Trip Development Director (Client Engagement Director)

TRIP DEVELOPMENT DIRECTOR*

(*Internal Title: Client Engagement Director)

Iconic Adventures – Steamboat Springs, CO

Iconic Adventures is hiring a senior account leader and trusted travel expert (“Client Engagement Director”) to lead complex travel planning for key partnerships and client relationships. This is an individual contributor role with substantial leadership responsibility. We are looking for someone with the poise and expertise to steward and grow valued client relationships, and the global destination knowledge and operational depth to execute on their own vision.

Our portfolio spans donor and impact travel, corporate and affinity groups, global charity challenge events, and luxury FIT experiences. Luxury & international trip design expertise is required for this hiring round; experience across other segments is a plus. (Candidates that meet all qualifications except Luxury/FIT expertise are welcome to apply and highlight this at the top of their cover letter - we will hold your resume for future consideration.) This role reports to the Managing Director.

Key Responsibilities

Trip Design and Development

• Own the design and development of your itineraries end to end, from first concept through final program execution and budget reconciliation.
• Bring first-hand destination expertise and supplier judgment to every itinerary, drawing on where you have traveled, guided, or operated.
• Set the vision and the standard for each trip project, and direct the development process that Trip Development Managers and Coordinators support you in executing.
• Select and negotiate contracting with ground operators, lodges, guides, and specialty suppliers.
• Stay current on destinations, properties, and operators through ongoing research and networking.

Client Management and Strategic Partnership

• Build consultative, long-term relationships with your private (B2C) and organizational (B2B) clients across design, sales, and delivery. Act as a trusted advisor and treat clients as valued partners.
• Present and sell itineraries directly, addressing highlights, tradeoffs and any operational challenges with tact and clarity.
• Act as a liaison between stakeholders, identifying decision-makers within groups or organizations and surfacing solutions.
• Develop a deep understanding of client needs and preferences to customize processes for trip development, registration, marketing, and more.
• Uphold discretion and confidentiality, safeguarding client privacy at all times.
• Maintain a big-picture perspective on the client’s goals and be proactive in identifying growth opportunities for the partnership, with a client-first mindset.

Proposals, Budgets, and Forecasting

• Build and present compelling itinerary and program proposals.
• Develop and manage complex trip budgets across the full lifecycle, owning pricing assumptions, margin targets, and post-trip reconciliation.
• Forecast revenue and margin across your portfolio and surface variances early.

Project Management

• Navigate and align trip planning with the client’s mission, values, internal structures, and approval processes.
• Oversee projects with multiple stakeholders, including clients, travelers, local partners, and internal teams, managing approvals and aligning with organizational goals.
• Manage expectations and control scope by aligning on deliverables and clearly communicating the implications of timeline or project changes.
• Anticipate and address client needs proactively and strategically.
• Manage challenges with diplomacy and sensitivity, demonstrating strong problem-solving and conflict-resolution skills.
• Communicate clearly and concisely with clients, participants, and internal teams to align expectations and logistics.

What You Will Bring

Required

• 8+ years of progressive experience within trip development and the travel industry, with a substantial portion of that spent designing and developing itineraries yourself.
• Expertise with international destinations and high-touch travel. You are well-traveled and fluent in the bespoke market.
• Demonstrated ability to manage clients, customers and complex programs, including the ability to lead cross-functional teams without formal authority.
• Demonstrated ownership of itineraries from concept through delivery.
• Proven ownership of complex trip budgets across the full lifecycle.
• Experience building and presenting client proposals that won or renewed business.
• Excellent written and verbal communication paired with highly developed presentation and negotiation skills.
• Bachelor’s degree or equivalent professional experience.
• Travel:
  2 to 4 weeks per year, as needed.
• Work authorization: Must be authorized to work in the United States. We do not sponsor employment visas for this position.
• Location: Remote, US-based. Working hours should substantially overlap with Mountain Time business hours.

Preferred

• Guiding or trip-leading experience.
• People or team management experience.
• Client presentation and travel conference experience.
• Event management background.
• Spanish language proficiency; other languages are a plus.

How You Work

• You lead through judgment, influence, and credibility, whether or not you formally manage the people supporting your work.
• You are a doer. You are as comfortable building an itinerary yourself as you are directing a team to build it, and you know when each is called for.
• You are tech-forward and systems-oriented. You adopt tools quickly and use AI tools thoughtfully in your administrative workflow. AI does not inspire or guide your trip design.
• You are extremely thorough. You elevate structure and take delight in organization.
• You are kind. Even better, you have a sense of humor and grow from your mistakes.
• You operate with a high degree of ownership and autonomy.
• You handle difficult conversations directly and hold scope without damaging the relationship.
• You work effectively in a remote environment, with flexibility for the occasional evening or weekend tied to live itineraries running in the field.

What We Bring to the Table

• Access to an incredible global network of suppliers, including DMCs and hotels, vetted partners, professional industry networks, and field staff to help you build your client’s dream trip.
• Trip development support that scales with your client portfolio.
• A dynamic environment with the technology and tools to do your best work.
• A path to growing your career in the travel industry. Iconic Adventures has a growing portfolio of sister companies and clients across private, corporate, and nonprofit travel. Join us for an exciting new phase of opportunity and partnership!

Benefits

• Health and dental coverage.
• Unlimited PTO.
• 401(k) plan with employer match.
• Paid parental leave.
• FAM opportunities.
• An annual discretionary allowance to support your working environment.
• An annual company retreat to reset and connect with colleagues.
• Optional use of our Steamboat Springs, Colorado office.

Employment Terms

Employees may not own or sell travel through a separate seller-of-travel certified business/travel agency while employed by Iconic Adventures.

Hiring Process and What to Expect

• We are hiring immediately and reviewing applications as they arrive. The window closes Friday, November 6, 2026, and may close sooner. Early applicants have the advantage.
• Due to the volume of interest, we are not able to respond to every application, but we read each one.
• Candidates are encouraged to highlight itineraries they personally designed and developed, trip budgets and travel programs they owned, and client relationships they grew.
• Be prepared to provide up to 3 professional references. We will not contact any reference without notifying you first.
• Candidates are encouraged to highlight itineraries they personally designed and developed, significant client relationships they owned and grew, and trip budgets for which they held primary responsibility.
• Be prepared to provide up to three professional references. We will not contact any reference without notifying you first.

Background Check Disclosure

Any offer of employment is contingent upon the successful completion of a job-related background check conducted in accordance with the Fair Credit Reporting Act and applicable state and local law.

Candidates will receive any required disclosures and authorization forms before a background check is conducted. Background information will be considered on an individualized basis and only to the extent permitted by law.

Equal Opportunity

The Iconic Adventures LLC, a Delaware limited liability company, is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.