Director of Customer Strategy & AI-Driven Operations

Leadout Capital; San Francisco (CA); On-site; USD 180,000 - 260,000; Full time

Job summary

Leadout Capital is seeking a Customer Strategy & Planning Director to lead the customer organization’s strategic planning and operating strategy within the Operations group (Regrello). The role partners with the CCO and Customer Success leadership to translate customer strategy into priorities, investments, and measurable outcomes.

The director will shape the value and Forward Deployed Engineer motions, ensure alignment with Sales and GTM, and drive AI-enabled capabilities to transform customer

Qualifications

• Proven ability to translate customer strategy into actionable plans and investments.
• Experience influencing senior leadership across multiple functions without direct authority.
• Strong understanding of enterprise Sales, GTM, and customer lifecycle.

Responsibilities

• Own annual, quarterly, and long-range planning for the Customer Success organization.
• Partner with the Chief Customer Officer and leadership to translate decisions into executable plans.
• Define and scale the customer value motion and FDE initiatives.
• Integrate customer strategy with Sales/GTM, pipelines, and revenue objectives.
• Design scalable operating models and cross-functional handoffs for scale.
• Drive cross-functional alignment across Sales, Product, Engineering, Finance, Data, and Ops.
• Identify risks, surface gaps early, and develop scalable solutions.
• Establish metrics with Data & Product to drive actions and outcomes.
• Lead AI strategy and predictive operations to optimize customer success and FDE allocations.

Skills

Strategic thinking

Executive communication

Cross-functional collaboration

Business acumen

Tools

Salesforce

Job description

Leadout Capital is seeking a Customer Strategy & Planning Director to lead the customer organization’s strategic planning and operating strategy within the Operations group (Regrello). The role partners with the CCO and Customer Success leadership to translate customer strategy into priorities, investments, and measurable outcomes.

The director will shape the value and Forward Deployed Engineer motions, ensure alignment with Sales and GTM, and drive AI-enabled capabilities to transform customer