Business Development Representative (BDR)

Stingrai; Toronto; Hybrid; CAD 60,000 - 110,000; Full time

Benefits offered by this job

Uncapped commission

2 weeks paid vacation

5 paid sick days

Founder mentorship

Career growth path

Job summary

Stingrai is transforming offensive cybersecurity by uniting AI-driven automation with elite human intelligence. As our first sales hire, you will work directly with the founder to shape the GTM playbook and drive net-new revenue from Toronto and beyond.

You will receive direct 1-on-1 coaching, pipeline strategy training, and technical mentorship while building an initial pipeline, qualifying inbound leads, and coordinating multi-channel outreach to security leaders.

Qualifications

• 1–3 years of B2B sales experience selling penetration testing services, offensive security, or technical SaaS.
• Must be a confident, relentless communicator comfortable with cold outreach to senior technical executives.
• Strong ability to articulate Stingrai’s value proposition to technical stakeholders.

Responsibilities

• Execute multichannel prospecting to engage security decision-makers.
• Qualify and convert inbound interest into product demos and discovery meetings.
• Attend local Toronto cybersecurity events to build executive relationships.
• Communicate Stingrai’s value combining CREST-certified human expertise with AI-driven pentesting.
• Partner with the founder to test outreach messaging and optimize the sales engine.

Skills

Outbound prospecting

Inbound lead qualification

Field networking

Technical articulation

GTM strategy

B2B sales

Sales coaching

Tools

LinkedIn Sales Navigator

ZoomInfo

Salesforce

HubSpot

Apollo

Job 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 discovery and 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.
• 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).
• 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.

What We Offer

• Compensation & Upside: Competitive base salary + uncapped commission structure with no ceiling on your earnings.
• 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.

All candidate evaluations are managed exclusively through LinkedIn.

Note: Direct emails, personal phone calls, or external solicitations will result in immediate application disqualification.