Technical Sales Specialist

🕒 June 26

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Workleap

WebsiteLinkedInAll Job Openings

201 - 500 employees

👥 HR Tech

☁️ SaaS

⚡ Productivity

💰 Private Equity Round on 2023-06

HR Tech • SaaS • Productivity

Workleap is a company that provides an integrated platform designed to improve the employee experience by focusing on engagement, performance, and development. Their suite of products includes Officevibe, Pingboard, and various Learning Management Systems (LMS) that help businesses tackle challenges like hybrid work, onboarding, professional development, and performance management. Workleap aims to create happier and more productive workplaces by making it easier for HR teams to manage and enhance their HR strategies. With a customer base exceeding 20,000 leaders globally, Workleap offers tools that are easy to implement and integrate with existing HR and productivity systems.

📋 Description

• Own every technical moment in the sales cycle — demos, advanced discovery, evaluation sessions — so prospects never leave a conversation with unanswered questions and no opportunity stalls for lack of technical depth; • Shorten deal cycles by delivering demos that become the internal gold standard — showcasing the platform's agentic capabilities in a way reps study, replicate, and learn from; • Drive deals to close as a technical co-closer — reinforcing the value of the Workleap Platform and Manager Agent, navigating gaps with roadmap and vision, and keeping momentum when the answer isn't a clean "yes, today"; • Cut rep ramp time by owning the technical track of sales onboarding and ongoing enablement, so reps handle the majority of product and AI conversations independently; • Shape the product roadmap by serving as the bridge between the field and product leaders — translating technical objections and field patterns into structured input PMs actually use, and closing the loop back to reps when things ship; • Compound the team's technical leverage by building reusable assets and AI-powered workflows — modelling internally the same agentic philosophy we sell to our customers; • Accelerate Manager Agent adoption by supporting expansion conversations and helping AEs and AMs articulate the value of our agentic approach compellingly.

🎯 Requirements

• Experience in a customer-facing technical sales role at a B2B SaaS company; • Genuine AI and agentic fluency — comfortable building your own workflows and explaining complex AI concepts to non-technical audiences, without needing a script; • Strong demo craft — you treat it as a discipline, not just a deliverable, and your demos become the references others copy; • High business acumen with a demonstrated track record of influencing deals to close (pre-sales, expansion, or both); • A builder mindset: you reach for systems and AI workflows that scale your knowledge rather than trading your own time for every problem; • Clear, confident communication across audiences — from HR leaders to C-suite; • Bonus: familiarity with HR tech, performance management, or employee engagement solutions.

🏖️ Benefits

• LTIP program, share in Workleap's long-term growth. • RRSP + Family health insurance + telemedicine + annual wellness budget. • Flexible vacation policy. • Remote work, with access to our Montreal office. • In-person gathering twice a year. • Claude access, for everyone.