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'll have the full powerhouse of Toast's scale, brand, and resources behind you, but you'll be the primary architect of how we operate, scale, and win. The decisions you make in this role aren't just incremental improvements; they will structurally shape how Toast competes and wins in retail for years to come.

This role focuses on the path from lead to live customer, unifying the operational infrastructure, handoff, and commercial goals of both the sales and onboarding ecosystems. You will operate across the full lifecycle, running the foundational operational layer and partnering with leadership to secure business outcomes across the transition. You will serve as a trusted strategic partner to Retail Sales and Onboarding leadership, owning the operational architecture connecting the Lead-to-Go-Live lifecycle.

This broad, autonomous role is designed for a sophisticated Revenue Operations operator who brings analytical skills alongside sales or onboarding expertise. This position is built around a North Star metric of increasing Productivity Per Rep (PPR), maximizing time moving deals versus managing administration to accelerate closed-won velocity and drive high-throughput onboarding. You will structure ambiguity, source workflow improvements from field leaders, and build the scalable systems required as the vertical expands. You will sit within a team that supports your analytical foundations, while working closely with Agentic GTM Operations to integrate applied AI capabilities into frontline workflows.

A day in the life (Responsibilities)

Strategic Partnership & Lifecycle Optimization

• Proactive Funnel Diagnostics: Analyze the end-to-end sales funnel from outbound prospecting through to contract close, identifying opportunities to increase pipeline quantity and improve stage conversion rates.
• Onboarding Throughput Optimization: Analyze the post-sale lifecycle to shorten implementation timelines, accelerate revenue recognition velocity, reduce pre-live churn, and optimize Onboarding Consultant (OC) efficiency.
• Field Intake & Prioritization: Establish and maintain an operational intake and vetting process for requests from sales and onboarding leaders, ensuring follow-through on high-impact vertical commitments.
• Performance Pattern Replication: Identify individual rep and consultant performance patterns—isolating what top performers do differently—and build the localized operational mechanisms required to scale those behaviors across the field.
• AI GTM Pod Contribution: Participate in the Retail AI GTM Pod, running agile field experiments, identifying workflows for automation, and sourcing frontline requirements to hand off to Agentic GTM Operations for production scaling.

Sales Operations & Outbound Program Architecture

• Sales Growth Programs & Funnel Development: Design and execute strategic projects, pilots, and programs to drive funnel growth by enhancing outbound motions for AE and XDR (SDR/BDR) teams, improving conversion rates, and expanding deal sizes across the organization.
• Productivity & Field Excellence: Partner with sales leadership and Enablement to isolate high-performer behaviors, scale best practices, and support RVPs and DMs in diagnosing productivity gaps. Structure internal field communications to help leadership deliver clear, unified direction in place of fragmented updates.
• Sales Systems & Tools Operations: Govern the Retail-specific layer of sales systems, managing Salesforce configurations, data integrity, hierarchy maintenance, and enhancement backlogs. Coordinate with Central Operations on shared infrastructure while managing unique third-party tools, vendor relationships, and vertical builds where footprints diverge.
• Central & Cross-Functional Coordination: Serve as the primary operational interface between the Retail vertical, Central Sales Operations, and cross-functional teams (Enablement, Marketing, Onboarding, BTT) to share context, leverage central foundations, and drive execution.
• Tooling & Workflow Opportunity Pipeline: Survey rep and manager layers to surface process friction, data gaps, and tool optimization use cases. Resolve immediate issues at the vertical level, align with Central Operations, and funnel advanced AI or automated workflow opportunities to the Agentic GTM Sales Engineer via the AI Pod Council.

Onboarding Infrastructure & Capacity Intelligence This is the first dedicated ops role for the Retail Onboarding org: building and improving the vertical layer of reporting, templates, playbooks, and capacity intelligence on top of the central foundation, ensuring Retail's operational needs are met as the org scales and the AI-first onboarding vision moves from pilot to production.

• Lifecycle Dashboard Infrastructure: Turn manual tracking into automated performance dashboards across all five onboarding lanes and twelve business categories, tracking Time-to-Go-Live (TTGL), First-Time Resolution (FTR), Customer Effort Score (CES), and milestone velocities.
• Project Template Design: Design and maintain vertical-specific Taskray project templates scaled to merchant milestones, segment deviations, and emerging market models like Wholesale B2B.
• Live Capacity Modeling: Maintain a bottom-up vertical capacity model integrating real-time workload limits, attrition trends, and consultant ramp curves to provide Finance with data-driven hiring signals.
• AI Tooling Enablement: Lead vertical field enablement and adoption tracking for Onboarding Consultants on emerging enterprise and localized AI capabilities (including AI Process Enhancements, AI Onboarding Coach, and Retail builds), providing structured documentation and floor support.
• Product Telemetry Tracking: Partner with Product and Analytics to operationalize core retention features (Retail Health 5: item library, AP loops, replenishment modules) into Salesforce and ToastWeb tracking to mitigate pre-live churn.
• Playbook Codification: Standardize, document, and maintain active execution playbooks turning siloed, technical knowledge into scalable training assets.

Lifecycle Governance & Cross-Functional Seams

• Handoff Process Governance: Own the Sales-to-Onboarding handoff as an end-to-end operational continuum, enforcing Notes-to-Services (NTS) artifact integrity, identifying friction points, and monitoring SLA standards.
• Cross-Functional Representation: Serve as the primary vertical liaison to central business technology (BTT) and Central Operations (COSO), managing technical backlogs to ensure Retail’s operational interests are prioritized in platform decisions.
• Offering Readiness Support: Provide operational scaffolding and SKU coordination for new product launches (e.g., Four Course readiness) and unique onboarding motions in partnership with Onboarding leadership and Enablement.

What you'll need to thrive (Requirements)

• Experience: 5–8 years of experience in revenue operations, sales operations, or GTM operations, with clear ownership of operational frameworks supporting high-velocity sales motions or complex customer implementation lifecycles.
• Analytical Self-Sufficiency: Functional SQL competency sufficient to extract data, audit funnel mechanics, and query cloud data sets to solve operational questions independently without core analytics team dependencies.
• Technical Surface Mastery: Deep operational familiarity with Salesforce architecture and enterprise project management infrastructure (Taskray or equivalent), including experience managing backlogs with technical teams.
• Autonomy: Proven track record of operating independently, self-generating workflows, structuring ambiguous problems, and confidently managing VP-level stakeholders.
• Cross-Functional Diplomacy: Exceptional communication skills with a proven ability to align competing priorities across Sales, Onboarding, Finance, and central IT stakeholders.

What will help you stand out (Nonessential Skills/Nice to Haves)

• 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