Weekend Remote Sales Development Representative Jobs in Toronto, ON

Security Compass solves a massive problem: we help organizations build secure software without slowing development teams down. Modern engineering teams move fast, but traditional security processes usually get in the way. We fix this by bringing security into the earliest stages of development so engineering and security teams can actually work together. Through our platforms, SD Elements and Devici, and our practical developer training, we build security directly into how software is designed and delivered.

We are growing fast and looking for our next superstar Sales Development Representative (SDR) to join our enterprise sales team. In this role, you will work in a dedicated 1:1 partnership with an Enterprise Account Executive (AE) to drive strategic, account-based pipeline growth.

Your primary objective is to build high-quality, qualified pipeline within targeted global enterprise accounts. This is not a high-volume "numbers game" call center; it is a highly consultative, strategic prospecting role that requires navigating complex enterprise environments, mapping stakeholders, and understanding the unique security challenges faced by product security, engineering, and compliance leaders.

This is an exciting opportunity for a motivated sales professional who thrives on deep research, tailored multi-channel outreach, and sophisticated value-based selling.

Location: We are open to candidates across Canada. We are a remote-first company with a head-office in Toronto.

• Strategic Account Mapping: Work closely with your dedicated Enterprise Account Executive to develop, execute, and continuously iterate on a tailored, account-based outbound strategy.
• Qualified Pipeline Generation: Identify, research, and penetrate target enterprise accounts to uncover high-value opportunities and build sustained sales momentum.
• Consultative Outreach: Executive outbound prospecting campaigns utilizing cold calling, highly personalized emailing, and digital networking tailored to senior product security stakeholders.
• Inbound Qualification: Partner with Marketing to seamlessly transition top-of-funnel leads and event attendees into fully qualified sales opportunities.
• Discovery Mastery: Execute initial discovery conversations to understand prospect pain points and effectively map them to Security Compass's core differentiators before scheduling technical briefings with your partner AE.
• Brand Ambassadorship: Represent Security Compass professionally at industry trade shows, conferences, and virtual customer events.

• Enterprise Prospecting Acumen: 1+ year of experience in B2B enterprise software sales prospecting is highly valued, particularly within cybersecurity, DevSecOps, or product security sectors.
• Value-Based Communication: Exceptional written and verbal communication skills with the ability to construct creative, compelling messages that resonate with senior leadership (CISOs, VPs of Development, AppSec Directors).
• The SDR Grit: A resilient mindset characterized by persistence, continuous curiosity, and an eagerness to learn complex technical concepts.
• Proven Track Record: Demonstrated success in meeting or exceeding quotas for generating qualified pipeline and enterprise-level opportunities.
• Modern Sales Tech Stack: Familiarity with CRM and advanced sales enablement tools such as Salesforce, Salesforce Sales Engagement, ZoomInfo, Nooks.ai, and LinkedIn Sales Navigator.
• Execution & Organization: Superior attention to detail with a proven ability to manage multiple account tracks and tasks simultaneously without dropping the ball.
• Comfort with the phone & rejection: You actually enjoy cold calling and hunting for new business. You don't take a "no" or a hang-up personally—it's just part of the job.
• Tech background: You've worked directly with or sold technology before. Ideally, you already understand how software is built or have a foundation in AppSec.

• Meaningful Work: We contribute towards making technology in the world more secure and our vision is one of a world where we can trust technology.
• Trust: It's important to us that you trust those you work with and are empowered to be yourself. We encourage open, respectful communication.
• Innovation: We encourage you to explore ideas and test new theories, both in your work and in your individual career development plan.
• Growth: We make your growth and learning a priority by allocating all our employees with a dedicated learning & growth budget.
• Life-Work Integration: We offer a hybrid or remote working model, flexible work hours, and unlimited vacation so you can integrate your work with life in a way that makes sense for you.
• Fun: Our casual atmosphere promotes camaraderie, fun, and helps bring people together.
• Embracing Diversity, Inclusion and Equity: Our goal is to create a safe, equitable workplace where everyone feels like they belong
• Building a team: We're in the midst of a building stage, and we want a team member that is open to continuing to build with the team.

1. Phone Interview (30 mins): A brief call with our Recruitment team to chat about your background and long-term career goals.
2. Hiring Manager Interview (45 mins): Meet with the Manager, Sales Development to dive into the role specifics, team structure, and your relevant experience.
3. Practical Assessment: A realistic enterprise prospecting exercise.
4. Hiring Manager & VP, GTM Strategy & Enablement interview (45 mins): A role-play activity and question period with the hiring manager and the VP of RevOps.
5. Culture-Add Interview (30 mins): This is a 30-minute virtual meeting with either our Chief People & Culture Officer or CEO to learn how your values align with our CCOAR values of Customer Focus, Collaboration, Ownership, Authenticity and Respect.
   

   Note: We use an AI-enabled interview tool (BrightHire) to support note-taking and review during the hiring process. The AI does not make decisions — it simply assists our hiring team. All decisions are made by people. Please let us know if you have questions about this"

   This posting is for an existing vacancy. Click here to start imagining your future at Security Compass!

   Security Compass is an equal opportunity employer. We are committed to meeting the accessibility needs of all individuals in accordance with the Accessibility for Ontarians with Disabilities Act (AODA) and the Ontario Human Rights Code (OHRC). Should you require any accommodation, please inform hr@securitycompass.com so that an inclusive and barrier free process can be provided for candidates taking part in all aspects of the hiring process. All information provided will be addressed confidentially.
   Base salary: $60,000–$65,000 CAD plus a variable compensation plan.