Head of Sales

JOB DESCRIPTION

Head of Sales – Global Charter & Revenue Growth

Transcend Cruises | Remote or Los Angeles vicinity based

ABOUT TRANSCEND CRUISES

Welcome aboard the future of river cruising.

Transcend Cruises is redefining the European cruise experience with a fully chartered, tech-enabled platform purpose-built for private group travel. Every sailing is a full-ship charter — serving corporate buyers, meeting planners, tour operators, affinity groups, and specialty travel partners.

As the only charter-only river cruise company, Transcend delivers unmatched customization, exclusivity, and operational control. Our growth is driven by high-value partnerships, disciplined sales execution, and a fundamentally different approach to selling the river — as a private venue, not a per-cabin product.

POSITION OVERVIEW

The Head of Sales is the #2 commercial leader at Transcend Cruises, reporting directly to the COO. This role is responsible for building, leading, and scaling global charter sales while directly contributing to revenue through owned accounts and strategic deals.

This is a player-coach role with equal parts leader, architect, and frontline seller. The Head of Sales will define how we sell, who we sell to, and how we scale while personally closing high-value charter business.

The role requires a proactive, process-oriented leader who thrives in ambiguity, builds structure where it does not yet exist, and brings both charter expertise and creative, out-of-the-box thinking to a category-defining product.

CORE RESPONSIBILITIES

1. Sales Leadership & Team Build-Out

• With COO, design and build a high-performing charter sales organization from the ground up
• Recruit, onboard, and develop a team of sales professionals across key verticals
• Establish clear roles, territories, and segment ownership
• Lead, coach, and hold the team accountable to performance standards
• Foster a culture of ownership, urgency, and disciplined execution

2. Revenue Generation & Strategic Selling

• Own and deliver against contracted charter revenue targets in partnership with the COO
• Personally originate and close a defined segment of charter sales (strategic accounts / high-value opportunities)
• Lead complex deal structuring and negotiations
• Drive multi-night, full-ship charter conversions across priority verticals
• Support team in advancing and closing key opportunities

·      Ensure all contracts are structured for successful downstream delivery and execution

3. Sales Systems, Process & KPI Development

• Build and implement scalable sales systems, processes, and playbooks through the ownership of a Transcend Sales Operating System

• Define and track KPIs across the full sales funnel, including:
• Pipeline value and coverage
• Conversion ratios by stage
• Sales cycle length
• Outreach and activity metrics
• Revenue forecasting accuracy
• Ensure CRM discipline and reporting integrity across the team
• Deliver structured reporting to COO for leadership, board and investor visibility

4. Pipeline Development & Market Expansion

• Identify and prioritize key revenue segments, including:
• Corporate & MICE
• Affinity & specialty groups
• Tour operators & trade partners
• Incentive and experiential buyers
• Build and scale a high-quality global pipeline with focus on growing Europe source market
• Drive proactive outbound strategies and account-based selling
• Create new demand segments beyond traditional cruise or hotel group buyers
• Expand Transcend’s reach into new and underpenetrated markets

5. Sales to Delivery Integration

·      Establish and enforce a seamless transition process from contracted sale to program planning and execution

·      Oversee Account Management to ensure complete and actionable handoff of all client and contract details

·      Support Account Management in ensuring continuity, satisfaction, and execution excellence

·      Identify opportunities for upsell, repeat business, and long-term account growth

·      Build feedback loops from delivery into sales strategy and positioning

6. Commercial Strategy & Collaboration

• Partner closely with the COO on overall sales strategy and go-to-market direction
• Collaborate with Marketing to align messaging, campaigns, and lead generation
• Work with Revenue and Operations to ensure feasibility, pricing alignment, and execution excellence
• Contribute to product positioning and evolution based on market feedback

7. Brand & Market Leadership

• Champion Transcend’s differentiated charter-only model in the marketplace
• Reframe buyer mindset from cabins to full-ship private venue
• Represent the brand at industry events, trade shows, and executive-level engagements
• Support development of sales materials, presentations, and trade education

QUALIFICATIONS

• 8–12 years of senior sales experience in charter sales, cruise, luxury travel, or group/MICE environments
• Proven track record of closing high-value B2B deals
• Experience building or scaling sales teams and processes
• Deep understanding of charter sales and group travel dynamics
• Strong relationships across relevant trade networks preferred
• Highly proficient in CRM systems and sales reporting
• Exceptional negotiation, communication, and presentation skills
• Comfortable operating in a startup or high-growth environment

LEADERSHIP PROFILE

The ideal candidate is:

• A leader and a doer, equally comfortable closing deals and building teams
• Proactive and self-directed, with a bias toward action
• Comfortable with ambiguity and building structure from scratch
• Process-oriented and data-driven, without losing commercial instinct
• A creative thinker who challenges traditional sales models

• A collaborative partner to executive leadership
• A credible industry presence with executive-level gravitas

SUCCESS IN THIS ROLE

Success will be measured by:

• Achievement of contracted charter revenue targets
• Strength and scalability of the sales organization
• Quality, depth, and velocity of the pipeline
• Implementation of clear systems, KPIs, and reporting discipline
• Market adoption of Transcend’s differentiated sales model
• Contribution to overall company growth and commercial strategy

WHY JOIN TRANSCEND

This is a rare opportunity to define and lead the sales engine of a category-creating company. As Transcend enters its launch phase and scales its fleet, the Head of Sales will directly shape revenue growth, team structure, and market positioning.

If you are ready to build, lead, and sell at the highest level in a transformative travel company we invite you to join us.