Advertising sales

Founding Account Executive, Advertising Sales

Build the Canadian advertising business from the ground up, developing a retained portfolio of brands and agencies while creating the GTM playbook that follows.

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Build a new market. Then do it again.

We are builders at heart, grounded in a passion for sales and business development. Going from 0→1, opening a market without a finished playbook, and turning first signals into a repeatable business is what energizes us. At Scale49, we get to do it again and again.

Our clients are funded companies from the US, Europe, and APAC entering Canada for the first time. We test the market, win the first customers, build the commercial system, scale what works, and eventually hand a functioning Canadian business back to the client. Then we start again.

If you want continuous opportunities to build GTM, sharpen your craft across new verticals, and sell greenfield opportunities without changing companies every two years, Scale49 may be the place for you.

Open the Canadian advertising market, close the first partnerships, and turn field learning into a repeatable sales motion.

You will be the full-cycle advertising seller driving Canadian revenue for a Scale49 client entering the market. You will create pipeline, build relationships with brands and agencies, develop compelling media solutions, close the first advertising partnerships, and help turn live market feedback into the Canadian GTM playbook.

This is for an AE who has already helped build a new market, territory, advertising product, or sales motion from 0→1 and wants to repeat that work across multiple businesses.

  • Build a focused Canadian advertiser and agency plan, generating your own pipeline through thoughtful outbound, industry events, relationships, and referrals.
  • Own the complete advertising sales cycle, from first contact and discovery through media planning, proposal development, negotiation, IO execution, and close.
  • Develop strong relationships with brand marketers, agency planners, investment teams, social leads, and other media decision-makers.
  • Learn each client’s audience, ad products, measurement capabilities, market position, and competitive context quickly enough to sell with credibility.
  • Run consultative discovery that connects advertiser objectives and audience needs to compelling media solutions and measurable results.
  • Respond to briefs and build persuasive proposals, presentations, and business cases.
  • Test advertiser ICP, positioning, pricing, packaging, objections, and deal strategy in the field.
  • Work closely with client, creative, insights, and AdOps teams to support a smooth transition from sale to campaign execution.
  • Maintain disciplined CRM hygiene, pipeline inspection, forecasting, and follow-up.
  • Bring structured advertiser, agency, and market feedback back to Scale49 and the client team.
  • Document the plays, talk tracks, proof points, and processes that future sellers can scale.
  • Proven advertising, media, adtech, or platform sales experience, with a track record of creating pipeline and closing new business.
  • Direct experience helping build a new territory, market, advertising product, or early-stage sales motion from 0→1.
  • Strong relationships across Canadian brands, media agencies, or advertising decision-makers.
  • Strong outbound instincts. You manufacture demand rather than wait for briefs or inbound opportunities.
  • Excellent discovery, presentation, storytelling, negotiation, and written communication skills.
  • The ability to translate audience insights, advertiser objectives, and product capabilities into compelling media solutions.
  • Comfort moving between senior marketing conversations and the operational details required to move campaigns forward.
  • High ownership, low ego, sound judgment, and the ability to move quickly without a finished playbook.
  • Fluency with CRM, sales engagement, research, media-planning, and AI-enabled selling tools.
  • A strong understanding of how Canadian advertisers and agencies evaluate, purchase, and activate media.
  • First 30 days: Build product, audience, and market fluency; map priority advertisers and agencies; launch outreach; and begin high-quality buyer conversations.
  • By 90 days: Create qualified advertising pipeline, respond to live briefs or opportunities, progress proposals, turn early market signals into sharper positioning and a clearer sales motion, and begin closing your first deals.
  • Within 6–12 months: Build and retain a meaningful portfolio of Canadian brands and agency relationships, establish referenceable campaign wins, and create a defined, repeatable GTM playbook that can scale or transfer to the client.
  • We push inputs aggressively, then turn one-to-one effort into one-to-many and one-to-ten output.
  • We build sales flywheels and rapidly reinvent the GTM based on direct internal and external signals.
  • Relationships open doors and accelerate deals; our real advantage is knowing when to use Challenger, consultative, Sandler, and other methods to move a buyer forward.
  • We operate comfortably in highly ambiguous, low-support environments without sacrificing action, judgment, or speed.
  • We document what works so every win makes the next market easier to build.

Apply for this role

Help build Scale49 from the beginning.

Share the experience that best demonstrates how you build, sell, and create trust. We’ll review your application against this specific founding role.

Questions? careers@scale49.com