WeTravel logo
WeTravel

The travel booking and payment platform powering client-focused multi-day group trip organizers and tour operators.

Chief of Staff

Chief of StaffChief of StaffFull TimeRemoteLeadTeam 51-200Since 2016H1B No SponsorCompany SiteLinkedIn

Location

Massachusetts

Posted

2 days ago

Salary

$75K - $135K / year

Seniority

Lead

Bachelor DegreeEnglish

Job Description

• 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.

Job 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.

Related Categories

Related Job Pages

More Chief of Staff Jobs

Chief of Staff2 days ago
Full TimeRemote

We are looking for an Owner’s Advisor to join our Advisory Services team. We partner with public and private sector clients across water/wastewater, transit and transportation, environmental services, and construction management—helping deliver critical infrastructure that st...

United States
$145K - $160K / year
EY logo

Global Assurance MS Chief of Staff

EY

Building a #BetterWorkingWorld by providing trust through assurance and helping organizations grow, transform & operate.

Chief of Staff2 days ago
Full TimeRemoteTeam 10,001+Since 1989H1B Sponsor

The Chief of Staff will support the Global Assurance MS leadership team with developing and executing strategic plans, engaging with leaders across regions to monitor strategy tracking for market success. This role is responsible for driving strategic investment initiatives, developing policies and processes, and ensuring effective teaming and execution of Assurance MS strategic plans.

United States
Mariner logo

Vice President, Chief of Staff

Mariner

Reducing Manufacturers' Cost of Quality

Chief of Staff3 days ago
Full TimeRemoteTeam 11-50H1B Sponsor

This Vice President role acts as a strategic proxy and force multiplier to the CIO, shaping priorities, accelerating execution, and ensuring alignment between technology, operations, and business strategy across the enterprise. Key duties include orchestrating cross-functional collaboration, driving executive alignment, leading strategic programs, overseeing the IT operating budget, and managing enterprise-wide IT communications.

United States
$150K - $175K / year
Jobgether logo

Senior Chief of Staff

Jobgether

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1 We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

Chief of Staff4 days ago
Full TimeRemoteH1B No Sponsor

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Remote Chief of Staff to the CRO. In this strategic partner role, you will significantly contribute to enhancing the operational efficiency of the global revenue organization. You ...

United States