Senior individual contributor

Founding Sr. Account Executive

Lead complex, high-value pursuits and become a trusted commercial operator for ambitious companies building their Canadian presence.

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Build a new market. Then do it again.

We are builders at heart, grounded in elite sales craft. 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.

Lead complex opportunities, build executive trust, and help define the playbook for enterprise growth in Canada.

You will be a senior full-cycle seller driving business for a Scale49 client entering Canada. Like every founding seller here, you will build pipeline and the GTM motion from the ground up. Your differentiator is access: you bring a deep, senior Canadian network and know how to turn trusted relationships into fast, credible paths to executive buyers, partners, and complex accounts.

  • Activate a relevant Canadian network to create early executive conversations, strategic introductions, and qualified opportunities.
  • Build a focused account strategy that combines relationship-led access with disciplined outbound and ecosystem development.
  • Own complex sales cycles from first meeting through discovery, validation, business case, security, procurement, negotiation, and close.
  • Multi-thread relationships across executive sponsors, functional leaders, technical stakeholders, finance, and procurement.
  • Create urgency without sacrificing trust, qualification quality, or long-term account value.
  • Advise Scale49 clients on Canadian buyer dynamics, competitive context, positioning, pricing, partnerships, and routes to market.
  • Use Challenger, consultative, Sandler, and other methods with judgment rather than relying on relationships alone.
  • Capture the motion so relationship-led wins become a repeatable system the broader team can execute.
  • A strong record of closing complex mid-market or enterprise B2B opportunities and consistently delivering against revenue targets.
  • A deep, current network of senior Canadian buyers, operators, partners, and market connectors relevant to technology and growth-stage businesses.
  • Evidence that you can activate relationships to open a new market quickly—not simply maintain an existing book of business.
  • Experience building a territory, market, or GTM motion where the playbook was incomplete.
  • Executive-level discovery, commercial judgment, negotiation, multi-threading, and deal-orchestration skills.
  • The discipline to self-source, maintain clean pipeline data, forecast accurately, and build beyond your network.
  • High ownership, low ego, discretion, and credibility with founders and senior client leaders.
  • Ability to rapidly learn and sell different products, verticals, and business models.
  • First 30 days: Map the client’s Canadian opportunity, identify relationship paths, build priority-account plans, and open senior conversations.
  • By 90 days: Establish meaningful qualified pipeline, progress multi-stakeholder opportunities, and sharpen the Canadian commercial strategy with direct market evidence.
  • Within 6–12 months: Win anchor customers, create referenceable executive relationships, and convert network-led access into a scalable sales system the client can inherit.
  • 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.

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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