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 of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

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.

In this role, you will shape the future of how our customers interact with their data—designing intuitive reporting products, delivering actionable insights, and building the APIs that empower internal teams to innovate on Toast’s data advantage. This role is pivotal to unlocking the full potential of our restaurant data for our customers and for Toast. You will collaborate with teams across Toast to transform complex data into meaningful insights that drive restaurant success while creating the foundational systems that fuel data-driven decision-making across Toast. If you’re passionate about delivering exceptional user experiences, thrive at the intersection of strategy and execution, and are eager to make an outsized impact, we’d love to have you on our team.

You are obsessed with customers and how they work. You wake up thinking about how to help our customers understand their data, and how we can bring the right amount of context to that data. You love solving complex problems, looking across experiences, and scaling simplicity for customers and for internal teams. You are grounded in user feedback, cross-functional partnership, and can translate customer and user needs and product vision into world-class experiences that work at scale.

You have a proven track record of building and shipping user-facing experiences that include explaining complex information in simple ways. You understand the power of AI and how to measure and evaluate the success of cross-cutting experiences like reporting. 

A day in the life (Responsibilities) 

• Own and drive the roadmap for reporting, helping to figure out how we can deliver a consistent, high quality customer experience across products and lines of business
• Work closely with customers, designers and developers to concept, prototype, ship, measure, and improve reporting and data experiences across Toast surfaces
• Partner with multiple teams to figure out how to bring insights and context to data for customers
• Help define and implement how we use data to power AI experiences
• Research and get to know customers (internal and external) directly 
• Champion customer needs across Toast by building strong relationships horizontally and vertically

What you'll need to thrive (Requirements)

• Experience as a product manager, including API design and management, reporting products, platform-thinking, as well as building customer-facing data experiences across web, mobile
• Experience developing and launching products with cross-functional constraints, not just technical constraints, and working collaboratively and effectively with cross functional teams  
• Exceptional communication skills, able to work well with architects, engineers, designers, customers, as well as executives and functional leaders outside of R&D
• Passion for and knowledge of the role data plays for R&D teams, including how to structure data for use in AI-driven products
• Entrepreneurial mindset and ability to create a compelling product vision
• Take ownership of an existing product, and figuring out how to improve and iterate on it including setting, measuring, and optimizing the right metrics

#LI-HYBRID
#BI-Hybrid

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 of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

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 launching a new initiative to bring the power of voice AI into the in-store restaurant experience. While voice has transformed drive-thru and phone ordering, we believe there’s a large opportunity to make in-store experiences better for guests and more proficient for restaurant teams. This team will explore voice capabilities across front-of-house (guest ordering, service interactions, POS assistance) and back-of-house (kitchen coordination, hands-free workflows, inventory signals). As the Principal Product Manager — Voice AI (In-Store) on the Commerce Platform, you’ll define strategy, evaluate vendors and partners, run zero→one discovery and pilots in real restaurants, and lead commercialization — creating a reusable voice platform that powers multiple use cases across the restaurant.

A day in the life (Responsibilities) 

• Define vision & portfolio strategy. Own the long-term vision and multi-quarter roadmap for in-store voice AI and the platform that enables multiple use cases across FOH/BOH. Balance short-term pilots with long-term platform investments.
• Run vendor & technical evaluation. Lead technical evaluation of voice and AI vendors (ASR, NLU, TTS, edge inference, on-device options) and create benchmarking frameworks for accuracy, latency, privacy, and cost.
• Lead commercial conversations. Drive vendor commercial discussions (pricing models, licensing, SLAs) and surface negotiation points — partnering with Procurement and Legal who finalize contracts and budget approvals.
• Drive zero → one discovery and pilots. Plan and execute discovery, rapid prototyping, and in-restaurant pilots; iterate based on operational feedback and scale successful experiments.
• Design a reusable voice platform. Define APIs, integration patterns, data flows, and tooling that make voice capabilities reusable across guest experiences, staff workflows, and integrations with POS, kitchen systems, and telemetry services.
• Lead GTM & commercialization. Define pricing, packaging, and go-to-market strategy with Product Marketing, Sales, and Operations; identify commercial models that fit restaurants of different sizes.
• Coordinate cross-functional delivery. Align Engineering, Hardware Ops, Reliability, Security, Data, Research, Design, Care/Onboarding, and GTM partners to de-risk delivery and adoption.
• Drive operational readiness & reliability. Define operational playbooks, observability, edge/online failover modes, and post-launch monitoring to ensure reliable in-store behavior and low support cost.
• Champion field research & validation. Spend time in restaurants to learn operational workflows, validate prototypes, and iterate with real staff and guests.
• Mentor & shape product practice. Coach senior PMs and engineers on voice/AI product development, vendor evaluation, and responsible AI practices; contribute to the Product Playbook.
• Embrace and advocate for the use of AI tools to accelerate product discovery, streamline execution, and explore new product experiences - helping shape how we build and what we build.

What you'll need to thrive (Requirements)

• AI product delivery experience. ~8+ years shipping complex software products with demonstrated ownership of multi-team programs or a major product portfolio, and experience delivering AI-enabled features or products.
• AI Model Evaluation. Hands-on experience defining and owning AI model evaluation (examples: WER/CER, intent accuracy, wake-word false accept/reject, latency, completion/task success), building continuous evaluation and model ops processes (drift detection, automated regression tests, A/B testing, rollback/mitigation playbooks), and partnering with ML teams to run experiments and error analysis.
• Zero → one experience. Proven track record taking a product from discovery through prototype and pilot to scale.
• Vendor evaluation & commercial acumen. Hands-on experience evaluating AI/voice vendors and participating in vendor commercial conversations (note: Procurement/Legal finalize contracts).
• Platform mindset. Ability to design reusable APIs and platform capabilities that enable multiple downstream use cases and teams.
• Customer & ops empathy. Experience conducting on-site discovery and validating prototypes in operational environments (restaurant or other physical venues).
• Cross-team leadership. Exemplary stakeholder management and ability to align senior partners across hardware, engineering, ops, and GTM, especially on high-visibility initiatives.
• Communication & influence. Clear, persuasive written and verbal communication; able to synthesize technical tradeoffs and business value for executives and partners.

Special Sauce* (Nice to Haves)

• Speech / voice product experience. Prior experience building voice AI products (ASR/NLU/TTS, or working directly with speech teams) is helpful but not required.
• Conversational UX & dialog design. Experience designing conversational flows, state management, turn-taking, error recovery and graceful degradation
• Exposure to hardware considerations for voice (far-field audio, beamforming, noise cancellation, embedded audio processing).
• Experience with on-device / edge inference and hybrid cloud/edge voice architectures (model quantization, latency/footprint tradeoffs).
• Familiarity with privacy, compliance, and PII handling for voice data (on-device vs cloud processing, country-level regulations).
• Background in restaurant, retail, or other physical-world operations.
• Experience with ML lifecycle tooling, continuous model evaluation, and production A/B testing strategies for AI features.

You’ll be measured on (suggested success metrics)

• Launch and adoption of successful in-store voice pilots (pilot → scale conversion).
• Measurable operational impact (e.g., staff time saved, reduction in order errors, throughput gains).
• Guest experience improvements (NPS/CSAT lift for voice flows, voice take rate).
• Platform reuse (number of distinct use cases / teams reusing core voice APIs).
• Reliability & support outcomes (uptime targets, reduction in Care tickets related to voice).
• AI health & model performance: model accuracy (WER/intent accuracy), latency, drift rate, and rate of regressions caught by CI/monitoring systems.

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 of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

^#LI-REMOTE