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Technical Sales Specialist
Location
Canada
Posted
11 days ago
Salary
$90K - $110K / year
Seniority
Senior
Job Description
Technical Sales Specialist
Workleap
• Cut rep ramp time by owning the technical track of sales onboarding and ongoing enablement, so reps handle the majority of technical conversations independently — without routing everything through TSS; • Eliminate the single point of failure on technical depth by taking real load off the existing TSS across pre-sales, expansion, and partner-led deals, so no deal stalls waiting on one person; • Shorten deal cycles by delivering demos that become the internal standard — the kind reps study, replicate, and learn from; • Drive deals to close as a technical co-closer, not just a validator — reinforcing value, navigating gaps with roadmap and vision, and keeping momentum when the answer isn't a clean "yes, today"; • Shape product roadmap by translating field patterns into structured input PMs actually use — and closing the loop back to reps when things ship; • Accelerate Migrate-to-Protect attach by supporting expansion conversations with existing customers and helping AEs and AMs connect the dots between products; • Compound the team's technical leverage by building reusable assets and AI-powered workflows so the same problem stops landing on the team's plate twice.
Job Requirements
- Experience in a customer-facing technical sales role at a B2B SaaS company;
- Familiarity with the Microsoft 365 platform (governance, migration, or adjacent experience is a strong plus);
- High business acumen with a track record of influencing deals to close;
- Strong demo craft — you treat it as a discipline, not just a deliverable;
- A builder mindset: you reach for systems and AI workflows that scale your knowledge rather than trading your own time for every problem;
- Genuine AI fluency — comfortable building your own workflows, not just using tools at surface level;
- Clear, confident communication across audiences, from IT admin to CIO to partner sales rep (bilingual French/English is a strong asset).
Benefits
- Health insurance
- Flexible work hours
- Remote work options
- Professional development opportunities
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• Reduce sales representatives' ramp-up time • Eliminate single points of failure for technical depth • Shorten sales cycles by delivering demos • Actively contribute to closing deals • Influence the product roadmap • Accelerate adoption of Migrate-to-Protect • Amplify the team's technical leverage
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