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're looking for a

Technical Support Specialist

who thrives on helping others, solving technical challenges, and delivering an exceptional client experience. In this role, you’ll serve as the frontline connection between Rentsync and our clients—providing support for our platform, rental websites, and data feed integrations. You'll engage with customers via email, phone, and video calls, and work closely with internal teams to resolve complex issues. The ideal candidate is a technical problem-solver passionate about customer success, demonstrating curiosity, coachability, and an entrepreneurial spirit, alongside resilience and accountability. Exceptional service and teamwork are fundamental. If you have a strong technical aptitude and a passion for customer success, we encourage you to apply. This role is a fixed-term contract position with a duration of

18 months

, with potential to convert to a permanent position at the end of the contract. 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 Rentsync’s office 2 days per week. Duties & Responsibilities Act as the

frontline support team

, handling inbound client inquiries while supporting and collaborating with all internal departments Respond to client inquiries via email, chat, phone, and video while meeting SLA targets Troubleshoot platform, website, data feed, and integration issues to ensure timely and effective resolution Partner with cross-functional teams (Product, Engineering, Sales, and Client Services) to resolve complex technical issues Educate clients on platform functionality, best practices,



and new features Support website quality assurance processes and assist with small implementation projects Gather and relay customer feedback to inform platform improvements and service enhancements Monitor client health and usage to make proactive, value-driven recommendations Assist with additional client support responsibilities as needed Perform other duties as assigned Required Knowledge, Skills & Abilities Advanced knowledge of internet technologies and web-based tools A solutions-oriented mindset with excellent listening and problem-solving skills Exceptional written and verbal communication abilities Strong attention to detail with excellent organizational skills Ability to work independently while contributing effectively to a collaborative team Ability to quickly learn and adapt to recent platforms, tools, and processes Comfort navigating software from the client's perspective with empathy and user-focused thinking Essential Qualifications 2+ years of experience in technical support or customer success, ideally within a SaaS, tech, or agency environment Strong technical understanding, with background or exposure to

data, code-related concepts, integrations, APIs, or web technologies Additional Preferred Qualifications Knowledge of the rental housing industry Experience supporting a CMS, property management system, or other rental industry platform Preferential consideration will be given to candidates who can report to one of Rentsync's regional offices 2 days/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. This is an open-ended job posting and may not represent a specific vacancy within the organization. Rentsync reserves the right to use Artificial Intelligence to screen and/or assess candidates.

#J-18808-Ljbffr

📌 Technical Support Specialist (Winnipeg)
🏢 Rentsync
📍 Winnipeg