POSITION OVERVIEWThe Director of FIT Sales is a senior leadership role responsible for driving revenue growth, developing sales strategy, and expanding market share across all distribution channels for the sightseeing and tour activity business. This role works closely with the Vice President of Sales and Marketing to align on company goals, set commercial strategy, and ensure sales initiatives are integrated with the broader marketing direction. The role oversees a multi-channel sales operation spanning Online Travel Agencies (OTAs), desk agents and concierge partnerships, and direct-to-consumer digital channels, with a strategic focus on accelerating direct online bookings.
In addition to owning the overall commercial strategy, the Director of Sales provides direct leadership to the Call Center Manager and the broader call center team, supporting a high-quality guest experience at every touchpoint. The role requires expertise in travel and tourism sales, a data-driven mindset, and the ability to build strong teams and scalable systems.
CROSS-FUNCTIONAL PARTNERSHIPThe Director of Sales works in close partnership with the Director of Marketing Technology. The Director of Sales owns revenue strategy, channel relationships, and the call center team, while the Director of Marketing Technology owns the digital infrastructure, demand generation, and customer data ecosystem that supports the sales funnel. Both roles share accountability for direct online booking growth and regularly align on campaigns, conversion performance, pricing promotions, and channel strategy.
Direct Online Booking Growth: The Director of Sales sets revenue targets and booking channel mix; the Director of Marketing Technology drives paid and organic traffic and conversion strategy.
Customer Data & CRM: The Director of Sales uses data for sales coaching and outreach; the Director of Marketing Technology owns the technology stack, segmentation, and automation.
OTA & Channel Management: The Director of Sales manages partner relationships and contracts; the Director of Marketing Technology manages digital listings, content, and reviews.
Promotions & Pricing: The Director of Sales defines offers, packages, and pricing strategy; the Director of Marketing Technology executes campaigns and landing pages.
Guest Experience Technology: The Director of Sales leads call center and concierge relationships; the Director of Marketing Technology implements booking flow and post-trip communications.
ESSENTIAL DUTIESSales Strategy & Revenue Growth- Work closely with the Vice President of Sales and Marketing to align on company-wide revenue goals, define sales strategy, and ensure commercial initiatives support the broader organizational direction.
- Develop and execute a comprehensive sales strategy aligned with company revenue targets and growth objectives across all channels.
- Lead the strategic shift toward direct online bookings, growing the channel mix and improving margin through owned digital channels.
- Set and monitor channel-specific performance goals, KPIs, and revenue targets, and report progress to executive leadership.
- Identify new market opportunities, partnership prospects, and revenue streams within the sightseeing and tour activity sector.
- Analyze the competitive landscape, pricing strategies, and market trends to maintain a strong competitive position.
Direct Online Channel Development- Champion the growth of direct-to-consumer online bookings as the primary strategic priority.
- Collaborate with marketing and digital teams to optimize the company website, booking funnel, and conversion rates.
- Define and drive promotional strategies, dynamic pricing, and packaging to incentivize direct bookings over OTA channels.
- Leverage CRM and analytics tools to build customer retention, repeat business, and loyalty programs.
- Stay current on digital booking trends, SEO/SEM strategies, and emerging technology platforms relevant to the travel industry.
Channel Management- Performs other job-related duties as assigned.
- Manage and optimize relationships across all distribution channels, including OTAs (e.g., Viator, GetYourGuide, Expedia), concierge/desk agents, and hotel partners.
- Negotiate and manage OTA contracts, commission structures, and inventory allocation to maximize net revenue.
- Build and maintain strong relationships with concierge teams, hotel front desks, and resort activity desks to drive referral bookings.
- Ensure channel parity, content quality, and brand consistency across all booking platforms.
Call Center & Team Leadership- Provide direct leadership and strategic direction to the Call Center Manager and the broader call center team.
- Set performance standards and service excellence expectations for inbound and outbound sales calls and reservation handling.
- Support the Call Center Manager in hiring, onboarding, training, and coaching team members.
- Review call center metrics, including conversion rates, average handle time, customer satisfaction scores, and upsell performance.
- Foster a high-performance, guest-centric culture across the sales and call center functions
Reporting, Analytics & Forecasting- Own sales forecasting and budget planning processes; provide accurate revenue projections to leadership.
- Build and maintain dashboards and reporting tools to track performance across all channels in real time.
- Use booking data, customer insights, and channel analytics to drive continuous improvement in sales strategy.
- Conduct regular business reviews with key partners and present results and recommendations to executive leadership
WHAT SUCCESS LOOKS LIKE- In the first 90 days, the Director of FIT Sales will have conducted a thorough audit of all sales channels, established baseline KPIs, and developed a prioritized roadmap for growing direct online revenue.
- Within six months, measurable progress toward direct booking growth targets will be visible, OTA relationships will be actively managed, and the call center team will be operating with clear performance goals and elevated coaching support.
- Over the first year, the Director of Sales will have meaningfully shifted channel mix toward direct bookings, improved overall margin, strengthened concierge and desk agent partnerships, and built a high-performing, motivated sales team culture aligned around delivering exceptional guest experiences. Ability to clearly and effectively present information and respond to questions from groups of managers, customers, employees, and the general public.
- Duties require a flexible work schedule to include working on nights, weekends, and/or holidays.
KNOWLEDGE, EXPERIENCE AND OTHER REQUIREMENTS- Bachelor's degree in Business, Hospitality, Tourism, or a related field is preferred, or an equivalent combination of education and experience.
- Minimum 10 years of related professional experience in a similar industry is required, preferably within tour operations, hospitality, or destination management companies (DMCs).
- Experience using Salesforce, Coach Manager, and Peek is strongly preferred.
The ideal candidate is outgoing, polished, and professional, with strong interpersonal skills, high emotional intelligence, and the ability to adapt to changing business needs and work effectively with diverse teams and stakeholders. Must be comfortable traveling as needed and working remotely when business requirements call for it.
BENEFITS- This role is bonus eligible. Total compensation is commensurate with experience and background.
- Medical, Dental, Vision and Drug Insurance
- 401(k) with a generous company match!
- Paid time off
- Employee Assistance Plan
- Pet Insurance
- Employee discount
- Advancement opportunities
- Free Parking
To apply, please click on the "Apply Now" link below.
We look forward to hearing from you and having you join Hawaii's best Tour and Transportation team! 
