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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