Senior Product Designer, Point of Sale

Toast•Boston, MA

10h•$125,000 - $254,000•Hybrid

About The Position

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. As a Senior Product Designer on the Point of Sale team, you will help define what world-class restaurant technology looks and feels like, shaping the experiences that thousands of servers, bartenders, and front-of-house staff depend on every single day to deliver excellent hospitality. Your mission is to raise the bar for how we think about speed, trust, and usability at the most critical touchpoint in the restaurant. Working within the POS team, you will bring both strategic vision and hands-on craft to some of Toast's most complex and high-impact design challenges. You'll partner with research, product, and engineering to deeply understand the workflows that define restaurant service, drive design direction across the platform, and help grow the quality and ambition of the work around you. You'll immerse yourself in the fast-paced reality of restaurant operations to ensure every design decision is grounded in the real world, not just what looks good on a screen. We are looking for a designer with a Founder's Mentality: someone who takes uncompromising ownership of their domain, influences beyond their immediate scope, and is relentlessly committed to customer success. If you are ready to lead at the intersection of craft and strategy and help build the future of restaurant operations, we want you on the line with us.

Requirements

You have a track record of driving measurable design impact — you can point to decisions you made that changed outcomes, not just deliverables you shipped.
You hold an exceptionally high bar for design excellence. Your portfolio demonstrates mastery of complex, real-world systems with fine attention to detail, edge cases, and long-term scalability.
You are a natural cross-functional leader. You build trust with product, engineering, and research peers, and you know how to influence direction without authority.
You excel at operating across multiple levels simultaneously — zooming out to shape strategy while zooming in to get the details right.
You have deep instincts for designing speed and reliability into products. You know that for front-of-house staff, a half-second matters.
You take an AI-first design approach to quickly create conceptual prototypes and possess strong visual design skills to polish beautiful and intuitive end-to-end journeys across multiple surfaces and contexts.
You are a mentor and force multiplier — your presence makes the design work around you better.
5+ years in product design, with clear progression from individual execution to owning product strategy and influencing org-wide design direction.
Please include a portfolio link with your application.

Responsibilities

Lead end-to-end design for Point of Sale experiences at a platform level, driving direction from early discovery through polished execution with significant autonomy and strategic influence.
Define how complex operational workflows — order taking, modifications, payments, table management, and beyond — should work across Toast's terminal and handheld surfaces, setting a high bar for the entire team.
Bring a systems mindset to the POS platform: identify patterns, build scalable solutions, and actively contribute to and evolve the Toast design system.
Partner with Product and Engineering leadership to shape roadmap direction, surface design risks early, and advocate for the user in prioritization decisions.
Design for the realities of restaurant service — high-pressure, time-sensitive, hardware-constrained — and set the standard for what reliable, trustworthy, front-of-house software should feel like.
Make work visible early and often, using prototypes, systems thinking, and clear storytelling to drive alignment and influence product direction across senior cross-functional stakeholders.
Mentor and develop designers on the team, raising the collective quality of process, craft, and judgment.
Champion the server and front-of-house perspective at every level of the organization, ensuring speed, clarity, and reliability remain non-negotiable design principles.
Integrate emerging AI-first tools and methods into your practice and help the broader team do the same.