Mid-Market Retail Solutions Engineer

About this role

Mid-Market Retail Solutions Engineer 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. After spending years building the best POS platform for restaurateurs, Toast has recently expanded its offerings into retail concepts. This role requires a founder’s mindset as we build the Retail Solutions Engineering team to support Toast’s growth in this new vertical.

The ideal candidate thrives in ambiguity, enjoys building processes alongside evolving products, and is energized by helping shape a new business line from the ground up. We are looking for a product and application expert who will serve as the technical lead within the mid-market sales process, with the objective of driving revenue. Mid-market retail deals are multi-location, multi-stakeholder, and technically complex, spanning integrations, data migration, network and hardware architecture, and enterprise-grade security review.

This role works cross-functionally with Sales, Product Management, Partnerships, and Implementation to ensure solutions are technically sound, scalable, and aligned to customer needs. As a Mid-Market Retail Solutions Engineer, you will be part of the founding team helping to revolutionize the way the retail industry does business by pairing technology with an unrivaled commitment to customer success. You will help multi-unit retail operators streamline operations, increase revenue, and deliver amazing customer experiences through our platform that combines retail point of sale, customer-facing technology, and award-winning customer support.

In this role, you will be challenged to take on meaningful projects that will help shape the future of the company. Join us as we empower the retail community to delight customers, do what they love, and thrive. A day in the life (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 What you'll need to thrive (Requirements) 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% What will help you stand out (Nonessential Skills/Nice to Haves) Prior Toast experience, or experience with a comparable retail/restaurant commerce platform Retail industry, retail SaaS sales, or related industry experience Experience with multi-unit or franchise retail operations Familiarity with ERP, inventory, e-commerce, loyalty, or accounting integrations common in retail Experience being an early hire on a new team or product line A strong spirit and energy to provide the best support in the retail industry Detail oriented AI at Toast At Toast, one of our company values is that we're hungry to build and learn.