Cybersecurity Sales Specialist

3 days ago


Remote, Oregon, United States Upside Business Consulting Inc. Full time

Job Title: Cybersecurity Sales Specialist (Remote – Winnipeg, MB)

Company: Upside Business Technologies

Location: Winnipeg, MB (Remote Eligible)

Salary: $120,000 base salary + $150,000 target incentive (OTE), uncapped commission potential

Job Type: Full-time, Permanent

About Us

Upside Business Technologies is a security-first Managed Service Provider helping small and mid-sized businesses protect their revenue from modern cyber threats. We deliver enterprise-grade cybersecurity protection with the simplicity and speed SMBs need to stay secure.

Our services include endpoint detection and response, 24/7 threat monitoring, incident response, data protection, and security awareness training. We're growing fast and looking for elite sales hunters who can drive pipeline, control the sales cycle, and close high-value deals.

What We Offer

  • $120,000 base salary + $150,000 target incentive (OTE)
  • No commission cap and clear accelerators
  • Minimum 3 weeks vacation + personal and wellness days
  • Comprehensive health, dental, and vision benefits
  • Company-matched pension and share purchase program
  • Fully remote or hybrid flexibility
  • Continuous professional development support

Key Responsibilities

  • Develop and execute a territory plan targeting SMBs across Canada
  • Build and manage a strong sales pipeline from prospecting to close
  • Conduct discovery calls, security presentations, and negotiations
  • Meet and exceed quarterly revenue targets
  • Collaborate with technical teams to ensure smooth customer onboarding
  • Maintain accurate forecasting and CRM discipline

Required Qualifications

  • 5+ years of success in cybersecurity or IT services sales to SMBs
  • Proven ability to ramp fast and close new business within 60–90 days
  • Documented record of $1M+ in closed annual recurring revenue or equivalent quota attainment
  • Exceptional communication, presentation, and negotiation skills
  • Bachelor's degree in Business or equivalent work experience
  • Experience with HubSpot or Salesforce CRM
  • Knowledge of endpoint protection, MFA, incident response, and cybersecurity best practices

Preferred Experience

  • Application security, data privacy, or IAM sales experience
  • Selling into regulated industries
  • President's Club or top-performer recognition in previous roles

Why Join Us

  • Sell a mission-critical cybersecurity solution
  • Work in a performance-driven culture that rewards results
  • Earn at the top of the market with unlimited commission potential
  • Be part of a fast-growing, security-focused team with national reach

Work Location: Remote (based in Winnipeg, MB)

Schedule: Monday to Friday, standard business hours

Travel: Minimal

How to Apply:

Submit your resume and a short summary of your top sales achievements. Only shortlisted candidates will be contacted.

Job Type: Full-time

Pay: $120, $270,000.00 per year

Benefits:

  • 401(k) matching
  • Dental insurance
  • Health insurance
  • Life insurance
  • Paid time off
  • Vision insurance
  • Work from home

Work Location: Remote


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