional driver of this transformation within the Retail vertical
• As an expert in applied AI, you will own the centralized deployment of AI applications to directly improve Productivity Per Rep (PPR)
• You will drive AI-powered productivity and automation across Retail sales, working with AEs and BDR/SDR teams to accelerate sales and with Onboarding to streamline the path to Customer Go-Live, with the opportunity to grow your impact across other GTM and client-facing teams as the vertical scales
• You will be the operational linchpin running the Retail AI GTM Pod, architecting a continuous feedback loop sourcing grassroots ideas from the frontline, filtering them through a business lens, and scaling them into production tools
• This is a technical, builder-focused role
• You will observe decentralized AI applications working across the organization and partner to accelerate their impact, making them structurally better, integrating them into core systems, and maintaining them long-term
• While you will partner with central corporate operations and marketing to advocate for Retail use cases and scale company-wide efficiencies, you will also possess the autonomous engineering capabilities to construct vertical-specific pipelines when distinct merchant workflows require it
• This role sits in Revenue Operations, but will also dotted-line report into engineering
• Leadership & Facilitation: Stand up the Retail AI GTM Pod to surface, qualify, and scale AI applications across the Retail field. The model could be a working group of AI-forward reps, managers, and leaders organized around defined themes in Sales & Onboarding, contributing domain expertise and frontline signals. The pod functions as an intake mechanism and sounding board, surfacing field experiments, pressure-testing priorities, and keeping your roadmap grounded in what moves the business
• Idea & Solution Sourcing: 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
• Build vs. Buy Evaluation: 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
• Roadmap Prioritization: Translate decisions into a sprint-based roadmap, prioritizing developments based strictly on their potential to drive vertical PPR and eliminate administrative friction
• Agile Sprint Execution: Maintain and execute against a technical scrum board, operating on defined sprint cycles to continuously ship, test, and iterate on AI-powered features
• Industrializing Frontline Wins: 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)
• Systems Integration: 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
• Data Integrity Architecture: Build & monitor data validation frameworks ensuring model inputs are pristine and outputs are entirely auditable and trusted by the field
• Application Security: 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). Ensure builds meet Toast's security standards given system proximity to payment and customer data workflows
• Enterprise Collaboration: 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
• Vertical Personalization: Monitor central enterprise tool developments (e.g., prospecting or enablement agent suites) to identify opportunities to clone, customize, or extend for Retail merchant types
• Bidirectional Knowledge Exchange: 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
• AI Fluency Leadership: Design and execute vertical-wide enablement tracks to build a baseline of confident, independent AI tool usage across sales reps, onboarding consultants, and managers
• Adoption Analytics: Build & monitor adoption tracking mechanisms for deployed AI solutions, ensuring training translates into consistent field usage and measurable reductions in level of effort (LOE)