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Head of Revenue Operations & Sales Enablement

Job in McLean, Fairfax County, Virginia, USA
Listing for: Wintermeyer Ventures
Full Time position
Listed on 2026-11-04
Job specializations:
  • Business
    Business Intelligence, Operations Management, Business Systems & Technology Analysis, AI Business & Operations
Salary/Wage Range or Industry Benchmark: 200000 - 250000 USD Yearly USD 200000.00 250000.00 YEAR
Job Description & How to Apply Below
About the Role

Lead the strategy, systems, processes, and enablement programs that support a global go-to-market organization at a B2B software company serving commercial and government markets. You will partner with executive leaders and teams across Sales, Customer Success, Marketing, and Product to build scalable, data-driven revenue operations.

What You'll Do
  • Develop the global Revenue Operations strategy and align teams around shared goals, operating rhythms, and scalable growth.
  • Own forecasting, pipeline governance, territory planning, capacity modeling, performance reporting, and executive dashboards.
  • Optimize the go-to-market technology ecosystem, including Salesforce, forecasting tools, AI-enabled workflows, and revenue intelligence platforms.
  • Build and lead Revenue Operations and Sales Enablement teams, supporting accountability, innovation, and continuous improvement.
  • Create enablement programs for onboarding, product readiness, sales methodology, manager development, certifications, and ongoing learning.
  • Partner with Product, Product Marketing, Customer Success, and Sales leaders on messaging, competitive positioning, selling capabilities, and enablement content.
  • Establish KPIs for forecast accuracy, pipeline quality, seller productivity, onboarding, deal velocity, and revenue performance.
  • Lead annual territory, quota, organizational capacity, and go-to-market planning.
  • Improve processes across the customer lifecycle through automation, AI adoption, and operational optimization.
  • Translate business data into strategic recommendations for executive leadership.
What We’re Looking For
  • 10 to 20 years of experience, including building and scaling Revenue Operations in high-growth B2B SaaS environments.
  • Experience supporting both enterprise and government or public-sector sales motions, ideally in regulated markets.
  • Advanced Salesforce architecture and optimization expertise, plus experience with tools such as Hub Spot, Gong, Clari, Outreach, CPQ, Tableau, Looker, SQL, and Excel.
  • Background in forecasting, pipeline analytics, executive dashboards, territory planning, quota setting, and capacity modeling.
  • Strategic sales enablement or training experience, with the ability to influence senior stakeholders and support seller development.
  • Experience with board reporting and late-stage growth or private-equity-backed environments is valuable; familiarity with compliance contexts such as FedRAMP is also relevant.
Compensation & Benefits

Base salary: $200,000 to $250,000 annually. Visa sponsorship is available.

Location

Hybrid role based in McLean, Virginia, with two days per week in the office.

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