Customer Support Specialist II

Customer Support Specialist II  

Function: Customer Experience  

Reports to: Manager, Customer Support  

Reviewed: 4.2026 

Location: Toronto Metro Area - Remote

Position Summary:  

• As Software Support Specialist Tier 2 for eScribe , 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 technical support experience in a SaaS or enterprise software environment, with at least 1 year of experience working in a Tier 2 capacity 

• 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  

AI Curiosity & Innovation

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:  

• Fully remote work with company provided equipment (laptop, software, etc.) 


• Employment with a growing, casual, fun, philanthropic minded company


• 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 
  
  


• CAN Based Employees
  
  
  • Employer paid Life and Accidental Death Insurance
  
  
  • Contribution to Health Care Spending Account
  
  
  • Dependent Life Insurance
  
  
  • Optional Life Insurance
  
  
  • LTD Insurance
  
  
  • Drug and Paramedical Coverage
  
  
  • Dental Insurance
  
  
  • Vision Insurance
  
  
  • EAP
  
  


• AUS Based employees
  
  
  
  • Superannuation rate of 12% 
  
  
  • Monthly stipend of $400 AUD to purchase private medical insurance 
  
  


• UK Based Employees (via EPG)
  
  
  
  • Pension - Aegon
    
    
    
    • Passageways/OnBoard contributes 8% of the employee's basic salary
    
    
    • Employees can contribute up to 100% of salary subject to max limits
    
    
    • Enrolled from Day 1 of employment
    
    
  
  
  • Private Medical Insurance
  
  
  • Life Assurance
  
  
  • Income Protection
  
  
  • Critical Illness
  
  
  • Employee Assistance Programme
  
  
  • Serious Illness Benefit
  
  
  • View email address on jobs.jobcopilot.com
  
  
  • Cashplan
  
  

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.

AI Use:
To ensure a fair and authentic assessment, the use of generative AI tools, real-time AI interview assistants, or third-party assistance is strictly prohibited during all stages of the interview process. Please note that all interviews will be recorded and securely stored for evaluation and training purposes. By applying for this position, you consent to these terms. If you require a reasonable accommodation due to a disability, please contact View email address on jobs.jobcopilot.com.