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 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

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The base salary range for this role is listed below. The starting salary will be determined based on ski