Cybersecurity Sales Specialist
@ Upside Business Technologies

Hybrid
$120,000
Hybrid
Full Time
Posted 22 days ago

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Email Hiring Manager

XXXXXXXXX XXXXXXXXX XXXXXXX****** @upsidebusinesstechnologies.com
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Job Details

About Upside Business Technologies

Upside Business Technologies is a security-first Managed Service Provider protecting SMBs from modern cyber threats. We deliver powerful, enterprise-grade cybersecurity solutions in a way that's simple, fast, and built for real business impact. We are expanding nationally and looking for elite closers who thrive in competitive environments and love winning big.

What’s in it for you

  • $120,000 base salary + $150,000 OTE with no commission cap and clear accelerators
  • 3+ weeks of vacation plus personal and wellness days
  • Comprehensive health, dental, and vision benefits
  • Flexible remote work (Winnipeg-based preferred)
  • Company-matched pension and share purchase program
  • Professional growth opportunities with advanced sales and cybersecurity training

What you’ll do

  • Own and execute your territory plan targeting SMBs across Canada
  • Prospect, run discovery, deliver compelling presentations, and close deals
  • Build urgency around risk exposure and position tailored security solutions
  • Exceed quarterly revenue goals and accelerate growth
  • Collaborate with technical teams to ensure client success
  • Maintain a clean, accurate pipeline with consistent forecasting

What we’re looking for

  • 5+ years of proven success in cybersecurity or IT services sales to SMBs
  • Strong hunter mentality and ability to close business fast
  • Documented record of $1M+ in ARR or equivalent quota attainment
  • Exceptional communication, presentation, and negotiation skills
  • Bachelor’s degree in Business or related field (or equivalent experience)
  • CRM experience (HubSpot, Salesforce)
  • Working knowledge of core security concepts (EDR, MFA, incident response, data protection)

Nice to have

  • Experience in application security, data privacy, or IAM
  • Selling into regulated industries or compliance-driven environments
  • Track record of top-performer or President’s Club achievement

Additional Information

This is not a maintenance role; it’s a hunter seat with real earning power. Enjoy the autonomy to drive deals, a leadership team that backs closers, Monday–Friday business hours, and minimal travel.

Key skills/competency

  • Cybersecurity
  • Sales
  • SMB
  • Prospecting
  • Closing
  • Negotiation
  • Pipeline
  • CRM
  • Presentation
  • IT Services
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How to Get Hired at Upside Business Technologies

🎯 Tips for Getting Hired

  • Tailor your resume: Highlight cybersecurity and sales achievements.
  • Research Upside: Understand their growth and culture.
  • Network effectively: Connect with current employees on LinkedIn.
  • Prepare case studies: Showcase your closing wins and pipeline success.

📝 Interview Preparation Advice

Technical Preparation

Review cybersecurity fundamentals and security protocols.
Study CRM systems like HubSpot and Salesforce.
Analyze SMB market trends and technical challenges.
Prepare on product and solution specifics.

Behavioral Questions

Describe a challenging sales negotiation.
Explain how you manage your sales pipeline.
Discuss your strategy under competitive pressure.
Share an experience with client relationship building.

Frequently Asked Questions