Sales Representative- Permanent Full-Time - (Supply Chain and Logistics B2B) - Ontario

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Chit Chats Express is seeking a permanent full-time Sales Representative in Ontario, onsite in Toronto, to identify, qualify and convert new business for its B2B shipping solutions. You’ll drive outbound and inbound outreach, conduct discovery calls, prepare proposals and pricing comparisons, and collaborate with Sales, Data, Product and Operations to ensure service fit before onboarding. The role offers a starting salary around $55,000 plus commission, benefits after 3 months, an annual bonus, two weeks’ vacation, birthday leave and GRSP eligibility. Key focus areas include strong communication, a customer-first mindset, CRM discipline, and multi-prospect management. To apply, tailor your resume with measurable results, highlight logistics or e-commerce sales, and demonstrate cross-team collaboration aligned with our mission.

Company Description

At Chit Chats Express, our mission is to empower Canadian entrepreneurs by making shipping simpler, more accessible, and more affordable. As a fast-growing, entrepreneurial company, we are proud to help businesses of all sizes reach customers around the world with confidence.

As e-commerce continues to eliminate borders, we believe Canadian entrepreneurs deserve a shipping partner that helps them compete globally without unnecessary complexity or high barriers to entry. Our goal is to create a seamless, borderless shipping experience that supports growth, opportunity, and long-term success for businesses across Canada.

If you are mission-driven, growth-oriented, and thrive in a collaborative environment, we’d love to hear from you.

Job Description

The role of the Sales Representative is essential in identifying, qualifying, and converting new business opportunities into active Chit Chats clients. This role is focused on building relationships with prospective clients, understanding their shipping needs, presenting relevant Chit Chats solutions, and guiding them through the decision-making process.

The Sales Representative’s responsibilities include: sourcing and following up with leads, conducting discovery calls, qualifying opportunities based on client fit, preparing proposals or pricing comparisons, and working with internal teams to ensure the client can be supported successfully.

Reporting to the Sales Manager – Business Development, the Sales Representative will contribute directly to revenue growth by turning qualified opportunities into active shipping clients and supporting the handoff to onboarding and account management once the client is ready to begin shipping.

Responsibilities

• Identify and pursue new business opportunities through outbound outreach, inbound leads, referrals, marketplace research, and reactivation campaigns.
• Conduct discovery calls to understand client shipping volume, current carriers, pain points, platforms, service needs, and growth potential.
• Qualify prospects based on commercial fit, shipping profile, compliance requirements, operational feasibility, and expected revenue.
• Present Chit Chats services clearly and professionally, tailoring the conversation to each client’s needs.
• Prepare basic pricing comparisons, savings summaries, proposals, and follow-up materials.
• Work with Sales Manager, Data, Product, and Operations to support more complex pricing or service-fit questions.
• Maintain accurate lead, opportunity, and client information in CRM.
• Track all outreach activity, follow-ups, next steps, and deal stages.
• Coordinate with Onboarding and Account Management to ensure a smooth transition after close.
• Follow up with prospects consistently and professionally to move opportunities through the pipeline.
• Identify client needs that may inform future products, service improvements, marketing campaigns, or partnership opportunities.
• Contribute to sales campaigns, vertical-specific outreach, and market research initiatives.
• Meet or exceed assigned activity, pipeline, conversion, activation, and revenue targets.

Requirements

• Strong written and verbal communication skills.
• Comfortable with cold outreach, discovery calls, follow-ups, and client presentations.
• Strong customer-first mindset with the ability to understand client pain points and recommend practical solutions.
• Good organizational skills and ability to manage multiple prospects at different stages.
• Ability to learn Chit Chats’ services, pricing structure, shipping workflows, compliance considerations, and operational requirements.
• Experience using CRM software, Google Workspace, Microsoft Office, and basic reporting tools.
• Strong problem-solving skills and ability to coordinate with internal teams.
• Self-motivated, resilient, and comfortable working toward sales goals.
• Ability to balance revenue growth with client fit, profitability, and operational feasibility.

Qualifications

• Post-secondary education or equivalent experience.
• 1–3+ years of experience in sales, business development, customer success, account management, or sales support.
• Experience in e-commerce, shipping, logistics, marketplaces, or small business services is an asset.
• B2B sales experience, preferably in logistics, transportation, or a related industry considered an asset.

Additional Information

Total Rewards and Compensation:

• Salary: Starting $55,000 per annum and Eligibility to participate in Sales Incentive Plan (Commission - tiered)
• Employer paid Group Benefits (Health, Dental and Vision; 80% coverage). After 3 months.
• Annual Year-End Bonus.
• Two weeks paid vacation (negotiable)
• Birthday leave (Paid)
• A rich GRSP plan eligibility after 3 months of employment

We thank you for your application, but only those candidates selected for an interview will be contacted.

Please note that the successful candidate will be subject to reference and criminal background checks prior to employment.

As a federally regulated employer, Chit Chats Express fully supports the principles of employment equity and encourages all qualified members of the designated groups to apply.