Customer Services Representative – Toronto

Location: Toronto, Canada – office-based

Vacancies: Two

Hours: One position from 9:00 AM to 6:00 PM and one from 10:00 AM to 7:00 PM

About Sterling

Sterling is a subsidiary of TransPerfect and serves as TransPerfect’s Virtual Data Room division.

We provide secure technology and specialist support for M&A;, due diligence, and other complex business transactions. Our clients rely on Sterling to manage and share sensitive information securely, often under significant time pressure.

We are expanding our Toronto team and looking for two Customer Services Representatives. This is a good opportunity for someone who enjoys working directly with clients, is comfortable with technology, and takes pride in solving problems and delivering excellent service.

The Role

As a Customer Services Representative, you will provide technical and operational support to clients and users of the Sterling Virtual Data Room platform.

You will help users navigate the platform, respond to support requests, deliver online training, and assist with important VDR workflows. You will also work closely with internal teams across different regions to make sure client requests are handled accurately and on time.

Our Toronto office serves as a North American Client Services hub, supporting users across the United States, Canada, LATAM, Europe, and other regions as required.

Your Responsibilities

- Support clients and users by phone and email.
- Advise clients on VDR processes and workflows.
- Help users with access, permissions, document management, Q&A;, reporting, and other platform features.




- Investigate support requests and escalate technical issues when required.
- Deliver online client training sessions.
- Take ownership of multiple client engagements and follow requests through to completion.
- Build positive and professional relationships with clients.
- Anticipate client needs and respond proactively.
- Coordinate with internal teams in different regions.
- Monitor progress and ensure client deliverables are accurate and completed on time.
- Maintain accurate records of client interactions, support requests, actions, and follow-up requirements.
- Keep job-tracking and billing information current and accurate.
- Follow established best practices and workflow procedures.

What We’re Looking For

- At least two years of experience in a B2B environment.
- Fluent English with excellent written and verbal communication skills.
- Confidence communicating with a wide range of business clients.
- Strong technical aptitude and the ability to learn new software quickly.
- Excellent attention to detail, accuracy, and active listening skills.
- The ability to manage several requests, work under pressure, and meet deadlines.
- A positive, practical approach and a willingness to take ownership.
- An interest in learning, developing, and building current skills.
- Previous experience in technology, software, or IT would be useful but is not required. Full training will be provided.

You must be based in or near Toronto and able to work from TransPerfect’s Toronto office each day. You must also be available for either the 9:00 AM–6:00 PM or 10:00 AM–7:00 PM schedule.

📌 Customer Service Representative (Toronto)
🏢 Sterling Technology | Virtual Data Rooms
📍 Toronto