Head of Revenue Operations & Sales Enablement

Wintermeyer Ventures; McLean (VA); Hybrid; USD 200,000 - 250,000; Full time

Job summary

Wintermeyer Ventures is seeking a seasoned Revenue Operations leader to design and scale global strategies for a B2B SaaS company serving commercial and government markets. You will partner with executives across Sales, CS, Marketing, and Product to build data-driven enablement and governance.

The role focuses on forecasting, territory planning, and KPI-driven management, with responsibility for tech ecosystem optimization and cross-functional enablement programs.

Qualifications

• 10 to 20 years of experience building and scaling Revenue Operations in high-growth B2B SaaS.
• Experience supporting enterprise and government or public-sector sales motions in regulated markets.
• Advanced Salesforce architecture and optimization expertise, plus experience with HubSpot, 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.
• Experience with board reporting and late-stage growth or private-equity-backed environments; familiarity with FedRAMP is relevant.

Responsibilities

• Develop the global Revenue Operations strategy and align teams around goals and operating rhythms.
• Own forecasting, pipeline governance, territory planning, capacity modeling, performance reporting, and exec dashboards.
• Optimize the go-to-market tech ecosystem (Salesforce, forecasting tools, AI workflows, revenue intelligence).
• Build and lead Revenue Ops and Sales Enablement teams, driving accountability and continuous improvement.
• Create enablement programs for onboarding, product readiness, sales methodology, manager development, certifications.
• Partner with Product, CS, Marketing on messaging, positioning, and enablement content.
• Establish KPIs for forecast accuracy, pipeline quality, seller productivity, onboarding, deal velocity.

Skills

Revenue Operations

Sales Enablement

Forecasting

Executive dashboards

Sales analytics

Tools

Salesforce

HubSpot

Gong

Clari

Outreach

CPQ

Tableau

Looker

SQL

Excel

Job description

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 HubSpot, 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.