Manager, Sales Operations and 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 : Enriching Lives Through Travel Our Values : Guest Obsessed, Open and Inviting, Fun-Loving and Focused, Light-Hearted and Genuine, Casual Yet Polished, Safe and Responsible. Windstar Cruises is dedicated to delivering unique and immersive travel experiences to our discerning guests. We are seeking a Manager of Sales Operations & Enablement to support Windstar Cruises’ global sales performance by executing and continuously improving core sales operations, enablement, and sales technology processes. This full-time, permanent role is responsible for translating commercial strategy into scalable processes, tools, insights, and enablement programs that help sales teams operate efficiently and effectively. The Manager works closely with Global Commercial, Sales leadership, Revenue Management, Marketing, Contact Center/VPC, IT, Finance, HR, Legal, Operations, and Itinerary Planning to ensure consistent execution across International, Global Accounts, Charters, and Travel Partners. The role focuses on driving adoption, improving seller experience, and delivering measurable gains in productivity, forecast accuracy, and revenue outcomes. This position will be fully remote, and must be located in the UK. Responsibilities Sales Planning & Operational Support Support International Sales leadership in executing annual and quarterly sales plans, pipeline management, and forecasting processes. Prepare operational inputs, materials, and analytics for pipeline reviews, QBRs, and sales planning cadences. Help translate commercial priorities into operational plans, timelines, and deliverables. Process Excellence & Standardization Document, maintain, and improve sales processes including lead management, partner engagement, opportunity management, quoting/contracting, and charter workflows. Identify opportunities to reduce manual effort and seller friction through process simplification and clear SOPs. Apply continuous-improvement practices to drive efficiency and consistency across regions. Sales Technology & CRM Administration Act as day-to-day business owner for sales tools such as CRM, partner/travel advisor tools, content management, forecasting, and sales automation platforms. Partner with IT on enhancements, integrations, testing, and releases to ensure tools meet business needs and scale globally. Support responsible use of AI and analytics features that improve seller productivity and insight quality. Monitor data quality and adherence to governance standards. Reporting, Analytics & Insights Build and maintain dashboards and reports that provide actionable insights for sales leaders and sellers. Analyze pipeline health, forecast trends, seller activity, and partner performance; surface risks and opportunities. Support forecast accuracy through consistent definitions, reporting cadence, and data discipline. Sales Enablement & Readiness Execute enablement programs including onboarding, ongoing training, certifications, playbooks, and role-based learning paths. Partner with Marketing and Product teams to align enablement content with messaging, itineraries, and brand standards. Coordinate partner and travel advisor enablement by delivering scalable content, tools, and communications. Track adoption and effectiveness of enablement initiatives. Commercial Operations Support (in partnership) Support territory design, quota setting, and capacity planning in collaboration with Sales and Finance. Assist with sales compensation administration in partnership with HR and Finance to ensure accuracy and timeliness. Support deal desk and charter approval workflows to improve cycle time while maintaining margin discipline. Change Management & Adoption Execute change management plans for new processes and tools, including communications, training, and feedback loops. Act as a point of contact for field questions, issues, and enhancement requests. Partner with field champions to reinforce adoption and continuous improvement. Teamwork, Leadership & Budget Support May manage or mentor analysts, enablement specialists, or system administrators. Support budget tracking and vendor management for sales operations and enablement initiatives. Model Windstar’s values and guest-first mindset; foster strong cross-functional collaboration. Qualifications Required Knowledge, Skills & Experience 7+ years of experience in Sales Operations, Revenue Operations, Sales Enablement, or related roles. Hands-on experience with CRM and sales technology platforms, including reporting and data management. Strong analytical skills with experience building dashboards and performance insights. Demonstrated ability to document and improve sales processes and support change adoption. Experience delivering sales training or enablement programs. Strong communication and organizational skills; ability to work effectively across functions and regions. Experience and knowledge of the UK and European travel trade distribution landscape. Preferred Qualifications Experience in travel, cruise, hospitality, luxury services, or B2B2C partner/channel environments. Familiarity with travel advisor ecosystems and consortia. Exposure to AI, automation, or analytics tools in a sales environment. Lean/Six Sigma, enablement, or project management certifications. Working Conditions Full-time, based in the UK (or as designated by Windstar). International travel as required to support sales teams, partners, and events. This job description may evolve based on business needs. EEO: Windstar is committed to a diverse and inclusive workplace. We are an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, pregnancy, genetic information, protected veteran status, or any other legally protected status.