We are currently seeking a motivated sales leader to serve as our Director of Sales Operations & Enablement. This role plays a pivotal role in driving Windstar Cruises' global sales transformation by integrating industry best practices across Sales Operations, Revenue Operations, Sales Enablement, and Sales Technology into a unified, future-ready function. This leader oversees the full Sales Operations & Enablement ecosystem-spanning process excellence, sales technology, analytics, readiness, seller experience, and go-to-market alignment-to enable high- performing global sales teams across North America, International, Global Accounts, Charters, and Travel Partners. The Director partners closely with Revenue Management, Marketing, Global Commercial, Contact Center/VPC, IT, Finance, HR, Legal, Operations, and Itinerary Planning to ensure unified commercial execution.

This role prioritizes initiatives that deliver the greatest impact on revenue and scalability while supporting three key pillars: Technology & Automation, Cost-Reducing Initiatives that allow us to scale, and Revenue-Driving strategies.

Responsibilities

• Sales Strategy, Planning & Governance
  • Partner with Sales leadership (NA, International, Global) to operationalize strategy, annual/quarterly planning, pipeline targets, and forecasting processes.
  • Facilitate a cross-functional commercial council that aligns Sales, Marketing, Revenue, Itinerary Planning, and Operations on unified go-to-market plans and calendars.
  • Translate business priorities into operational roadmaps, resourcing plans, and change initiatives with clear success criteria and timelines.
• Process Excellence & Global Standardization
  • Design, document, and optimize global sales processes-including lead management, partner engagement, opportunity progression, quoting/contracting, and charter workflows.
  • Reduce seller friction by simplifying workflows, removing manual effort, and establishing standard operating procedures (SOPs) across sales motions and regions.
  • Apply Lean/Six Sigma and continuous-improvement methods to identify bottlenecks and drive measurable efficiency gains.
• Sales Technology Ownership & Data Integrity
  • Serve as business owner for sales technologies (e.g., CRM, partner/travel advisor tools, content management, forecasting, sales automation, analytics; do not name vendors).
  • Partner with IT to evaluate, select, implement, and optimize solutions that increase productivity, enable automation, and scale globally while maintaining security and compliance.
  • Champion responsible use of AI and advanced analytics to improve forecasting, territory/partner insights, and seller effectiveness.
  • Establish data governance, quality standards, integrations, and interoperability to unlock reliable reporting and decision intelligence.
• Reporting, Analytics & Decision Intelligence
  • Define and manage dashboards and KPIs that provide actionable, role-based insights for executives, managers, and sellers.
  • Analyze seller productivity, partner performance, pipeline health, mix/segment trends, and opportunity gaps; recommend actions to improve outcomes.
  • Improve forecast accuracy and cadence; establish common definitions, guardrails, and rhythms (QBRs, pipeline reviews).
• Global Sales Enablement & Readiness
  • Own the enablement strategy: onboarding, continuous learning, certifications, sales playbooks, product/itinerary training, and role-based competencies.
  • Align enablement with marketing messaging, brand standards, and product strategy; ensure tools/process adoption through blended learning and field coaching.
  • Coordinate channel/partner enablement for travel advisors, consortia, and key accounts; provide scalable content and toolkits for trade partners.
• Commercial Operations: Territories, Quotas & Compensation (in partnership)
  • Partner with Finance and Sales leaders to support quota methodology, territory design, and capacity planning.
  • Oversee sales compensation administration with HR/Finance; ensure plans are accurate, timely, and aligned to growth priorities and profitability.
  • Support deal desk/charter processes, approvals, and exception governance to accelerate cycle time while protecting margin.
• Change Management, Communication & Adoption
  • Lead change plans for new processes and tools: stakeholder mapping, readiness assessments, communications, and success measures.
  • Establish a network of field champions and feedback loops to accelerate adoption and continuous improvement.
• Leadership, Team Building & Budget
  • Hire, develop, and lead a high-performing team (analysts, enablement managers, CRM admins, program managers, sales tech owners).
  • Manage function budget; prioritize investments across technology, data, training, and enablement content for ROI.
  • Model Windstar's values and guest-first mindset; foster collaboration across global and matrixed teams.

Qualifications

• 10+ years in Sales Operations, Revenue Operations, Sales Enablement, Commercial Strategy, or comparable leadership roles; global or multi-region experience preferred.
• Proven track record leading sales transformation and cross-functional initiatives with measurable impact on revenue, efficiency, and seller productivity.
• Deep expertise with CRM and sales technology ecosystems; experience driving adoption, data quality, and value realization.
• Strong analytical capability-dashboard design, KPI frameworks, forecasting, and executive storytelling.
• Demonstrated success in process design, workflow optimization, and organizational change management.
• Experience building enablement programs (onboarding, readiness, content, certifications) and measuring behavior change and outcomes.
• Excellent communication and facilitation skills; ability to influence at senior levels and across geographies.

Preferred Qualifications

• Experience in travel, cruise, hospitality, luxury services, or B2B2C partner/channel environments highly desired.
• Familiarity with travel advisor ecosystems, consortia, and channel enablement.
• Background with AI/automation in sales processes; Lean/Six Sigma, PMP, or enablement certifications.
• Experience with BI/analytics tools and learning/enablement platforms.

Benefits:

For full-time employees, Windstar offers a comprehensive benefits package including: Medical, Dental & Vision; HSA & FSA; Life & Disability; Accident, Hospital & Critical Illness; Pet Insurance; Vacation, Sick Time and paid Holidays; 401(k) with Company Match; Employee Assistance Plan; Education Assistance and Employee Discounts & Travel Deals.