Technical Sales Specialist - Workleap
About The Position
Workleap is seeking a Technical Sales Specialist who will serve as the technical authority for the entire sales organization. This role requires a deep understanding of their agentic HR platform and AI concepts, with the ability to engage in technical sales activities when necessary and to build systems and training that empower sales representatives to handle technical conversations independently. The specialist will be responsible for owning technical moments in the sales cycle, shortening deal cycles through effective demos, acting as a technical co-closer, reducing rep ramp time, shaping the product roadmap, and accelerating adoption of the Manager Agent. This is a foundational role in building Workleap's technical sales function, working closely with sales and product teams.
Requirements
- Experience in a customer-facing technical sales role at a B2B SaaS company.
- Genuine AI and agentic fluency, comfortable building workflows and explaining complex AI concepts to non-technical audiences.
- Strong demo craft, treating it as a discipline.
- High business acumen with a demonstrated track record of influencing deals to close.
- A builder mindset, utilizing systems and AI workflows for scalability.
- Clear, confident communication across various audiences, from HR leaders to C-suite.
Nice To Haves
- Familiarity with HR tech, performance management, or employee engagement solutions.
Responsibilities
- Own every technical moment in the sales cycle, including demos, advanced discovery, and evaluation sessions.
- Deliver demos that become the internal gold standard, showcasing agentic capabilities for reps to learn from.
- Act as a technical co-closer to reinforce value, navigate gaps, and maintain deal momentum.
- Own the technical track of sales onboarding and ongoing enablement to reduce rep ramp time.
- Serve as the bridge between the field and product leaders, translating technical objections into structured input for product managers.
- Build reusable assets and AI-powered workflows to compound the team's technical leverage.
- Support expansion conversations and articulate the value of the agentic approach to accelerate Manager Agent adoption.
Benefits
- Base salary: $90 to $110k
- Eligible for commission, bringing total on-target earnings (OTE) to approximately $100–120k CAD.
- LTIP program
- RRSP
- Family health insurance
- Telemedicine
- Annual wellness budget
- Flexible vacation policy
- Remote work
- Access to Montreal office
- In-person gathering twice a year
- Claude access
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
