Director of Operations - Insider Expeditions

Spyglass Ops; United States; Remote; USD 90,000 - 120,000; Full time

Job summary

Spyglass Ops seeks a Director of Operations for Insider Expeditions, responsible for optimizing operational efficiency across remote teams. This role prioritizes strategic thinking and data-driven decisions while ensuring the successful execution of travel programs. Candidates should excel in remote team management and possess strong financial acumen.

Benefits

Health Insurance

3 Weeks of PTO

Professional Development Opportunities

Qualifications

• Experience managing remote teams across multiple time zones.
• Proven results increasing team efficiency and generating scalable growth.
• Exceptional attention to detail and organizational skills.

Responsibilities

• Define KPIs and measure data per department.
• Recruit, manage, train, and discipline personnel effectively.
• Oversee finance and client billing to increase profitability.

Skills

Efficiency

Data-Driven Decision-Making

Remote Team Management

Financial Literacy

Risk Management

Job description

Director of Operations - Insider Expeditions

Director of Operations - Insider Expeditions

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Link to apply listed at the bottom of this Job Description. Only applications submitted through this link will be considered.

WHO WE ARE

Welcome to Insider Expeditions, where extraordinary journeys come to life and dreams become unforgettable realities. Our passion lies in crafting one-of-a-kind adventures that are as unique as you are, guiding you through uncharted territories and opening doors to breathtaking moments.

We are not your ordinary travel company. Our dedicated team of creative experience designers are true masters of their craft, obsessed with the tiniest details, weaving together bespoke trips that shatter the mold of traditional itineraries. For more than 17 years, we have offered people the chance to host community or brand or board meetings all over the world, led fundraising trips and non-profit donor experiences, music festivals in remote locations, creative brainstorming adventures for entrepreneurs, epic birthday celebrations, university alumni gatherings, and remote wellness and longevity retreats.

We also take sustainable travel seriously, making a continual conscious commitment to responsible tourism. Experience a journey that not only enriches your soul but also uplifts the well-being of local communities and raises awareness for global causes. We are the number #1 tour operator raising funds for climate change through our epic, carbon neutral, and leave-no-trace trips to Antarctica,and this is just one example. Together we can explore the world while preserving its beauty for generations to come.

With over 500 awe-inspiring experiences spanning all seven continents, Insider Expeditions stands as a beacon of trust and reliability in the boutique travel space. Our carefully designed itineraries, guided by experienced hosts, promise seamless logistics and renown experiences that keep our travelers and clients coming back year after year.

We are on a mission to give people some of the very best days of their lives. We are inspired and motivated to ensure Insiders have memories they will keep for the rest of their lives from our expeditions.

The Insider Advantage:

• Commitment to Our Clients: Our commitment of providing world-class service to our clients is our highest priority. From tour conception and marketing strategies to tour implementation and program evaluation, we partner with our clients to make sure they are included at every stage and ensure that their expectations are exceeded.
• Planning Once-In-A-Lifetime Itineraries: We pay attention to the little details that make any journey extraordinary. From early engagement materials to the itineraries themselves – every detail is refined and curated. Our itineraries are filled with exclusive opportunities not feasible through independent travel or with another operator.
• Executing With Ease While You Enjoy: We provide opportunities to engage with industry experts, renowned artists, and local communities. Enjoy relevant discussions and interactive activities that enhance every program. Most of our itineraries also contain an impact component, honoring both our traveler’s interests and our commitment to the communities we visit and the planet we love.

**If our culture and mission does not resonate with you, please do not bother applying.

JOB DESCRIPTION

The Insider Expeditions team is looking for a results-driven and detail-oriented Director of Operations. The Director of Operations is responsible for optimizing the team’s day-to-day execution across the business. They design and implement company infrastructure & processes to boost productivity & efficiency, while reducing friction and mitigating/preventing day-to-day fires. We're seeking a leader who can implement data-driven processes while preserving our creative approach to extraordinary travel experiences

The Director of Operations’ goal is to make the company operate as smoothly and efficiently as possible. The Director of Operations leads major company initiatives / projects, and holds the team accountable to completing them. The application code word is EMPOWER. The Director of Operations is a highly skilled strategic thinker. They anticipate and solve problems in a self-directed way. The Director of Operations is obsessed with data. They empower and build a team around them. The Director of Operations manages people effectively and creates ascension and disciplinary plans.

This remote position is full-time. Our team operates across multiple time zones with program directors in Fiji, Europe, and the USA, requiring excellent remote communication skills. This is a critical position within the business, as such, we host a rigorous, 4-part application process. This role does not require any travel.

RESPONSIBILITIES (TASKS ASSOCIATED WITH THE ROLE):

• This position will work very closely with the CEO
• Define KPIs and measure data per department, creating dashboards to deliver insights
• Recruit, manage, promote, train, develop, and discipline people effectively
• Implement management systems that hold people accountable to projects and tasks
• Complete company objectives and projects on time
• Set agendas, facilitate, and optimize meetings
• Find new opportunities for efficiency gains
• Oversee finance and client billing, cutting waste and increasing profitability
• Serve as a strategic buffer between the visionary CEO and the operational team, translating creative ideas into executable plans
• Manage upward effectively, providing structure to the CEO's innovative vision while maintaining team focus on priorities
• Establish clear strategic direction, accountability frameworks, and transparency across all departments while holding the team accountable towards this strategic vision.
• Oversee a portfolio of group travel events, ensuring consistent quality and profitability across diverse programs
• Review and prepare contracts, insurance policies, and terms & conditions with meticulous attention to detail
• Lead negotiations with clients, vendors, and suppliers to optimize pricing and service delivery
• Identify, assess, and mitigate risks related to travel proposals and event projects
• Build data-based decision-making workflows to improve operational efficiency
• Directly oversee the team, ensuring they are fulfilling responsibilities, meeting requirements, and producing expected results.
• Document company procedures and build upon/update as necessary.
• Ensure that the team is correctly following all workflows & SOPs

REQUIREMENTS (EXPECTED PROFICIENCIES):

• Proven results increasing team efficiency & performance, and generating scalable growth as a digital Director of Operations or similar position.
• Understanding of group travel operations is a must, experience working in the industry is a ++
• Exceptional attention to detail, time-management and organizational skills.
• Mindset & drive -- you hold yourself accountable to the highest standards of performance and are resilient in the face of obstacles or failure.
• Experience managing remote teams across multiple time zones
• Proven ability to establish and uphold accountability systems in a creative environment
• Financial literacy, including ability to analyze P&Ls and identify profit optimization opportunities
• Risk management experience, particularly in travel or event planning contexts
• Program/portfolio management skills to oversee multiple concurrent travel experiences
• Strong manager, and a keen interest to develop this skill set even further.
• Candid & direct communicator, with strong interpersonal, verbal, and written communication skills in English
• Highly resourceful, a natural problem-solver who loves learning new things.
• Data-Driven
• Nuanced discerner – you have the ability to “see around corners” and ensure that the team and company are working toward the right things
• Our organization works on the US time zones, however this role may require you to work some evenings & weekends due to the nature & location of our travel itineraries.
• This is a fully remote full time position. Ability to work across multiple time zones is must and some weekend work required

A+ PLAYER COMPETENCIES

• Honesty / Integrity
• Organization and Planning
• Strategic Vision
• Empathy
• Decision-Making
• Balance
• Follow through on commitments
• Analytical skills
• Persistence
• Proactivity

BENEFITS

• $90K to $120K commensurate with experience, with bonus structure based around growth metrics. Year 1 on track earnings of $150K
• This is a Fulltime Position, 1099 or W2 Role available if you are eligible to work in the US.
• Health Insurance, Vision, Dental Package available for W2 Eligible Candidates.
• 3 Weeks of PTO, 3 more days added per year of time served with the organization.
• Most US Federal Holidays are observed by our team.
• Professional Development: This role will be supported by an external Ops program that includes Ops mentorship, community, and live coaching.
• Potential for growth into a COO position for the right candidate
• Opportunity to help shape the strategic direction of an established boutique travel company
• Access to a network of global travel professionals and unique industry insights

HOW TO APPLY

If you are interested in this position, please submit an application at the following link.

Our team will review your application and get back to you shortly. We look forward to hearing from you!

DISCLAIMER:

Spyglass Ops is an authorized representative of Insider Expeditions. We are an Operations Hiring Agency, working on behalf of startup businesses to find and hire Operations Positions. All of our roles are full-time, salaried, leadership positions within growing business. We also filter the businesses we work with, to ensure they provide long-term positions, growth opportunities, and a strong working environment / culture. Our company qualifies and interviews candidates, then connects finalists with our clients for final interviews and job offers. Our highest priority is creating win-win matches for both our candidates and clients.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Management and Manufacturing

• Industries

  Operations Consulting

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