Weekend Technical Support Engineer Jobs in Toronto, ON

 Wisedocs is a fast-growing, venture-backed AI platform that transforms how insurance companies analyze claims. With ~$20M USD raised, 100+ team members globally, and 90+ customers across North America and Australia, we're doubling revenue year over year.  

Founded by experts who've experienced the claims process firsthand, Wisedocs combines deep domain knowledge with next-gen AI trained on 100M+ documents. Our platform turns complex medical records into clear, structured insights-backed by expert human oversight.  

Join a mission-driven team building intelligent products that cut through complexity, accelerate decision-making, and make a real impact when it matters most.   

Role Summary 

Wisedocs is expanding how insurers, IME firms, and defense legal practices understand and act on medical information - and as the platform grows in complexity and serves more sophisticated accounts, the demand for technical depth in our post-sale team is growing too. 

The Technical Support Engineer role sits between a Support Specialist and Technical Account Manager on the post-sale track. You own escalated support for a set of assigned accounts, investigating complex technical issues that Tier 1 cannot resolve. You are not a ticket resolver - you are a technical investigator and configuration contributor who catches what the team misses. 

What you'll be doing: 
Escalated Technical Support 

• Own Tier 2 support: triage, investigate, and resolve issues that require platform knowledge beyond standard troubleshooting 

• Manage escalated tickets end-to-end - diagnosis, communication, resolution, and documentation - with clear SLA ownership 

• Partner with Support Specialists to pull escalations out of the queue early and prevent customer-facing delays 

• Serve as the technical bridge between support and the engineering team when issues require deeper investigation or a product fix 

• Act as an escalation resource and technical mentor for Support Specialists, helping develop troubleshooting skills and technical proficiency across the team 
  

Configuration & Technical Operations 

• Manage and maintain customer-specific platform configurations - instance settings, workflow rules, and output logic 

• Support the Technical Configuration Specialist on complex builds, particularly during implementation and migration periods 

• Execute configuration changes independently for established customers and validate behavior in staging environments before release 

• Contribute to configuration documentation and internal knowledge base to improve scalability across the team 

 
Customer-Facing Technical Guidance 

• Run technical calls independently: configuration walkthroughs, troubleshooting sessions, and feature training 

• Translate complex platform behavior into clear, non-technical language for customer teams 

• Proactively surface configuration improvement opportunities to CSMs for named accounts 

• Support implementation handoffs by providing technical continuity from onboarding into steady-state support 

 
Internal Collaboration & Knowledge 

• Document customer interactions, root-cause findings, and resolution patterns for the team knowledge base 

• Provide structured feedback to Product on recurring issues and configuration limitations 

• Identify recurring customer friction points and partner with Product and Engineering to advocate for scalable solutions 

• Work closely with the Director of Technical Success and CSMs to flag account health signals tied to technical blockers 

 
You're a great candidate if you have

• 3+ years in a technical support, platform support, or support engineering role in a SaaS environment 

• Demonstrated ability to own and resolve complex, multi-system technical issues independently 

• Comfort working with configuration logic, JSON structures, or similar platform-level tooling 

• Strong written and verbal communication - you can explain technical issues clearly to both technical and non-technical audiences 

• Experience managing escalations, prioritizing competing requests, and communicating status to customers under pressure 

• Familiarity with ticketing systems (Jira, HubSpot, or similar) and a structured approach to documentation 
  

Nice to Have 

• Experience with SQL, prompt engineering, or workflow automation tools 

• Background in insurance, claims, legal tech, or another regulated industry 

• Exposure to implementation or onboarding workflows in a B2B SaaS context 

• Experience working alongside or growing toward a TAM, CSE, or Solutions Engineer role 
  

What we offer: 

• Flexible hybrid environment to collaborate in-person at our Toronto HQ. 

• Modern employee benefits, including health and dental coverage  

• Competitive compensation, with valuable stock options, as we're still a young company growing very quickly.   

• An opportunity to develop very rapidly in your career. We can offer you a super-immersive learning environment, and when you thrive there, you will have the opportunity to rapidly develop this opportunity into senior practitioner or management opportunities as you choose.   

• Access to a learning and professional development fund to help you level up your career while you're working with us. We hope to be an incredible step up in your career if you decide to come and work with us.   

• Company events   

• Generous Paid Time Off   

• Paid Sick Days   

• Casual Dress code   

• Employee Referral Bonus   

• Tuition Assistance   

• Plus, many other Recognition Programs!   
  

Recruitment Journey at Wisedocs: 

We're excited to meet you and explore the possibilities together!  At Wisedocs, honesty is one of our core values. Our Recruitment process is transparent to ensure you are set up for success:    

• Round 1 - People & Culture Chat: 20-30 min conversation about your background, goals, and the role.  

• Round 2 - Interview with the Hiring Manager:  Diving into your work experience and learning more about you (30-45min)

• Round 3 - Take Home Case Study Presentation: Present your take home assignment to our implementation and support teams (1hr) 

Compensation  

Our target base salary range for this role is $60,000 - $75,000 CAD. This range reflects the full growth journey within the role - from building and developing skills early on, to becoming highly proficient and ultimately achieving excellence. Where an offer lands within the range is based on your experience, skills, and impact, which we assess throughout the hiring process.   

We're committed to fair and transparent pay and ongoing career development. If your expectations fall outside this range but you're excited about the role, we still encourage you to apply.   

Note: We use AI-powered tools alongside human review to support a fair, inclusive, and efficient hiring process, helping us work smarter and create better experiences for our customers and team.  

This posting is for current and future opportunities at Wisedocs. Even if there isn't an immediate opening, we're always excited to meet great people. If your experience lines up, we encourage you to apply - we'll reach out when a role opens that's a good fit.  

*Wisedocs AI is an equal opportunity employer and are committed to providing employment accommodation in accordance with AODA. If you require an accommodation, please notify us and we will work with you to meet your needs.