Onboarding Specialist

About Rentsync:
Rentsync is an award-winning, high-growth organization that provides high quality websites, marketing services, and software solutions to the rental and property management industry throughout Canada and the United States.

About the Role:

We are looking for a new Onboarding Specialist to join our Customer Success team. You’ll own the full client onboarding lifecycle, and you’ll also help build and improve the processes that make onboarding scalable, manage client relationships, and identify and close expansion opportunities

This is a great opportunity for you if you are a strong communicator with technical competence. We value curiosity and a builder mentality. If you default to automation, use AI tools in your daily work, and get excited about the challenge of improving existing processes into more efficient, repeatable playbooks, this role was built for you!

This is a hybrid/remote position, all qualified candidates are encouraged to apply, however preferential consideration may be given to individuals who can report to one of Rentsync’s regional offices (located in Toronto, St. Catharines and Montreal) 2 days per week on average.

Duties & Responsibilities:

Client Onboarding

• Own and execute full-cycle client onboarding from kickoff to go-live, ensuring timely implementation and accurate platform configuration.
• Deliver structured platform training sessions to new clients and provide refresher sessions as needed.
• Translate client needs into onboarding plans aligned with platform best practices and client timelines.
• Troubleshoot onboarding-related platform issues in collaboration with Support and Product.
• Collect and maintain all required documentation for client KYC (Know Your Customer) compliance.
• Identify and escalate risks, blockers, or delays in the onboarding pipeline to the department head proactively.
• Ensure clear documentation and context are handed off to support ongoing client needs after onboarding is complete.

Process Building & Operations

• Design, document, and continuously improve onboarding workflows, templates, and playbooks to increase consistency and reduce cycle time.
• Maintain data quality and pipeline accuracy across all active onboarding accounts.
• Create and update client-facing onboarding documentation, knowledge base articles, how-to guides, and self-serve resources.
• Identify opportunities to automate or streamline recurring onboarding tasks using AI tools, scripts, or platform features.

Expansion & Account Management

• Identify, demo, and close upsell and expansion opportunities (new features, add-ons) during onboarding, with proper documentation and communication of the sale.
• Track and report onboarding progress across multiple accounts using internal tools and dashboards.
• Collaborate with Sales, Product, and Support to position clients for long-term success and retention.

Required Knowledge, Skills & Abilities

• Comfortable using AI tools (e.g., ChatGPT, Claude, Copilot, or equivalent) as part of your daily workflow to move faster, draft content, analyze data, or solve problems.
• Strong organizational skills with the ability to manage multiple concurrent onboarding projects without dropping context.
• Clear, professional communication skills (written and verbal) with the ability to train non-technical users on a software platform.
• Technical curiosity and a willingness to get hands-on. You're comfortable reading API documentation, troubleshooting platform configurations, writing basic formulas or scripts, and working directly with data to identify patterns or solve problems. 
• Comfort operating in an environment where scope shifts, priorities change, and people wear multiple hats.

Essential Qualifications

• 2+ years in a client-facing onboarding, implementation, or customer success role within a SaaS environment.
• Demonstrated experience building or improving operational processes.
• Legally entitled to work in Canada

Additional Preferred Qualifications

• Bilingual fluency in English and French (written and spoken).
• Experience with property management, real estate, or proptech platforms.
• Experience working with CRM, pipeline management, or project tracking tools
• Able to work at one of Rentsync's regional offices 2 days per week on average

Rentsync is an equal opportunity employer. If you are selected to participate in the interview process and require unique accommodations, please don’t hesitate to let us know. 

Successful candidates may be required to complete a criminal background check in the final phase of the interview process.