About the Role
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.
What You'll Do
- 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
What You Bring
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 sponsorships
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, HubSpot, or equivalent) and comfortable with pipeline reporting
GTA-based with an established network of local agency and brand contacts
Experience selling branded content, sponsorships, 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
Required
Preferred
What This Is Not
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.
Ideal Backgrounds
- 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
We would be particularly interested in candidates coming from:
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.
The Sales Factory Toronto, Ontario, CAN Office
20 Camden St, Toronto, Ontario, Canada, M5V 1V1
