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

• Make every sales call — demo, advanced discovery, evaluation session — a moment of trust for the prospect so that no technical question goes unanswered and no opportunity stalls; • Shorten sales cycles by delivering demos that become the internal standard — demos that showcase the platform’s agentic capabilities in a way that reps study, replicate, and draw inspiration from; • Directly help close deals as the technical co-closer — reinforcing the value of the Workleap platform and the Agent Manager, navigating gaps with product vision, and keeping momentum when the answer is not yet a “yes”; • Reduce ramp time for sales reps by owning the technical component of onboarding and ongoing training, so they can handle the majority of AI conversations autonomously; • Influence the product roadmap by acting as a bridge between the field and product leaders — translating technical objections and trends into structured data that PMs actually use; • Multiply the team’s technical leverage by building reusable resources and AI workflows — embodying internally the same agentic philosophy we sell to customers; • Accelerate adoption of the Agent Manager by supporting expansion conversations and helping AEs and AMs articulate the value of our agentic approach convincingly.

🎯 Requirements

• Experience in a technical sales role with direct customer-facing responsibilities at a B2B SaaS company. • Genuine fluency with AI and agentic solutions — comfortable building your own workflows and explaining complex AI concepts to non-technical audiences without relying on a script. • Mastery of the demo craft — you treat demos as a discipline, not just a deliverable, and your demos become reference points others copy. • Strong business acumen with a proven track record of influencing deal outcomes (pre-sales, expansion, or both). • Builder mindset: you create systems and AI workflows that scale your knowledge rather than trading your time for every problem. • Clear, confident communication with a range of audiences, from HR leaders to executives. • Nice to have: familiarity with HR tech, performance management, or employee engagement.

🏖️ Benefits

• LTIP (Long-Term Incentive Plan) — a stake in Workleap’s long-term growth. • RRSP + group family insurance + telemedicine + annual wellness budget. • Flexible vacation policy. • Remote work, with access to our Montreal offices. • In-person company gatherings twice a year. • Company-wide access to Claude (AI assistant).