Director, Strategy & Operations - Trailhead Ecosystem

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About Salesforce

We're Salesforce, the Customer Company, inspiring the future of business with AI+ Data +CRM. Leading with our core values, we help companies across every industry blaze new trails and connect with customers in a whole new way. And, we empower you to be a Trailblazer, too - driving your performance and career growth, charting new paths, and improving the state of the world. If you believe in business as the greatest platform for change and in companies doing well and doing good - you've come to the right place.

The Trailhead Ecosystem organization is seeking a highly organized, proactive, and strategic Director of Strategy & Operations to support our dynamic and impactful team, which includes Trailhead Product & Engineering, Trailhead Content, and the Trailblazer Community & Workforce Development. This leader will be instrumental in driving operational excellence, ensuring strategic alignment, and facilitating effective communication across the organization. If you thrive in a fast-paced environment, possess exceptional analytical and communication skills, and are passionate about enabling high-performing teams, this role is for you.

This role is a critical partner to the leadership team across Trailhead Product & Engineering, Trailhead Learning Content, and Trailblazer Community & Workforce Development. You will work closely with the respective VPs and their leadership teams to streamline operations, manage resources effectively, and drive strategic initiatives forward. The ideal candidate is a detailed-oriented, strategic executor with a strong planning and budgeting background, and adept at building strong relationships across diverse teams.

Here's some of what you'll be responsible for:

• Operations & Chief of Staff Support: Partner with the SVP to drive leadership operations and act as a right-hand.

• Rhythm of the Business: Define and manage the cadence, forums, communication, and follow-up for business reviews of KPIs and major initiatives.

• Strategic Planning & V2MOM: Own annual and quarterly planning cycles, including V2MOM definition, tracking, and reporting, as well as budget and staffing.

• Budget Management: Oversee the consolidated budget, including allocation, forecasting, prioritization, and expenditure tracking across all teams.

• Data Analysis, Reporting, and Metrics: Analyze KPIs and business data to provide actionable insights, create clear reports, define and track key metrics beyond V2MOM, and develop dashboards to visualize performance and progress.

• Operational Excellence: Design, implement, and manage key operational processes (annual planning, bi-weekly ops reviews, MBRs, QBRs) to ensure efficiency and accountability.

• Executive Communications: Develop and deliver executive-level presentations and communication on strategy, business performance, and monthly team updates.

• Internal Communications Strategy: Develop a broader internal communications strategy beyond the monthly summaries, including town halls, all-hands meetings, or internal newsletters.

• Cross-Functional Collaboration: Foster strong relationships and facilitate collaboration across the Trailhead Ecosystem and other Salesforce organizations.

Required Skills & Experience

• 5+ years of experience in operations, strategy, program management, or a Chief of Staff role, preferably within a technology or product-focused organization.

• Proven experience in developing and managing rhythm of the business processes, including annual and quarterly planning cycles.

• Demonstrated ability to manage complex budgets and financial processes.

• Hands-on experience in creating compelling, data-driven presentations for executive audiences.

• Strong understanding of strategic planning methodologies, such as V2MOM.

• Excellent verbal and written communication skills, with the ability to communicate effectively across various levels and functions.

• Exceptional organizational skills and attention to detail, with the ability to manage multiple priorities and deadlines.

• Strong analytical and problem-solving skills, with the ability to translate data into actionable insights.

• Ability to influence and drive results in a matrixed environment.

• Proficiency in productivity and collaboration tools (e.g., Google Workspace, Slack, Salesforce).

• A proactive and self-starter mentality with a strong sense of ownership.

• Comfortable working in a fast-paced and evolving environment.

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