Tier 2 Technical Customer Support Specialist

We are looking for a technically skilled and customer-focused individual to join Rewind’s support team as a Tier 2 Technical Customer Support Specialist. The ideal candidate is analytical, proactive, and enjoys both solving technical challenges and helping teammates grow. You will play a key role in resolving escalated support cases while building automation tools, integrating systems into our Zendesk interface, and performing data analysis.

This is a full-time on-site position based in Toronto with potential growth to include on-call rotations, weekend support, and expanded hours of operation. Some work on statutory holidays may also be required.

About You

You have a relentless focus on the customer and do whatever you can to make sure their experience with Rewind is the best it can possibly be at all times. You possess the technical expertise to troubleshoot complex issues through a variety of methods including the usage of SQL to understand how to unblock customers and then work with our Tier 3 Customer Engineering team to document root cause issues for preventative work in the future. If you ever suspect an issue may be more easily or quickly resolved by jumping on a call, you won’t hesitate to offer one and work through issues real-time. Finally, you’re a player-coach who enjoys helping teach and guide others how to find information or resolve issues more effectively. 

A Typical Day:

Solving complex technical issues and working with customers: Dive into advanced problems and drive empathy with customers to provide outstanding levels of customer service.

• Investigating and resolving escalated tickets that require complex troubleshooting techniques including but not limited to running SQL queries, executing scripts and more

• Engaging directly with customers via email, live chat, or phone to guide them through technical resolutions.

• Breaking down technical concepts into clear, digestible steps, personalizing communication to ensure customer understanding.

• Using empathy and active listening to build strong relationships with customers, ensuring they feel supported throughout their journey with Rewind.

Supporting Tier 1 agents and documenting processes: Act as a mentor and resource for your teammates while sharing knowledge with the broader team.

• Providing guidance and troubleshooting support for Tier 1 agents as they work through customer issues, helping them learn along the way.

• Assisting in documenting technical processes and creating knowledge base content to ensure Tier 1 agents can handle a broader range of issues independently.

• Offering input on best practices for handling complex cases and system workflows, ensuring consistency across the team.

• Building scripts to automate repetitive tasks and improving the efficiency of support workflows.

• Identifying and integrating additional tools into our Zendesk interface, improving agent efficiency and customer experience.

• Analyzing support data to uncover trends, optimizing processes, and delivering insights to management.

Collaborating with internal teams and customers: Work closely with Product, Engineering, and customers to ensure smooth resolutions.

• Collaborating with the Tier 3 and Engineering teams on issues that require deeper technical expertise and development knowledge.

• Escalating high-priority or complex technical cases when needed, while keeping customers informed and engaged throughout the process.

• Gathering feedback from customers and internal stakeholders to continuously improve the support process and product experience.

We are looking for candidates who have 2-4 years of experience in an elevated customer support or technical support role, preferably in the B2B SaaS or tech startup space.

You are:

• Collaborative and proactive team player, eager to mentor and contribute to the continuous improvement of the team.
• Excellent verbal and written communicator with ability explaining technical concepts to both customers and team members.
• Customer-centric, passionate about delivering exceptional service and maintaining long-term relationships.
• Able to work evenings, weekends, and public holidays when required, with flexibility to meet business needs.

You have:

• Experience running SQL queries, working with APIs, and developing automation scripts
• Familiarity with customer support systems like Zendesk or Salesforce, with experience integrating tools or optimizing workflows.
• Strong problem-solving and troubleshooting skills, with the ability to simplify complex technical issues.
• Proficiency in Apple/Mac OS, Google Suite, and experience with CRM and support tools such as Zendesk or Salesforce.
• Ability to manage a high volume of work, prioritize tasks, and work efficiently in a fast-paced environment.

Nice to have: 

• A CS degree or a completed bootcamp with exposure to Ruby-on-Rails
• Familiarity with programming languages for automating tasks and integrating tools into support workflows

Where You’ll Work
This role will be based out of our Ottawa or Toronto Office.  

How Rewind Will Support You
We know that enjoying the journey is just as important as reaching our goals. We work hard to create a positive, inclusive environment where fun and laughter are part of our everyday routine. We also offer a variety of benefits to support your success both at work and in your personal life which includes but is not limited to: 

• Flexible working hours 
• Employee stock options
• Health benefits
• 3 weeks vacation
• 7 life leave days
• 2 Level Up days for professional development
• 1 volunteer day
• Summer hours (off every other Friday from June - September) and office closed during the holiday break in December
• 4 week sabbatical after 4 years with us
• Paid parental leave
• $5000/year professional development allowance (you can take courses, buy books, attend conferences, cover certifications, etc)
• $1000/year wellness/home office allowance

Rewind is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career. We value how each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. We strongly encourage candidates of all different backgrounds and identities to apply.