Head of Operations

Note: Please apply directly to our website: https://explorerchick.com/dream-team-jobs/head-of-operations/. Only applications submitted through our website will be considered.-Explorer Chick is a premium women’s adventure travel company with a 10+ year track record and a fiercely loyal community. We design transformative, high-touch adventure travel experiences for women around the world.We are hiring a Director of Operations to run the operational engine of the company.Explorer Chick has strong demand, a proven product, and an experienced team. As the company grows, we need operational leadership that can lead people effectively, maintain structure, and ensure the business executes consistently while delivering the exceptional guest experience our brand is known for.This role reports directly to the CEO and is responsible for overseeing the day-to-day operations of the company.What You Will OwnOperations LeadershipYou will lead the operational side of the company, including teams responsible for:Destination ManagementGuest ServicesGuide ManagementOperations SystemsHR administrationYour role is to ensure the team is aligned, supported, and executing at a high level.Responsibilities include:Leading weekly operations meetings and maintaining team alignmentSetting priorities and ensuring the team is focused on the most important workRemoving operational bottlenecks and supporting team decision-makingStructuring the team effectively as responsibilities evolveEnsuring work remains visible and deadlines are honoredYou will act as the operational leader responsible for maintaining clarity, accountability, and execution across the organization.Team Performance & AccountabilityYou will be responsible for maintaining a high-performing operations team.This includes:Establishing clear performance expectations and role ownershipConducting employee evaluations and performance reviewsDeveloping compensation structures and role clarity as the company growsAddressing performance issues directly and constructivelySupporting hiring and onboarding as the organization evolvesYou should be comfortable managing people, setting expectations, and maintaining strong professional boundaries.Guest Experience & Trip Design StandardsExplorer Chick trips are designed to feel thoughtful, engaging, and premium. Operational decisions must protect that experience.You will work closely with Destination Managers and Guide Management to ensure operational choices support both guest satisfaction and brand standards.Responsibilities include:Reviewing and approving itinerary adjustments when neededEvaluating accommodations, trip pacing, and logistics through a hospitality lensEnsuring operational decisions enhance the guest experience rather than dilute itMaintaining high standards for lodging, service levels, and trip flowSupporting the team in designing trips that feel intentional, engaging, and memorableExplorer Chick trips combine logistics, hospitality, and storytelling. Strong operational judgment is required to maintain that balance.Project Management & ExecutionExplorer Chick operates through structured projects and operational priorities. You will ensure the team focuses on the right work and that initiatives move forward consistently.Responsibilities include:Leading operational projects with clear scope, ownership, and deadlinesEnsuring projects move forward on schedule and reach completionPrioritizing initiatives based on business impactEliminating work that does not support current prioritiesEvaluating and implementing the company’s project management system to support visibility, accountability, and executionThe goal is disciplined execution and consistent follow-through.Systems, Playbooks & Operational StructureExplorer Chick is building operational playbooks that support consistent execution across the company.Playbooks are developed collaboratively across the team. Your role is to ensure they are built, maintained, and used effectively.Responsibilities include:Maintaining playbook standards and documentation structureEnsuring operational processes are clearly documentedTranslating processes into repeatable routines and workflows within the project management systemImproving processes where inefficiencies existEnsuring systems remain simple, usable, and consistently followedPlaybooks should not simply document work — they should improve how the company operates.Our goal is clarity and simplicity, not unnecessary complexity.Operational Judgment & Risk ManagementThe operations team frequently brings forward questions, challenges, or proposed changes.You will evaluate these situations and determine the best path forward.Responsibilities include:Assessing operational risks and potential impactsHelping the team distinguish between real problems and lower-priority concernsGuiding the team toward solutions that balance guest experience, efficiency, and riskEnsuring operational decisions align with company standards and prioritiesStrong operational judgment is essential in this role.Trip Operations & Financial PerformanceYou will oversee the operational performance of the trip portfolio.Responsibilities include:Understanding trip-level budgets and marginsMonitoring operational spending and vendor termsSupporting Destination Managers in negotiations and cost controlIdentifying opportunities to improve margins, efficiency, and guest experienceOperational decisions should consider both return on investment and long-term sustainability.How You WorkYou are:Structure and systems-first, not reactiveFocused on outcomes over activityCalm under pressureDirect, decisive, and proactive in communicationComfortable prioritizing and eliminating work that does not move the business forwardAble to assess risk and make sound operational decisionsComfortable being handed a problem, not a processWilling to say, “This isn’t working. Here’s what I recommend instead.”Focused on execution and completion — not just ideasCurious about inefficiencies and motivated to improve themData-literate and comfortable using metrics and performance data to guide decisionsYou understand that operations requires balancing people leadership, systems, and judgment.This is not a task-taker role. You are expected to lead, make decisions, and ensure the work and business moves forward.You must also have experience operating in a fully remote team environment. Virtual work requires strong self-direction, communication discipline, and structured follow-through.Required Experience7+ years in operations leadership, business management, or operational roles in a service-based businessExperience managing teams and performance systemsPersonal familiarity with outdoor or active travel experiencesAbility to understand physical activity levels, trip flow, and the operational realities of adventure travelStrong operational judgment and risk awareness in dynamic environmentsExperience building or maintaining operational systems, processes, or playbooksStrong project management and execution skillsFinancial awareness, including budgets, margins, and operational spendingComfort working directly with a founder/CEO in a fast-moving environmentExperience operating successfully in a fully remote team environmentExperience implementing or managing project management systemsPreferred:Experience in travel, hospitality, tourism, or experiential businessesExperience managing logistics-heavy or multi-day guest experiencesCompensation & StructureFull-Time, Salaried PositionBase Salary: $85,000–$95,0003% IRA Match100% Remote (Cincinnati-area preferred for occasional in-person strategy sessions)Travel opportunitiesThis is a senior leadership role with direct access to the CEO and real ownership over operational performance, team leadership, and the systems that support Explorer Chick’s growth.Compensation is aligned with experience and demonstrated ability to drive operational excellence, accountability, and disciplined execution across the organization.