Director, AI Strategy & Enablement

Taskrabbit • San Francisco, CA

3h • $180,000 - $250,000 • Hybrid

About The Position

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.
The Director of AI Strategy and Enablement will be a critical leader in developing, championing, and executing Taskrabbit’s AI strategy, governance, and priority use cases across all functions. This role reports directly to the CEO and serves as a strategic thought partner to the Senior Leadership Team on all AI efficiency and productivity initiatives. You will lead the company’s most critical cross-functional AI initiatives from concept to execution, working closely with the CEO and SLT. This leader is not only highly analytical, execution-oriented, and hands-on, but also technically strong. You will be responsible for turning AI strategy into measurable outcomes by identifying and prioritizing high-impact use cases. You’ll build AI-based solutions and teach others how to scale this way of working.
You also have a bias for action, an appetite for risk and innovation, and a passion for AI tools. You use and test them regularly and are seen as an expert in the domain. You’re able to ideate at the executive level, build a plan, orchestrate workstreams across departments, and personally drive initiatives to completion.

Requirements

• 15+ years in technology, innovation, or transformation roles, with 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.

Responsibilities

• Develop and execute AI strategy, partnering with the Senior Leadership Team to ensure alignment across all initiatives. You will create clarity in uncertainty by translating complex AI trends into actionable strategies that align with business priorities.
• 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, incorporating the latest innovations in AI and identifying opportunities where AI can help accelerate strategic business priorities.
• 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 by building AI solutions across the organization
• Lead the establishment and execution of operational frameworks and governance, ensuring cross-functional communication and integration across functions. Evaluate tools that will help the company scale more effectively.
• 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, inspiring resilience and continuous improvement.
• Stay current on AI trends and implement relevant technologies (e.g., LLMs, RPA, ML platforms).
• 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 across the organization.

Benefits

• Taskrabbit is a Hybrid Company. We value flexibility and choice but also stay committed to regular in-person connection.
• The People. You will be surrounded by some of the most talented, supportive, smart, and kind leaders and teams -- people you can be proud to work with!
• The Diverse Culture. We believe that we make better decisions when our workforce reflects the diversity of the communities in which we operate. Women make up half of our leadership team and our diversity representation is above that of the tech industry average.
• The Perks. Taskrabbit offers our employees with employer-paid health insurance and a 401k match with immediate vesting for our US based employees. We offer all of our global employees generous and flexible time off with 2 company-wide closure weeks, Taskrabbit product stipends, wellness + productivity + education stipends, IKEA discounts, reproductive health support, and more. Benefits vary by country of employment.

What This Job Offers

• Job Type: Full-time
• Career Level: Director