About the RoleWe 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 current 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 DoOwn a defined book of business and pipeline, driving new logo acquisition and growing revenue within existing advertiser accountsDevelop and execute account plans for mid-market and enterprise brands and agency holding group partnersBuild solid relationships across the buying committee — brand, media, performance, and procurement stakeholdersLead consultative discovery to understand client marketing objectives, audience strategies, and measurement prioritiesCraft and present tailored advertising proposals — including custom integrations, programmatic packages, and sponsorships — aligned to client goalsTranslate audience insights, reach metrics, and attribution data into compelling sales narrativesNegotiate deals and close agreements with discipline, managing pricing, added value, and make-goods within defined parametersCollaborate with internal teams — editorial, marketing,



ad ops, and analytics — to deliver against campaign commitments and renewal targetsManage pipeline accurately in CRM and provide reliable revenue forecasts to sales leadershipRepresent the brand at industry events, upfronts, and client entertainment as neededWhat You BringRequired3–6+ years of advertising or media sales experience in a quota-carrying, client-facing roleTrack record of selling to both direct brand clients and media/creative agencies in the GTA marketDemonstrated ability to manage a full sales cycle — from prospecting and discovery through proposal, negotiation, and closeStrong understanding of digital advertising products: display, video, native, programmatic, social, and email/newsletter sponsorshipsAbility to use audience and performance data to build compelling, insight-led presentationsExperience working with multi-stakeholder clients, including procurement and senior marketing leadershipProficient with CRM tools (Salesforce, HubSpot, or equivalent) and comfortable with pipeline reportingGTA-based with an established network of local agency and brand contactsPreferredExperience selling branded content, sponsorships, or integrated packages beyond standard display unitsFamiliarity with programmatic advertising, private marketplace (PMP) deals,



or data targeting productsBackground 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 presentationsComfort pitching C-suite and VP-level marketing stakeholders at major Canadian brandsWhat This Is NotThis 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.$80,000 - $90,000 a yearBase Salary:$80,000 – $90,000 depending on experienceCommission Plan:$50,000 target variable, tied to closed revenue and renewal performanceOn-Target Earnings (OTE):$130,000 – $150,000Location:Greater Toronto Area — in-person role with regular client-facing activity across the GTA and Ontario marketThis 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.#J-18808-Ljbffr

📌 Sales Executive - Advertising - C$80,000 - C$90,000 A Year (Winnipeg)
🏢 The Sales Factory
📍 Winnipeg