Strategic Services Director - Enterprise Strategy & Execution

Workboard; Chicago (IL); On-site; USD 150,000 - 175,000; Full time

Benefits offered by this job

Flexible PTO

Paid holidays

Health insurance

Employer 401K match

Quarterly bonuses

All-hands meetings

Job summary

WorkBoard is seeking a Director of Strategic Services for WorkBoardAI to guide strategic initiatives with senior executives. You will shape how customers formulate objectives, operationalize plans, and measure impact using data-driven operating models.

The role emphasizes strategic advisory, portfolio alignment, and driving tangible business outcomes across large enterprises. You will partner with Success, Sales, and Product teams to accelerate growth, influence executive decisions, and ensure

Qualifications

• Minimum 10+ years of work experience in strategy, consulting, or related roles.
• Experience leading enterprise-level engagements in SaaS or strategy execution domains.
• Ability to connect business value to technology and influence senior leaders.

Responsibilities

• Lead executive conversations and workshops with C-Level leaders.
• Coach client teams to define, communicate, and operationalize strategic objectives.
• Drive value realization through ROI-based value journeys and renewals.

Skills

Executive stakeholder management

Strategy development

SaaS experience

Tools

Salesforce (SFDC)

Job description

WorkBoard is seeking a Director of Strategic Services for WorkBoardAI to guide strategic initiatives with senior executives. You will shape how customers formulate objectives, operationalize plans, and measure impact using data-driven operating models.

The role emphasizes strategic advisory, portfolio alignment, and driving tangible business outcomes across large enterprises. You will partner with Success, Sales, and Product teams to accelerate growth, influence executive decisions, and ensure