Travel Sales Specialist


Ciclismo Classico seeks energetic and team orientated individuals with experience in active travel to join our team in Travel Sales Specialist on a full-time basis for immediate start. Candidates should reside in New England and will work remotely combined with time at our Arlington office.

Our number one core value is to ensure that our guests have an unforgettable experience throughout their journey with Ciclismo Classico from initial inquiry to post trip feedback. With your knowledge and experience of the destinations we offer you will seek to understand customer needs, communicate the Ciclismo brand values, match customers with the perfect trip, close the sale and support customers at every touch point with the highest level of service ensuring that they have a fantastic experience and return again and again. 

Are you a natural at sales and customer service person? Ciclismo Classico’s Travel Advisors manage sales leads with the key objective of growing incremental and new sales and improve traveler retention. Collaborating with the CEO, marketing and operations Ciclismo Classico’s Travel Advisors share their knowledge, ideas and continuously contribute to all aspects of the company to ensure the delivery of world-class travel experiences. 

This is a great opportunity to launch or grow your career in the booming and exciting active travel business, the fastest growing niche in the travel business.


The Team:

Our Ciclismo team is a customer focused, passionate, organized and collaborative group with a hands-on attitude who make things happen together. The travel advisor works closely with operations, product, marketing and customer service. Key external relationships include our guests, travel agents and trade partners and suppliers.

Objectives and Responsibilities of the Travel Advisor: 

  • Increases revenue and retains loyal travellers by demonstrating travel expertise and the highest levels of front-line service.
  • Identifies, responds to and engages with all leads. 
  • Develops and maintains in-depth knowledge of the Ciclismo portfolio of trips; stays on top of consumer, competitor, and market trends
  • Builds and delivers creative sales strategies that are focused on brand expertise and the highest levels of traveller experience, and identifies areas of improvement; 
  • Supports sales efforts by completing all related administrative tasks accurately and efficiently.
  • Tracks sales activities to support strategic decision-making; 
  • Acts as a brand ambassador to avidly promote the business, share its vision, increase awareness, and establish more relationships; as required, participates in tradeshows and other industry events.
  • Plays a collaborative role with all individuals in the organization to ensure that sales strategies and objectives are aligned to the business’s overall objectives.
  • Works closely with the European operations in the creation of new sales strategies and approaches.

Your day-to-day role will include:

  • Building rapport and understanding the needs of your guests.
  • Preparing quotes for private tours and customizing them with our Italian team to ensure they meet the needs of your guests.
  • Following up on and converting leads to bookings.
  • Working with operations team, ensure that your customer’s trip is arranged to perfectly meet their needs.
  • Supporting your guests with all pre, during and post trip questions, amendments and issues.
  • Connecting with your guests pre and post trip to ensure all goes to plan and listening to their feedback to ensure we continually improve our trips.
  • Building strong relationships with our guests that ensure they return again and again.
  • Ensuring that every detail of your guest’s trip is perfectly organized and documented, including the administrative tasks this involves.

Who are we looking for?

  • You have a super positive attitude and are excited and curious to grow with the Ciclismo Classico community.
  • You like working hard, rolling up your sleeves, are collaborative and driven by delivering the highest quality service
  • You have a passion for the outdoors with experience and knowledge of some of the destinations of our tours (we will teach you the rest).
  • You care about the environment, preserving local cultures and promoting tourism that makes a difference (like bicycle tourism).
  • Experience in sales or customer facing roles where you have demonstrated your ability to understand and exceed customer needs, propose solutions, overcome objections and close sales.
  • An excellent eye for detail and administrative skills.
  • Able to multitask, prioritize and establish deadlines to ensure competing objectives are met.
  • Interpersonal and team skills which enable you to build great relationships internally and externally.
  • Highly confident, competent and articulate individual who can communicate professionally across all levels.
  • Able to work under pressure, motivated to achieve targets
  • Learning orientated
  • Resilient and flexible
  • A hands on individual willing to go the extra mile for guests, colleagues and Ciclismo Classico (a win: win: win approach) 

The Ciclismo Classico team is passionate and driven to make a difference in the world and in people’s lives. 


If you are looking for a challenging, fast paced environment, where you are making a difference in people’s lives, then Ciclismo Classico will be a great fit for you. We are looking for individuals who share our travel vision of delivering the highest quality, educational experiences and connects people with transformative active travel experiences in Europe and New England

Some of the things you can expect when you join our team:


  • Onboarding including sales, product and systems training.
  • Ongoing training and development throughout your career.
  • Annual bike tours to Europe!
  • Learning about the adventure travel business from an industry pioneer

Salary Package: 

The starting salary for the travel advisor is between $55,000 to $70,000 depending on experience increasing by $5,000 after successful completion of your initial six-month training and onboarding period. Our experienced high performing senior specialists earn between $65,000 and $80,000 after two years+ with Ciclismo Classico.


  • Initially 15 days PTO increasing to 20 days after 3 years’ service, plus federal holidays
  • An extra day off on your birthday
  • 50% employer paid health insurance
  • Great discounts on Ciclismo Classico tours for family and friends
  • A flexible work culture. You choose office, home or co-working mix
  • Regular company meetings
  • An innovative, fast growth, international and solution focused culture
  • Regular learning and development opportunities
  • The opportunity to make a difference to people’s lives and the planet.

Some of the things we expect from you:

  • At least two years in a fast-paced customer facing travel sales or sales environment
  • Excellent knowledge and fluency in the Microsoft Office suite of applications.
  • Experience working with travel booking such as Peak 15 and CRM software is an asset
  • Excellent sales, communication and customer service skills
  • Passionate for active travel
  • In depth knowledge and experience of travelling, living or working in the destinations we offer trips
  • The flexibility to work some evening and weekends for Ciclismo Classico events
  • You are based in New England and legally permitted to work in the USA (We may consider strong out of state candidates, depending on location)

Does this sound like your dream job? Please send your CV, an awesome cover letter to com explaining why you would be a perfect match for this role.

We look forward to you joining us on our adventure.


About Ciclismo Classico

As a specialized “boutique” bicycle tour operator since 1989, we passionately provide the most authentic, unique and exciting vacations in the adventure travel industry. Our well-crafted educational trips in Europe (the majority of tours are in Italy) and New England are active immersions into local art, language, music and, of course, delicious cuisine. By combining legendary service and rare cultural experiences, our Ciclismo philosophy continues to energize and transform each and every guest.

We warmly embrace our active-travel niche and family-style company culture. Our strengths and excellent reputation lie in our 34 years of active travel expertise, superior and personalized customer service, and multi-talented staff and members of our tour leadership team. Our entire Ciclismo US and 26 bilingual guides are passionate about doing things the Ciclismo Way-with a sense of fun, creativity and total dedication to quality.


Ciclismo Classico


Full Time

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(not necessarily associated with the tour operator)

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