Head of Revenue Operations

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop and implement a revenue operations strategy encompassing acquisition, implementation and go-live, facility expansion, supplier enrollment and monetization, renewal, and retention.

• Take ownership of and enhance the go-to-market technology stack, which includes Salesforce, Pardot/Marketing Cloud Account Engagement, and Gong, alongside integrations with the Casechek platform, Google Workspace, and Slack.

• Focus on automation, ensuring a unified source of truth, and promoting adoption within the commercial team.

• Collaborate with Product and Engineering to incorporate platform usage data into the CRM, enabling visibility of expansion, renewal risks, and ROI for Sales and Customer Success.

• Create the operating model, data structure, and reporting framework for supplier-side enrollment, adoption, and revenue opportunities.

• Establish a deal desk in partnership with Sales, Finance, and Legal to enhance pricing, quoting, approvals, and contracting processes.

• Work closely with the President and Finance on bookings and ARR forecasting, territory and account planning, quota strategies, capacity modeling, and compensation plan design.

• Define and track business KPIs such as pipeline coverage and velocity, win rates, time-to-go-live, net revenue retention, facility penetration, and supplier adoption.

• Implement a win/loss process and maintain consistent loss-reason documentation within Salesforce.

• Align Marketing, Sales, Customer Success, Implementation, and Product teams on definitions, handoffs, and lifecycle stages.

• Begin as a hands-on individual contributor, then develop and structure the RevOps function across systems, analytics, and deal operations.

• Report to the President & Chief Growth Officer while collaborating with Operations, Finance, Product, Engineering, Security, Legal, and commercial teams.

⛳️ Requirements

• Over 10 years of experience in revenue, sales, or business operations.

• At least 5 years in a leadership role.

• Ability to work directly as an individual contributor while progressively building a team.

• Proven experience in scaling RevOps within a growth-stage B2B SaaS organization.

• Experience managing complex enterprise sales processes involving long cycles, multiple stakeholders, and procurement-heavy buyers.

• Extensive knowledge of Salesforce.

• Practical experience with Pardot and Gong.

• Strong understanding of integrations, automation, data architecture, and practical AI applications in go-to-market workflows.

• Proficient in forecasting, SaaS metrics (ARR, NRR, CAC, LTV), and compensation/territory design.

• Familiarity with regulated data environments such as HIPAA, BAAs, and SOC 2.

• Ability to collaborate effectively with Security and Legal teams.

• Preference for candidates with experience in healthcare, health-tech, or hospital-facing enterprise SaaS.

🏝️ Benefits

• Annual bonus.

• Opportunity for equity or long-term incentive plans.

• 401(k) match.

• Flexibility to work from home with hybrid (Chicago) or remote (National) options.

• Unlimited paid time off.

• Fully paid parental leave options.

• Comprehensive medical and dental benefits.

• Brand-new pro-level laptop.

• Annual education budget for courses, certifications, and learning resources.