Head of Revenue Operations

Founding Revenue Operations & Enablement

Location: Chicago, IL — Onsite

Reports to: CEO

Company Stage: Series A, profitable

About the Role

We’re looking for a Founding Revenue Operations & Enablement hire to build and optimize the infrastructure that supports our growing go-to-market organization.

This is a highly hands-on role with broad ownership across RevOps systems, sales enablement, analytics, and AI-driven process automation. You’ll work directly with the CEO and partner closely with AEs and BDRs to improve how the team operates, sells, and scales.

What You’ll Do

• Own and optimize core GTM systems including HubSpot, Clay, Gong, and other sales technology.
• Build and maintain dashboards, reporting, and analytics for leadership to track pipeline, productivity, conversion, and revenue performance.
• Partner with AEs and BDRs on sales enablement, including processes, workflows, playbooks, training, and onboarding.
• Run system and process trainings for the go-to-market team and drive adoption of new tools and workflows.
• Identify opportunities to use AI and automation to streamline sales processes, improve productivity, and eliminate manual work.
• Support the development of whitepapers, sales collateral, and other GTM content.
• Analyze sales data and translate findings into actionable recommendations for leadership.
• Build and improve the processes, infrastructure, and documentation needed to scale the revenue organization.
• Serve as a cross-functional partner between sales, leadership, and technology, ensuring systems and processes support the needs of the business.

What We’re Looking For

• 3+ years of experience in Revenue Operations, Sales Operations, Sales Enablement, or a similar GTM function.
• Hands-on experience managing CRM and GTM systems; HubSpot experience strongly preferred.
• Experience with tools such as Clay, Gong, Salesforce, Outreach, Apollo, or similar sales technologies.
• Strong analytical skills and experience building dashboards and reporting for leadership.
• Experience supporting AE and/or BDR teams through enablement, training, and process development.
• Interest and experience in using AI and automation to improve sales workflows.
• Comfortable operating in a high-ownership, early-stage environment where you’ll build processes rather than inherit them.
• Strong written and verbal communication skills with the ability to work directly with executive leadership.

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Tagged as: Data Analysis, HubSpot, Salesforce