WorkSpan

Director AI PLG

WorkSpan

full-time

Posted on:

Location Type: Remote

Location: United States

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Job Level

Lead

About the role

  • 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
  • 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
  • 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

Requirements

  • 5+ years in revenue, sales, or marketing operations with recent, hands-on experience implementing AI tools
  • Proven experience at a Product-Led Growth company, ideally at the Series C stage
  • Strong background in data analysis, aligning data models, and evaluating model performance
  • Data-driven and experimentation-minded with specific experience in freemium/trial conversion models
  • A 'scrappy' approach to execution with the ability to manage vendor relationships and lead change management
Benefits
  • 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
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
AI technology stackdata pipelinesmodel governanceAI toolsdata analysisfreemium conversion modelsautomated communicationsAI-driven experienceshealth monitoring strategiesperformance metrics
Soft Skills
data-drivenexperimentation-mindedscrappy executionvendor relationship managementchange managementcustomer empathyrecommendation skillscommunicationleadershiporganizational skills