Team Lead, Sales

At Fresh Tracks Canada, we craft tailor-made Canadian vacations for people from all over the world. Since 1996, our team of Canadian Insiders have helped our customers plan their vacations and enjoy life-changing travel experiences.

ABOUT THE ROLE

Fresh Tracks Canada is looking for a Sales Team Lead to help scale and support a high-performing sales organization through its next phase of growth.

This is not a traditional people-management role. The Sales Team Lead acts as a coach, operational expert, trainer, problem-solver, and trusted resource for the sales team. The role bridges the gap between frontline sales execution and leadership, helping agents navigate processes, systems, technology, product knowledge, and client scenarios while contributing to broader organizational initiatives.

As our sales organization continues to grow, we are looking for someone who thrives in a fast-paced environment, enjoys helping others succeed, and can balance day-to-day support with longer-term process improvement and operational excellence.

Salary Range: $70,000 CAD annually, plus sales commission, based on experience and qualifications.

RESPONSIBILITIES

Sales Team Support & Coaching

• Serve as a primary point of contact for sales agents requiring support with product knowledge, processes, systems, trip builds, pricing, and booking workflows

• Provide ongoing coaching through call reviews, side-by-side support, and skill development conversations

• Help agents strengthen consultative selling skills, value proposition delivery, objection handling, and closing techniques

• Support performance improvement initiatives and reinforce best practices across the team

• Assist with escalated client situations and internal problem-solving

Training & Enablement

• Support onboarding and training of new sales team members

• Reinforce adoption of sales processes, systems, and tools

• Assist in developing, maintaining, and improving training content, documentation, and learning resources

• Identify coaching and development opportunities across the team

• Contribute to ongoing sales enablement initiatives that improve team effectiveness and performance

Operational Excellence

• Support daily operational troubleshooting and help identify practical solutions to recurring challenges

• Assist with process creation, process improvement, and documentation updates

• Help maintain consistency across sales workflows and operational standards

• Participate in testing, rollout, and adoption of new systems, tools, and technology enhancements

• Act as a subject matter expert for key sales processes and systems

Cross-Functional Collaboration

• Partner closely with Product, Operations, Marketing, Finance, and Leadership teams

• Help communicate operational changes, process updates, and new initiatives to the sales team

• Participate in cross-functional projects and provide frontline sales insights

• Support organizational initiatives that improve efficiency, customer experience, and business performance
  

Leadership & Team Development

• Foster a collaborative, positive, and accountable team environment

• Support team engagement, morale, and culture-building initiatives

• Help identify opportunities for growth and development within the sales team

• Lead by example through professionalism, adaptability, and a solutions-oriented mindset

• Act as a trusted resource and informal leader across the organization

REQUIREMENTS

• Demonstrated experience in sales leadership, coaching, training, or team development

• Strong ability to build credibility and influence without relying solely on formal authority

• Experience supporting teams in a fast-paced, customer-focused environment

• Excellent communication, coaching, and relationship-building skills

• Strong organizational skills and ability to manage multiple priorities simultaneously

• Experience creating or improving processes, systems, and documentation

• Comfortable navigating technology platforms, CRM systems, reporting tools, and operational workflows

• Ability to think strategically while remaining highly operational and hands-on
• Positive, resilient, and adaptable approach to problem solving

REWARDS

You may be eligible to receive the following benefits, based on your contract type:

• 3 weeks vacation (4 weeks after your first year)
• Extended health benefits package
• Paid anniversary day off
• “Pawternity leave” days for your new furry family members
• Friendly and fun team environment with company celebrations and social events
• Access to Canadian travel industry discounts!
• Community (volunteer) Hours
• Paid Maternity & Parental leave
  
• Paid Pregnancy loss leave

DIVERSITY, EQUITY, AND INCLUSION

We are an equal opportunity workplace. We strongly encourage applications from under-represented communities, diverse backgrounds, identities, and experiences. We don’t judge based on race, religion, ethnic background, sexual orientation, age, marital status, disability, gender identity or anything else that you might bring to the table. We don’t care about where you went to college, your degree, your age, or what names you might have on your resume. Instead, we’re looking for motivated, compassionate people who can execute from the ground up. We also know that everyone has a unique career journey and experience comes in many forms.

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