Cybersecurity Sales Specialist (Remote – Winnipeg, MB)
Cybersecurity Sales Specialist (Remote – Winnipeg, MB)
About Us: Upside is a leading provider of IT support and cybersecurity solutions for small and medium-sized businesses. We are committed to delivering enterprise-level IT practices and solutions at affordable prices.
Position Overview: We are seeking an experienced and results-driven Cybersecurity Sales Specialist to drive new business and revenue growth. This full-time, permanent role focuses on identifying opportunities, managing the full sales cycle, and delivering impactful security solutions to SMB clients across Canada. The position follows a Monday to Friday schedule with standard business hours and minimal travel requirements.
Key Responsibilities:
Develop and execute a territory plan targeting SMBs nationwide.
Build and manage a strong sales pipeline from prospecting to close.
Conduct discovery calls, lead security presentations, and negotiate deals.
Meet and exceed quarterly sales and revenue targets.
Collaborate with technical teams to ensure seamless customer onboarding.
Maintain accurate forecasting and CRM discipline throughout the sales process.
Qualifications:
Minimum 5 years of successful sales experience in cybersecurity or IT services targeting SMBs.
Proven ability to ramp quickly and close new business within 60–90 days.
Documented track 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 professional experience.
Experience using HubSpot or Salesforce CRM.
Strong knowledge of endpoint protection, MFA, incident response, and cybersecurity best practices.
Preferred Experience:
Experience in application security, data privacy, or IAM sales.
Previous sales into regulated industries.
President’s Club or top-performer recognition in prior roles.
Why Join Us:
Highly Competitive Compensation: $120,000 base salary + $150,000 target incentive (OTE), with no commission cap and clear accelerators.
Comprehensive Benefits: Health, dental, and vision coverage, company-matched pension, and share purchase program.
Flexibility: Fully remote or hybrid work options.
Time Off: Minimum 3 weeks vacation plus personal and wellness days.
Company-matched pension and share purchase program.
Professional Development: Continuous growth and training opportunities.
High-Impact Role: Sell a mission-critical cybersecurity solution in a performance-driven culture.
How to Apply: Send your resume and a short summary of your top sales achievements to connect@upside-business.com with the subject line "Cybersecurity Sales Specialist". Only shortlisted candidates will be contacted.