Sales leadership

Founding Sales Director

Help shape the commercial operating system, lead client engagements, and build the standards and team behind Scale49’s sales execution.

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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.

Build the operating rhythm, coach the founding sales team, and remain close enough to the work to lead critical pursuits personally.

You will lead the commercial build for a Scale49 client entering Canada while remaining personally accountable for revenue. This is a player-coach role: you will set the market strategy, carry and close critical deals, establish the operating cadence, coach the founding sales team, and turn field learning into a repeatable Canadian GTM engine.

  • Translate the client’s ambition into a focused Canadian ICP, account strategy, market narrative, and execution plan.
  • Personally generate pipeline and lead priority opportunities from first conversation through close.
  • Establish the sales operating system: stages, qualification, metrics, forecasting, pipeline reviews, CRM discipline, and deal inspection.
  • Coach Account Executives in discovery, messaging, account planning, executive engagement, negotiation, and closing.
  • Design and test outbound, partner, event, community, and relationship-led growth motions.
  • Create tight feedback loops between buyers, Scale49, and client leadership to improve positioning, pricing, packaging, and product priorities.
  • Identify the inputs producing disproportionate output and turn them into repeatable sales flywheels.
  • Build the playbook, team standards, and handoff plan that allow the Canadian business to scale beyond its founding team.
  • A proven record building and leading 0→1 or early-stage B2B sales motions while personally closing meaningful business.
  • Experience launching a new market, territory, product, or business line with limited infrastructure and incomplete information.
  • Strong command of full-cycle selling, enterprise deal strategy, pipeline creation, forecasting, and sales operations.
  • Demonstrated ability to coach sellers, raise performance standards, and build a high-accountability operating rhythm.
  • Executive presence and the ability to advise founders and client leadership using direct market evidence.
  • Fluency across Challenger, consultative, Sandler, and related sales methodologies, with judgment about when each is useful.
  • Strong Canadian market relationships and an understanding of local buyer behaviour, ecosystems, and commercial nuance.
  • Builder energy, low ego, high velocity, and comfort switching between strategy, management, and frontline execution.
  • First 30 days: Establish market priorities, operating cadence, target accounts, team expectations, and the first active pipeline motion.
  • By 90 days: Build measurable qualified pipeline, progress lighthouse opportunities, improve the team’s execution, and validate the core Canadian sales thesis.
  • Within 6–12 months: Deliver meaningful revenue, create reference customers, establish a predictable commercial engine, and prepare a documented team and playbook for scale or client handoff.
  • 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