Director of Sales Operations & Enablement

Windstar Cruises•Miami, FL

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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).
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.
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.
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.
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.