Technical Sales Specialist

🕒 May 14

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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

• 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.

🎯 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