Pickering, On Cybersecurity Jobs – 77 Openings This Week

Cybersecurity Sales Executive
Oppos Inc. —Scarborough, ON
- $60,000–$90,000 a year
- Full-time
- Hybrid work
- Bilingual
- Salesforce
- Research
- Dental care
Quick apply
10d
Cybersecurity Investigator, International Cybersecurity & Data Investigations
Scotiabank —Toronto, ON
- Spanish
- Customer service
- English
- Tuition reimbursement
IT Specialist
ID Logistics Canada —Ajax, ON
- $50,000–$55,000 a year
- Full-time
- Data analysis skills
- Maintenance
- No university degree
Quick apply
Senior OT Cybersecurity & Network Security Analyst
Atlantic Packaging Products Ltd —Scarborough, ON
- $104,759–$130,949 a year
- Hybrid work
- Manufacturing
- Communication skills
- Wellness program
- Dental care
Quick apply
IT Security Analyst- Zscaler
Tekstaff IT Solutions —Toronto, ON
- $65–$85 an hour
- Contract
- Hybrid work
- Bilingual
- Spanish
- Computer Science
Quick apply
Senior IT Auditor
ISG Search Inc —Markham, ON
- $90,000–$115,000 a year
- Full-time
- Hybrid work
- Computer Science
- Analysis skills
- Presentation skills
- Dental care
- Vision care
Quick apply
Senior Cloud Engineer
BMO Financial Group —Ontario
- $75,900–$141,900 a year
- Remote
- Analysis skills
- Mentoring
- Software development
- Tuition reimbursement
- Life insurance
Senior Cloud Engineer
BMO Financial Group —Ontario
- $75,900–$141,900 a year
- Full-time
- Remote
- Analysis skills
- Mentoring
- Software development
- Tuition reimbursement
- Life insurance
IT Support Specialist
360°kids —Markham, ON
- $57,832–$65,350 a year
- Full-time
- Azure
- Inventory management
- Maintenance
Quick apply
IT Support Specialist
BGIS —Markham, ON
- $54,185–$67,732 a year
- Full-time
- Microsoft Word
- Azure
- Microsoft Outlook
10d
Principal Investigator, Cybersecurity
Durham College —Oshawa, ON
- $57.41 an hour
- Part-time
- Azure
- Master's degree
- AWS
IT Laboratory Technician
Ontario Tech University —Oshawa, ON
- $90,525 a year
- Weekends as needed
- Management
- Computer Science
- Inventory management
12d
IT Support & Systems Administrator
BV USA Enterprises —Markham, ON
- $55,000–$70,000 a year
- Full-time
- Google Suite
- Computer Science
- Engineering
- Paid time off
- Life insurance
Quick apply
4d
Cyber Security Analyst (L2)
CDW —Toronto, ON
- $66,000–$91,600 a year
- 12 hour shift
- Computer Science
- Engineering
- English
7d
Specialist IT II
Signet Jewelers —Markham, ON
- Full-time
- Inventory management
- Maintenance
- Windows
Information Security Analyst
CAA SCO Systems & Services Inc —Thornhill, ON
- $49,500–$76,200 a year
- Research
- Communication skills
- Analytics
- Wellness program
- Tuition reimbursement
Quick apply
OT Cyber Security Analyst/Engineer
Alithya —Pickering, ON
- $120,000–$140,000 a year
- Full-time
- Hybrid work
- Computer Science
- Sales
- Engineering
- Tuition reimbursement
Business System and IT Specialist
Canaweld Inc. —Whitby, ON
- $88,000–$89,000 a year
- Full-time
- Azure
- Computer Science
- Engineering
- Disability insurance
- Dental care
Quick apply
12d
Sessional Lecturer - INFR 4680U - IT Security Policies and Procedures - Fall 2026
Ontario Tech University —Oshawa, ON
- Contract
- Remote
- Computer science
- Management
- Computer Science
Sales Executive – IT & Cybersecurity Services
CyberISolve Inc. —Markham, ON
- $40,000–$80,000 a year
- Full-time
- Hybrid work
- Salesforce
- English
- Research
- Work from home
- Flexible schedule
Quick apply
3d

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Cybersecurity Sales Executive

Oppos Inc.
Scarborough, ON

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Job details

Permanent | Full-time
$60,000–$90,000 a year
10 days ago

Qualifications

Bilingual
Pre-sales stakeholder presentations
Pre-sales solution discovery
Outbound sales
Inbound selling
Customer retention
PCI
Salesforce Platform
Salesforce
Post-secondary education
Lead generation
Research
Business development
Sales pipeline
Requirements analysis
Sales orientation
Forecasting
Prospecting
ISO 27001
Client consultation
HubSpot
Cybersecurity
Business
Client interaction
Negotiation
Bid preparation (Technical proposal processes)
Technology sales

Full job description

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

Quick apply

Refine Your Search

cybersecurity jobs in pickering, on

Cybersecurity Sales Executive

Cybersecurity Investigator, International Cybersecurity & Data Investigations

IT Specialist

Senior OT Cybersecurity & Network Security Analyst

IT Security Analyst- Zscaler

Senior IT Auditor

Senior Cloud Engineer

Senior Cloud Engineer

IT Support Specialist

IT Support Specialist

Principal Investigator, Cybersecurity

IT Laboratory Technician

IT Support & Systems Administrator

Cyber Security Analyst (L2)

Specialist IT II

Information Security Analyst

OT Cyber Security Analyst/Engineer

Business System and IT Specialist

Sessional Lecturer - INFR 4680U - IT Security Policies and Procedures - Fall 2026

Sales Executive – IT & Cybersecurity Services

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