ph3JOB DESCRIPTION /h3 pABOUT CONTEXT TRAVEL /p pContext 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.
/p pContext is a long-standing company founded in ****.
We have been backed by growth equity since ****.
/p h3ROLE: /h3 pRegional Senior Associate - Italy, Southern Europe and Africa /p h3LOCATION: /h3 pRemote role /p h3SCHEDULE /h3 p: Monday-Friday, 9:00 AM - 6:00 PM CET /p h3SALARY: /h3 p Commensurate with experience /p h3JOB DESCRIPTION /h3 pContext'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.
/p pThe 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 fulfilable, working directly with our experts, and using data and tools to improve our regional operations.
/p pThe 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.
/p h3ROLE AND RESPONSIBILITIES /h3 ul liOwn 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.
/li liServe as the primary, proactive contact for clients and advisors, ensuring all proposals are commercially sound, operationally feasible, and accurately tracked.
/li liMaintain expert knowledge of the ISEA portfolio to ensure fulfilability, support product development, and turn recurring custom requests into repeatable products.
/li liMonitor backend configurations and flag seasonality risks or portfolio gaps before they impact bookings.
/li liManage 1:1 expert communications and build trusted relationships with the regional community,



thoughtfully matching experts to clients based on context and expertise.
/li liProvide clear briefings on custom content and collect expert feedback to drive continuous product improvement.
/li liTriage the regional inbox daily by urgency and value, maintaining strict data hygiene through consistent tagging and accurate information transfer.
/li liMaintain communication templates and canned responses to ensure high-quality, reportable regional data.
/li liAnalyze regional trends and root causes to identify client and operational pain points, providing actionable recommendations for cross-functional resolution.
/li liFluently utilize the tech stack and AI tools to optimize drafting, research, and data tasks, sharing best practices with the team.
/li liDesign, document, and lead new regional workflows and efficiency projects to improve the overall client experience.
/li liMentor and train seasonal contractors and Delivery colleagues.
/li liSupport onboarding of new regional teammates and act as a resource for best practice.
/li liActively contribute to weekly Delivery team and cross-regional meetings.
/li liParticipate in region-agnostic initiatives and lead project working groups.
/li /ul h3KEY STRENGTHS AND IMPACT AREAS /h3 ul liCommercial instinct.
Converts custom enquiries into confirmed, profitable bookings without losing the personal touch.
/li liPortfolio depth.
Knows the Italian, Greek, Turkey and Africa product well enough to answer most questions without escalating.
/li liTechnical fluency.
Adopts tools, including AI, and turns them into time saved for the whole team.
/li liData discipline.
Tags, records, and reports accurately, so regional decisions are based on real numbers.
/li liPattern recognition.
Sees the trend behind the individual complaint and proposes the structural fix.
/li liExpert relationships.
Trusted by the expert community, and able to brief them well under time pressure.
/li /ul h3WHAT YOU'LL BRING /h3 pRequired /p ul li2+ of experience in travel, hospitality, or a comparable client-facing commercial role.
/li liProven experience selling or building custom,



high-value travel or service proposals with an eagerness to close the sale and celebrate the win /li liNative-level English and Italian written and spoken (required), with strong professional judgement in sensitive client and expert-facing communications /li liDeep familiarity with and passion for Italy (required), including 3+ years lived or directly relevant professional experience, with a knack for inspiring others to visit.
/li liDemonstrated autonomous ownership: can triage, decide, and close loops without heavy supervision.Sincere enthusiasm for connecting with clients both via email and over the phone /li liConfident with CRM, booking, and communication platforms; fast to learn new systems.
/li liComfortable working with data: building a report, reading it, and explaining what it means.
/li liYou 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.
/li liResilience and composure—you handle unhappy clients with empathy and a thick skin /li liCultural sensitivity—you have experience and/or interest in working with colleagues and people from around the globe /li liA curious, learning-driven mindset—you'd happily be one of our clients yourself /li /ul pPreferred /p ul liKnowledge of Greece or other Southern Europe destinations.
/li liGreek or another regional language.
/li liExperience writing SOPs or training material.
/li liBackground in cultural heritage, art history, archaeology, or a related field.
/li /ul pIn exchange, we are thrilled to offer: /p ul liA supportive, mission-oriented work environment with colleagues who care /li liUnlimited access to digital lectures and, audio guides, and in-person small group tours /li liAnnual enrichment stipend to pursue personal and professional interests /li liTech stipend /li liFlexible PTO (with no caps, encouraged minimums, and parental leave) /li liA remote-first work policy - we have colleagues based in all four corners of the world /li liAn 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 **** we took the whole company to our birthplace, Rome, to celebrate our 20th anniversary.) /li /ul pContext 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.
/p /p #J-*****-Ljbffr

📌 Italy, Southern Europe, Africa Regional Senior Associate (Lazio)
🏢 Context Walks
📍 Lazio