Territory Sales Manager (Canada)

Territory Sales Manager – Canada

Location: Alberta or Saskatchewan, Canada (ideally between Calgary and Edmonton)
Compensation: $50,000 base salary plus a $50,000 commission guarantee for the first 12 months (See below)
Travel Requirements: 60–80% travel throughout the assigned territory
Work Arrangement: Remote when not traveling, with extensive field-based customer engagement

Compensation

• Base salary: $50,000 annually.
• Commission guarantee: $50,000 during the first 12 months, in addition to base salary.
• First-year compensation opportunity: $100,000 in guaranteed base salary and commission, with additional earning potential based on sales performance and the applicable commission plan.

Position Overview

We are seeking a highly motivated, self-directed Territory Manager to drive sales growth and expand market presence across Canada. This role is critical to the company's continued growth and is ideal for a high-energy sales professional who thrives in the field, builds lasting customer relationships, and takes ownership of territory performance.

The Territory Manager will manage the full sales cycle, develop new business opportunities, strengthen existing customer relationships, and represent the company's livestock and gooseneck trailer product lines throughout the assigned territory.

This is a field-focused sales position that requires significant travel, strategic planning, and disciplined follow-through. The successful candidate will be comfortable working independently, managing a flexible schedule, and maximizing productivity by coordinating multiple customer visits within each trip.

Key Responsibilities

• Develop and execute a territory sales plan to achieve revenue, sales, and market growth objectives.
• Identify, prospect, and develop new business opportunities across the assigned Canadian territory.
• Manage the full sales cycle, from lead generation and customer outreach through quoting, negotiation, order placement, and ongoing customer communication.
• Build and maintain strong relationships with customers, dealers, and key accounts to generate repeat business and long-term growth.
• Promote livestock and gooseneck trailer product lines by understanding customer needs and communicating product features, benefits, and value.
• Plan and coordinate territory travel efficiently, scheduling multiple customer visits and maximizing face-to-face selling time.
• Maintain consistent follow-up with prospects and customers to move opportunities through the sales pipeline.
• Track sales activities, opportunities, and customer interactions in the CRM system, ensuring accurate and timely documentation.
• Monitor pipeline progress, sales performance, and territory opportunities to identify areas for improvement and growth.
• Collaborate with sales leadership and internal teams to address customer needs, resolve issues, and support business objectives.
• Attend customer meetings, industry events, trade shows, and other relevant activities to strengthen market presence.
• Follow established sales processes and core activity expectations to maintain consistency, accountability, and strong territory performance.

Qualifications and Experience

• Proven experience in territory sales, outside sales, business development, or a related customer-facing sales role.
• Trailer sales experience is highly preferred.
• Experience selling agricultural equipment, heavy machinery, or other high-value capital equipment, such as tractors, combines, or similar products, is strongly preferred.
• Demonstrated ability to manage the complete sales cycle and develop new business independently.
• Strong prospecting, negotiation, presentation, and relationship-building skills.
• Self-motivated, energetic, and results-oriented, with a strong work ethic and the ability to execute a sales plan without extensive supervision.
• Excellent planning, organizational, time-management, and follow-up skills.
• Experience using CRM systems is required. Familiarity with Pipedrive or the ability to learn and adopt new CRM technology quickly is essential.
• Ability to work independently while maintaining regular communication and accountability with sales leadership.
• Valid driver's license and a driving record that meets company requirements.
• Ability and willingness to drive a company-provided pickup truck and, when necessary, set up or haul gooseneck or livestock trailers.
• Must reside in Canada, preferably in Alberta or Saskatchewan, with proximity to the Calgary–Edmonton corridor considered an advantage.
• Must have a clean driving record as you will be pulling trailers.
• Must have CRM experience.

Travel and Work Expectations

This position requires 60–80% travel, with an expectation of spending approximately three to four days per week traveling throughout the territory and three to four nights per week in hotels.

The Territory Manager will work remotely when not on the road but must be comfortable with a schedule that extends beyond traditional 8 a.m. to 5 p.m. hours. Customer availability, territory demands, and travel schedules will determine daily working hours.

Success requires proactive planning, efficient route management, regular customer engagement, and consistent follow-through. Candidates should understand that frequent travel is a fundamental requirement of the position and a key driver of success.

The role offers autonomy and flexibility in managing day-to-day activities, supported by regular communication with sales leadership and established sales processes.

The goal is for the Territory Manager to develop a productive sales pipeline and generate enough commission to exceed the guarantee within the first 12 months. Because trailer manufacturing can take at least 90 days, commission timing will depend on production and the applicable commission payment terms.

What Success Looks Like in the First Year

• Establish a strong presence across the assigned Canadian territory.
• Build a healthy sales pipeline through consistent prospecting and customer engagement.
• Develop lasting relationships with customers and generate repeat business.
• Demonstrate effective territory planning, efficient travel, and consistent execution of required sales activities.
• Maintain accurate CRM records and reliable reporting of sales activities and opportunities.
• Develop a thorough understanding of the company's products, sales processes, and customer base.
• Progress toward independently generating commissions that exceed the first-year guarantee.
• Contribute measurably to revenue growth and expansion of the company's Canadian market presence.

Ideal Candidate Profile

The ideal candidate is a driven outside sales professional who enjoys being on the road, building relationships, and developing business in a large geographic territory. They are organized, proactive, and comfortable balancing independent work with clear performance expectations.

Candidates with experience selling trailers, agricultural equipment, heavy machinery, or other high-value products will be particularly well suited to this opportunity. Above all, the successful Territory Manager will bring energy, accountability, strategic planning, and a commitment to growing the business through consistent field activity and excellent customer service.
Benefits and Perks

• Stable and growing company with long-term career potential
• Cross-training and skill development opportunities
• Team-oriented environment focused on quality and continuous improvement
• 401(k) with company match
• Seven paid holidays plus one floating holiday annually
• Medical, dental, and vision insurance
• Health Savings Account (HSA) option
• Company-paid life insurance
• Voluntary short-term and long-term disability insurance
• Vacation and sick time accruing upon hire
• Employee Assistance Program (EAP)
• Employee Referral Bonus Program
• Wellness Program, including annual health fair screenings to support a healthy lifestyle

Company Description

Since 1995, Lakeshore has provided Staffing, Recruiting and Payrolling services to employers in Denver and Chicago across multiple industries. We are committed to achieving success by matching top talent with the right opportunities. In 2017, Lakeshore re-branded as Lakeshore Talent after a management buyout, becoming a woman owned company. We have a dynamic team of Account Executives focused on sales and the client experience and a talented team of Recruiters focused on candidate recruitment and candidate experience. We are able to offer a higher level of service as a result, and take pride in building strong relationships worthy of loyalty with both clients and candidates.

Company DescriptionSince 1995, Lakeshore has provided Staffing, Recruiting and Payrolling services to employers in Denver and Chicago across multiple industries. We are committed to achieving success by matching top talent with the right opportunities. In 2017, Lakeshore re-branded as Lakeshore Talent after a management buyout, becoming a woman owned company. We have a dynamic team of Account Executives focused on sales and the client experience and a talented team of Recruiters focused on candidate recruitment and candidate experience. We are able to offer a higher level of service as a result, and take pride in building strong relationships worthy of loyalty with both clients and candidates.