Commercial Lead

Boston, MA Preferred, but open to remote 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. Toast is transforming how people experience dining—from the moment they walk in, to how they order, pay, and engage with hospitality brands. Our Commerce group sits at the center of this evolution, building technology that seamlessly connects service, payments, and operations to create entirely new ways for guests to dine and pay. We’re looking for a Commercial Lead to help shape and bring to life the next generation of in-store payment and hospitality experiences. In this role, you’ll work directly with a range of innovative restaurant concepts, from immersive entertainment venues to emerging hospitality brands and established operators, to rethink how dining flows—from ordering to checkout and everything in between. You’ll play a key role in defining how technology can unlock faster, more intuitive, and more engaging guest experiences. This is a highly hands-on, exploratory role where you’ll operate across the full customer journey—testing new ideas in real environments, partnering closely with operators, and helping translate those learnings into scalable solutions. A day in the life (Responsibilities) Own the end-to-end experience with pilot customers—introducing new ways to order, pay, and interact in-venue, and ensuring successful rollout and adoption Partner with a diverse set of hospitality operators—including eatertainment venues and forward-thinking restaurant groups—to design and refine new service and payment flows Gather real-time insights from customers and guests, turning feedback into actionable recommendations that shape product direction and commercial strategy Collaborate cross-functionally with product, engineering, and go-to-market teams to bring new concepts to life and ensure they can scale effectively Build business cases and financial models to evaluate new opportunities, pricing approaches, and customer segments Help define repeatable playbooks that enable broader rollout of new in-store experiences across the Toast ecosystem What you’ll need to thrive (Requirements) Experience in sales, customer success, onboarding, professional services, or growth—ideally in hospitality, payments, or SaaS A builder mindset with a strong bias for action; you’re comfortable navigating ambiguity and testing ideas in live environments Passion for reshaping in-person experiences, particularly how guests interact with restaurants and complete transactions Proven ability to work closely with product teams to iterate quickly and find product-market fit Deep curiosity about hospitality trends and emerging restaurant formats Strong operational instincts, with experience creating processes that can scale Excellent communication and stakeholder management skills, with the ability to build trust across internal teams and external partners Experience working with experiential dining, venue-based entertainment, or innovative restaurant concepts Familiarity with POS systems, payments technology, or hospitality operations Background in early-stage initiatives or building new programs from the ground up In this role, you’ll help redefine what it feels like to dine out—creating seamless, engaging, and entirely new ways for guests to experience hospitality and complete their transactions. AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part o ... (truncated, view full listing at source)