Senior AI GTM Architect for Retail Solutions

WinsAbove; Toronto; Hybrid; CAD 136,000 - 218,000; Full time

Job summary

Toast is seeking a GTM Sales Engineer & AI Solutions lead to deploy AI across the Retail organization, accelerating productivity per rep and enabling onboarding to go live with frontline teams.

You will architect AI pipelines, evaluate build vs buy, and drive adoption while maintaining strong security practices and collaboration with Marketing, Revenue Operations, and engineering. This hybrid role requires travel and a hands-on engineering mindset.

Qualifications

• 4+ years in a technical, analytical, or GTM operations role owning full AI deployment lifecycles.
• Hands-on with modern AI toolchains and production AI backend systems.
• Knowledge of security best practices for AI-native systems and agile engineering.

Responsibilities

• Lead the Retail AI GTM Pod to surface, qualify, and scale AI apps across Retail.
• Evaluate build vs buy options; drive roadmaps and adoption tracking.
• Ship and iterate AI features with sprint cycles and reliable release practices.
• Coordinate integration with Salesforce, Snowflake, Taskray and related platforms.
• Build data validation and security controls; monitor model inputs/outputs.
• Partner with Revenue Operations, Marketing AI, and Business Tech to align roadmaps.
• Drive AI fluency and adoption analytics across sales and onboarding teams.
• Travel to US as needed.

Skills

Applied AI Deployment

AI Toolchain

Deployment Stack

Security Awareness

Agile Operations

Strategic Diplomacy

Travel

Tools

Gemini Suite

Claude Cowork

Claude Code

Job description

Toast is seeking a GTM Sales Engineer & AI Solutions lead to deploy AI across the Retail organization, accelerating productivity per rep and enabling onboarding to go live with frontline teams.

You will architect AI pipelines, evaluate build vs buy, and drive adoption while maintaining strong security practices and collaboration with Marketing, Revenue Operations, and engineering. This hybrid role requires travel and a hands-on engineering mindset.