Technical Support Engineer
Sidetrade
Technical Support Engineer
Sidetrade
AI-powered SaaS optimizing order-to-cash
Sidetrade · Calgary, Canada (Hybrid) · Full-time · Posted 2026-11-02
Workplace: hybrid
Department: Customer Success
Do you thrive on solving complex technical problems and turning customer challenges into success stories? At Sidetrade, we're looking for a driven Technical Support Engineer to join our global Support team. You'll work with enterprise customers across North America and Europe, troubleshoot technical and functional issues, and partner with cross-functional teams to ensure customers achieve maximum value from our innovative AI platform.
About Sidetrade
Sidetrade (Euronext Growth: ALBFR.PA) is an AI-native company dedicated to Order-to-Cash (O2C). Its platform combines O2C applications, autonomous AI agents, and Aimie IQ, an intelligent natural-language interface that helps multinationals accelerate their cash generation, all built on SAFE, the Sidetrade Agentic Framework for Enterprise. Sidetrade operates the world's largest proprietary O2C Data Lake, built on $9 trillion in B2B transactions and millions of buying companies. We use this data to train specialized AI models that monitor, analyze, decide, and act autonomously throughout the O2C cycle. Sidetrade supports companies in 85 countries with 450 employees across Europe, North America, and Asia-Pacific.
We’re proud of our 38 nationalities, and these diverse perspectives drive our innovation, one-team culture, and customer-first mindset. Sidetrade has been positioned as a Gartner® Magic Quadrant™ Leader since 2022. We value passion over perfection. So, if you’re eager to learn and bring great energy, we want to hear from you. Be you. Grow with us.
Curious about Sidetrade? Catch Aimie in motion: Aimie Video
The role:
As part of Sidetrade’s Support team, you will work closely with our customers to understand the challenges they face every day and help them succeed with our platform. You will troubleshoot technical and functional issues, guide customers through solutions, and clearly explain product features to resolve problems.
You will collaborate with Customer Experience, Product, and R&D teams to investigate issues and ensure customers receive timely and effective support.
This role participates in a rotating shift schedule to help provide extended coverage across time zones.
This position is based in our Calgary office with an expectation of between three to four days in office per week.
What you will be doing:
Provide technical and functional support to our customers
Provide innovative solutions for the customer’s functional and technical challenges
Resolve complex issues applying analytical problem-solving skills
Manage the escalation process working with Customer Experience, Product and R&D
Become a Product Expert and share best practices with your colleagues
Translating complex technical workflows into clear, structured documentation (process maps, SOPs, runbooks, and user guides)
Collaborating with technical and business stakeholders to validate understanding and keep documentation accurate and up to date
Based in North America, you will ensure the 24x5 and eventual 24x7 coverage with your Europe-based colleagues
You should apply if:
2–3 years of experience is required in enterprise-level B2B technical support, application support, or a similar customer-facing technical role
Strong analytical and troubleshooting skills with a structured approach to problem solving
The ability to work in a shift rotation Monday-Friday and occasional weekends:
Day shift: 8-hour shift beginning at 8am
Evening shift: 8-hour shift beginning at 4pm
Strong written and verbal communication skills, with the ability to explain technical issues clearly to customers
Technical knowledge of SQL, Linux, or web application support
A proactive mindset and the ability to take ownership of issues through resolution
Fluency in English
Nice to have:
Because when you thrive, we all succeed!
We’re committed to providing a welcoming and inclusive experience for every candidate.
If you need any accommodation during the hiring process, just let us know.
Agencies
We only accept applications from invited agencies via our Workable portal. Unsolicited CVs sent to managers or HR won’t be subject to fees.
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Sidetrade provides an AI-powered SaaS platform for optimizing the order-to-cash (O2C) process, called Augmented Cash. It uses its proprietary AI assistant, Aimie, trained on a large data lake of B2B payment transactions, to forecast customer payment behavior, recommend collection strategies, automate dunning, resolve invoice disputes, and improve cash flow. The product is delivered as a subscription SaaS and targets finance departments in large, international companies across multiple industries. Sidetrade differentiates itself with its data-driven Aimie assistant, its global reach (over 85 countries), and recognition as a Gartner Leader in Invoice-to-Cash. The company's goal is to help businesses reduce payment delays, manage credit risk, and accelerate cash collection by providing actionable insights and automated workflows within the O2C cycle.
Explore more opportunities at Sidetrade