Senior Manager, GTM Sales Engineer & AI solutions

About the role

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. Retail is Toast's biggest bet and we are growing rapidly. The opportunity is massive, and the category is ours to define. You will have the backing of Toast's scale, brand, and resources but you will be on the team architecting how we operate, scale, and win. The decisions you make in this role will shape how Toast competes in retail for years to come. Toast is prioritizing AI integration across the enterprise to redefine GTM velocity. As part of this strategy, multiple business units are pursuing specialized AI initiatives tailored to market challenges. This model balances corporate-wide coordination with vertical accountability: teams work in lockstep to scale efficiencies and aggregate impact, while remaining responsible for developing, building, and launching solutions optimized for unique operating environments. 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.

Key facts

What you'll do

Drive the operational ownership and governance of the Retail AI GTM Pod, establishing intake mechanisms and prioritization frameworks for AI ideas sourced from frontline teams.

Champion the evaluation of AI use cases by coordinating with field teams to pressure-test hypotheses and align solutions with business outcomes that directly impact PPR.

Lead technical discovery for build versus buy decisions, determining efficient paths for problem statements through custom agents, API stitching, or vendor partnerships.

Architect and deploy scalable AI applications into production environments, integrating them with core Toast systems to ensure reliability, maintainability, and performance.

Establish continuous feedback loops between field execution and corporate strategy, surfacing data-driven insights to refine solution design and adoption.

Define and manage sprint-based roadmaps for AI initiatives, prioritizing developments that reduce administrative friction and accelerate sales productivity in Retail.

Collaborate closely with Enablement to launch non-technical end-users into new AI tools, ensuring clear onboarding paths and active ownership of adoption metrics.

Partner with Onboarding teams to streamline the path to Customer Go-Live by embedding AI workflows that accelerate time-to-value for retail merchants.

Act as the vertical-specific technical liaison between distributed AI experiments and centralized corporate operations, standardizing practices while preserving local adaptability.

Translate field feedback and performance data into iterative product improvements, maintaining active ownership of tool lifecycle management from inception through scale.

Coordinate cross-functional alignment with Revenue Operations, corporate marketing, and engineering to ensure Retail AI strategies support enterprise-wide objectives.

Evaluate emerging AI technologies and methodologies, determining when to experiment, pilot, or scale solutions based on clear ROI indicators.

Provide thought leadership and data-backed recommendations to leadership on AI GTM strategy, influencing investment and resourcing decisions for Retail.

Champion best practices in AI governance, security, and compliance within the Retail vertical, ensuring solutions meet organizational standards.

Drive the definition of success metrics for AI deployments, establishing measurement frameworks that link tool usage to productivity and revenue outcomes.

Requirements

Bring 8 or more years of professional experience in technology, sales engineering, or solutions architecture, with a proven track record of driving complex implementations.

Hold a Bachelor's degree in Computer Science, Engineering, or a related technical field, or demonstrate equivalent practical experience through a combination of training and work history.

Possess deep expertise in applying AI and machine learning concepts to real-world business problems, with hands-on experience in at least one modern AI stack.

Demonstrate fluency in interpreting business requirements and translating them into technical specifications that engineering teams can execute against.

Show a strong track record of working autonomously and influencing stakeholders without direct authority, managing multiple priorities in a fast-paced environment.

Exhibit exceptional communication skills, able to distill technical concepts for non-technical audiences while maintaining rigor in discussions with engineers.

Have experience navigating ambiguous problem spaces and making timely decisions with incomplete information to keep initiatives moving forward.

Commit to working closely with cross-functional teams, aligning priorities between field sales, onboarding, and corporate operations to ensure cohesive execution.

Nice to have

Experience with retail point-of-sale systems, commerce platforms, or customer engagement technologies.

Background in managing AI product roadmaps or data-driven GTM initiatives in B2B environments.

Familiarity with Toast's product suite and retail-specific workflows.

Practical notes

This is a full-time role located in Remote.

Employees may be required to travel up to 25% of the time.

Visa sponsorship may be considered for eligible candidates.