Job Details

Lead with Heart. Drive Results. Create Lifelong Memories.

At Trilogy, we're celebrating 52 years as a Lahaina-based, family-owned and operated company. Rooted in tradition and Aloha, we've built a legacy of creating lifelong memories that span generations—and we're just getting started.

We're seeking a Director of Sales & Marketing to help write the next chapter of our story. Join our Executive Leadership Team and help lead the vision, strategy, and execution behind how we engage guests, grow revenue, and elevate our brand across Hawaii and beyond.

About You:

You're a strategic leader and passionate storyteller. You blend creativity with analytics, brand with business, and vision with execution. Whether you come from hospitality, consumer brands, travel, or lifestyle marketing, you know how to inspire teams and connect with audiences. You lead with heart—and you know how to deliver results.

What You'll Do:

Drive Trilogy's marketing and sales strategies across all platforms and guest segments
Lead branding, campaign development, digital marketing, PR, and product positioning
Mentor and manage a high-performing team across Sales, Group Sales, and Guest Services
Represent the company at industry events, in the community, and in media
Champion new guest experiences and product offerings that reflect Trilogy's values and growth goals

Why Trilogy?

At Trilogy, we are more than excursions. We are stewards of shared moments—sunset sails, family celebrations, and first-time ocean experiences. Our company is guided by four principles:

Leading with Heart – We lead with compassion, care, and community.
Driven to Excellence – We aim higher, think smarter, and act with purpose.
Professional and Fun – We take our work seriously, and find joy in the journey.
Engaging Hospitality – We do more than simply serve guests, we create authentin connections.

You'll join a team that's proud of where we come from and excited about where we're going.

Compensation & Perks:

Base Salary: $110,000 – $125,000
Bonus Potential: 22% of base salary
One week of vacation frontloaded at time of hire
Relocation assistance available
Fully Company Paid Health Insurance for Employee and all Dependents

The chance to live and work where others vacation.

What We're Looking For:

10+ years of progressive experience in sales, marketing, or brand leadership
Bachelor's degree required; MBA preferred
Strong communication and presentation skills
Track record of leading teams, launching campaigns, and driving revenue
Data-driven mindset with creative flexibility
Industry knowledge of hospitality or tourism is a plus—but not required