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Hotel Regional Director of Sales - Remote (Canada)

June 27, 2026

About Gillis At Gillis, we believe that sales is the lifeblood for all organizations. Our mission is to make sales accessible and achievable to all hotel owners. We also believe that our associates are our biggest asset and we put our people first over profit. If you are looking for a company that invests in its culture in a fast-paced, supportive, and dynamic environment, we would love to hear from you. Our clients trust us to increase their revenue and build both short-term and long-term business. We embrace the dynamic nature of our industry and always ask ourselves, “How can this be done better?” and “How can we provide more value?” Role Overview <ul> <li>The Regional Director of Sales (RDOS) will provide strategic, outbound and proactive sales for 6 multi-branded hotels, located across Canada and/or the USA.</li> <li>This position is home-based and reports to an Executive Director of Sales Performance.</li> </ul> What’s in it for you? <ul> <li>Position is home-based (remote) during client’s business hours and requires travel for in-market visits (2-4 visits per year).</li> <li>Working within a fun and fast-paced environment, Gillis’ culture offers dynamic training, ongoing coaching, and a deep commitment to taking care of our employees.</li> <li>Base salary of $70K CAD, quarterly incentives and an annual profit-sharing bonus.</li> <li>31 paid days off annually: <ul> <li>15 PTO Days</li> <li>13 Holidays/Gillis Days</li> <li>3 Wellness Days</li> </ul> </li> <li>Comprehensive benefits package.</li> <li>Team offsites.</li> </ul> Responsibilities <ul> <li>Provide strategic, outbound and proactive sales for a portfolio of 6 multi-branded hotels while also creating a sales-focused culture with the General Managers and Front Desk staff by sharing best practices and peer to peer coaching.</li> <li>Accountable for driving ROI for hotel partners while achieving revenue milestones on a shortened sales cycle of 6 months.</li> <li>Activate new accounts in the local market and increase market share from existing accounts through intentional and strategic prospecting. Deliver bi-weekly sales strategy presentations over MS Teams with each of your designated hotels to report progress.</li> <li>Develop and nurture a sales pipeline utilizing Salesforce CRM to manage accounts and shorten the sales cycle.</li> <li>Support the Dynamic Sales Solution model by working closely with your assigned POD (team) to drive revenue across our portfolio of hotels.</li> <li>Create remarkable client experiences, manage client expectations, and maintain a high level of client satisfaction by acting as a seamless extension of the hotel and representing your clients with professionalism and integrity.</li> <li>Ability to travel for in-market visits to elevate and strengthen client relationships.</li> </ul> What You'll Bring <ul> <li>3+ consecutive years of hotel guestroom sales experience across all market segments; multi-property sales experience preferred.</li> <li>Proven ability to generate new business, grow market share, and achieve revenue goals.</li> <li>Strong knowledge of hotel sales strategies, RFP processes, brand tools, account management, and hotel operations.</li> <li>Experience building trusted relationships with hotel owners, General Managers, and key local accounts.</li> <li>Proficiency with Salesforce (or similar CRM), Microsoft Office, AI tools, and sales technology.</li> <li>Excellent communication, organization, and presentation skills, with the ability to manage priorities and deliver results in a remote, fast-paced environment.</li> <li>Ability to work at a computer and participate in virtual meetings for extended periods.</li> <li>Reside in Canada and able to travel for client visits approximately 2-4 times annually. </li> </ul> Our Commitment to Fair Hiring <ul> <li>At Gillis, we may use technology, including AI, to support aspects of our recruitment process; however, all interviews and hiring decisions are conducted by people.</li> <li>Gillis is committed to fostering an inclusive and accessible workplace. Accommodations are available through the recruitment process upon request.</li> </ul>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

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This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...