AI Automation Senior Lead

About Taskrabbit: Taskrabbit is a marketplace platform that conveniently connects people with Taskers to handle everyday home to-do’s, such as furniture assembly, handyman work, moving help, and much more. At Taskrabbit, we want to transform lives one task at a time. As a company we celebrate innovation, inclusion and hard work. Our culture is collaborative, pragmatic, and fast‑paced. We’re looking for talented, entrepreneurially minded and data‑driven people who also have a passion for helping people do what they love. Together with IKEA, we’re creating more opportunities for people to earn a consistent, meaningful income on their own terms by building lasting relationships with clients in communities around the world. Taskrabbit is a hybrid company with employees distributed across the US and EU and a Built In — Best Places to Work (2022, 2023, 2024) continually ranked across multiple national and regional categories. Join us at Taskrabbit, where your work will be meaningful, your ideas valued, and your potential unleashed! This is a hybrid role that will sit out of our San Francisco office. Hybrid in‑office Tuesdays and Wednesdays of each week. About the Role We are looking for a builder to help lead our ‘AI for Work’ efforts. Together with the Director of AI Strategy and Enablement, you will build the internal AI infrastructure that makes our teams more efficient. That means building, evaluating vendors, and continuously evolving the AI systems our teams run on with the goal of maximizing every person’s efficiency and scaling our ability to deploy agents across the business. You will embed directly within business functions across the organization, deeply understand how teams operate today, and fundamentally reimagine how they should operate tomorrow. This is not about bolting automation onto existing processes; it’s about redesigning how work gets done with agentic tooling transforming (and eliminating) workflows. You will partner with leaders across the business to surface high‑impact opportunities, architect intelligent solutions, and deliver measurable gains in productivity, output quality, and the experiences we deliver to our employees. You will define what "AI-native operations" looks like inside Taskrabbit. As the AI Productivity and Business Automation Lead, you will also own a critical role in scouting, evaluating, testing, and piloting third‑party AI tools to unlock significant productivity gains across Taskrabbit. You’ll work closely with the Director of AI Strategy and Enablement and functional leads to map high‑value process bottlenecks and identify AI solutions. You’ll also help create structured experiments and pilot programs that demonstrate measurable business impact. In addition, you’ll help bring cutting‑edge AI technology into practical application, supporting implementation and tracking success to drive our AI Strategic Plan. You will be responsible for "mining" the business for efficiency opportunities while simultaneously helping to build the centralized orchestration layer that ensures our enterprise AI spend is governed, consistent, and scalable. This is a high‑impact IC role designed for a "scrappy builder" who thrives on turning internal complexity into streamlined, automated excellence. What You Will Do: Partner multiple functional leaders to define new standards for how teams operate in an AI‑augmented environment. Reporting to the Director of AI Strategy and Enablement, you will establish the "AI-first" baseline for daily execution, ensuring that ways of working are clearly defined and consistent across all non‑engineering functions. Conduct structured discovery, shadowing teams, interviewing stakeholders, and mapping end‑to‑end processes, to identify where AI can eliminate, redesign, or dramatically accelerate work. Embed within internal business functions to develop a deep, firsthand understanding of current workflows, pain points, and decision‑making processes to map high‑value process bottlenecks. Reimagine workflows from first principles rather than automating existing steps; challenge assumptions about what requires human involvement and what doesn’t. Design, build, and deploy AI‑powered automations, agents, and internal tools that reduce time spent on repetitive, low‑value‑add tasks while improving the quality and consistency of outputs. Integrate large language models, agentic frameworks, and automation platforms into internal workflows with appropriate guardrails, error handling, and human‑in‑the‑loop checkpoints. Measure everything: establish baselines before intervention, track adoption and usage patterns post‑deployment, and quantify productivity impact in terms of hours saved, error rates reduced, and cycle times compressed. Serve as a trusted advisor to functional leaders on what AI can and cannot do for their teams; translate business problems into technical solutions and technical constraints into business language. Stay abreast of the rapidly evolving AI tooling landscape (e.g., LLM capabilities, orchestration frameworks, RPA‑to‑AI convergence, no‑code/low‑code platforms) and calibrate our internal stack accordingly. Build reusable patterns, templates, and playbooks so that successful automations in one function can be adapted and scaled across others. Collaborate closely with the engineering and product organizations to ensure internal automation efforts align with our broader technology strategy and do not create shadow IT risk. Help to define the framework for evaluating the success and health of our workforce transformation. You will determine the key signals that demonstrate progress, partnering with Finance and Data Science to ensure that operational shifts deliver validated value to Taskrabbit. You will focus on moving beyond tool adoption to fundamental change, ensuring our teams are positioned to focus on high‑value, high‑judgment work that drives enterprise performance. Beyond individual projects, you will focus on helping to build the mindset and capability for teams to lead their own evolution. You will create the models that allow the organization to stay agile, ensuring the workforce can continuously adapt as technology and market conditions change. Skills Required: Educational Foundation: You hold a Bachelor’s degree in Computer Science or a comparable technical field, with demonstrated interest in Business Analytics, Finance, Data Science, applied AI, or related disciplines. Experience: You bring 5+ years of professional experience, including 1–2 years of direct, relevant experience in AI, data, or analytics‑driven roles. GenAI Fluency: You have hands‑on experience with generative AI tools (e.g., Gemini, ChatGPT, Claude) through professional, academic, or personal projects, with a strong understanding of concepts such as state management and prompt versioning. AI & ML Knowledge: You possess a solid understanding of AI technologies and machine learning concepts, and can apply them effectively in business contexts. Analytical Thinking: You demonstrate a strong analytical mindset, with the ability to design experiments, interpret metrics, and distinguish meaningful signals from noise. Communication Skills: You communicate clearly and concisely, translating complex technical insights into actionable recommendations for non‑technical stakeholders. Ownership & Drive: You exhibit curiosity, a bias for action, and a strong sense of ownership in fast‑moving, ambiguous environments. #J-18808-Ljbffr