Technical Sales Specialist (AI)

TL;DR

Technical Sales Specialist (AI): Acting as the technical authority for the sales organization to drive deals through deep agentic platform expertise and high-impact demos with an accent on AI fluency and sales enablement. Focus on bridging the gap between field objections and product roadmaps, building scalable technical assets, and accelerating the adoption of AI-powered HR tools.

Location: Must be based in Canada (Remote)

Salary: Base $90,000 – $110,000 CAD (OTE approx. $100,000 – $120,000 CAD)

Company

Montreal-based tech company building agentic HR platforms and Microsoft 365 migration solutions.

What you will do

• Lead all technical moments in the sales cycle, including advanced discovery, evaluations, and high-stakes demos.
• Create "gold standard" demo assets that showcase agentic capabilities for the sales team to replicate.
• Act as a technical co-closer, reinforcing platform value and navigating roadmap gaps to drive deals to completion.
• Own technical onboarding and enablement to reduce ramp time for AEs and AMs.
• Bridge the gap between the field and product leaders by translating technical objections into structured product input.
• Build reusable assets and AI-powered workflows to scale technical knowledge across the organization.

Requirements

• Experience in a customer-facing technical sales role at a B2B SaaS company.
• Must be based in Canada.
• Genuine AI and agentic fluency, with the ability to explain complex concepts to non-technical audiences.
• Expert-level demo craft and strong business acumen with a track record of influencing closed deals.
• Builder mindset focused on creating scalable systems rather than manual problem-solving.
• Clear, confident communication skills for interacting with HR leaders and C-suite executives.

Nice to have

• Familiarity with HR tech, performance management, or employee engagement solutions.

Culture & Benefits

• Remote work flexibility with access to the Montreal office and twice-yearly in-person gatherings.
• Comprehensive benefits package including RRSP, family health insurance, telemedicine, and an annual wellness budget.
• Long-term incentive program (LTIP) sharing in the company's growth.
• Flexible vacation policy.
• Company-wide access to Claude AI.

Hiring process

• Initial conversation with a recruiter.
• Virtual interviews with the hiring manager and one additional interviewer.
• Completion of a take-home case study followed by a collaborative discussion with potential teammates.