This job has expired

This position was posted on March 18, 2026 and is likely no longer accepting applications. We've kept it here for historical reference. Check out the similar jobs below!

Chief of Staff

WeTravel, Inc.

Job Overview

Location

Boston

Job Type

Full-time

Full Job Description

📋 Description

• The Chief of Staff at WeTravel, Inc. serves as the CEO’s operational counterpart and a central hub for strategic execution, ensuring leadership priorities are translated into action across the organization. This role is critical for maintaining alignment, driving accountability, and enabling the leadership team to focus on high-impact initiatives in a fast-moving, high-growth environment.
• Day to day, the Chief of Staff will act as an ‘air traffic controller’ for the CEO by coordinating leadership meetings, setting agendas, and ensuring follow-through on decisions; lead the preparation of board and investor materials, including data gathering and cross-functional input; drive the company’s OKR process from planning to tracking and reporting; lead cross-functional strategic initiatives, identify bottlenecks, and drive solutions; and maintain and improve internal documentation systems like Confluence to support organization-wide knowledge sharing and AI adoption efforts.
• WeTravel is an international, mission-driven company headquartered in Amsterdam with a strong presence in Boston, passionate about transforming the travel industry through innovation and adventure. The leadership team values operational excellence, transparency, and cross-functional collaboration, and the Chief of Staff will play a key role in enabling this culture by connecting teams, clarifying priorities, and ensuring consistent execution.
• In this role, the individual will develop deep expertise in executive operations, strategic planning, and organizational scaling within a high-growth tech environment. They will gain visibility into board-level dynamics, investor relations, and global operations while building influence across functions without formal authority—positioning them for future leadership roles in operations, strategy, or general management.

🎯 Requirements

• Based in Boston or East Coast and willing to travel to Portsmouth, NH, Amsterdam, Chicago, Denver/SLC as needed.
• Strong operator with experience in strategy, operations, consulting, or high-growth startups.
• Exceptional organizational and project management skills with ability to work across teams and influence without formal authority.
• Strong written communication and executive-level presentation skills.
• Comfortable operating in fast-moving, ambiguous environments and willing to be flexible with working hours to collaborate with global teams in Amsterdam or Sydney.

🏖️ Benefits

• 100% employer-covered HDHP medical, DHMO dental, and standard vision coverage (or choice of plans) for US team members.
• Generous "Time to Recharge" policy with unlimited paid time off.
• Amsterdam Program: opportunity to visit WeTravel’s HQ in Amsterdam for 2–4 weeks annually, staying in company apartments.
• Extensive paid family leave and three paid volunteer days per year.
• Employer-sponsored 401(k) plan with 2% company match.
• Two-week cross-functional onboarding program and cutting-edge equipment provided.
• Ability to work remotely for up to 4 weeks per calendar year.

Skills & Technologies

REST

Senior

Remote

Ready to Apply?

Apply Externally

You will be redirected to an external site to apply.

AI Job Fit Analysis

Pro

See exactly how your profile matches this role — strengths, skill gaps, and what to do about them.

WeTravel, Inc.

Visit Website

About WeTravel, Inc.

WeTravel is a San-Francisco-based fintech-travel platform that provides payment, booking and itinerary management tools for group travel organizers and tour operators. Its SaaS solution enables travel companies to collect funds, manage client documents, create custom booking pages and automate supplier payouts while offering travelers multi-currency payment options. Founded in 2016, the company focuses on small to mid-size travel businesses worldwide, integrating banking, payment processing and customer management into one dashboard.

View Company Profile

Get more remote jobs like this

Subscribe to the weekly newsletter for similar remote roles and curated hiring updates.

Weekly remote jobs and featured talent.

No spam. Only curated remote roles and product updates. You can unsubscribe anytime.