Chief of Staff in Boston

The Chief of Staff partners closely with the CEO and leadership team to drive strategic execution, operational alignment, and cross‑functional coordination across the company. This role acts as the CEO’s operational counterpart—ensuring priorities move forward, information flows effectively, and key initiatives are executed with speed and clarity. The Chief of Staff serves as a central hub for communication, planning, and accountability across teams, helping leadership stay focused on the highest‑impact work.

Key Responsibilities

• Executive & Leadership Support: 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.
• Investor Relations & Board Coordination: 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.
• Strategic Planning & OKRs: 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.
• Cross‑Functional Project Leadership: 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.
• Internal Systems & Documentation: 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.

What Success Looks Like

• Leadership team operates with clear priorities, strong coordination, and consistent follow‑through.
• Strategic initiatives move forward without bottlenecks or misalignment.
• Board and investor communications are timely, accurate, and well‑organized.
• Company knowledge and documentation remain structured and accessible.
• Cross‑functional progress is tracked and communicated effectively.

Ideal Candidate

• 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.

Please note: At this time, we are not accepting applications from candidates residing in the following states: Alaska, California, Colorado, New York, or Washington. For this role, we can only consider candidates with the legal right to work in the United States. Unfortunately, WeTravel is not able to offer visa sponsorship or relocation assistance at this time.

Equal Opportunities

WeTravel is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome applicants from all backgrounds, experiences, and perspectives. If you're excited about this opportunity and believe you're a good fit, we encourage you to apply and join us in transforming the travel industry!