Director of Strategic Accounts – Hospitality (Hybrid)
Position Type: Independent Contractor / Commission-Only
Industry Focus: Hospitality, Hotels, Resorts, Hotel Management Companies, and Hospitality Ownership Groups
Reports To: President & CEO
Position Overview
Daryl May & Associates Inc. is seeking a highly connected and experienced hospitality sales professional to join our team as Director of Strategic Accounts – Hospitality.
This role is focused exclusively on identifying, developing, and securing new hotel and hospitality clients requiring managed IT services, cybersecurity, cloud solutions, infrastructure support, and strategic technology consulting.
The ideal candidate will have an extensive network within the hospitality industry, including relationships with hotel owners, management companies, general managers, regional operators, and hospitality decision-makers. The successful candidate will leverage their industry expertise and existing contacts to generate qualified opportunities and close new recurring revenue business.
This is a commission-only position designed for an entrepreneurial sales professional who thrives on relationship-building, business development, and long-term account growth.
Work Environment
This is a hybrid position with a primarily remote work environment.
The Director of Strategic Accounts – Hospitality will be expected to work independently from their home office while managing prospecting activities, relationship development, sales meetings, proposals, and client communications.
While the majority of the role can be performed remotely, occasional travel will be required, including:
- In-person meetings with prospective and existing clients
- Hotel property visits and site tours
- Industry conferences, trade shows, and networking events
- Hospitality association meetings and business development opportunities
- Company meetings, training sessions, and strategic planning events
The successful candidate should be comfortable building relationships both virtually and in person and understand that face-to-face engagement remains an important component of developing and maintaining strategic hospitality partnerships.
Travel requirements will vary based on business opportunities and territory coverage but are expected to be moderate and focused primarily on revenue-generating activities.
Key Responsibilities
Strategic Business Development
- Identify and secure new hotel, resort, and hospitality management clients.
- Develop and maintain relationships with:
- Hotel Owners
- Hotel Management Companies
- General Managers
- Regional Directors of Operations
- Directors of Finance
- Ownership Groups
- Franchise Operators
- Hospitality Consultants
- Generate new business opportunities through existing industry relationships, networking, referrals, and strategic outreach.
- Conduct discovery meetings to identify client business and technology needs.
- Present Daryl May & Associates' hospitality-focused IT solutions and services.
- Prepare proposals, pricing presentations, and service agreements.
- Negotiate contracts and close new recurring revenue opportunities.
Client Relationship Management
- Serve as the primary relationship owner during the sales process.
- Ensure a smooth transition of newly signed clients to the company's service delivery and operations teams.
- Maintain executive-level relationships with key client stakeholders.
- Identify opportunities for account growth, referrals, and additional service offerings.
Market Development
- Represent Daryl May & Associates at hospitality conferences, networking events, trade shows, and industry functions.
- Monitor industry trends and emerging opportunities within the hospitality sector.
- Provide market intelligence and competitive insights to leadership.
Required Qualifications
Experience
- Minimum 5 years of experience in hospitality sales, hospitality technology sales, hotel operations, hotel technology, managed IT services, or business development.
- Demonstrated success generating new business and closing recurring revenue agreements.
- Established network of hospitality industry contacts and decision-makers.
- Experience selling into hotels, resorts, hospitality management companies, or related organizations.
Knowledge & Skills
- Strong understanding of hotel operations and hospitality technology environments.
- Exceptional networking, communication, and relationship-building skills.
- Strong negotiation and presentation abilities.
- Ability to work independently and manage a sales pipeline.
- Self-motivated with a proven hunter mentality.
Preferred
- Experience with Managed IT Services (MSP).
- Experience selling Microsoft 365, cybersecurity, cloud, networking, infrastructure, or technology solutions.
- Existing relationships within Canadian hospitality markets.
Compensation Structure
Commission
This position is compensated exclusively through commissions and recurring account royalties.
Initial Client Acquisition Commission
The Director of Strategic Accounts – Hospitality will receive:
100% of the first month's recurring revenue for each new client secured.
Example:
- Monthly Managed Services Agreement: $7,880/month
- Commission Earned: $7,880
Annual Recurring Royalty
On each client anniversary, the Director will receive a commission equal to the client's current monthly recurring service value, provided they remain actively engaged with Daryl May & Associates Inc.
Example:
Year 1:
- Client Monthly Revenue: $7,880
- Commission: $7,880
Year 2:
- Client Monthly Revenue: $8,450
- Commission: $8,450
Year 3:
- Client Monthly Revenue: $9,000
- Commission: $9,000
Account Ownership
Following the first anniversary of the client relationship, and provided the Director remains actively engaged with the company, they will become the designated Account Holder for that client.
The Director will continue to support strategic relationship management and business growth opportunities, while all day-to-day service delivery, support, projects, and operational responsibilities will be managed by Daryl May & Associates' internal teams.
Performance Expectations
Success in this role will be measured by:
- New Monthly Recurring Revenue (MRR) generated.
- Number of qualified hospitality opportunities created.
- Number of new hotel properties secured.
- Number of hospitality management companies secured.
- Client retention and account growth.
- Referral generation and strategic partnerships developed.
Additional Compensation & Company Support
While this is a commission-only position, Daryl May & Associates Inc. is committed to providing the tools and support necessary for success.
The successful candidate will receive:
- Company-issued laptop
- Company-issued mobile phone
- Company email account and business software access
- Mileage reimbursement for approved business travel
- Reimbursement for approved business expenses incurred while conducting company business
- Access to company marketing materials, sales collateral, and proposal templates
- Administrative, operational, and technical support from internal teams
- Access to company-sponsored networking and business development opportunities, where applicable
The Director of Strategic Accounts – Hospitality will be expected to follow all company expense reimbursement policies and procedures, with all expenses requiring appropriate documentation and approval in accordance with company guidelines.
Why Join Daryl May & Associates Inc.
- Uncapped earning potential.
- Recurring royalty-based compensation model.
- Opportunity to build a long-term portfolio of hospitality accounts.
- Backed by an experienced technical and operational team.
- Ability to focus on sales and relationship development while the company handles service delivery and support.
Pay: $60,000.00-$150,000.00 per year
Benefits:
- Company events
- Flexible schedule
- Work from home
Application question(s):
- Are you comfortable working in a commission-only compensation structure with no base salary?
Language:
Work Location: Hybrid remote in Mississauga, ON
