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Casechek

Head of Revenue Operations

Casechek

. Build and run a revenue operations strategy across acquisition, implementation and go-live, facility expansion, supplier enrollment and monetization, renewal, and retention .

Posted 11/4/2026full-timeRemote • United StatesLead💰 $160,000 - $190,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

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Demonstrates extensive expertise in Revenue Operations, including strategy development, data architecture, and integration of go-to-market technology stacks. Proficient in managing complex enterprise sales processes and forecasting SaaS metrics while ensuring compliance in regulated environments.

Highest-signal resume keywords
Revenue Operations StrategySalesforce ExpertisePardot ExperienceGong ProficiencySaaS Metrics Fluency

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills
Revenue OperationsData ArchitectureForecastingAutomationIntegrationsCompensation DesignTerritory PlanningKPI ReportingEnterprise Sales SupportSupplier Enrollment
Soft Skills
Team LeadershipCollaborationHands-On ContributionStrategic ThinkingCommunication
Tools & Technologies
SalesforcePardotGongGoogle WorkspaceSlackCasechek
Industry Keywords
B2B SaaSHealthcareHealth-TechRegulated DataHIPAABAAsSOC 2

Tech Stack

Tools & technologies
Cloud

About the role

Key responsibilities & impact
  • Build and run a revenue operations strategy across acquisition, implementation and go-live, facility expansion, supplier enrollment and monetization, renewal, and retention
  • Own and evolve the go-to-market technology stack, including Salesforce, Pardot/Marketing Cloud Account Engagement, and Gong, plus integrations with the Casechek platform, Google Workspace, and Slack
  • Prioritize automation, a single source of truth, and commercial-team adoption
  • Partner with Product and Engineering to bring platform usage data into the CRM and make expansion, renewal risk, and ROI visible to Sales and Customer Success
  • Build the operating model, data, and reporting for supplier-side enrollment, adoption, and revenue opportunities
  • Build a deal desk with Sales, Finance, and Legal to streamline pricing, quoting, approvals, and contracting
  • Partner with the President and Finance on bookings and ARR forecasting, territory and account planning, quota plans, capacity modeling, and compensation-plan design
  • Define and report business KPIs including pipeline coverage and velocity, win rates, time-to-go-live, net revenue retention, facility penetration, and supplier adoption
  • Establish a win/loss process and consistent loss-reason recording in Salesforce
  • Align Marketing, Sales, Customer Success, Implementation, and Product on definitions, handoffs, and lifecycle stages
  • Start as a hands-on individual contributor, then design and build the RevOps function across systems, analytics, and deal operations
  • Report to the President & Chief Growth Officer and collaborate with Operations, Finance, Product, Engineering, Security, Legal, and commercial teams

Requirements

What you’ll need
  • 10+ years in revenue, sales, or business operations
  • 5+ years leading a team
  • Comfort working hands-on as an individual contributor while building a team over time
  • Experience scaling RevOps at a growth-stage B2B SaaS company
  • Experience supporting complex enterprise sales motions with long cycles, multiple stakeholders, and procurement-heavy buyers
  • Deep Salesforce expertise
  • Hands-on experience with Pardot and Gong
  • Strong grasp of integrations, automation, data architecture, and practical AI use in GTM workflows
  • Fluency in forecasting, SaaS metrics (ARR, NRR, CAC, LTV), and compensation/territory design
  • Working knowledge of regulated-data environments including HIPAA, BAAs, and SOC 2
  • Comfort partnering with Security and Legal
  • Healthcare, health-tech, or hospital-facing enterprise SaaS experience strongly preferred

Benefits

Comp & perks
  • Annual bonus
  • Opportunity for equity or long-term incentive plans
  • 401(k) match
  • Work-from-home flexibility with hybrid (Chicago) or remote (National) setup
  • 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