Workleap

12 open remote positions

Workleap is a Montreal-based tech company that builds HR and Microsoft 365 migration software. With over 15,000 customers and a builder culture, they value autonomy and impact.

Salary Distribution 9 of 12 jobs

PTO Distribution 11 of 12 jobs

Unlimited PTO 11 jobs (92%)

Benefits Overview 12 of 12 jobs

RRSP (10) Telemedicine (10) LTIP (7) Wellness Budget (7) Health Insurance (5) Wellness budget (4) Annual Bonus (3) Flexible vacation (3) Remote work (3) Dental (2) Flexible PTO (2) Flexible Vacation (2) Health insurance (2) Medical (2) PTO (2) Vision (2) 401(k) (1) Annual bonus (1) Claude Access (1) Family Health Insurance (1)

Open Positions

Content Marketing Manager

$62,050–$76,650/yr
Canada Unlimited PTO

  • Shape Workleap's content presence across the entire funnel, from thought leadership to paid campaigns and customer communications.
  • Identify the best angle and format for each message, then produce and distribute across all relevant channels with consistency.
  • Build and pilot a content engine that maximizes the value of every idea, transforming internal signals and product launches into multi-format assets.

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Bilingual Associate Account Manager, Renewal Desk

$75,000–$85,000/yr
Canada Unlimited PTO

  • Own the end-to-end renewal motion for the Flash segment, running proactive 90/60/30-day cycles to protect GRR and surface expansion potential.
  • Accelerate pricing migration conversations, moving legacy per-seat customers to the new platform pricing model and closing them.
  • Maintain a clean HubSpot pipeline, identify expansion signals with Account Managers, and use AI tools like Claude to personalize outreach at scale.

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Gestionnaire de compte - ShareGate

$115,000–$138,000/yr
Canada Unlimited PTO

  • Drive portfolio growth by leading renewals and identifying expansion opportunities to increase overall ARR.
  • Accelerate adoption and retention by proactively guiding accounts from onboarding through expansion using usage data and engagement signals.
  • Conduct strategic conversations with contacts using a rigorous discovery approach that connects real IT challenges to concrete outcomes ShareGate can deliver.

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Account Manager - ShareGate

$75,000–$90,000/yr
Canada Unlimited PTO

  • Own the full revenue relationship with your accounts, leading renewals and uncovering expansion opportunities to increase ARR.
  • Drive adoption and retention through proactive engagement and strategic conversations with IT teams.
  • Collaborate with internal teams and use AI tools to improve outreach, maintain clean CRM, and position Pro/Enterprise offerings.

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Software Developer II (Web), Migrate - ShareGate

$100,000–$130,000/yr
Canada Unlimited PTO

  • Ship full-stack features ensuring quality and UX from the first milestones of a new web app, partnering closely with Product Manager and Designer.
  • Lay solid technical foundations from day one by contributing to architecture decisions and engineering practices.
  • Integrate Microsoft APIs reliably and build a quality culture through testing, code reviews, and AI tool usage.

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Spécialiste en ventes techniques

Canada Unlimited PTO

  • Serve as the lead technical authority across the sales team, mastering our agentic platform and AI language to decide when to step into a deal and when to build systems that empower reps.
  • Shorten sales cycles by delivering demos that become internal benchmarks, showcasing the platform's agentic capabilities in ways reps study, replicate, and draw inspiration from.
  • Directly contribute to deal closure as a technical co-closer, build reusable resources and AI workflows, and bridge field insights with product leaders to influence the roadmap.

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Technical Sales Specialist

Canada Unlimited PTO

  • Own every technical moment in the sales cycle, including demos, advanced discovery, and evaluation sessions to build trust and close deals.
  • Cut deal cycles by delivering gold-standard demos that reps study and replicate, showcasing agentic capabilities.
  • Drive deals to close as a technical co-closer, reinforcing platform value and navigating gaps with roadmap and vision.

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Manager, Revenue Accounting & Billing - Finance Canada

Canada Unlimited PTO

  • Own the end-to-end revenue accounting and billing operations, ensuring every subscription, renewal, and amendment is priced, invoiced, and recognized correctly.
  • Lead a small team of three, drive DSO reduction, and automate collections by fixing issues at the CRM-to-ERP handoff.
  • Execute structural projects like US-entity tax initiatives and revenue tech stack reviews as the central coordination point across Finance, RevOps, and Customer Success.

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