Company: Oppos Inc.
Location: Toronto / Scarborough, ON (Hybrid — 1–2 days per week in office)
Employment Type: Full-time, Permanent
Reports to: VP, Cybersecurity Sales
Compensation: $60,000–$90,000 base + 10% commission on sales
About Oppos
Oppos is a Toronto-headquartered cybersecurity assessment and compliance company with over 60 years of combined industry experience serving both public and private sector organizations. We help startups, scale-ups, SMBs, and enterprise clients become and stay audit-ready across frameworks like SOC 1 & 2, ISO 27001, FedRAMP, CMMC, PCI-DSS, HIPAA, GDPR, and Quebec Bill 25.
We sell a high-demand solution that businesses genuinely need, including penetration testing, vCISO, threat modelling, red team engagements, and executive tabletop exercises — all delivered on a transparent, fixed-fee model rather than the traditional hourly billing of the Big 4. Our mission is simple: make compliance and security readiness feel less like chaos and more like an enabler of growth.
We work as a hybrid team, collaborating out of our Scarborough office 1–2 days per week for planning, client sessions, and team building, with the flexibility to do focused work remotely the rest of the time.
The Opportunity
We are looking for a results-driven Cybersecurity Sales Executive to own a book of business and personally drive new revenue for Oppos' assessment, compliance, and managed security services. This is an individual-contributor, quota-carrying role with no direct reports: you'll manage the full sales cycle end to end — from prospecting and qualification through solutioning, negotiation, and close. You'll report to the VP, Cybersecurity Sales and work closely with Service Delivery and Marketing departments to win and grow accounts.
Key Responsibilities
Prospecting & Lead Generation
- Research and identify high-potential prospects through strategic outbound campaigns, social selling, and inbound lead qualification across multiple channels.
- Initiate contact with key decision-makers and influencers — including CISOs, security architects, compliance leaders, and data protection officers — to uncover security and compliance challenges and opportunities.
Qualification & Discovery
- Conduct discovery conversations to understand prospect pain points, technical requirements, and business priorities, determining fit and readiness for Oppos' services and RegAI platform.
- Establish consultative relationships with client stakeholders, up to and including senior executives (CISO, CIO, CFO), based on a clear understanding of their compliance obligations and business needs.
Sales Cycle & Pipeline
- Own the full sales cycle end to end, from first contact through solution design, proposal, negotiation, and close.
- Build and qualify a healthy pipeline of sales-ready opportunities by clearly articulating Oppos' value proposition and converting conversations into scoped, progressing deals.
- Position Oppos' portfolio — SOC 2, ISO 27001, penetration testing, vCISO, and the RegAI platform — translating framework requirements into clear business value and ROI.
- Lead and coordinate RFX and proposal responses, partnering with Service Delivery and subject-matter experts to ensure quality and timeliness.
- Drive renewal and expansion activity across all accounts to maximize retention and lifetime value.
- Apply a consistent sales methodology (e.g., MEDDIC / MEDDPICC) to qualify and advance opportunities.
Activity, Forecasting & CRM
- Consistently meet or exceed individual sales quota and activity metrics, including calls, emails, social touches, and qualified meetings booked.
- Maintain accurate, detailed records of all prospect interactions, opportunities, activities, and forecasts in the CRM (e.g., HubSpot), ensuring disciplined pipeline and data hygiene.
- Manage an accurate personal pipeline and forecast, and report on progression, risks, and accelerators to the Director of Sales.
Product Knowledge & Collaboration
- Develop a deep understanding of Oppos' RegAI platform, services portfolio, competitive landscape, and cybersecurity and compliance trends to engage in credible, value-driven conversations with technical and executive audiences.
- Partner closely with Service Delivery, Marketing, and Sales leadership to optimize messaging, refine target accounts, and continuously improve conversion rates.
- Partner with channel and alliance partners where relevant to extend reach and accelerate deals.
Qualifications
- Post-secondary education in Business, Commerce, or a related field, or an equivalent combination of education and experience.
- Minimum 3-5 years of progressive, quota-carrying sales experience, with a track record of meeting or exceeding targets.
- Demonstrated success managing a full sales cycle and closing new-logo and expansion business in complex, multi-stakeholder environments.
- Experience selling cybersecurity, compliance, IT services, or managed services is strongly preferred.
- Strong CRM proficiency (HubSpot, Salesforce, Microsoft Dynamics, or equivalent) and disciplined pipeline and data hygiene.
- Ability to communicate and present effectively to stakeholders at all levels, including senior executives.
- Familiarity with compliance frameworks (SOC 2, ISO 27001, PCI-DSS, HIPAA, GDPR) and/or services such as penetration testing and vCISO is an asset.
- Experience with sales methodologies such as MEDDIC, MEDDPICC, or SPIN Selling.
- Comfortable working independently in a hybrid, fast-paced, growth-stage environment.
- Bilingual (English/French) is an asset but not required.
What We Offer
- Comprehensive health and dental benefits.
- Hybrid work model — 1–2 days per week in our Scarborough office, with remote flexibility.
- Competitive compensation: $60,000–$90,000 base salary, 10% commission on sales, and a profit-share bonus structured to reward driving $1.5–2M in annual sales.
- The chance to sell a differentiated, fixed-fee offering platform in a fast-growing security and compliance market.
- A collaborative, mission-driven team that treats compliance as an enabler, not a distraction.
Oppos is an equal opportunity employer. We are committed to providing accommodations for applicants with disabilities throughout the recruitment process — please let us know if you require any accommodation.
Pay: $60,000.00-$90,000.00 per year
Benefits:
- Casual dress
- On-site parking
Experience:
- Cybersecurity: 1 year (required)
- Sales: 3 years (required)
Work Location: Hybrid remote in Scarborough, ON M1W 3W6
