Retail Solutions Engineer, Mid-Market Growth

WinsAbove; United States; Hybrid; USD 100,000 - 160,000; Full time

Job summary

Toast is seeking a Mid-Market Retail Solutions Engineer to serve as the technical lead in the sales process, building end-to-end architectures for multi-location retailers and delivering tailored demonstrations that map Toast’s platform to each prospect’s workflows.

As part of the founding team, you’ll work across Sales, Product, Partnerships, and Implementation to ensure scalable solutions, drive pilots, address security reviews, and hand off to Delivery to realize what was sold.

Qualifications

• 3+ years in solutions engineering, sales engineering, pre-sales consulting, or a comparable technical customer-facing role.
• Working POS knowledge and the ability to speak credibly about retail operations
• Demonstrated success supporting complex, multi-stakeholder sales cycles with longer timelines and formal evaluation processes
• Practical fluency with integrations and APIs, with the ability to read documentation, reason about data flows, and scope what’s possible without engineering support
• Ability to handle complex customer communications fluently while maintaining high levels of customer satisfaction
• Ability to translate between technical and business audiences, including executive stakeholders
• Ability to manage multiple active opportunities simultaneously in a fast-paced environment
• Strong problem solving and troubleshooting skills
• Ability to work with minimal supervision
• Excellent communication and customer service skills
• Willingness to travel for onsite discovery, demos, and industry events - up to 25%

Responsibilities

• Serve as the technical lead on mid-market retail opportunities, partnering with Account Executives from discovery through close
• Run structured technical discovery with multi-stakeholder buying groups (operations, IT, finance, merchandising, and executive sponsors) to uncover business challenges and technical requirements
• Build and deliver tailored demonstrations and demo environments that map Toast’s retail platform to a prospect’s specific workflows, rather than standard product walkthroughs
• Design end-to-end solutions for multi-location retailers, including integration architecture, API and data flows, catalog and data migration, hardware configuration, and network requirements
• Scope and position the Toast partner ecosystem where native functionality doesn’t fully meet a requirement, and clearly frame trade-offs and effort
• Lead pilots and proofs of concept: define success criteria, manage technical validation, and drive them to a decision
• Own the technical components of RFPs, RFIs, security questionnaires, and vendor review processes
• Document technical scope and solution design, and lead clean handoffs to Implementation and Onboarding so what was sold is what gets built
• Clearly communicate gaps in product/market fit to Product Management and Product Marketing, and advocate for roadmap priorities grounded in real deal loss and risk
• Partner with Sales Enablement to build training, demo assets, and technical playbooks as the retail motion matures
• Become an expert in the product with complete knowledge of the technologies and the application software
• Attend trade shows and other events as a Toast brand ambassador
• Operate comfortably in an entrepreneurial environment where process, tooling, and product are still being built

Skills

Solutions engineering

Retail operations knowledge

Stakeholder management

APIs & integrations

Technical discovery

Job description

Toast is seeking a Mid-Market Retail Solutions Engineer to serve as the technical lead in the sales process, building end-to-end architectures for multi-location retailers and delivering tailored demonstrations that map Toast’s platform to each prospect’s workflows.

As part of the founding team, you’ll work across Sales, Product, Partnerships, and Implementation to ensure scalable solutions, drive pilots, address security reviews, and hand off to Delivery to realize what was sold.