PayShepherd envisions a future where heavy industrial sites operate with maximum efficiency and minimal administrative burden. Our strategy focuses on building a comprehensive and user-friendly contractor management platform, fostering better relationships between contractors and clients and ensuring project success.

We have an aggressive growth plan and are looking to add to our team. You’d be a great fit to execute on this vision if you:

● Thrive in a fast-paced, ever-evolving environment

● Are passionate about bringing innovation to transitional industries

● Have experience in Heavy Industry or Technology

● Are proactive in creating creative solutions to complex problems

● Are client-focused; our success is built on strong relationships between us, our clients and their contractors. If you excel at collaboration and are committed to delivering exceptional service, you’ll fit right in

● Treat AI as a core part of how you work, not a side experiment. We expect everyone here to use AI to do their best work and to keep getting better at it.

We are looking for a Technical Product Support to join our Customer Success team. You are the front line of the PayShepherd platform and the first person our contractors and customer administrators turn to when something blocks their work. Your focus is fast, high-quality resolution, root cause fixes, and turning everyday problems into a better product and a smaller queue.

● Customer-centric: strives to create delightful experiences, make customers' lives easier, and be a trusted partner to clients and their contractors.

● Builds Trust: demonstrates open and clear communication in all interactions, holds themselves accountable, and is respectful to colleagues, customers, and partners.

● Bias for Action: moves work forward by taking the next step rather than stopping at opinions, keeps timelines tight, and maintains deliberate momentum to drive results.

● Growth Mindset: values resilience and believes effort leads to improvement; treats mistakes as stepping stones, welcomes feedback, and prioritizes outcomes over ego by evaluating ideas on their merit.

● Deep Curiosity: asks a lot of questions, digs into hard problems, challenges their own thinking, and keeps experimenting rather than settling for what is already known.

● Resolve support requests across every channel. Own each conversation from first response to confirmed resolution across email, live chat, and phone, for both contractors and customer administrators.

● Troubleshoot the core platform. Diagnose and resolve issues across purchase orders and ingestion, rates, LEMs and timesheets, invoices and proformas, approvals, anomaly and hard block rules, user access, and CSV mapping.

● Diagnose, reproduce, and escalate. Capture the problem clearly with recordings and reproduction steps, file well-formed engineering tickets, drive them to resolution with the Dev team, and close the loop with the customer.

● Reconcile data and ingestion. Validate customer PO reports, correct approver assignments, and chase ingestion failures so customer source data flows cleanly into the platform.

● Own your account context. Build and hold institutional knowledge for your assigned accounts, including their configuration quirks and reporting exceptions.

● Enable self-service. Create templates, short video walkthroughs, and guides so contractors and admins can resolve common tasks without a ticket.

● Advocate for the customer inside PayShepherd. Surface recurring issues, product gaps, and churn signals to Customer Success, Product and/or Engineering using existing idea and incident processes.

● Build and maintain AI-assisted support workflows across triage, drafting, summarizing, and self- serve content, so you resolve more issues faster and your time goes to the hard diagnostic work only a human can do.

● Use AI to spot patterns across conversations, surface recurring issues and churn risk, and turn them into clear actions and customer-ready summaries.

● Automate the repetitive parts of your work such as first-pass responses, ticket summaries, and status updates, and help tune the AI support agent rather than compete with it.

● 2+ years in a technical or product support, SaaS support, or a technically demanding operations role

● Strong troubleshooting instincts; you can trace a symptom to a root cause across data, configuration, and workflow

● Understanding of heavy industry (oil and gas, mining, manufacturing, pulp and paper, etc.)

● Comfort with data, reading reports, spotting mismatches, and working in spreadsheets and CSV files

● Clear and patient written and verbal communication; you can explain a technical block to a non- technical contractor

● Strong organizational skills and follow-through in a high-volume queue; internal and external teams will depend on you

● Self-driven commitment to keep learning; our product evolves fast, and so do our customers

● Creative problem-solving skills resulting in practical and innovative solutions

● Eagerness to climb the AI proficiency ladder quickly. The expectation for this role is that you reach Builder level, automating real parts of your own job, and keep going

● Exposure to ERP or procurement data (SAP, Avantis), contractor or field workflows, or support tooling (Intercom, Dialpad, Jira) would set you apart

● Bilingual in English with French or Spanish would be considered an asset, although not required.

● Remote work

● Flexibility, professional development, internal mobility, high growth environment, intrinsically rewarding work, self-determination, day to day variety, stock options

● Best-in-class AI tools and a culture that funds and celebrates building with AI

● Full-time, Permanent, base salary

● Extended Health Benefits Package

● Apply through the PayShepherd website https://www.payshepherd.com/careers#open-positions