Senior Travel Sales Consultant – Luxury Cycling & Active Vacations

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 (Hub Spot) 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 (Hub Spot 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.
• 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.