Manager, AI Chatbot Experience

Summary

Join Wealthsimple's Systems Design & Optimization Team as the Manager, AI Chatbot Experience! You will own the chatbot's performance, user experience, and continuous improvement, leading a dedicated team. Responsibilities include QA, testing, enhancing prompts and content, system integrations, vendor management, and collaboration with Product Management. This role requires a Bachelor's degree in a related field, experience in conversational AI and chatbot optimization, strong NLP understanding, API integration experience, and proven leadership skills. Wealthsimple offers competitive salary, top-tier health benefits, retirement savings matching, generous paid time off, wellness and professional development budgets, an international work program, and various employee resource groups.

Requirements

• 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

Responsibilities

• 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

Benefits

• 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