Director of Sales Operations & Enablement

Overview

Awarded World’s Best Small Ship Cruise line, Windstar Cruises is known for intimate yacht style experience and unique voyages to the world’s best small ports and hidden harbors. Its three sailing yachts and four all-suite yachts carry just 148 to 342 guests and cruise around the world. Our mission is to imagine and deliver personalized and immersive experiences 180 degrees from ordinary.

We enrich people’s perspective through inspired travel.

Our Mission:
We imagine and deliver personalized and immersive experiences 180 degrees from ordinary

Our Vision:
Enriching people’s perspective through inspired travel

Our Values:
Welcoming, Innovative, Now, Discipline, Serve, Teamwork, Authentic, Responsible

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.

• 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…