Senior Customer Onboarding Specialist at pebl. About the role Pebl is on the hunt for a Senior Customer Onboarding Specialist who will take ownership of guiding high-value enterprise clients through their initial journey with the company's Global Work Platform. This position serves as the critical bridge between contract signing and full platform adoption, ensuring that organizations can seamlessly hire, pay, and manage distributed teams spanning more than 185 countries worldwide. You will act as the primary relationship holder during the implementation phase, combining strategic advisory capabilities with hands-on project execution to deliver exceptional client experiences. The role demands someone who thrives in fast-paced environments and possesses deep expertise in navigating complex international employment landscapes while maintaining unwavering attention to compliance requirements.
Key facts Location: Toronto, Ontario (Hybrid arrangement)
Engagement: Full-time permanent position
Compensation: CA$88,000 to CA$125,000 annually
Team: Customer Onboarding department
What you'll do Own the complete onboarding lifecycle for strategic enterprise accounts beginning immediately after contracts are finalized, shepherding clients through every phase until they achieve full operational independence on the platform.
Lead structured kickoff sessions and ongoing client meetings where you will collaboratively define project timelines, clarify mutual expectations, assign ownership of deliverables, and establish communication cadences that keep all parties aligned throughout implementation.
Serve as a trusted advisor on international expansion initiatives, helping clients determine which markets to prioritize based on their business objectives while educating them on jurisdiction-specific hiring regulations, employment laws, and compliance obligations.
Guide clients through comprehensive benefits benchmarking exercises that compare mandatory statutory entitlements against competitive local market practices, enabling them to craft attractive compensation packages that resonate with talent in each target country.
Deliver thorough training sessions on the Pebl platform, walking client teams through core functionality, reporting capabilities, employee management workflows, and self-service features to ensure they can confidently operate without constant support intervention.
Maintain rigorous oversight of project milestones, proactively identifying potential blockers or risks before they escalated,



and communicating transparent status updates to both internal leadership and client stakeholders on a regular basis.
Orchestrate seamless collaboration across multiple internal teams including Sales, Product Management, Finance, Legal, and Customer Experience to guarantee that every aspect of the client implementation receives appropriate attention and resources.
Systematically capture client insights, pain points, and feature requests during the onboarding process, synthesizing this feedback into actionable recommendations that inform Product and Engineering roadmap decisions.
Design, document, and continuously refine standardized onboarding playbooks, templates, and process workflows that enhance operational efficiency and enable the team to scale effectively as client volume increases.
Identify opportunities to accelerate time-to-value for clients by streamlining implementation steps, automating repetitive tasks, and introducing best practices gleaned from successful previous engagements.
Build lasting relationships with client stakeholders that extend beyond the onboarding phase, setting the foundation for robust ongoing partnerships and potential expansion opportunities.
Contribute to team knowledge sharing by mentoring junior specialists, leading internal training sessions, and documenting lessons learned from challenging implementations.
Requirements A minimum of five years of hands-on professional experience in customer-facing positions where operational excellence and client satisfaction were primary success metrics.
Undergraduate degree in business administration, human resources, communications, or a related discipline, though equivalent real-world experience will be considered for candidates with exceptional track records.
Demonstrated history of success in project management, program management, or client implementation roles, ideally within software-as-a-service companies or technology-driven organizations.
Exceptional ability to juggle multiple complex projects simultaneously, each involving numerous stakeholders with competing priorities and tight deadlines.
Native or near-native English fluency combined with polished written and verbal communication abilities that enable you to build rapport quickly and convey complex information clearly.




Self-directed work style characterized by strong personal accountability, creative problem-solving instincts, and a bias toward taking initiative rather than waiting for direction.
Comfort operating in ambiguous situations where processes may still be evolving and flexibility is essential.
Strong analytical capabilities that allow you to interpret client data, identify patterns, and make evidence-based recommendations.
Nice to have Previous professional experience within human resources technology, global mobility services, international payroll processing, or workforce management operations.
Familiarity with employment regulations across multiple jurisdictions or experience supporting multinational organizations with distributed teams.
Background working with employer-of-record models or professional employer organizations.
Additional language proficiency beyond English, particularly in languages relevant to key global markets.
Certification in project management methodologies such as PMP, PRINCE2, or Agile frameworks.
Experience with change management principles and helping organizations adopt new technologies successfully.
Skills & tools Pebl Global Work Platform (proprietary technology stack)
Project management methodologies and associated software tools
Stakeholder relationship management across organizational hierarchies
Cross-functional coordination and internal advocacy
Strategic client consultation and advisory services
Process documentation and workflow optimization
Data analysis and reporting
Training development and delivery
Practical notes The compensation package includes a comprehensive benefits suite featuring flexible paid time off policies that respect work-life balance, generous parental leave provisions for growing families, full health and dental insurance coverage, retirement savings programs with employer contributions, and participation in an employee equity incentive plan that allows you to share in the company's success.
Pebl maintains a hybrid working model in Toronto, offering flexibility while preserving opportunities for in-person collaboration with colleagues.
This role offers significant growth potential within a rapidly expanding company operating at the intersection of technology and global workforce solutions.
The organization is firmly committed to equal opportunity employment principles and evaluates all candidates based solely on qualifications and merit, without discrimination based on any protected characteristic.

#J-18808-Ljbffr

📌 Senior Customer Onboarding Specialist (Ontario)
🏢 Pebl
📍 Ontario