VP, Revenue Operations
Accelerate Performance.

About the Role

CAI Software is seeking a VP, Revenue Operations to lead our go-to-market operations function. This role owns the systems, processes, and analytics that connect Sales, Marketing, Finance, and Technology into a single, high-performing engine built to scale with the business.

The VP, Revenue Operations will partner directly with the senior leadership, turning complexity into clarity and data into decisions that move the business forward. This is a hands-on leadership role that treats AI and automation as tools to deploy now - not just evaluate - to eliminate manual work, sharpen forecasting, and give the GTM team a durable operational advantage.

What You'll Do

AI-Driven Operations & Process Optimization

• Champion AI and automation across RevOps - pipeline analysis, forecasting, lead scoring, reporting, and workflow automation.
• Identify high-friction, manual processes and replace them with intelligent, scalable solutions.
• Evaluate and deploy AI-native tools that boost seller productivity and reduce operational overhead.
• Build a culture where the team defaults to automation before headcount.
• Own the end-to-end sales process: lead management, pipeline governance, and stage progression - continuously optimizing at every stage.

Sales Strategy & Planning

• Partner with the CRO and Sales Leadership on territory design, resource allocation, quota setting, and capacity modeling.
• Own the annual and quarterly sales planning cycle, ensuring team goals align tightly to business objectives.
• Develop, track, and manage KPIs across the sales organization; lead performance forecasting.

Compensation Plan Ownership & Distribution

• Own end-to-end design, documentation, and governance of sales compensation plans, ensuring alignment with company strategy and quota targets.
• Partner with Finance, HR, and Sales Leadership to model plan economics, pay mix, and payout curves before rollout.
• Manage annual plan distribution and rep-level acknowledgment, plus communication of any mid-year plan changes.
• Own compensation calculation, validation, and payout processing in partnership with Finance and Payroll, ensuring accuracy and on-time payment.
• Field and resolve compensation disputes and inquiries, maintaining clear documentation and audit trails.
• Evaluate compensation plan performance against desired seller behavior and recommend adjustments each planning cycle.

Deal Desk Management

• Own the deal desk function, including deal structuring, non-standard pricing, and contract review approvals.
• Establish and enforce deal approval workflows and escalation paths across Sales, Finance, and Legal.
• Partner with Sales, Finance, and Legal to accelerate quote-to-cash cycle time while managing commercial risk.
• Monitor discounting, deal terms, and margin impact; provide guardrails and guidance to sales reps and leadership.
• Continuously improve deal desk tools, templates, and playbooks to reduce deal friction and cycle time.

Sales Tools & Technology

• Evaluate, implement, and manage the RevOps tech stack: CRM, sales automation, analytics platforms, and AI tools.
• Ensure the sales team is equipped with the right technology to perform at their best.
• Lead system integrations that improve productivity and reporting accuracy.
• Lead RevOps integration for newly acquired businesses, including CRM, ERP, and sales process consolidation onto CAI's unified systems.

Data Governance & CRM Data Quality

• Establish and enforce CRM data governance standards, including field-level ownership, naming conventions, and data hygiene protocols.
• Maintain high data integrity across accounts, contacts, opportunities, and pipeline stages to support accurate reporting and forecasting.
• Proactively identify and resolve data quality issues that impact reporting, compensation calculations, or sales execution.
• Partner with IT and Marketing Operations to align CRM data structure with downstream systems and reporting needs.

Budget & Vendor Management

• Own the RevOps technology budget, including license utilization, renewal negotiations, and cost optimization across the tech stack.
• Manage vendor relationships and contracts for CRM, sales engagement, analytics, and AI tools, ensuring accountability to SLAs and ROI.
• Evaluate new vendors and tools, building the business case for adoption, consolidation, or retirement of platforms.

Analytics & Reporting

• Build dashboards and operational frameworks that give sales leaders and executives real-time visibility into pipeline health, performance, and forecast accuracy.
• Lead board-level reporting and executive business reviews.
• Drive data-driven decision-making across the GTM organization - from rep-level metrics to revenue forecasts.

Sales Enablement

• Lead strategy for sales and channel enablement, including onboarding programs, training, and continuous skill development.
• Ensure new hires ramp quickly; ensure tenured reps stay sharp and process-adherent.
• Align with Marketing on pipeline generation, lead management, and demand strategy.
• Partner with Finance on forecasting, budgeting, and revenue recognition.
• Collaborate with Product and Customer Success to bring the customer voice into GTM planning.

Team Leadership & Development

• Lead and develop the RevOps team - coaching for performance, building a bench, and creating clear paths for growth.
• Build a high-performing, scalable organization that grows with the business.
• Model a culture of operational excellence, continuous improvement, and bold thinking.

What We're Looking For

• 7-10 years in Sales or Revenue Operations, with at least three years in a global leadership role.
• Demonstrated experience deploying AI tools and automation to improve GTM operations - not just evaluating them.
• Strong hands-on experience with Salesforce, Gong, and NetSuite, with the ability to integrate these platforms across sales, marketing, and finance workflows.
• Proven track record of process optimization in a high-growth, fast-paced environment.
• Strong analytical skills - able to move from raw data to executive-ready insight.
• Strong experience with sales compensation design and incentive structures.
• Exceptional cross-functional communicator and collaborator.
• Experience owning sales compensation administration and tools (e.g., Xactly, CaptivateIQ, Spiff) a plus.

Compensation

The compensation range reflects the Company's good faith belief at the time of posting. Individual base pay depends on various factors, including primary work location, complexity and responsibility of the role, job duties and requirements, and relevant experience, knowledge, skills, and education. Base pay ranges are reviewed and typically updated each year, and offers are made within the applicable range at the time of hire. Certain roles are eligible for additional rewards, including discretionary merit increases, bonus, and/or stock, and certain roles are eligible to earn sales variable compensation incentives under the terms of the applicable plan.