Customer Support Specialist II

Function: Customer Experience

Reports to: Manager, Customer Support

Reviewed: 12.2025

Location: Toronto Metro Area - Remote

Position Summary:

• As Software Support Specialist Tier 2 you will act as a subject matter expert on our platform, providing high-quality, second-line technical support for escalated customer issues. You'll troubleshoot complex technical problems, support cross-functional teams, and advocate for customer needs with Product and Engineering.

• The ideal candidate is customer-obsessed, highly technical, and thrives in a collaborative environment. You'll play a key role in ensuring our customers receive timely, effective, and thoughtful support that aligns with our commitment to a top-tier experience.

• Our current support hours are 8:30am – 8pm ET. You must be available to work a shift that falls within those hours. The team will rotate on-call shifts approximately 1 week/month. (8pm – 11pm ET).

Key Responsibilities:

• Technical Support & Troubleshooting

• Diagnose, troubleshoot, and resolve complex software and technical issues escalated from Tier 1 support.

• Investigate environmental factors affecting performance (e.g., networks, browser settings, APIs, integrations).

• Respond to customer inquiries via ticketing system, phone, and video conferencing.

• Document technical issues thoroughly, including steps to reproduce, system logs, and customer impact.

• Product Knowledge & Enablement

• Become an expert in our product suite, features, and customer use cases.

• Stay current with product updates and actively contribute to internal knowledge sharing.

• Create and maintain detailed documentation, internal troubleshooting guides, and customer-facing help articles.

• Customer & Cross-Functional Collaboration

• Act as a technical liaison between Customer Experience, Product, Engineering, and QA.

• Provide clear updates to customers and internal stakeholders on ticket status and resolution timelines.

• Participate in customer feedback loops to inform product enhancements.

• Support product release readiness and identify potential risks from a support perspective.

Skills and Experience Needed**:**

• 5+ years of Tier 2 technical support experience in a SaaS or enterprise software environment.

• 3+ experience in technical customer support tools like Zendesk, Azure DevOps, and CRM/ticketing platforms.

• 1+ experience with livestream platforms, encoders (OBS, Wirecast, vMix), and protocols (RTMP, HLS). is strongly preferred.

• Knowledge of AV and networking systems and troubleshooting (router settings, switch ports, troubleshooting VLAN, etc.)

• Knowledge of Microsoft SQL Server, Windows Server 2008-2016, IIS Web Server, HTML.

• Strong analytical, diagnostic, and troubleshooting abilities.

• Excellent communication skills with the ability to explain technical issues to non-technical audiences.

• Experience in cross-functional collaboration with Product, Engineering, and QA teams.

• Proven ability to prioritize and manage multiple issues in a fast-paced environment.

• Strong technical documentation and writing skills.

• Strong technical documentation &writing skills.

• Preferred: Demonstrated knowledge and hands-on experience with artificial intelligence tools and concepts (such as machine learning, NLP, or automation)

Competencies:

Accountability

Adaptability

Applied Learning

Business Acumen

Collaboration

Customer Focus

Dealing w/Ambiguity

Decision Making

Driving for Results

Initiating Action

Planning & Organizing

Technical/Professional Knowledge/Skills

About the company:

Boards set the standard for what organizations can achieve. At OnBoard, our board management software helps boards function at a higher level so every organization can make a bigger difference in the world.

Launched in 2011, today, OnBoard serves as the board intelligence platform for more than 5,000 organizations and their 12,000 boards and committees in 60 countries worldwide. With customers in higher education, nonprofit, healthcare systems, government, and enterprise business, OnBoard is the leading board management provider.

OnBoard has grown from a class project at Purdue University in West Lafayette, Indiana in 2003 into the world's leading board management software platform today. Backed by JMI Equity and the acquisitions of eScribe and Govenda, OnBoard is positioned to become the industry leader in Board Management and Meeting Solutions for private and public sector entities.

Benefits and Perks:

• Company provided equipment (laptop, software, etc.)
• Employment with a growing, casual, fun, philanthropic minded company
• Employer paid extended health benefits, including health spending account (CAN based employees)
• US Based Employees
  • Comprehensive, high-quality medical/prescription drug plan options, as well as dental and vision plan offerings.
  • An employer contribution to your Health Savings Account (HSA) if you participate in a High Deductible Healthcare Plan.
  • Medical Flexible Spending Accounts available.
  • Dependent Care Flexible Spending Accounts available.
  • Basic life insurance in the amount of $50,000 or 1 X's your salary (whichever is higher).
  • Short and long-term disability and Accidental Death and Dismemberment benefits at no cost to you.
  • 401K Retirement Savings Plan with automatic enrollment at the first of the month following 60 days of employment at 5% to help you secure your financial freedom. We offer a generous company match that starts on the first of the month following 60 days of employment. The company match is dollar for dollar on the first 3% of your pay that you contribute and $0.50 on the dollar on the next 2%, for a total match of 4%.
  • Paid Time Off (PTO)/Holiday

Diversity Statement - Culture of Togetherness:

At OnBoard, our mission is to encourage and celebrate a culture of togetherness. We acknowledge that uniqueness is powerful, and we welcome, foster, and appreciate all. Diversity, Equity, and Inclusiveness fuel the Pathfinder atmosphere and all our efforts. Our power is in our people and we Pledge 1% to give back to our communities and across the globe.

OnBoard is an equal opportunity employer and committed to a diverse and inclusive working environment. Passageways does not discriminate based on race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. For individuals with disabilities who would like to request an accommodation please email peopleops@passageways.com.