Group Specialist, Success at Pilot. Vancouver, Canada. On-call, hourly, flexible schedule (roughly 10-25 hrs/week, more in peak season). Hybrid. We are remote-first and flexible either way, but you would join us in person 1 to 3 times a week, depending on the time of year and what you are working on. CA$20.00 - CA$30.00 per hour, with potential for performance bonuses.

The role. The goal. 🛣️

Here’s what we’re looking for from you:

It is very simple. We want someone to own group bookings end to end, and to win more of them. Retreats, conferences, weddings, sports teams, and larger friend and family trips keep finding us on their own, and we have never had anyone dedicated to them. That is what this role is.

Half the job is looking after the groups that come to us. The other half is going and finding more, through business development and marketing. It is some of the best business we get, and nobody owns it yet. You would.

What you’ll be doing and learning 🧑‍💻

You don’t necessarily need to already have experience doing these (but it helps), and they are entirely subject to change based on what gets the most results. But here goes. The job duties are:

Drumming Up New Business

• Go and find group business rather than waiting for it to arrive
• Build relationships with the kinds of organisations that travel in groups: companies, clubs, teams, event organisers, wedding planners
• Work with marketing on campaigns, partnerships, and content aimed at group travel
• Follow up with past groups and turn one trip into the next one
• Bring us ideas for where group demand is hiding, then go and get it

Owning Group Requests

• Respond quickly to group, retreat, and wedding block enquiries
• Work out what the group actually needs: dates, size, budget, flexibility, and who makes the call
• Put together options and quotes a group can decide from, not a wall of links
• Follow up until they decide, without being pushy

Sourcing & Holding Inventory

• Source rooms, rates, and holds with hotels and our distribution partners
• Negotiate group rates and terms
• Get confirmed options into Pilot so the group can plan around them
• Keep track of what we are holding and when it expires

Booking & Vendor Operations

• Place bookings, confirm them with the property, and keep good records
• Get on the phone with hotels and partners when that is what resolves it
• Sort out booking errors, availability problems, and special requests
• Handle changes and cancellations all the way through to travel

Support During & After the Trip

• Be reachable when a group is travelling and something goes wrong
• Handle escalations calmly and with urgency
• Make sure people feel informed and taken care of
• Follow up afterwards and turn a good trip into repeat business

Making It a System

• Build the templates, processes, and documentation so the next one is easier
• Flag recurring problems to product and engineering
• Keep an eye on how the pipeline is converting and what it is worth
• Anything else as needed. We are a startup, so this is subject to change!

One important thing about all of the above

Treat everything above as a starting point, not a job spec carved in stone. It is not exhaustive, and it will change.

We’re a startup. We do more of what works and less of what doesn’t, and that means the shape of this role will move as we learn, sometimes quickly. You’ll pick up things that aren’t on this list, and some of what is on this list will turn out not to matter. So you need to be genuinely adaptable, and ideally you should enjoy that rather than just tolerate it. If what you want is a fixed list of duties that stays fixed, this won’t be the job for you, and that’s okay.

You’ll need to be eager, ready to work hard, and able to work independently. We’re moving fast, and that means doing a lot more in less time, sometimes cutting corners to do so.

Still, work-life harmony is important, so you’ll be the one setting your own goals to make sure they can be reasonably accomplished during your working hours.

“Should I apply??!??!?” 🤯

First of all, obviously.

It’s easy, and you can do it here: https://forms.gle/D1HrBVbDteJqXwZYA

Second of all, as long as you think you have either the necessary skills, or the ability to learn them very quickly to do this role, you’re good. We care about your ability to execute, not your experience, though it certainly can be an indicator.

That said, the ideal candidate probably has these traits…

Core Traits and Working Style

• Calm under pressure and emotionally steady, even when a group of 30 needs an answer tonight
• Highly reliable, detail aware, and follows things through to completion
• Acts with urgency and does not let issues linger
• Comfortable working without perfect information and making good judgment calls
• Polite, respectful, and empathetic with guests and partners, while still being firm when needed
• Low ego. Focused on solving the problem, not defending themselves

Business Development and Marketing

• Comfortable generating business, not just servicing it. Happy to go out and find the next group
• Comfortable asking for the business without being pushy
• Can negotiate rates and terms with a hotel and hold a position
• Has ideas about where demand comes from, and is willing to test them
• Motivated by closing and by margin, not just by clearing a queue

Communication and Execution

• Very strong written communication. Clear, concise, and human
• Comfortable getting on the phone with guests, hotels, and partners
• Knows when async is enough and when a call resolves things faster
• Able to explain issues and next steps clearly to non-technical people

Availability and Responsiveness

• Genuinely available on an on-call basis, including some evenings and weekends when a group is travelling
• Comfortable working Pacific time hours for North American groups
• Comfortable with fast-moving environments and shifting priorities
• Understands group travel is time sensitive and that dates expire

Experience and Background

• Prior experience in group sales, hotel sales, events, travel agency work, hospitality, or customer support is strongly preferred
• Experience dealing directly with customers or external partners is a plus
• Travel or hospitality experience is helpful but not required
• Based in or near Vancouver, and able to be with us in person 1 to 3 times a week

If you meet even 50-70% of these you could be a great fit!