About the Role

Are you a driven skilled who thrives on closing deals and scaling revenue on your own schedule? We are seeking a high-energy Outbound Sales Representative for a flexible freelance or part-time contract role to monetize our rapidly growing web traffic.In this role, you will own the entire closing cycle—from outbound prospecting to contract signature. You will pitch premium display ads, programmatic inventory, and custom sponsorships directly to brands and agencies.

Focus 100% on Sales: This is a pure revenue-generating role. We have dedicated operational teams for tech, creative, campaign execution, and reporting. Your only focus is crushing your outbound targets and maximizing your commission.What You’ll Do:

- Prospect and engage advertisers, media agencies, and programmatic partners through aggressive outbound outreach.
- Pitch and sell customized advertising packages, sponsorships, and digital campaigns.
- Close new business across both direct and programmatic categories.
- Negotiate pricing, placement tiers, and contract terms to maximize contract value.
- Build an active pipeline of repeatable brand and agency clients.

What You Bring:

- 3+ years of experience in media, advertising, or heavy outbound sales.




- Proven success closing deals and generating revenue in a quota-driven environment.
- Strong prospecting, negotiation, and communication skills.
- Ability to independently manage a pipeline from a cold lead to a final close.
- Results-driven mindset with total comfort working toward strict revenue targets.

Nice-to-Have Advantages:

- Bilingualism (English and French).
- Experience selling website inventory, sponsorships, or media blocks.
- Familiarity with programmatic systems, agencies, or reseller networks.

Important Note

This is a dedicated freelance/part-time outbound sales closing role. It is not an account management, campaign coordination, design, or development position. Only candidates with proven outbound closing experience will be considered.How to Apply

Apply via Indeed and include:

- Your resume.
- Examples of sales performance, quotas hit, or deals you have closed (if available).

Job Type: Part-Time / Freelance / Contract

Compensation: $36,000- $55,000 + commission (Base salary meets all Ontario general minimum wage requirements)

Location: Hybrid (Toronto, ON)

Work Location: Hybrid remote in Toronto, ON M6L 1B8

Pay: $36,000.00-$55,000.00 per year

Work Location: Hybrid remote in Toronto, ON

📌 Outbound Sales Representative (Freelance / Part-Time) (Toronto)
🏢 Out o'The Box
📍 Toronto