Head of Revenue Operations

What You'll Be Doing

Own the revenue operating system, designing and scaling the processes, metrics, and infrastructure that drive consistent, predictable performance across the business
Partner with Systems Engineering to drive end-to-end improvements and scalability in Salesforce, including structure, data hygiene, workflow automation, and adoption across the sales org
Evaluate the current ecosystem of tools and technology supporting commercial and revenue operations, and make recommendations on the optimal, AI-native tech stack for the function
Serve as the accountable owner of that tech stack and roadmap, partnering closely with Product and Tech to build the AI-native operating system rather than building it in isolation
Own pricing strategy, SKUs, and the end-to-end quote-to-cash process, ensuring pricing structures and deal execution are clean, consistent, and scalable
Own the forecasting cadence and develop robust, repeatable forecasting models (pipeline, bookings, ARR) that improve accuracy and predictability
Build the AI-powered operating layer — automated briefings, pipeline intelligence, meeting prep, and reporting dashboards — that gives the commercial organization real-time visibility
Establish and maintain a unified KPI framework, ensuring alignment on definitions, visibility, and accountability across the funnel
Act as connective tissue across live opportunities, coordinating Marketing, Finance, the RFP team, Value Enablement, and Sales Engineering so they're effectively leveraged
Partner with Sales, Marketing, Customer Success, and Finance leadership to align execution with company goals and financial plans
Analyze pipeline health, conversion rates, and sales efficiency to identify opportunities and drive improvements
Design and manage sales compensation and incentive plans that align with business objectives and drive desired behaviors across GTM teams
 
What Success Looks Like
In 3 months
Build a deep understanding of Arcadia's GTM model, revenue streams, and key SaaS metrics (ARR, NDR, GDR, pipeline coverage, win rates, sales cycle)
Assess current RevOps infrastructure, CRM configuration, reporting, and forecasting methodologies
Map the current ecosystem of tools and technology supporting commercial and revenue operations, and begin forming a point of view on the optimal, AI-native tech stack
Establish trust across Sales, Marketing, Customer Success, and Finance leadership
In 6 months
Own the CRM and forecasting cadence end-to-end, with a unified KPI framework giving clear visibility into pipeline health, revenue performance, and GTM efficiency
Ship the first version of the AI-powered operating layer (automated briefings, dashboards, and reporting tools) that reduces manual reporting burden for commercial leadership
Improve forecast accuracy through enhanced pipeline modeling and data-driven insights
In 12 months
Operate a scalable revenue operating system — process, CRM, forecasting, and AI tooling — that enables predictable growth and aligns planning across GTM and Finance
Deliver consistent, high-confidence forecasts and actionable insights that directly inform the executive team's decisions
Improve key performance metrics (e.g., pipeline coverage, conversion rates, sales productivity, retention) through data-driven optimizatio

What You'll Bring

The Role, Done Before
• You have held this exact role — Head/Director of Revenue Operations or equivalent — at a company of similar growth stage, and can point to what you built and owned.
Growth-Stage Fluency
• Track record of operating at growth-stage speed and ambiguity — scrappy, resourceful, and comfortable building infrastructure from scratch rather than administering something already built. Candidates whose experience is exclusively at large, mature organizations without growth-stage exposure are not a fit for this seat.
Deep SaaS Metrics Expertise
• Strong command of key SaaS metrics including ARR, NDR, GDR, CAC, LTV, pipeline coverage, and sales productivity, and how they connect to business performance.
Forecasting & Modeling Rigor
• Proven ability to build and operationalize forecasting models (e.g., pipeline velocity, ARR forecasting) that improve accuracy and predictability.
CRM & Systems Ownership
• Deep, hands-on experience owning a CRM (Salesforce or equivalent) and the broader GTM tech stack — configuration, data integrity, and workflow design, not just consumption of dashboards.
Pricing & Quote-to-Cash Experience
• Hands-on experience owning pricing strategy, SKU structure, and the quote-to-cash process, ideally in a company that scaled or restructured its pricing model.
AI-Forward
• Comfortable using AI tools to build operational leverage — automating reporting, briefings, and workflows rather than relying solely on headcount to scale.
Cross-Functional Leadership
• Track record of partnering effectively with Sales, Marketing, Customer Success, Finance, and executive leadership to drive alignment and results.
Operator Mindset
• Ability to move between strategy and execution, translating insights into action and driving measurable impact.

Would Love for You to Have

8–12+ years of experience across Revenue Operations, Sales Operations, or GTM analytics in a SaaS environment
Experience supporting a high-growth SaaS company through key milestones (e.g., post-acquisition integration, scale-up, or M&A)
Familiarity with modern BI, AI, and planning tools (e.g., Sigma, Adaptive, Salesforce ecosystem, AI-native reporting/agent tools) and building self-service analytics environments
Experience designing and optimizing sales compensation plans at scale

What You'll Get

• The mandate to build a consistent, predictable commercial engine — including its AI-powered tooling — rather than inherit and maintain one
• A growth path from individual contributor to leading the people and functions that support sales operations as Arcadia scales
• A mission-driven culture where your work supports better healthcare outcomes
• Competitive compensation and strong benefits, including Flexible Time Off
• A collaborative, data-driven environment focused on impact, ownership, and continuous improvement