Technical Solutions Specialist
Company shown to members 🔒 · Remote · Canada only
Apply free: 3 jobs are on us✨ Tailor my resume for this job🎤 Practise the interview question, free
✓ Straight from the company's own careers page. No middlemen, no “we'll send you a check for equipment”. How we check jobs
✓ Sent 100 applications and heard nothing? Make this one count: tailor your resume to this ad in one tap, free.
✨ Not sure this is the one? Get your remote job matches in 30 seconds →
First recorded by Psst: 5 November 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
Practise the first interview question for this job
If the company replies, the first call usually starts with a question like this. Vague answers are the easiest to reject. Write yours and get an AI score in under a minute.
The 20-second read
- Experience
- 3+ years required
- Where you can live
- Canada only
- Skills and tools
- sql, upsell, saas, documentation, scheduling, compliance
- Job type
- Full-time
Read from the ad by Psst's rules. Check the full ad below before applying.
Job details
- Where you can work
- Canada
- Employment type
- Full-time
- Advertised pay
- Not stated by the employer
- Experience
- 3+ years required
- Employer publication date
- 4 November 2026
- First recorded by Psst
- 5 November 2026
- Last checked at the source
- 8 November 2026
About the job
Position Summary
The Technical Solutions Specialist is part of the company's Projects team and provides hands-on technical troubleshooting, configuration, and implementation support across the company product suite. This position works directly with clients and internal teams to resolve issues, configure system features, and support upsell installations, while building the technical depth needed to take on increasingly complex, higher-level work over time.
Key Responsibilities
Configuration & Implementation
- Configure system settings, forms, workflows, user roles, and integrations (e.g., SSO) to meet client needs.
- Set up and maintain vehicle, driver, and route-related data, subscriber notifications, and translation/localization settings.
- Support new feature rollouts, product updates, and upsell installations across all product lines.
- Help build and configure environments used to support product demos and sales presentations (this role does not conduct demos or sales activities directly).
Client & Cross-Functional Collaboration
- Partner with senior technical staff, developers, and client success teams to resolve escalated or cross-product issues.
- Communicate clearly with clients to understand reported issues, set expectations, and confirm resolution.
- Help build and maintain a technical documentation repository, including training materials, templates, and frameworks that support consistent processes and cross-coverage across the team.
Product Support & Troubleshooting
- Diagnose and resolve client-reported issues across the company product suite, including routing, scheduling, student data, GPS/live tracking, and reporting features.
- Investigate and troubleshoot application errors, system messages, and unexpected behavior, escalating complex or system-level issues as needed.
Reporting & Compliance Support
- Assist with government and ministry reporting cycles and related data validation as required.
- Support seasonal and cyclical processes (e.g., school-year setup, grade rollovers, annual update cycles) as assigned.
Requirements
- 3-5 years of experience in technical support, software implementation, solutions consulting, or a related client-facing technical role.
- Strong troubleshooting and analytical skills, with the ability to diagnose issues across multiple interconnected systems.
- Comfort working with SaaS applications; familiarity with databases, SQL, or system administration concepts is an asset.
- Excellent written and verbal communication skills, with a client-service mindset.
- Strong organizational skills and the ability to manage multiple priorities in a fast-paced environment.
- Experience in the K-12 transportation, education technology, or SaaS support space is a plus, but not required.
Benefits
- Competitive salary and performance-based bonuses.
- Full health and wellness benefits.
- Flexible work hours and remote-friendly setup.
- Full access to Claude Code and modern AI tooling, and the autonomy to shape how our team uses it.
- A collaborative team culture focused on modernizing software that drivers, parents and school districts rely on every day.
Apply free: 3 jobs are on us✨ Tailor my resume for this jobPrepare with the Apply kit
- No pay listed
A resume that gets past the first 6 seconds
Recruiters skim. The Psst resume coach fixes what makes them skip you, line by line, and one tap tailors it to the exact job you're applying to.
- 1Every line checkedWeak starts, clichés and AI-sounding phrases flagged, with a 3-question fix.
- 2Tailored to the jobSee which skills and tools from the ad your resume is missing. Try it free on one of your matches.
- 3Ready for remoteTime zone, tools and proof you work on your own, the things remote teams look for.
- 4Looks the partOne page, 6 designs, 8 colours and a matching cover letter, free to build. Premium downloads the PDF and Word files.
Example with made-up details. The score is the builder's own check, not an ATS rating or a promise of an interview.