Entry Level Technical Support jobs in Toronto, ON

Technical Support & Client Success Representative (12:00pm-8:00pm)

About WeVend

WeVend is a fintech company specializing in cashless payment solutions, self-serve vending technology, and point-of-sale integrations. We work with merchants, venues, and enterprise clients across North America to deploy and support our CasHUB platform and next-generation vending infrastructure. We move fast, solve real problems, and take pride in keeping our clients’ operations running smoothly — around the clock.

The Role

We’re looking for a technically sharp, client-focused Technical Support & Client Success Representative to join our growing support team. This is primarily a hands-on technical support role — you’ll be the person our merchant and business clients rely on to diagnose, troubleshoot, and resolve issues with their WeVend payment terminals and integrated systems. You’ll own problems end-to-end rather than just triage them.

Working the afternoon-to-evening shift (12:00 PM – 8:00 PM), you’ll be the go-to technical resource during peak client operating hours — when equipment issues have the highest business impact and clients need fast, competent resolution, not escalation loops. You’ll also carry a share of our weekend on-call rotation to ensure our clients always have a knowledgeable person in their corner.

This role suits someone who gets genuine satisfaction from solving problems, communicates clearly with non-technical clients under pressure, and knows the difference between a configuration issue and a hardware fault.

What You’ll DoTechnical Support — Primary Responsibility

• Diagnose and resolve technical issues with WeVend payment terminals, POS integrations, network connectivity, and peripheral hardware.
• Walk clients through structured troubleshooting steps via phone, email, and live chat; own the resolution through to confirmation that the issue is fully closed.
• Perform remote configuration, software resets, terminal re-provisioning, and account-level troubleshooting within WeVend’s systems.
• Identify root cause on recurring technical issues and document findings clearly for the engineering team, flagging patterns that require a product or infrastructure fix.
• Escalate only when a resolution genuinely requires backend engineering access — and when you do, hand off with complete, accurate technical notes so nothing gets repeated.

Client Onboarding & Account Support

• Support new client onboarding and equipment deployment — guiding merchants through hardware setup, account activation, network configuration, and first-use walkthroughs of WeVend products including CasHUB.
• Handle billing inquiries, account changes, and payment-related questions with accuracy and professionalism.
• Maintain accurate client records, case notes, and resolution documentation in the ZenDesk CRM; follow up to confirm issues are fully resolved and clients are satisfied.

On-Call & Continuous Improvement

• Participate in the weekend on-call rotation, responding to urgent technical and client issues within agreed SLA windows.
• Surface recurring technical and client-experience issues to the operations and product teams to drive continuous improvement.

What We’re Looking ForRequired

• 2–4 years of experience in a technical support, helpdesk, or field support role — ideally in payments, fintech, SaaS, POS systems, or unattended/vending technology.
• Demonstrated ability to independently diagnose and resolve hardware, software, and connectivity issues — you are a solver, not a ticket router.
• Solid understanding of payment terminal operations, network troubleshooting (Wi-Fi, LAN, cellular), and basic POS or SaaS platform administration.
• Excellent written and verbal communication — you can walk a non-technical merchant through a technical fix clearly and calmly, without jargon or condescension.
• Comfortable with CRM and ticketing tools (Zendesk, Salesforce, HubSpot, or similar); quick to learn new internal systems.
• A composed, methodical problem-solving mindset — you stay structured under pressure and take full ownership of issues from open to close.
• Availability for the 12:00 PM – 8:00 PM shift, Monday through Friday, and willingness to participate in the weekend on-call rotation.

Assets

• Experience with Help Desk systems including ZenDesk.
• Experience with payment terminal brands such as Ingenico, Verifone, Castles Technology, or PAX.
• Familiarity with cashless payment systems, EMV/contactless standards, or unattended retail technology.
• Bilingual (English/French) — strongly preferred given our Canadian client base.
• Experience in a startup or scale-up environment where processes are still being built.

Pay: $45,000.00-$55,000.00 per year

Benefits:

• Casual dress
• Company events
• Dental care
• Employee assistance program
• Extended health care
• Flexible schedule
• Life insurance
• Paid time off
• Vision care
• Wellness program
• Work from home

Work Location: Hybrid remote in North York, ON