Retail Revenue Operations: Sales & Onboarding Operations

About the Role

Toast builds technology that helps restaurants and local businesses grow and run more effectively in an increasingly digital market. The company’s retail business is a major strategic priority, and this position plays a central part in shaping how that business scales and performs.

This role sits at the intersection of retail sales and onboarding, with responsibility for the operational framework that connects the lead-to-go-live journey. You will partner closely with leadership across sales and onboarding to improve handoffs, streamline workflows, and support commercial outcomes across the customer lifecycle.

The position is intended for an experienced revenue operations professional who combines strong analytical capability with practical sales or onboarding experience. The main objective is to improve Productivity Per Rep (PPR) by reducing administrative burden, increasing deal velocity, and enabling efficient high-volume onboarding. You will help define scalable operating mechanisms, surface improvement ideas from the field, and work alongside AI-focused GTM operations teams to bring automation into frontline workflows.

Strategic Partnership and Lifecycle Optimization

• Review the full sales funnel from outbound activity to closed business, identifying ways to improve pipeline volume and conversion at each stage.
• Examine the post-sale journey to reduce implementation timelines, speed up revenue recognition, lower churn before go-live, and improve Onboarding Consultant efficiency.
• Create and manage a structured intake process for requests coming from sales and onboarding leaders, with emphasis on the highest-impact priorities.
• Study top performer behaviors across reps and consultants, then translate those patterns into repeatable operating practices.
• Contribute to the Retail AI GTM Pod by testing field workflows, identifying automation opportunities, and feeding requirements into production-ready operations work.

Sales Operations and Outbound Program Design

• Build and run programs, pilots, and projects that strengthen outbound performance, increase conversion, and expand deal size across AE and XDR teams.
• Work with sales leadership and enablement partners to identify best practices, close productivity gaps, and create clearer communication for field teams.
• Own the retail-specific layer of sales systems, including Salesforce configuration, data quality, hierarchy maintenance, and enhancement prioritization.
• Act as the main operational connector between the retail vertical, central sales operations, and partner teams such as enablement, marketing, onboarding, and business technology.
• Capture process pain points, data issues, and workflow improvement ideas from managers and reps, and route larger automation opportunities to the appropriate AI operations partners.

Onboarding Infrastructure and Capacity Planning

• Replace manual tracking with automated dashboards across all onboarding lanes and business categories, measuring TTGL, FTR, CES, and milestone speed.
• Create and maintain vertical-specific Taskray templates that align with merchant milestones, segment differences, and new market models such as wholesale B2B.
• Maintain a bottom-up capacity model that reflects workload limits, attrition, and ramp trends so Finance can make informed hiring decisions.
• Support onboarding consultant adoption of new AI tools and retail-specific capabilities through documentation, enablement, and floor support.
• Work with Product and Analytics to bring product telemetry into Salesforce and ToastWeb tracking in order to reduce pre-live churn.
• Document and standardize playbooks so that technical knowledge becomes reusable training material and operating guidance.

Governance and Cross-Functional Coordination

• Own the sales-to-onboarding handoff as a complete operational process, protecting Notes-to-Services artifact quality and monitoring SLA expectations.
• Represent the vertical in conversations with central business technology and central operations, including management of technical backlog priorities.
• Support readiness for new product launches and special onboarding motions by coordinating operational setup with onboarding leadership and enablement.

Requirements

• 5 to 8 years of experience in revenue operations, sales operations, or GTM operations, with ownership of systems and processes that support either fast-moving sales motions or complex implementation lifecycles.
• Working SQL ability strong enough to pull data, inspect funnel mechanics, and answer operational questions without depending on a core analytics team.
• Deep working knowledge of Salesforce and project-management tooling such as Taskray or similar platforms, including experience handling technical backlogs with engineering or systems teams.
• Demonstrated ability to work independently, build structure in ambiguous situations, and manage senior stakeholders with confidence.
• Strong communication and stakeholder management skills, with the ability to align competing priorities across sales, onboarding, finance, and central IT.

Preferred Background

• A broad operational background spanning both pre-sale and post-sale lifecycle systems.
• Direct experience in frontline sales, sales management, onboarding, or implementation before moving into operations.
• Experience in complex B2B SaaS environments or verticals with matrixed routing, supply chain complexity, or inventory-heavy workflows such as retail, grocery, convenience, or fuel.
• Hands-on familiarity with generative AI tools, prompt design, or automation frameworks that reduce administrative work.

Compensation and Benefits

The role includes a base salary range that varies by geographic pay zone:

• Zone A: USD 120,000 to 192,000
• Zone B: USD 105,000 to 168,000
• Zone C: USD 94,000 to 150,000

Starting pay depends on skills, experience, and location. Total compensation may also include overtime, bonus or commissions if eligible, equity, and benefits. The company also provides a broader rewards package designed to support employee wellbeing and retention.

Additional Information

The company uses AI tools during hiring to help recruiters and interviewers with note-taking, summarization, and interview documentation. Hiring decisions are made by people.

The workplace model is hybrid, with in-person collaboration balanced against individual flexibility. Regional office expectations vary by location.

The company emphasizes diversity, equity, and inclusion as part of its culture and aims to create equitable opportunities for employees across the restaurant community.

Reasonable accommodations are available for candidates with disabilities during the application or interview process. Applicants needing support can contact the hiring team through the designated accommodation email.

For U.S. roles, Massachusetts law prohibits requiring or administering a lie detector test as a condition of employment or continued employment.