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JOB DESCRIPTION

ABOUT CONTEXT TRAVEL

Context Travel is a global day tour operator that connects intellectually curious travelers with local subject matter experts in over 60 destinations around the world. Our guests often tell us that we are the best part of their trip, and we take great pride in creating unforgettable moments that are treasured for a lifetime.

Context is a long-standing company founded in 2003. We have been backed by growth equity since 2017.

ROLE: Regional Senior Associate - Italy, Southern Europe and Africa
LOCATION: Remote role
SCHEDULE: Monday-Friday, 8:00 AM - 5:00 PM GMT
SALARY: Commensurate with experience

JOB DESCRIPTION

Context’s Delivery team ensures the seamless execution of exceptional cultural experiences for all stakeholders—clients, travel advisors, guides, vendors, venues, and partners. We create highly personalized experiences while maintaining smooth and efficient operations.

The Regional Senior Associate - Italy, Southern Europe and Africa is a key member of the Italy, Southern Europe, Africa Delivery team. This is a hybrid commercial and operational role. You will own high-value custom requests from first enquiry to confirmed booking, and you will hold deep knowledge of the regional portfolio. The role has two equal halves. The first is client-facing and commercial: converting custom enquiries, advising clients and advisors, and maximizing the value of each booking. The second is behind the scenes: keeping the regional portfolio accurate and fulfillable, working directly with our experts, and using data and tools to improve our regional operations.

The role reports to the Regional Senior Manager - Italy, Southern Europe and Africa, and will work closely with the Regional Director and the Regional Delivery team.

ROLE AND RESPONSIBILITIES

• Own the end-to-end journey for custom and high-value regional requests, from initial qualification and proposal design to closing the sale and identifying upsell opportunities.
• Serve as the primary, proactive contact for clients and advisors, ensuring all proposals are commercially sound, operationally feasible, and accurately tracked.
• Maintain expert knowledge of the ISEA portfolio to ensure fulfillability, support product development, and turn recurring custom requests into repeatable products.
• Monitor backend configurations and flag seasonality risks or portfolio gaps before they impact bookings.
• Manage 1:1 expert communications and build trusted relationships with the regional community, thoughtfully matching experts to clients based on context and expertise.
• Provide clear briefings on custom content and collect expert feedback to drive continuous product improvement.
• Triage the regional inbox daily by urgency and value, maintaining strict data hygiene through consistent tagging and accurate information transfer.
• Maintain communication templates and canned responses to ensure high-quality, reportable regional data.
• Analyze regional trends and root causes to identify client and operational pain points, providing actionable recommendations for cross-functional resolution.
• Fluently utilize the tech stack and AI tools to optimize drafting, research, and data tasks, sharing best practices with the team.
• Design, document, and lead new regional workflows and efficiency projects to improve the overall client experience.
• Mentor and train seasonal contractors and Delivery colleagues.
• Support onboarding of new regional teammates and act as a resource for best practice.
• Actively contribute to weekly Delivery team and cross-regional meetings.
• Participate in region-agnostic initiatives and lead project working groups.

KEY STRENGTHS AND IMPACT AREAS

• Commercial instinct. Converts custom enquiries into confirmed, profitable bookings without losing the personal touch.
• Portfolio depth. Knows the Italian, Greek, Turkey and Africa product well enough to answer most questions without escalating.
• Technical fluency. Adopts tools, including AI, and turns them into time saved for the whole team.
• Data discipline. Tags, records, and reports accurately, so regional decisions are based on real numbers.
• Pattern recognition. Sees the trend behind the individual complaint and proposes the structural fix.
• Expert relationships. Trusted by the expert community, and able to brief them well under time pressure.

WHAT YOU’LL BRING

Required

• 2+ of experience in travel, hospitality, or a comparable client-facing commercial role.
• Proven experience selling or building custom, high-value travel or service proposals with an eagerness to close the sale and celebrate the win
• Native-level English and Italian written and spoken (required), with strong professional judgement in sensitive client and expert-facing communications
• Deep familiarity with and passion for Italy (required), including 3+ years lived or directly relevant professional experience, with a knack for inspiring others to visit.
• Demonstrated autonomous ownership: can triage, decide, and close loops without heavy supervision.Sincere enthusiasm for connecting with clients both via email and over the phone
• Confident with CRM, booking, and communication platforms; fast to learn new systems.
• Comfortable working with data: building a report, reading it, and explaining what it means.
• You are someone who does not stop at the task in front of them. This person spots patterns, brings them to the team, and proposes the process or the tool that fixes the problem for good. Comfort with technology — including AI tools — is central to the role, not a nice to have.
• Resilience and composure—you handle unhappy clients with empathy and a thick skin
• Cultural sensitivity—you have experience and/or interest in working with colleagues and people from around the globe
• A curious, learning-driven mindset—you’d happily be one of our clients yourself

Preferred

• Knowledge of Greece or other Southern Europe destinations.
• Greek or another regional language.
• Experience writing SOPs or training material.
• Background in cultural heritage, art history, archaeology, or a related field.

In exchange, we are thrilled to offer:

• A supportive, mission-oriented work environment with colleagues who care
• Unlimited access to digital lectures and, audio guides, and in-person small group tours
• Annual enrichment stipend to pursue personal and professional interests
• Tech stipend
• Flexible PTO (with no caps, encouraged minimums, and parental leave)
• A remote-first work policy - we have colleagues based in all four corners of the world
• An annual company retreat to connect and celebrate with colleagues in person. (Past locations include New York City, Philadelphia, Lisbon, Barcelona, Mexico City, and Berlin. In 2024 we took the whole company to our birthplace, Rome, to celebrate our 20th anniversary.)

Context Travel is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you have a disability or special need that requires accommodation, please let us know.

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