About the Role
We are building a dedicated advertising sales function and looking for a driven Sales Executive to lead direct and agency client relationships across digital, print, and integrated media. This role sits at the centre of our revenue growth strategy — you will be responsible for generating new business, deepening existing client relationships, and positioning our advertising products as essential to the media plans of brand, agency, and performance marketing buyers.
This is not a role for order-takers. The ideal candidate understands how advertisers think, can speak credibly to performance outcomes and brand metrics, and is comfortable navigating multi-stakeholder deals across brand managers, media planners, and procurement. If you've thrived in a competitive media sales environment where storytelling and data work together, this role is for you.
What You'll Do
Own a defined book of business and pipeline, driving new logo acquisition and growing revenue within existing advertiser accounts
Develop and execute account plans for mid-market and enterprise brands and agency holding group partners
Build strong relationships across the buying committee — brand, media, performance, and procurement stakeholders
Lead consultative discovery to understand client marketing objectives, audience strategies, and measurement priorities
Craft and present tailored advertising proposals — including custom integrations, programmatic packages, and sponsorships — aligned to client goals
Translate audience insights, reach metrics, and attribution data into compelling sales narratives
Negotiate deals and close agreements with discipline, managing pricing, added value, and make-goods within defined parameters
Collaborate with internal teams — editorial, marketing, ad ops, and analytics — to deliver against campaign commitments and renewal targets
Manage pipeline accurately in CRM and provide reliable revenue forecasts to sales leadership
Represent the brand at industry events, upfronts, and client entertainment as needed
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.
The Sales Factory Toronto, Ontario, CAN Office
20 Camden St, Toronto, Ontario, Canada, M5V 1V1
