Chief of Staff
WeTravel
full-time
Posted on:
Location Type: Remote
Location: Massachusetts • United States
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Salary
💰 $75,000 - $135,000 per year
Job Level
About the role
- Serve as an operational partner to the CEO, acting as an “air traffic controller” for leadership priorities, initiatives, and communications.
- Coordinate leadership meetings, agendas, and follow-ups to ensure decisions translate into action.
- Support alignment across the executive team and maintain visibility into strategic priorities.
- Lead preparation and coordination of board materials and investor updates, including board decks, data gathering, and cross-functional inputs.
- Manage timelines and ensure leadership teams provide accurate reporting and metrics.
- Maintain consistency and quality of communications with investors and board members.
- Drive the company’s OKR process, including planning cycles, alignment across teams, and tracking progress.
- Monitor cross-functional initiatives and provide regular reporting to leadership on key outcomes and blockers.
- Help ensure company priorities translate into clear, measurable execution across departments.
- Lead and manage company-wide strategic initiatives that require coordination across multiple teams.
- Identify operational bottlenecks and drive solutions to keep projects moving forward.
- Ensure leadership visibility into progress, risks, and outcomes.
- Support organization-wide AI adoption efforts, ensuring agentic tools are adopted.
- Maintain and organize Confluence to ensure key documentation, processes, and company information remain accurate and accessible.
- Improve documentation standards and knowledge-sharing practices across teams.
Requirements
- Based in Boston or East Coast and willing to travel to Portsmouth, NH, Amsterdam, Chicago, Denver/SLC as needed.
- Comfortable being uncomfortable, and operating in a fast-moving, ambiguous environment.
- Strong operator with experience in strategy, operations, consulting, or high-growth startups.
- Exceptional organizational and project management skills.
- Ability to work across teams and influence without formal authority.
- Strong written communication and executive-level presentation skills.
- Willing to be flexible in working hours. Work early or late in the day to facilitate collaboration with Amsterdam or Sydney-based colleagues.
Benefits
- Your health matters – US team members get 100% employer-covered HDHP medical, DHMO dental, and standard vision coverages or a choice of plans that suit your needs.
- Generous “Time to Recharge” policy — enjoy unlimited paid time off to rest and recharge.
- Amsterdam Program – visit us in Amsterdam (HQ) for 2–4 weeks annually, staying in one of our WeTravel apartments.
- Work remotely for a maximum of 4 weeks per calendar year.
- Extensive paid family leave.
- Three paid volunteer days per year.
- Two-week cross-functional onboarding program.
- Cutting-edge equipment and tools to set you up for success.
- Join an international, travel-loving team with a passion for adventure and innovation.
- Employer-sponsored 401(k) plan with a 2% company match to support your long-term financial goals.
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
project managementstrategic planningOKR processdata gatheringreportingmetrics trackingdocumentation standardsknowledge-sharing practicescross-functional coordinationoperational bottlenecks
Soft Skills
organizational skillsinfluencing without authoritywritten communicationexecutive-level presentationadaptabilityproblem-solvingcollaborationleadershipflexibilitycomfort with ambiguity