Job Description

About the opportunity

Help people take the best trip of their lives, and get paid to talk about travel, cycling, food, and Europe all day.

• Ciclismo Classico is a boutique leader in premium cycling and active travel experiences, designing award-winning biking journeys in Italy and across Europe since 1989. We’re growing, and we’re hiring a Senior Travel Sales Consultant to turn qualified inquiries, travel dreamers and more into booked adventures, build long-term guest relationships, and help shape the next stage of our brand.

• If you’re a high-touch, relationship-driven salesperson who loves Europe, and cycling, this is a rare chance to sell something you can be proud of rather than the normal travel package.

What you’ll do

In this role, you will:

• Convert warm leads from web inquiries, past travelers, referrals, and partner channels into booked trips (FIT, private departures, and scheduled group departures).
• Own the full sales conversation: discovery, itinerary guidance, objection handling, closing, and post-booking care.
• Build long-term relationships with sophisticated, repeat travelers and turn them into raving “I’m coming back with my friends” guests.
• Collaborate with our trip designers in Europe to customize private groups and bespoke itineraries.
• Partner with marketing: share what guests are asking for, influence messaging, and identify high-potential themes and departures.
• Represent Ciclismo Classico at select rides, events, and guest evenings in key markets (Boston area and beyond; some evenings/weekends).
• Use our CRM (HubSpot) to manage pipeline, follow-ups, and conversion performance.

What success looks like in your first 6–12 months

• You consistently hit and exceed monthly booking and revenue targets.
• You’ve built a personal “book of guests” who request you by name.
• You’re feeding product/itinerary feedback straight from the traveler into the business.

What you bring

You’re a great fit if you have:

• 5–10 years of consultative phone / interactive sales experience (ideally travel, luxury experiences, adventure, or high-end consumer services).
• Proven track record meeting or exceeding revenue or conversion targets.
• Strong written and verbal communication; you’re confident guiding discerning travelers.
• Working knowledge of Europe (Italy strongly preferred: culture, regions, food, terrain).
• Ability to juggle details for multiple clients without dropping service quality.
• Comfortable using CRM tools (HubSpot or similar), and online booking / operations platforms.

Nice to have:

• You speak Italian, French, or Spanish.
• You’ve sold or led active / cycling / adventure travel.
• You’ve sold FITs, private groups, or custom itineraries.

Why this role is exciting

• You’re selling high-value, high-repeat product in one of the fastest-growing segments in travel: active, experiential, small-group European trips. Demand for “do something meaningful, not sit on a bus” travel is surging, and we’re built exactly for that.
• You’ll learn directly from a founder-led team with 35+ years of brand equity and guest loyalty.
• You get to help shape new departures and custom trips — you’re not just reading a script.

Comp & benefits

• Competitive base salary + commission/bonus structure (top performers earn significantly above base).
• Medical insurance (partially employer paid).
• Familiarization / educational travel: eligibility to join an annual Ciclismo Classico European trip.
• Opportunity for growth into Sales Leader / Sales Manager as we scale.

Location

This role is based in Arlington, MA. Hybrid arrangements or remote for exceptional candidates will be considered. Some travel (events, hosted rides) is required.

How to apply

Email your resume to lauren@ciclismoclassico.com with the subject line “Senior Travel Sales Consultant.”

Optional but helpful: in 4–5 sentences, tell us about a trip (yours or one you sold) that changed someone’s life.

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