Retail Revenue Operations: Sales & Onboarding Operations

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. Retail is Toast's biggest bet and we are growing rapidly. The opportunity is massive and the category is ours to define. You will have Toast's scale, brand, and resources behind you, with real influence over how we operate, scale, and win.

This is a hands-on Revenue Operations business partner role. You will work alongside Retail Sales and Onboarding leaders to help them hit their goals, not only by advising on what should change, but by identifying opportunities, developing a point of view, and personally driving the work required to make those changes real.

You will own two connected domains: Sales Operations for Retail's AE and BDR/SDR teams, and Onboarding Operations for the Retail Onboarding organization, including the Lead-to-Go-Live handoff between them. The mandate is straightforward: help Retail Sales and Onboarding hit their goals and scale effectively. Your remit spans creating pipeline, improving conversion and deal size, increasing onboarding throughput, replicating what top performers do, reducing administrative drag on reps and consultants, and getting customers live and generating revenue faster. Much of this shows up in Productivity Per Rep (PPR), a core operating metric for our team, though the remit is broader than any single measure. It also means identifying what we should start doing, not only what has been identified. 

This is not a strategy-only or delegation-heavy Principal role. You will move between senior-level thought partnership and detailed execution: analyzing problems, designing pilots, managing projects, defining process and system requirements, influencing cross-functional partners, and driving work through launch and adoption. You will be given broad focus areas rather than a task list, and expected to build and prioritize your own roadmap while managing real day-to-day operational demands.

Applied AI is part of how this team works. You will use AI tools in your own workflow, identify where automation can eliminate effort for the field, and partner with our Agentic GTM Sales Engineer, a technical builder, to turn the strongest ideas into production tools. You will also have analytics partners for heavier data infrastructure and modeling work.

A day in the life (Responsibilities) 

• Business Partnership & Roadmap Ownership: Work across frontline teams and senior leadership to understand goals, identify growth opportunities and operational problems, prioritize the highest-value work, and own initiatives from problem definition through rollout, adoption, and measurement.
• Sales Growth & Productivity: Diagnose funnel performance, design and run growth programs and pilots, replicate top-performer behaviors, and reduce the workflows and administrative work limiting AE and BDR/SDR productivity.
• Onboarding Throughput & Scale: Partner with Onboarding leadership to improve Time-to-Go-Live, consultant productivity, capacity planning, and performance visibility across five onboarding lanes and twelve business categories, building the processes and operating mechanisms Retail needs as it scales.
• Lead-to-Go-Live & Cross-Functional Execution: Improve the Sales-to-Onboarding handoff and identify where process, systems, data, or AI can strengthen the motion. Translate business needs into clear requirements and work with Business Technology, Analytics, Enablement, Central Operations, and our Retail AI Council to get solutions delivered and adopted.

What you'll need to thrive (Requirements)

• Revenue Operations Experience: 5 to 8 years in Revenue Operations, Sales Operations, GTM Operations, or a closely related role, with meaningful ownership of cross-functional GTM work. Experience supporting high-velocity Sales and/or Onboarding organizations is highly valued.
• Ownership & Execution: Proven ability to take broad or ambiguous problems, develop a point of view, identify and prioritize the work, and drive initiatives end to end without requiring a predefined roadmap.
• Analytical Self-Sufficiency: Comfortable working directly with operational data to investigate questions, identify patterns, test hypotheses, and make recommendations without depending on an analyst for every answer. Functional SQL competency required.
• GTM Systems Fluency: Able to recognize where process or system design is causing problems, shape a solution, write clear business requirements, partner with technical teams through delivery, validate what is built, and drive adoption. Strong Salesforce experience and familiarity with enterprise project or implementation management tooling, such as Taskray or equivalent, expected.
• Applied AI Fluency: Hands-on use of generative AI to improve your own work, structure and solve operational problems, and identify opportunities to reduce manual effort or improve field productivity.
• Communication & Influence: Able to move comfortably from frontline operational detail to VP-level strategy and drive action across teams you do not directly manage.

• A comprehensive operational background reflecting a cross-section of both pre-sale (Sales/Outbound Ops) and post-sale (Onboarding/Implementation Ops) lifecycle systems.
• Prior experience directly within frontline sales roles (AE, DM, or Sales Management) or onboarding/implementation roles, with subsequent operational depth built on top of that domain experience.
• Experience operating within complex B2B SaaS verticals or industries featuring intricate supply chain, matrixed routing, or inventory footprints (e.g., retail, grocery, convenience, or fuel).
• An active personal baseline of leveraging generative AI tools, prompt engineering, or modern automation frameworks to systematically reduce daily administrative drag.

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.