Italy, Southern Europe, Africa Regional Senior Associate

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