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Founding Sales Development Representative (Remote)

PragmatikeCanada🇨🇦Canada

Why this role stands out

As a Founding Sales Development Representative, you'll have the unique opportunity to build Pragmatike's outbound sales engine from the ground up, directly influencing go-to-market strategy and seeing your impact immediately. This remote role is perfect for an entrepreneurial and resourceful individual eager to shape a company's growth trajectory while developing valuable skills and gaining direct access to leadership. Apply today to become an integral part of a fast-growing team and forge a path for significant career advancement.

Quick overview

SeniorityMid Senior
Employment typeTemporary/Casual
Work modeRemote
LocationCanada, Canada
Business DevelopmentHubSpotLinkedIn Sales NavigatorOutreachProspecting

Job description

Founding Sales Development Representative

Pragmatike is on a mission to help early-stage startups and scaleups win the talent war and build exceptional tech teams.

About the Role

We're looking for a Founding Sales Development Representative (SDR) to help build our outbound sales engine as we enter our next phase of growth. We're looking for someone entrepreneurial, resourceful, and relentless—someone who enjoys opening doors, building relationships, and creating opportunities from scratch.

You'll work directly with the founders to identify and engage startup founders, CTOs, and hiring leaders across Europe and North America, helping them discover how Pragmatike can accelerate their hiring.

Why This Role Is Different

  • Build the sales engine from zero to one: Help define our outbound strategy, messaging, prospecting workflows, and sales playbook.

  • Direct access to founders: Work closely with company leadership, influence go-to-market strategy, and see your impact immediately.

  • High ownership: Experiment, iterate, and continuously improve how we generate new business.

  • Join a fast-growing company: Become an early member of the team with the opportunity to grow alongside the business.

You’re a Fit If You…

  • Have 2+ years of experience in outbound sales, business development, or SDR roles, ideally selling B2B services or SaaS.

  • Enjoy prospecting and consistently generating new opportunities through LinkedIn, email, and cold outreach.

  • Are highly organized, proactive, and comfortable managing your own pipeline.

  • Communicate exceptionally well, both in writing and verbally, with a consultative approach.

  • Thrive in startup environments where speed, ownership, and experimentation are valued.

  • Are self-motivated and comfortable working remotely with minimal supervision.

  • Have excellent English communication skills.

Nice to Have

  • Experience selling recruitment, staffing, HRTech, or talent acquisition solutions.

  • Previous experience working with startups, founders, or technology companies.

  • Familiarity with tools such as LinkedIn Sales Navigator, Apollo, HubSpot, Clay, or similar outbound platforms.

  • Interest in AI, startups, and the future of work.

Compensation & Benefits

  • Flexible freelance contract with competitive performance-based compensation.

  • Opportunity to shape Pragmatike's outbound sales function from the ground up.

  • Fully remote work environment with flexible hours.

  • Direct collaboration with founders and meaningful ownership from day one.

  • High-growth environment with significant career progression opportunities.

Ready to help startups build world-class teams while building Pragmatike's sales engine? Apply now and join us at the beginning of our journey. 🍜🏴‍☠️

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