At a Glance
- Tasks: Manage custom travel requests and ensure exceptional cultural experiences for clients.
- Company: Join Context Travel, a global leader in unique travel experiences.
- Benefits: Enjoy flexible PTO, tech stipends, and unlimited access to enriching resources.
- Other info: Be part of a diverse, mission-driven team with excellent growth opportunities.
- Why this job: Make unforgettable memories for travellers while working remotely with a passionate team.
- Qualifications: 2+ years in travel or hospitality, fluent in English and Italian.
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
- 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.
Italy, Southern Europe, Africa Regional Senior Associate in Edinburgh employer: Context Travel
Context Travel is an exceptional employer that fosters a supportive and mission-driven work environment, perfect for those passionate about travel and culture. With a remote-first policy, flexible PTO, and opportunities for personal and professional growth, employees enjoy a unique blend of autonomy and collaboration. The company also offers enriching experiences such as annual retreats and access to educational resources, making it an ideal place for intellectually curious individuals looking to make a meaningful impact in the travel industry.
StudySmarter Expert Advice🤫
We think this is how you could land Italy, Southern Europe, Africa Regional Senior Associate in Edinburgh
✨Get Involved in Local Travel Events
Join local tourism fairs or travel expos in your area. These events are a treasure trove for networking, and you can often meet hiring managers from companies like Context Travel who are looking for fresh talent for roles like Italy, Southern Europe, Africa Regional Senior Associate.
✨Showcase Your Travel Know-How
Create a travel blog or use social media to share your experiences and insights about different destinations. This can help you stand out to recruiters in the travel industry, demonstrating your passion for the sector and your ability to engage with an audience.
✨Connect with Alumni from Your School
Check out alumni groups linked to the travel and tourism sectors. Often, these connections can lead to inside info about opportunities at companies like Context Travel and give you a leg up for your Italy, Southern Europe, Africa Regional Senior Associate application.
✨Don’t Shy Away from Cold Emails
If there's a dream company you want to join, don’t hesitate to send a friendly email to their HR or recruitment team. Express your interest in their vision and mention that you’re keen on any Italy, Southern Europe, Africa Regional Senior Associate openings they might have. It's a bold move, but it might just pay off!
We think you need these skills to ace Italy, Southern Europe, Africa Regional Senior Associate in Edinburgh
Some tips for your application 🫡
Show Your Passion for Travel:In the travel and tourism industry, your love for exploration and different cultures should shine through in your application. Make sure to share personal anecdotes or experiences that highlight your enthusiasm for travel—this can really set you apart when applying for the Italy, Southern Europe, Africa Regional Senior Associate role at Context Travel.
Highlight Your Customer Service Skills:Customer service is king in travel and tourism. When detailing your work experience, focus on situations where you provided outstanding service or resolved customer issues, as this demonstrates your ability to ensure client satisfaction. Include specific examples in your CV to show that you're ready to face the challenges of the Italy, Southern Europe, Africa Regional Senior Associate position at Context Travel.
Keep Your CV Travel-Themed:When it comes to CV conventions in the travel industry, think of including any relevant certifications or training you've completed, like first aid or tour guiding courses. If you've travelled widely yourself, don't hesitate to mention that—it's all about showing your background fits the globetrotting vibe of Context Travel.
Craft a Compelling Cover Letter:Your cover letter should not only explain why you're a great fit but also reflect your personality! Use this space to express what excites you about the travel sector and how you can contribute to Context Travel's adventures. Share any unique perspectives or ideas you have to enhance the travel experience, especially as a full-time Italy, Southern Europe, Africa Regional Senior Associate.
How to prepare for a job interview at Context Travel
✨Show Off Your Travel Knowledge
For a role in travel and tourism, it’s vital to demonstrate your knowledge of different destinations, cultures, and travel trends. Brush up on popular destinations and recent changes in travel restrictions. We suggest bringing some interesting travel stories or experiences to share—this can help you connect personally with the interviewer!
✨Prepare for Customer Scenarios
Expect to be hit with customer service scenarios during the interview. They might ask how you'd handle a challenging traveller or resolve a booking issue. Think of a few real-life examples from your experiences, even if they’re just from customer service roles. This will show that you're ready for the field and have the right mindset to tackle on-the-ground challenges!
✨Highlight Your Flexibility and Passion
In a full-time travel position, there are often irregular hours and spontaneous travel opportunities. Be sure to convey your flexibility and willingness to embrace the unpredictable nature of this industry. Let’s showcase that enthusiasm for travel and how it drives your decision-making!
✨Know the Tools of the Trade
Get familiar with travel booking systems and tools, such as Amadeus or Sabre. If you have experience using any specific software or even social media for travel promotions, bring that up! We want to show that you can hit the ground running and adapt quickly to their processes at Context Travel.
