Head of Revenue Operations

About the Role

As Head of Revenue Operations, you will build, optimize, and scale the operational, data, and technology foundation across our entire go-to-market organization—including Sales, Marketing, Customer Success, Finance, and Partnerships. Reporting directly to executive leadership, your mission is to transform our systems, billing infrastructure, reporting, and GTM strategy into a clear, high-performing growth engine.

You will lead a small but high-impact RevOps team (2 direct reports) while personally owning the architecture and execution of our RevTech stack (including HubSpot and Chargebee), lead management, funnel optimization, enablement and ramp, and AI deployment. This is not a traditional admin role—we are looking for a builder, strategic systems architect, and AI-forward operator who rationalizes existing tools before adding new ones, replaces manual reporting with automated signal, and shortens new-hire time-to-productivity as a core business metric.

This role is 100% remote and available to US-based candidates. (Boston, MA preferred)

You Are

• An Operational Builder & AI-Forward Architect: Highly organized and system-minded, you thrive on taking complex, disconnected processes and building simple, scalable workflows. You actively identify, test, and deploy AI tools and automated knowledge systems to eliminate manual work and boost team productivity.
• A Strategic Systems Thinker: You look beyond basic CRM administration to understand broader business goals, connecting executive priorities to billing infrastructure, tech stack rationalization, and RevOps strategy.
• A Hands-On Problem Solver: You balance executive strategy with technical execution—equally comfortable presenting to leadership or personally building automations, forecasting models, and CRM workflows.
• A Growth & Ramp Driver: You view new-hire time-to-productivity as a business metric, using automated measurement, early success signals, and modern systems to ramp revenue teams faster.
• A Collaborative Leader: You manage, mentor, and elevate a team of RevOps professionals while bridging the gap between technical data systems and business leadership to align GTM operations.

You Will

• Own Revenue Systems, Billing Infrastructure & AI Innovation: Lead full ownership and architecture of core revenue systems (HubSpot, Chargebee, and broader RevTech). Continuously inspect, consolidate, and optimize current platforms before evaluating new spend. Build advanced automation workflows across Marketing, Sales, CS, Finance, and Partnerships, and deploy AI tools (such as living AI knowledge bases/Claude skills libraries) to streamline operations.
• Drive Enablement, Ramp & Team Productivity: Own new-hire ramp time with a clear, measurable path to reduction. Design onboarding, coaching, and exception-based reporting workflows that run through systems rather than headcount. Partner with Sales leadership on structural changes (comp design, team placement) that raise pipeline productivity per rep.
• Optimize Funnel Performance & Revenue Intelligence: Diagnose pipeline leaks and conversion bottlenecks across all channels. Build executive dashboards, forecasting models, and predictive analytics to improve speed-to-lead, decision-maker contact rates, expansion efficiency, and retention outcomes. Ground all recommendations in data first.
• Lead Data Strategy & Governance: Define how data is captured, structured, and managed across the customer lifecycle, improving CRM hygiene, billing accuracy, reporting integrity, and system interoperability.
• Manage & Develop the RevOps Team: Lead, hire, and mentor 2 direct reports. Build a culture of innovation, systems thinking, accountability, and technical excellence, raising team competency across AI, automation, and systems architecture.
• Partner Cross-Functionally: Collaborate closely with Sales, Marketing, CS, Finance, Product, and Executive Leadership to support product-led growth (PLG) motions, upgrade paths, monetization strategies, and long-term GTM infrastructure.

You Have

Must Have

• RevOps Leadership Experience: 5–8+ years of experience in Revenue Operations, Sales Operations, GTM Systems, or Revenue Enablement, with proven experience leading teams or major strategic initiatives.
• Systems & Tech Stack Mastery: Deep expertise configuring and managing HubSpot, along with strong experience in billing/subscription management platforms (Chargebee or similar) and operational architecture.
• AI & Automation Curiosity: Hands-on track record implementing modern automation tools and proactive experience deploying AI solutions (including AI-powered knowledge or enablement systems).
• Enablement & Ramp Ownership: Experience owning, measuring, or influencing new-hire ramp time and onboarding outcomes as core operational metrics.
• Data & Analytics Proficiency: Strong analytical background with direct experience querying raw data, building forecasting models, and designing board-level/executive dashboards (SQL, BI tools, or advanced analytics platforms).
• Stack Rationalization Skills: Proven track record evaluating, consolidating, or replacing major GTM and business software platforms.

Nice to Have

• Billing Operations: Direct experience with Chargebee, subscription management, and revenue recognition workflows.
• Product-Led Growth (PLG): Experience supporting PLG motions, automated upgrade paths, and expansion loops.
• Early-Stage / High-Growth Scaling: Experience scaling a RevOps function in a fast-growing SaaS tech company.
• Multi-Segment GTM: Background supporting multi-segment environments (SMB, Mid-Market, and Enterprise).
• Marketing Attribution & Demand Gen: Deep understanding of marketing attribution models and demand generation tech stacks.

Interview Process

• Initial Screen: 30 min with the Lead Recruiter
• Hiring Manager Interview: 45 min with the CRO
• Problem Solving Interview: 60 min with the Director of People
• Cross-Functional Interviews: 30 min with the Head of Sales & 30 min with the CEO

*We also require completion of the Wonderlic Assessment before the end of the process. This is done independently and takes about 20–30 min.

We Offer

• 100% remote work environment
• Medical, Dental, and Vision insurance within 30 days (100% employer-paid medical)
• Equity package
• Flexible PTO with a 15-day minimum
• Generous Parental Leave
• FSA and HSA options
• 401(k)
• Growth & Wellness Stipend
• WFH Equipment stipend
• Chance to work with the latest technology and AI tools
• A collaborative, high-ownership culture with clear opportunities for career growth