About the position
Toast is driven by building the restaurant platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. Toast built its reputation by delivering a world-class Point-of-Sale experience purpose-built for restaurants. Now, we're expanding our platform to serve a new and exciting audience: retail businesses. Toast is making a bold investment in this space—expanding to thousands of retail locations, starting with convenience stores, bottle shops, and grocers, with plans to extend into additional segments in the future. This is not an incremental extension; it’s a ground-up opportunity to reimagine what POS can be for the modern retailer. We’re looking for a Principal Product Manager to lead this transformation. You’ll own the product vision and roadmap for our Retail POS offering. This team will be embedded within our POS product and engineering org to leverage Toast’s core platform strengths, while working in close partnership with Retail Line of Business (LOB) leadership to deliver a product that meets the unique demands of retail environments. If you’re excited by the opportunity to build something foundational, drive a cross-functional product strategy, and help Toast expand into a new vertical, this role is for you.
Responsibilities
- Define the Product Strategy: Set the vision and roadmap for Toast’s Retail POS, aligning with both platform capabilities and market needs.
- Lead Cross-Functional Execution: Partner with engineering, design, and analytics teams to build and deliver exceptional products, from discovery through launch and iteration.
- Bridge Teams and Verticals: Work closely with POS product teams and Retail LOB stakeholders to align on priorities, share insights, and ensure integrated decision-making.
- Understand the Customer: Conduct user research and gather input from sales, support, and retail customers to inform product direction.
- Drive Measurable Outcomes: Define success metrics and use data to evaluate performance, inform tradeoffs, and continuously improve.
- Communicate the Vision: Share plans, progress, and decisions clearly across stakeholders, including executive leadership, go-to-market teams, and customer-facing orgs.
Requirements
- 10+ years of product management experience in B2B SaaS, ideally in POS, commerce platforms, or embedded payments.
- Experience launching and scaling new products or verticals from zero to one in dynamic, fast-paced environments.
- Proven ability to influence across teams, lead with clarity, and make data-informed decisions.
- Exceptional communication and stakeholder management skills—comfortable navigating between technical and business conversations.
- Strong product instincts, customer empathy, and bias for action.
Nice-to-haves
- Experience in retail software or POS systems (including retail-specific workflows, compliance, or inventory management).
- Background in launching verticalized products across diverse customer segments.
- Familiarity with hardware integrations, mobile-first interfaces, or hybrid commerce models.
- Deep understanding of retail operations and store-level employee workflows.
Benefits
- Competitive compensation and benefits programs.
- Cash compensation (overtime, bonus/commissions, if eligible).
- Equity (if eligible).
- Flexible benefits to meet changing needs.
