AI Automation Senior Lead, Taskrabbit
$192-250k
+ Bonus
ChatGPT
Senior and Expert level
New York
San Francisco Bay Area
More information about location
Outsourcing marketplace for everyday tasks
Be an early applicant
Outsourcing marketplace for everyday tasks
1001+ employees
B2CMarketplaceHome improvementOutsourcing
Be an early applicant
$192-250k
+ Bonus
ChatGPT
Senior and Expert level
New York
San Francisco Bay Area
More information about location
1001+ employees
B2CMarketplaceHome improvementOutsourcing
Company mission
To transform lives, one task at a time, by connecting millions globally with trusted Taskers every year.
Role
Who you are
- 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
What the job involves
- 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
- 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
Application process
- 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
Our take
Back in 2011, TaskRabbit took full advantage of a growing trend - that technology enables consumers to do more commerce in their homes than ever before. Its marketplace connects users to "Taskers" that can perform virtually any role customers require, such as heavy lifting and cleaning.
TaskRabbit's product is diverse, with the potential to enter any commerce sector in the world. In 2017, the company was acquired by IKEA, which gave it the resources to undergo a data-driven European expansion which included launching in Germany and France, as well as increasing services in densely-populated UK areas.
By developing internationally, while also emphasising its offerings as a delivery service, the company has set itself up on the world stage. Having continued to grow and expand its offerings, TaskRabbit remains a key player in the gig economy, with every sign that it will continue its successes into the future.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
Led by a woman
Top investors
3% employee growth in 12 months
Company
Funding (2 rounds)
Jul 2012
$14.1m
Dec 2011
$19.3m
Total funding: $33.3m
Company benefits
- Remote first and highly connected
- Employee-covered health care
- 401k with match
- Flexible PTO
- Paid holidays & recharge weeks
- Wellbeing allowance and free access to HeadSpace and Spring Health
- Paid parental leave, adoption assistance, and reproductive health assistance
- Speaker series, career paths, and an annual education allowance
- IKEA discount, Taskrabbit credit, and productivity stipend
Company HQ
Potrero Hill, San Francisco, CA
Leadership
Ania Smith
(CEO)Several years of experience in leadership at companies like Expedia, Uber, Airbnb and Walmart.
Salary benchmarks
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