Mid-Market Retail Solutions Engineer

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