Technical Operations Lead

We are looking for a full-time Technical Operations Lead .

As Technical Operations Lead, you will be accountable for the effective operation, continuous improvement, and evolution of the Technical Operations function supporting CanadaHelps’ B2B, D2C, and CHE platforms and internal tools.

This is a player-coach role that combines hands-on technical and operational work with strategic ownership, requiring you to remain close to day-to-day issues while also identifying broader opportunities to improve how our products, processes, and operations function.

You will work closely with Product, Engineering, DevOps, QA, Data, Customer Support, Customer Success, and other stakeholders to investigate and resolve complex issues, identify customer and operational trends, manage risk, and drive improvements.

You will serve as a key advocate for customers and frontline teams, ensuring operational insights and customer-impacting issues are effectively represented in product and technology decisions.

With a small team, this role requires a high degree of autonomy, judgment, and ownership.

The successful candidate will be comfortable moving between tactical problem-solving and strategic thinking—investigating an issue, identifying the broader operational or customer impact, bringing the right stakeholders together, and driving the issue or opportunity through to resolution or improvement.

The annual salary range for this role is $67,000 - $72,000.

Where an offer falls within this range is determined through the interview process.

Candidates are benchmarked by the hiring team based on role scope, relevant experience, skill alignment, and expected impact, using consistent and objective criteria.

This is an existing vacancy.

This position is remote but may require to be in-office in Toronto for team collaborations.

Responsibilities will include but are not limited:

• Own the day-to-day effectiveness and health of Technical Operations across B2B, D2C, CHE, and relevant internal tools. Act as a senior escalation point for complex technical, product, and operational issues, driving investigation and resolution with the appropriate internal teams and external partners.
• Proactively monitor operational trends, recurring issues, escalations, and customer-impacting problems to identify patterns, risks, and opportunities for improvement. Ensure risks and dependencies are identified early and that appropriate mitigation or contingency plans are established.
• Coordinate Technical Operations’ participation in significant incidents, ensuring appropriate escalation, cross-functional communication, documentation, and follow-up. Maintain strong working knowledge of CanadaHelps’ products, systems, workflows, and operational dependencies.

• Serve as a key operational partner to Product, Engineering, DevOps, QA, Data, and customer-facing teams by bringing forward meaningful customer and operational insights that can inform product decisions, priorities, and improvements.
• Identify recurring customer and operational pain points and help translate them into clearly defined problems, requirements, or opportunities for improvement. Advocate for customer and operational needs during product and technology discussions while balancing customer impact, business priorities, technical considerations, and operational sustainability.
• Manage weekly & bi-weekly meetings with QA, DevOps, and Product teams to ensure appropriate team members are attendees. Ensure team members are actively participating and bringing necessary tickets onto the radar.
• Participate in relevant product discovery, planning, testing, releases, and post-release evaluation. Identify operational impacts, edge cases, risks, dependencies, and support requirements associated with proposed product and technology changes.

• Analyze operational data, including Salesforce cases, Jira activity,Aha! Ideas, incidents, recurring issues, and other available sources, to identify trends and opportunities to improve customer experience, efficiency, and scalability.
• Lead and contribute to initiatives that simplify, standardize, automate, or eliminate inefficient operational processes. Identify opportunities to reduce recurring support demand through product improvements, automation, self-service, documentation, or process changes.
• Continuously evaluate existing tools, workflows, and processes to ensure they remain effective and fit for purpose as CanadaHelps’ products, technology, and operating model evolve.

• Identify and escalate operational, customer, financial, privacy, fraud, compliance, and technology risks relevant to Technical Operations. Partner with appropriate stakeholders to assess risks, establish mitigations, and strengthen operational controls.
• Support the development and maintenance of escalation paths, decision frameworks, contingency plans, and operational controls for significant issues and incidents. Contribute to post-incident reviews and other follow-up activities to identify systemic improvements and reduce the likelihood of recurrence.

• Own the quality, accuracy, and sustainability of Technical Operations documentation, processes, training materials, and knowledge resources. Ensure operational changes are reflected in documentation and communicated effectively to impacted teams.
• Identify knowledge gaps and opportunities to improve internal enablement and customer self-service. Support the adoption and effective use of new support, automation, AI, and operational tools.

• Lead, coach, and develop the Technical Operations team by establishing clear expectations, priorities, and development objectives. Remain hands-on in the work and provide subject-matter expertise, coaching, and support on complex issues.
• Identify opportunities to strengthen team capabilities, knowledge coverage, and operational resilience. Support recruitment, onboarding, performance management, and professional development as required.

• Partner with the Senior Director, CX & Operations and cross-functional leaders on strategic operational and technology initiatives. Lead or contribute to initiatives that improve scalability, customer experience, operational efficiency, risk management, technology adoption, and organizational effectiveness.
• Assess the operational implications of organizational, product, and technology changes and help establish practical implementation and change-management plans. Bring forward opportunities where Technical Operations can create greater organizational leverage through automation, AI, self-service, process redesign, or other approaches.

• 4–5+ years of experience in technical operations, technical client services, business operations, digital operations, technology, eCommerce, SaaS, or a related environment.
• Minimum 2 years of experience in a supervisory or leadership role.
• Experience working cross-functionally with Product, Engineering, QA, DevOps, Data, Customer Support, Customer Success, or similar technical and operational teams.
• Experience investigating complex issues, identifying contributing factors, and coordinating resolution across multiple stakeholders.

identifying process improvement opportunities and translating them into practical operational or technology solutions.

• Strong technical aptitude and the ability to understand complex systems, workflows, integrations, and dependencies.

with Jira, Salesforce, Google Workspace, and an aptitude for learning new systems and technologies.

• Strong analytical and problem-solving skills, with the ability to use operational data to identify trends, patterns, risks, and opportunities.
• Strong verbal and written communication skills, with the ability to communicate technical and operational information clearly to both technical and non-technical audiences.
• Demonstrated ability to influence stakeholders without direct authority, advocate effectively for customer and operational needs, and build strong cross-functional relationships.
• Strong prioritization and judgment, with the ability to distinguish urgent issues from systemic problems and balance immediate operational needs with longer-term improvements.
• A continuous improvement mindset, with a demonstrated interest in simplifying processes, increasing scalability, reducing unnecessary work, and exploring opportunities through automation, AI, self-service, and technology.
• Experience leading or coordinating projects, initiatives, incidents, or other cross-functional work is an asset. Familiarity with Agile product development and collaboration with Product and Engineering teams is an asset.

We believe in everyone

At CanadaHelps, we commit to pursuing deliberate efforts to ensure that our company is a place where differences are welcomed, different perspectives are respectfully heard and where every individual feels a sense of belonging and inclusion .

We know that by creating a vibrant climate of inclusiveness, we can more effectively advance our collective capabilities.

AI in Recruitment :

CanadaHelps does not use AI-enabled tools to screen, assess, rank, or select candidates in our recruitment process.

Our hiring teams make all hiring decisions.