About this opportunity
sunday lists this Head of Revenue Operations opportunity in chicago, Illinois. Review the employer’s description below for duties, qualifications and application requirements.
Job description
About Us
sunday is building the fastest, simplest way to pay in restaurants. With a quick scan of a QR code, diners can pay, tip, and leave in about 10 seconds. We believe great products should feel obvious, not complicated, and we focus relentlessly on keeping things simple while earning trust from restaurants and guests at every interaction. Today, sunday powers payments in thousands of restaurants across the US, UK, and France, helping operators turn tables faster, increase tips, and unlock valuable insights. We push ourselves to go beyond what’s expected, building with ownership, moving fast, and scaling with ambition as we tackle our biggest growth opportunity in the US.
About The Role
As Head of Revenue Operations , you will be responsible for instrumenting, designing, and managing our key GTM systems (e.g., Salesforce, Salesloft, Nooks) to support and align our teams across the revenue funnel. You will also be tasked with ensuring these systems support our workflows and processes, and are driving operational excellence. Your focus will be on working with team leaders to optimize our processes to create a more scalable high-growth company. This is a pivotal role for a seasoned RevOps leader and builder capable of translating ambitious business strategy into robust, scalable operational frameworks that directly enable our expansion across SMB, mid-market, and enterprise clients.
Systems & Technology Oversight
Own the Revenue Operations tech stack strategy, including CRM, sales enablement, and analytics tools.
Set priorities and direction for system enhancements, integrations, and data governance, and optimize for scale, adoption, and business impact.
Ensure system reliability and scalability to support global growth.
Ensure GTM data is clean, auditable, and decision-grade across all systems.
Implement controls to maintain data integrity and compliance.
Process Improvement & Change Management
Anticipate growth bottlenecks and build infrastructure to support 2x, 5x, 10x scale.
Lead process improvements and automation to enable hyper-growth and drive cross functional GTM coordination.
Partner with GTM leaders to support rollout of new processes, tools, and programs.
Lead change management efforts to ensure adoption and long-term success of operational initiatives.
Communicate clearly and effectively across stakeholders at all levels.
Systems Strategy & Architecture
Define the long-term GTM systems architecture, ensuring tools, data, and processes align with how sells, renews, and grows.
Establish frameworks for governance, security, and change control, ensuring sustainable scale and system integrity.
Partner with the GTM, Sales, Finance, and Data teams to align systems and processes with company growth objectives.
Identify opportunities for automation, consolidation, and efficiency across the GTM stack.
Systems Integration & Expansion
Extend Salesforce to the broader GTM stack - integrating systems that enable seamless execution from Lead to Opportunity and Quote to Cash.
Design clean, reliable data flows between Marketing, Sales, Success, and Finance, creating a single source of truth for customer and revenue data.
Evaluate and manage vendors, ensuring integrations meet standards for data quality, scalability, and governance.
Salesforce & Ownership
Serve as the architect and owner of Salesforce, the core platform at the center of the GTM stack.
Manage Salesforce end-to-end - including data model, automation, security, and reporting frameworks.
Design and maintain scalable, auditable workflows for lead routing, opportunity lifecycle, quoting, billing, and renewals.
Define roles, permissions, and data hygiene standards to ensure security, accuracy, and consistency across all GTM functions.
Establish documentation, change management, and version control to maintain reliability and traceability of system changes.
Leadership & Enablement
Build and mentor a future GTM Systems & Data team as the company scales.
Partner with Enablement and Ops leaders to drive adoption, training, and system hygiene.
Serve as a trusted advisor to GTM and Finance leadership - balancing innovation, control, and data-driven insight.
Own and evolve our revenue tech stack (e.g. Salesforce, CPQ, integrations) with a focus on automation, scalability, and usability
Use data to drive strategic decisions and establish clear KPIs for pipeline health, conversion, and rep productivity
Ensure data hygiene, process integrity, and compliance across GTM systems
Collaborate cross-functionally with Marketing, Product, and Customer Success to align revenue strategies and optimize acquisition, expansion, and retention efforts
Define and execute the GTM technology strategy and multi-year roadmap, ensuring alignment with Plaid’s scaling needs, evolving GTM motions (sales-assisted, enterprise, partnerships), and long-term business objectives.
Architect, evolve, and maintain scalable CRM (Salesforce) and GTM system solutions across the full go-to-market stack, including integrations with billing, CPQ, marketing automation, analytics, and internal data platforms.
Own GTM systems governance and data integrity, including tooling standards, data models, access controls, and operational hygiene. Establish guardrails that balance speed and flexibility with consistency, compliance, and long-term maintainability.
Lead, mentor, and grow a high-performing GTM Systems team, including managers, admins, engineers, and analysts.
Manage GTM technology vendors and budgets, including tool evaluation, contract negotiation, renewal planning, and ROI assessment.
Partner closely with Sales, Marketing, Customer Success, RevOps, Finance, Product, and Engineering to intake demand, prioritize initiatives, and deliver solutions that improve GTM workflows, seller productivity, and customer outcomes.
Lead a cross-functional AI enablement effort across GTM, responsible for evaluating emerging AI tools and capabilities, designing scalable processes, and overseeing technical deployment. Drive responsible adoption of AI automation to improve seller efficiency, data quality, forecasting accuracy, and customer engagement.
Drive change management and adoption, ensuring new systems, tools, and processes are successfully rolled out, documented, and embraced by GTM teams through enablement, training, and feedback loops.
Oversee and optimize key systems (e.g., Salesloft, Salesforce, Hubspot, Nooks, Docusign) and processes supporting marketing, sales, and account management, including CRM, automation tools, and analytics platforms
Lead the design, implementation, and scaling of revenue operations infrastructure to support growth from $25M to $50M+ ARR
Support sales and revenue and technical implementation leadership with sales enablement and training where appropriate to help ramp new hires up on our tools and sales playbook
Drive Salesforce customization, integration, and optimization to align with business needs, including building sales methodologies into the platform
Join early, grow fast, and shape the journey!
Key Responsibilities
Own and lead the RevOps technical function across three teams, Engineering, Systems, and Analytics, spanning US and EU. Act as connective tissue between Sales and technical systems.
Rebuild and modernize the CRM and data infrastructure to support a scaling GTM org, while building reporting and analytics from the ground up.
Eliminate manual processes through
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Worksite address
chicago, IL, 60290, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.