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 Cana dian 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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