Sales Development Representative | REMOTE (Ontario)

Gatekeeper is the only unified Vendor and Contract Lifecycle Management solution, trusted by lean Finance, Procurement and Legal teams with enterprise-sized responsibilities. Backed by Vista Equity Partners, we bring Vendor Risk & Compliance, Contract Lifecycle Management, and Vendor Performance & Savings together in one AI-powered platform.

Gatekeeper keeps every stage of the vendor lifecycle whole. Due diligence shapes the contract, the contract stays connected to obligations, performance and spend, and a continuous view of what every vendor delivers and costs helps teams strengthen governance and identify actionable savings.

Built on this unified foundation, Gatekeeper AI turns data into answers, while more than 50 specialist Gatekeeper Agents turn those answers into action. From due diligence and contract review to compliance monitoring and supplier performance, our technology helps organisations strengthen compliance, accelerate contracting, drive savings and stay audit-ready.

We are proudly AI-first in how we build, work, and innovate. Every employee has access to the latest AI tools and technologies, with no restrictive token limits or barriers to adoption. We encourage our teams to embrace AI as part of their everyday workflow; accelerating learning, driving innovation, automating repetitive tasks, and enabling more impactful work across every function.

Please note: This is a remote role, open to candidates living in Ontario only.

Role Overview

In this role you will:

• Use our playbook and your incredible communication skills to build brand new relationships between Gatekeeper and potential clients
• Partner closely with an Account Executive in the region, learning how opportunities progress through the full sales cycle and playing an important role in building pipeline together
• Drive business through outbound prospecting via cold calling, email and social selling
• Continuously test and improve our go-to-market messaging and targeting
• Build the foundations for a long-term career in technology sales through hands-on coaching, exposure to the wider sales cycle and opportunities to take on new responsibilities as you develop

• Experience – Previous exposure to B2B sales or another customer-facing environment is a plus, not a prerequisite. This role is also a great fit for recent graduates or anyone looking to launch their career in technology sales
• Growth mindset – You’re curious, coachable and motivated to learn. You’re excited by the opportunity to develop your commercial skills, learn from experienced colleagues and build a career in sales.
• Attitude - First and foremost. Optimistic, resilient and high achieving
• Communication – You enjoy connecting with new people and are keen to develop confident, engaging communication skills across phone, email and social channels
• Drive – You’re motivated by ambitious goals and excited to develop the skills to engage and sell to sophisticated buyers
• AI first – You have a genuine curiosity about AI and are excited to learn how new tools can make you more effective, accelerate your development and evolve the way you work
• A true team player - we support and push each other to be our best and do not hesitate to step in to help

• Generous remuneration
• 100% remote working: no offices and no commute
• Generous holiday allowance
• Monthly health and wellbeing perk
• Learning & Development opportunities for lifelong learners
• Technology: we provide everything you need to do your best work
• Gatekeeper for Good: Match funding to support non-profit organisations in your local community
• Gatekeeper retreats

We live by our company vision and values. If these ring true to you, then we’d like to talk to you.

Gatekeeper offers a diverse and multicultural working environment, currently spanning 15 countries. We respect each other’s differences and welcome candidates from all backgrounds.