Business Development Representative (BDR)

Company Description Stingrai is transforming offensive cybersecurity by uniting AI-driven automation with elite human intelligence. We are one of only four CREST-accredited offensive security firms in Canada, a gold-standard designation reserved for top-tier security practices. Our Penetration Testing as a Service (PTaaS) platform pairs our proprietary AI pentesting agent (Snipe) with white-hat hackers to deliver real-time, zero-noise vulnerability validation at the speed attackers move. Backed by active security researchers who present at DEF CON, BSides, and NATO Locked Shields, Stingrai enables security, engineering, and compliance leaders to find, validate, and patch vulnerabilities before adversaries exploit them. As we scale our go-to-market engine, we are hiring our very first sales team member to build our pipeline from the ground up. Role Description As our first sales hire, you will not be rep #50 in a crowded bullpen. You will work directly alongside our founder to shape Stingrai's GTM playbook and drive net-new revenue. You will receive direct 1-on-1 sales coaching, pipeline strategy training, and technical mentorship from the founder. This role carries high visibility, direct organizational impact, and a clear trajectory for rapid promotion into an Account Executive (AE) role as our sales org scales. What You’ll Do Outbound Pipeline Generation: Execute multichannel prospecting via cold calling, targeted email campaigns, and strategic LinkedIn outreach to engage security decision-makers (CISOs, VPs of Engineering, IT Security Directors). Inbound Lead Qualification: Rapidly qualify and convert inbound interest into scheduled product demonstrations and discovery meetings. In-Person Field Networking: Attend local Toronto cybersecurity conferences, tech meetups, and industry events to build organic executive relationships. Technical Value Articulation: Communicate Stingrai’s value proposition, combining CREST-certified human expertise with AI-driven continuous pentesting, to technical stakeholders with clarity and credibility. GTM Strategy & Iteration: Partner directly with the founder to test outreach messaging, analyze field insights, and optimize our sales engine. Who You Are Preferred Experience: 1 to 3 years of B2B sales experience selling penetration testing services, offensive security, or technical SaaS. Alternative Backgrounds Welcome: No commercial cybersecurity experience? You are still encouraged to apply! You must use your cover letter to answer "Why You?" by proving your raw sales drive, past quota achievements, and high technical aptitude. Toronto-Based: Currently residing in the Greater Toronto Area (GTA), working remotely today with flexibility for a hybrid model in Toronto as our local footprint grows. Relentless Communicator: Confident, articulate, and highly comfortable making cold calls to senior technical executives. Coachable & Resilient: Thrives in fast-paced startup environments, treats rejection as a learning loop, and is eager to absorb coaching from leadership. Bonus If You Have Familiarity with offensive security concepts (pentesting, PTaaS, vulnerability management, cloud security, SOC 2 / ISO 27001 compliance frameworks). Hands-on experience with modern sales engagement tools (LinkedIn Sales Navigator, Zoominfo, Salesforce, HubSpot, or Apollo). What We Offer Compensation & Upside: Competitive base salary + uncapped commission structure with no ceiling on your earnings. Health & Benefits: Comprehensive medical, dental, and health benefits package. Paid Time Off: 2 weeks paid vacation per year + 5 paid sick days Founder Mentorship: Direct 1-on-1 sales execution training and executive career mentorship from the founder. Career Growth: A defined path for promotion into an Account Executive (AE) closing role. Application & Hiring Process All candidate evaluations are managed exclusively through LinkedIn. Submit Application: Apply via our official LinkedIn Job Post with your Resume and a Cover Letter detailing "Why You?" LinkedIn Screening: Initial screening interviews will be conducted directly through LinkedIn messaging/calls. Founder Interview: A final, in-depth interview with Stingrai's founder. Note: Direct emails, personal phone calls, or external solicitations will result in immediate application disqualification.

The BDR will drive net-new revenue by executing multichannel outbound prospecting and qualifying inbound leads. They will also partner with the founder to optimize the go-to-market playbook and attend industry events to build executive relationships.

Candidates should ideally have 1 to 3 years of B2B sales experience in offensive security or technical SaaS, though high technical aptitude and sales drive are accepted. Must be based in the Greater Toronto Area and possess strong communication skills for engaging senior technical executives.

• Medical Insurance • Dental Insurance • Health Benefits • Paid Vacation • Paid Sick Days • Founder Mentorship

Identified from the job description. Confirm important requirements above.

• Outbound Pipeline Generation
• Cold Calling
• Lead Qualification
• B2B Sales
• Technical Value Articulation
• GTM Strategy
• LinkedIn Outreach
• Email Campaigns
• Field Networking
• CRM Management

• Sales
• Technology
• Security & Safety
• Software
• Consulting

Minimum experience

2+ years

Apply by

Feb 19, 2027

Posting language

English

Working hours

40 hours per week

Seniority

Entry level

Application method

Direct apply is available