Windstar Cruises · 15 hours ago
Director of Sales Operations & Enablement
Miami, FL
Full-time
Onsite
Director/Executive
10+ years expWindstar Cruises, awarded World’s Best Small Ship Cruise line, is seeking a motivated sales leader to serve as the Director of Sales Operations & Enablement. This role is crucial in driving global sales transformation by integrating best practices across multiple sales functions and ensuring unified commercial execution to enhance revenue and scalability.
Travel
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
Qualification
Required
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
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
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
Employee Discounts & Travel Deals
Company
Windstar Cruises
Windstar Cruises is a travel & tourism company specializing in cruise vacation packages.
1001-5000 employees
Funding
Current Stage
Late StageLeadership Team
Janet Bava
Chief Commercial Officer (CCO)
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