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Senior Manager, Web Strategy & AI Experience

AppDirect - Toronto, ON, Canada - In-office - posted 2026-09-11

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Salary: CAD 129,000 - 161,000 / annual

AppDirect is a subscription commerce platform enabling digital entrepreneurs worldwide to sell any product through any channel on any device as a service. The company powers millions of subscriptions globally and operates with a values-driven culture. As Senior Manager of Web & AI Experience, you will lead the strategy, roadmap, and execution of AppDirect's corporate website and cornerstone sales and marketing applications. You'll manage a small, agile web development team responsible for end-customer and partner experiences, transforming the team to adopt an AI-first mentality. Key responsibilities include: - Owning the strategy and execution of AppDirect's corporate website and sales/marketing applications, ensuring alignment with business goals and measurable outcomes - Leading AI integration across team workflows—identifying, testing, and implementing tools for development acceleration, content generation, prototyping, and UX personalization - Driving LLM-aware content strategy (AEO/GEO) and SEO to ensure discoverability by both human audiences and AI systems - Managing and mentoring web developers working with latest AI and web technologies, setting performance standards and supporting professional development - Partnering with design and UI teams to evolve the component library and design system for consistency, accessibility, and responsiveness - Improving site performance through technical optimization, structured data, experimentation, and conversion testing - Leveraging AppDirect's proprietary AI platform (devs.ai) and leading vibe-coding environments to unlock creative and technical potential This is a highly cross-functional role requiring close collaboration with marketing, technical teams, product, and leadership to deliver measurable strategic outcomes. You'll blend strategic thinking with hands-on execution, balancing roadmap development with technical problem-solving. Requirements: - 5+ years of experience leading web strategy, design, or digital product management, ideally in a B2B SaaS environment - Hands-on experience with common web technologies including React, Next.js, web infrastructure, vibe-coding tools, and database/CMS systems - Demonstrated experience integrating AI tools into development or content workflows, including LLM-driven coding tools (e.g., Cursor, Lovable, devs.ai) - Proven experience with technical SEO, performance optimization, structured data, and LLM-aware content strategies - Experience managing technical teams and driving cross-functional initiatives with product, design, and marketing stakeholders - Strong communication skills to translate complex technical decisions into clear direction for non-technical partners and senior leadership - Comfort with ambiguity and iterative working practices, as the AI landscape shifts rapidly and requires continuous tool and approach evaluation

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