Sales Executive - Advertising

Overview

We are building a dedicated advertising sales team and are looking for a driven media sales professional to help grow advertising revenue across digital, print, sponsorship, branded content, and integrated media solutions.

This is a highly client-facing role focused on developing new business and growing relationships with advertisers and agencies across the GTA. Success in this role comes from your ability to open doors, build trust with marketing decision-makers, uncover opportunities, and close revenue-generating partnerships.

We are looking for someone who already understands the advertising ecosystem, has experience working with agencies and brand advertisers, and enjoys the challenge of building business through proactive outreach and relationship development.

• Generate new advertising revenue from both direct advertisers and agency partners
• Build and manage a pipeline of opportunities across the GTA market
• Develop relationships with media buyers, planners, account directors, marketing managers, and senior brand stakeholders
• Lead client discovery conversations to understand campaign objectives and business goals
• Create and present integrated advertising solutions including digital, branded content, sponsorship, event, and custom media opportunities
• Negotiate and close advertising agreements while managing revenue forecasts and pipeline activity
• Partner with internal teams to develop compelling proposals and ensure successful campaign execution
• Represent the organization at client meetings, industry events, and networking opportunities

• 3–6+ years of advertising or media sales experience in a quota-carrying, client-facing role
• Track record of selling to both direct brand clients and media/creative agencies in the GTA market
• Demonstrated ability to manage a full sales cycle — from prospecting and discovery through proposal, negotiation, and close
• Strong understanding of digital advertising products: display, video, native, programmatic, social, and email/newsletter sponsor ships
• Ability to use audience and performance data to build compelling, insight-led presentations
• Experience working with multi-stakeholder clients, including procurement and senior marketing leadership
• Proficient with CRM tools (Salesforce, Hub Spot, or equivalent) and comfortable with pipeline reporting
• GTA-based with an established network of local agency and brand contacts

• Experience selling branded content, sponsor ships, or integrated packages beyond standard display units
• Familiarity with programmatic advertising, private marketplace (PMP) deals, or data targeting products
• Background in a media category experiencing audience or format evolution (digital publishing, streaming, OOH, podcast, or emerging channels)
• Experience using media planning tools (e.g., Comscore, Nielsen, Similar Web) to support client presentations
• Comfort pitching C-suite and VP-level marketing stakeholders at major Canadian brands

• This is not a campaign management or ad operations role — you are in market, owning revenue.
• This is not a role where success comes from servicing inbound RFPs — you will build pipeline from scratch and develop clients proactively.
• This is not a remote position. In-person client meetings, agency visits, and event presence are core to how this role drives results.

We would be particularly interested in candidates coming from:

• Media and publishing organizations
• Digital media companies
• Broadcast and streaming media
• Out-of-home advertising
• Sponsorship and partnership sales
• Advertising technology companies with direct agency relationships

This is a rare chance to build — not just sell. You’ll step into a high-impact role with real ownership, shaping both your book of business and the trajectory of our advertising revenue. We’re investing in a modern, competitive media offering, and you’ll be at the centre of taking it to market — backed by a collaborative team that moves quickly and values strong ideas.

If you’re energized by the thrill of the chase, confident in the room with senior marketers, and motivated by turning insight into revenue, you’ll thrive here. This is a role for someone who wants to win — and help define what winning looks like as we scale.