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Director, AI Strategy & Enablement

United States, New York 180000.00 - 250000.00 USD / Year · Job Posted February 18, 2026
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Job Description

We are seeking a visionary technology leader to define, drive, and execute our company-wide AI strategy and enablement. This role is pivotal in transforming how we work, serve customers, and deliver value through the integration of AI, automation, and intelligent workflows. It supports not only our employees and their ability to use AI, but also our clients and Taskers, as we increasingly leverage AI across our Product teams to improve the user experience. You will operate cross-functionally to identify opportunities, build capabilities, and embed AI-driven thinking into the company’s strategic and operational core.

Job Responsibility

  • Develop and execute AI strategy, partnering with the Senior Leadership Team to ensure alignment across all initiatives
  • Partner with process owners and functional leaders to reimagine workflows using AI, automation, and intelligent decisioning
  • Assist teams in identifying, enabling, testing and scaling commercial opportunities via AI
  • Communicate to inspire action by evangelizing AI’s potential across Taskrabbit, influencing stakeholders at all levels, and fostering a culture of innovation and responsible enablement
  • Support functional and business unit leaders in developing and continually refreshing their AI strategies
  • Apply your expertise in Machine Learning, Data, Generative AI, and Agentic AI, to contribute to innovative solutions to drive individual productivity across Taskrabbit and functional efficiencies
  • Lead the establishment and execution of operational frameworks and governance
  • Monitor, analyze, and report on the progress and impact of AI initiatives
  • Directly lead a small team and indirectly lead broader teams through ambiguity and change
  • Stay current on AI trends and implement relevant technologies
  • Identify high-impact opportunities, pilot solutions, and scale successful initiatives
  • Define and track metrics to measure the value and ROI of AI initiatives
  • Serve as a trusted advisor to executives and educate teams on AI’s role and value
  • Establish AI ethics, security, and compliance guidelines in partnership with Legal, Security, and Data Governance
  • Define ways to scale the use of AI tools across the company, including partnering with the L&D team on training

Requirements

  • 15+ years in technology, innovation, or transformation roles
  • 3–5 years in AI/ML or intelligent automation
  • Proven success in implementing enterprise AI strategies that deliver measurable business value
  • Strong foundation in business process engineering and automation platforms
  • Highly skilled with AI technologies, including NLP, generative AI, ML, and computer vision
  • Experience collaborating across business, engineering, and product teams
  • Executive presence and ability to influence at all levels
  • Knowledge of AI ethics and governance frameworks is a must
  • Bachelor’s degree in Computer Science, Engineering, Data Science, Business, or related field
  • Broad passion for and understanding of emerging technologies in AI/ML
  • Effective project management and teamwork skills, with the ability to communicate across multiple management levels and thrive in cross-functional settings

What we offer

  • Employer-paid health insurance
  • 401k match with immediate vesting
  • Generous and flexible time off
  • 2 company-wide closure weeks
  • Taskrabbit product stipends
  • Wellness + productivity + education stipends
  • IKEA discounts
  • Reproductive health support

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