AI-Powered Technical Product Support (Remote)

Payshepherd; Canada; Remote; CAD 60,000 - 90,000; Full time

Benefits offered by this job

Extended Health Benefits Package

Stock options

Remote work

Job summary

PayShepherd is seeking a Technical Product Support specialist to join the Customer Success team. You will be the first line of contact for contractors and customer administrators, delivering fast, high-quality resolutions across multiple channels and driving product improvements.

You will leverage AI-assisted workflows and implement self-service resources while maintaining strong customer relationships and ownership of account context in a remote, high-growth environment.

Qualifications

• 2+ years in a technical or product support, SaaS support, or a technically demanding operations role.
• Strong troubleshooting instincts; trace a symptom to a root cause across data, configuration, and workflow.
• Experience with heavy industry or technology domains is a plus.
• Comfort with data, reports, CSV files, and spreadsheets.
• Ability to explain technical blocks to non-technical stakeholders.
• Willingness to learn and adapt in a fast-growing environment.

Responsibilities

• Resolve support requests across email, live chat, and phone for contractors and admins.
• Troubleshoot core platform: POs, ingestion, rates, invoices, approvals, user access, and mappings.
• Capture problems clearly, file engineering tickets, and drive resolution with the Dev team.
• Reconcile data and ingestion; validate reports and chase ingestion failures.
• Own account context and maintain configuration knowledge for assigned accounts.
• Create templates and guides to enable self-service.
• Advocate for customers and surface issues to CS, Product, or Engineering.
• Build AI-assisted workflows for triage, drafting, and self-serve content.
• Use AI to spot patterns and translate issues into actionable steps.
• Automate repetitive tasks and tune the AI support agent.

Skills

Technical support

SaaS support

Troubleshooting

Data analysis

Clear communication

Organizational skills

AI proficiency

ERP/Procurement data

Support tooling

Tools

Intercom

Dialpad

Jira

SAP

Avantis

Job description

PayShepherd is seeking a Technical Product Support specialist to join the Customer Success team. You will be the first line of contact for contractors and customer administrators, delivering fast, high-quality resolutions across multiple channels and driving product improvements.

You will leverage AI-assisted workflows and implement self-service resources while maintaining strong customer relationships and ownership of account context in a remote, high-growth environment.