Director AI PLG

About WorkSpan The next era of growth is being driven by business interoperability. Cloud, genAI, solutions combining services and software- more and more, companies outpace their competition not just through building superior products, but by creating stronger partnerships, paths to market, and better business models for winning together. Cloud providers, service providers, tech partners and resellers are teaming up to win more deals together through co-selling. WorkSpan is building the world’s largest, trusted co-selling network. WorkSpan already has seven of the world’s ten largest partner ecosystems on our platform and $50B of customer pipeline under active management. AWS, Google, Microsoft, MongoDB, PagerDuty, Databricks and dozens of others trust WorkSpan to accelerate and amplify their ecosystem strategies. With a $30M series C and backing from world class investors Insight Partners, Mayfield, and M12, WorkSpan is poised to drive the future of B2B. Come be a part of it. Join our team for the opportunity to: ● Own your results and make a tangible impact on the business ● Develop a deep understanding of GTM working closely with leadership across sales & marketing ● Work with driven, passionate people every day ● Be a part of an ambitious, supportive team on a mission About the role: Key Responsibilities AI Infrastructure & Platform Strategy Design and maintain an AI technology stack that supports automated customer life cycles and product-led engagement. Unify customer data into a definitive system of record to power all automated communications and buyer journeys. Evaluate and implement AI tools and data constructs that solve specific friction points in the freemium and trial conversion process. Establish data pipelines and model governance to ensure reliable, scalable, and automated insights. PLG AI Enablement & Support Implement AI-driven experiences within the application to communicate directly with users based on real-time behavior. Develop AI-powered health monitoring and expansion strategies to drive engagement beyond the initial sales meeting. Scale operations through automation, focusing on "human-in-the-loop" workflows rather than managing a large manual team. Provide recommendations to product and marketing teams on building the foundation for new, automated GTM motions. Cross-Functional AI Strategy Serve as the AI subject matter expert, "charting the path" for growth by translating business requirements into technical AI solutions. Conduct a 90-day "listening tour" to map out current onboarding processes, data availability, and build customer empathy. Establish performance metrics and continuously optimize AI models based on business outcomes and ROI. Required Experience 5+ years in revenue, sales, or marketing operations with recent, hands-on experience implementing AI tools. PLG Background: Proven experience at a Product-Led Growth company, ideally at the Series C stage. Technical Acumen: Strong background in data analysis, aligning data models, and evaluating model performance. Mindset: Data-driven and experimentation-minded with specific experience in freemium/trial conversion models. Execution: A "scrappy" approach to execution with the ability to manage vendor relationships and lead change management.