Job Summary

The Regional Director of Sales (RDOS) at Gillis Sales is a strategic, remote leadership position focused on driving revenue for a portfolio of six multi-branded hotels across North America. Operating within the “Dynamic Sales Solution” model, the RDOS acts as a proactive, outbound sales engine, shortening sales cycles and embedding a sales-focused culture within each hotel’s local team. This role is ideal for a high-performing “hunter” who excels at remote relationship management, Salesforce-driven pipeline development, and translating prospecting efforts into actualized revenue.

Job Details

Employer: Gillis Sales
Location: Remote (Applicant can reside anywhere in Canada or the USA)
Position Type: Full-time, Home-based
Salary & Benefits:
- Annual Salary: $70,000 CAD.
- Incentives: Quarterly performance incentives and an annual profit-sharing bonus.
- Time Off: 15 accrued PTO days plus “Gillis Days” in months without statutory holidays.
- Wellness: Comprehensive benefits package and a culture focused on mental and financial well-being.
- Travel: Requires travel for in-market visits 2–4 times per year to strengthen client relationships.
Reporting Structure: Reports to an Executive Director of Sales Performance; works within a collaborative “POD” team structure.

Core Responsibilities

Portfolio Management: Execute proactive outbound sales for six hotels, focusing on business transient, crew, and government segments.
Revenue Generation: Achieve revenue milestones on a shortened 6-month sales cycle and drive high ROI for hotel partners.
Strategic Prospecting: Activate new local market accounts and increase market share from existing accounts through intentional prospecting.
Sales Coaching: Create a sales-driven culture by coaching General Managers and Front Desk staff on best practices and lead conversion.
Account Management: Utilize Salesforce CRM to manage the pipeline, track daily activities, and maintain accurate follow-ups.
Reporting: Deliver bi-weekly sales strategy presentations via MS Teams to report progress and strategy to hotel stakeholders.
Relationship Building: Act as a seamless extension of the hotel brand, managing client expectations with high integrity and professionalism.

Candidate Requirements

Hotel Sales Experience: * 3+ consecutive years of hotel guestroom sales (Business Transient, Crew, and Government segments).
- Experience in Select Service hotels is required.
- 2 years in a Dual or Area hotel sales role is highly preferred.
Technical Proficiency: * Expertise in Salesforce or similar CRM systems.
- Strong command of Microsoft Office (especially Excel and PowerPoint) and MS Teams.
- Deep understanding of the RFP process and hotel brand tools.
Professional Skills: * Proven track record of meeting/exceeding sales targets.
- Excellent negotiation and verbal/written communication skills.
- Strong organizational and time management skills to handle a remote, multi-property portfolio.

Job Description

Are you a strategic sales leader who thrives on the hunt and values the freedom of a remote workspace? Gillis Sales is seeking a Regional Director of Sales to help us redefine how hotel owners achieve their revenue goals. At Gillis, we believe sales is the lifeblood of any organization, and we put our people first, investing in a culture that prizes integrity, professional growth, and work-life harmony.

In this role, you aren’t just a salesperson; you are a consultant and a coach. You will be the proactive force behind six different hotels, navigating the complexities of multi-brand environments to find and secure high-value business. Whether you are delivering a strategy presentation over MS Teams or walking a local market during one of your bimonthly visits, your focus remains on one thing: shortening the sales cycle and maximizing revenue. We provide the dynamic training and coaching; you provide the “hunter” instinct and the discipline to manage a thriving pipeline from your home office.

Joining Gillis means joining a team that values your mental and financial health. We offer the flexibility of remote work alongside the excitement of team offsites and a profit-sharing model that ensures when the company wins, you win. We are looking for collaborative team players who are eager to contribute to a “fun and fast-paced” environment while acting as a professional extension of our clients’ brands.

If you have a proven track record in select-service hotel sales and the technical savvy to leverage CRM data into sales victories, we want to hear from you. Help us make sales accessible and achievable for hotel owners across North America.

Gillis Sales | Calgary Regional Operations

Gillis Sales is a specialized hospitality sales performance partner that provides “Dynamic Sales Solutions” (DSS) for hotel owners across North America. Rather than operating as a traditional brick-and-mortar agency, Gillis functions as a fully remote, virtual sales organization. In Calgary, the company acts as a strategic recruitment and operational hub, hiring local hospitality experts to provide remote, high-impact sales support for multi-brand hotel portfolios.

Company Culture: “Cultivating a Culture of Selling”

The culture at Gillis is built on the belief that “sales is the lifeblood of every organization.” It is designed for proactive “hunters” who thrive in an entrepreneurial, results-oriented environment.

Supportive Autonomy: While the roles are 100% home-based, the culture emphasizes a “POD” structure where team members receive 3 weeks of intensive onboarding and ongoing peer-to-peer coaching via MS Teams.
People Over Profit: The organization prides itself on being “unconstrained,” allowing staff the freedom to pursue creative solutions for clients. Leadership emphasizes a “People-First” approach, investing in employee well-being to ensure they can deliver an average 4x–8x ROI for hotel partners.
Grit and Accountability: The environment is fast-paced and high-pressure, requiring “grit” and a solutions-focused mindset. Staff are expected to be “market insiders” who move beyond selling “rates, dates, and space” to provide genuine consulting value.

Unique Location & Hub Status

While the global headquarters is in Dallas, TX, and the Canadian administrative base is in Waterloo, ON, Calgary serves as a vital Regional Talent Hub.

Remote-First Connectivity: Gillis leverages Calgary’s deep pool of hospitality talent—particularly those with experience in the city’s major energy and airport hotel corridors—to fill senior Regional Director of Sales (RDOS) positions.
Strategic Time Zone Advantage: Calgary-based associates are uniquely positioned to manage hotel portfolios across both the Western Canadian and US Mountain/Pacific markets, ensuring seamless communication with General Managers and clients across multiple time zones.
Industry Alignment: The company maintains a Platinum Allied Membership with the IHG Owners Association, making its Calgary-based team essential for supporting Holiday Inn, Holiday Inn Express, and Staybridge Suites properties throughout Western Canada.

Core Service Offerings

Service	Impact
Dynamic Sales Solution (DSS)	A turnkey, virtual sales team that acts as an extension of a hotel’s on-site staff.
Sales Training	Specialized programs to enable front-line desk staff to capture and convert leads.
Sales Consulting	Strategic audits to uncover market issues and develop long-term revenue processes.

To apply for this job please visit gillissales.com.