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AI Automation Senior Lead

New York, New York, United States; San Francisco, California, United States

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!

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. 
  • Hands-on Builder Mindset: You are a scrappy, execution-oriented builder who can take ideas from stakeholders and independently develop working agentic workflows without relying on external engineering resources. 
  • Business Acumen: You translate complex AI capabilities into clear business value, articulating ROI and impact for diverse stakeholders. 
  • Operational Excellence: You bring rigor to operations, including managing vendor relationships, forecasting technical costs (e.g., token usage), and maintaining system reliability and SLAs. 
  • Strategic AI Perspective: You stay current with rapid advancements in AI (e.g., LLMs, agents), proactively identifying implications for business and workforce transformation. You effectively bridge the gap between what is technically possible and what is practically scalable. 
  • Leadership & Influence: You are a self-starter who thrives in ambiguity and can lead high-stakes discussions with senior leaders, using structured thinking and compelling storytelling to drive alignment and change. 
  • Impact Orientation: You are deeply data-driven, partnering effectively with Finance and Data Science to define success metrics and ensure initiatives deliver measurable productivity gains and business impact. 
  • Continuous Learning: You demonstrate strong intellectual curiosity and a commitment to continuous learning, staying ahead of emerging technologies to ensure long-term organizational readiness.

Compensation & Benefits: 

At Taskrabbit, our approach to compensation is designed to be competitive, transparent, and equitable. Total compensation consists of base pay + bonus + benefits + perks. The base pay range for this position is $192,000 - $250,000. This range is representative of base pay only, and does not include any other total cash compensation amounts, such as company bonus or benefits. Final offer amounts may vary from the amounts listed above and will be determined by factors including, but not limited to, relevant experience, qualifications, geography, and level.

You’ll love working here because:

  • 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. 

Taskrabbit’s commitment to Diversity and Inclusion:

An Active Commitment to Equity within our Company and Platform. We are an inclusive community where all who share our mission and values belong. Our diverse team represents the communities we serve, breaking down systemic barriers, and transforming lives- one action at a time.

Taskrabbit is an equal opportunity employer and values diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, ancestry, citizenship, sex, gender, gender identity, sexual orientation, age, marital status, military/veteran status, or disability status. Taskrabbit is committed to working with and providing reasonable accommodation to applicants with physical and mental disabilities. 

Taskrabbit will consider for employment all qualified applicants with criminal histories in a manner consistent with applicable law. 

Taskrabbit will never use text or chat applications to conduct interviews. We have a thoughtful and interactive interview process that includes an initial recruiter phone screen and several video-based interviews with our hiring teams. Communications will always be conducted by taskrabbit.com domain names.

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