Manager - AI Chatbot Experience

Your career is an investment that grows over time!

Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 4 million users who trust us with more than $50 billion in assets.

Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.

The Systems Design & Optimization Team is responsible for managing the various systems within the Customer Experience Operations organization including but not limited to: Zendesk, Five9, and our client-facing AI chatbot. This team is responsible for ensuring that our CS workflows are streamlined and efficient, facilitating a seamless experience for both our Clients and our internal teams.

About the Manager, AI Chatbox Experience role:

• As the Manager, AI Chatbot Experience, you will take full ownership of the chatbot's performance, user experience, and rapid ongoing improvement

• You will lead a dedicated team that is ultimately responsible for ensuring high-quality client responses and seamless integrations with our other CXO systems and tools

• Responsibilities of this role and team include but are not limited to:  Continuous QA, testing, and “bot bashing”, making enhancements to underlying prompts and content, integrating the chatbot with other systems and platforms, ongoing vendor management and, collaborating with Product Management on the entirety of the chatbot experience 

• This position offers a unique opportunity to shape and refine our chatbot’s role in delivering exceptional user experiences and driving business value.

As the Manager, AI Chatbox Experience, you will:

• Own the end-to-end chatbot experience. Define and implement a strategic roadmap for the chatbot to align with organizational goals and user needs. Continuously test, monitor and analyze chatbot conversations and performance metrics to identify areas for improvement and innovation.

• Manage and mentor a team conducting continuous quality assurance (QA) to ensure chatbot responses are accurate, consistent, and aligned with brand voice.

• Optimize chatbot prompts and content. Oversee the development, testing, and refinement of chatbot prompts and underlying content to enhance conversational quality. Collaborate with cross-functional teams (e.g., marketing, product, and support) to align with broader business initiatives.

• Configure and maintain integrations between the chatbot and other platforms, tools, and systems to enhance functionality and provide seamless experiences. Work closely with vendors and internal development teams to ensure technical stability and compliance with security standards.

• Serve as the primary point of contact for chatbot vendors, negotiating contracts, managing budgets, and ensuring delivery of agreed-upon services. Stay informed about vendor updates, new features, and emerging technologies to identify opportunities for innovation.

• Drive continuous improvement Gather user feedback and translate insights into actionable improvements. Stay updated on industry trends, best practices, and emerging technologies to maintain a competitive edge in chatbot experience design.

What you bring:

• Bachelor’s degree in Computer Science, Information Systems, Business Administration, or a related field

• Experience and passion for conversational AI, chatbot optimization, product management, or a related field

• Strong understanding of natural language processing (NLP) concepts and frameworks

• Demonstrated experience in configuring API integrations and managing technical implementations

• Analytical mindset with experience leveraging data to drive decision-making

• Excellent communication, organization and stakeholder management skills

• Experience in vendor management, including contract negotiations and performance monitoring

• Proven leadership experience with the ability to manage and motivate a team

Why Wealthsimple?

🤑 Competitive salary with top-tier health benefits and life insurance

📈 Retirement savings matching plan using Wealthsimple Work

🌴 20 vacation days per year and unlimited sick and mental health days

📚 Up to $1,500 per year towards wellness and professional development budgets respectively 

🛫 90 days away program: Employees can work internationally in eligible countries for up to 90 days per calendar year 

🌎 A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)

💖 Company-wide wellness days off scheduled throughout the year

We’re a remote-first team, with over 1,000 employees coast to coast in North America. Be a part of our Canadian success story and help shape the financial future of millions — join us!

Read our Culture Manual and learn more about how we work.

DEI Statement

At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. 

Accessibility Statement

Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.