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Instawork — Chicago Illinois
Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works.
We are seeking a Senior Manager of Product Operations to help us transition from an app-based marketplace to an agent-first world. We believe the future of work isn't about browsing feeds or tapping buttons - it’s about having intelligent agents that work on your behalf. We need a technical operator who can bridge the gap between high-level business goals and this new user interface.
You won't just optimize processes; you will prototype the logic, agents, and automation layers that fundamentally change how our Pros and Partners experience the platform.
Who You Are
: An Architect of the "Agent-First" World: You understand that the next iteration of the internet is not point-and-click, but intent-and-action. You see a future where users interact with our marketplace through conversation and delegation, not just navigation. A UX Builder, Not Just a Process Fixer: You realize that in an AI world, "Operations" is the Product.
You are obsessed with reducing user friction, believing that if a human has to manually search or sift through data, the agent has failed. An AI Pragmatist: You know how to deploy the right model for the job. You distinguish between where a reasoning model is needed to handle complex user intent versus where a deterministic script suffices.
A "Hands-On" Visionary: You don't just write specs for Engineering; you prototype the solution yourself. You are comfortable building the first version of an agentic workflow to prove it works before we scale it globally.
What You’Ll Do
: Build the Agent-First Interface: Design and deploy agentic workflows that proactively manage the "work" for our users - turning passive browsing into a hands-free, autonomous experience where the app works for them. Solve Marketplace Complexity: Prototype and implement intelligent systems that handle complex reasoning tasks (like liquidity balancing, preference matching, or real-time negotiation) to make the market feel alive and responsive. From Strategy to Code: Act as the technical bridge, translating high-level business objectives into functional AI prototypes and automated pipelines that you build, test, and validate yourself.
Drive Data-Led Evolution: Use programmatic analysis to identify exactly where the current user journey is broken and deploy intelligent, self-healing layers to fix it in real-time.
Qualifications
: Technical Engineering Fluency: 2+ years of engineering experience (or equivalent proficiency) with the ability to write code (Python/TypeScript) and use AI-native IDEs (Cursor, Replit) to build your own tools. Applied AI Experience: Demonstrated history of building agents or automated workflows that take action, not just generate text. You know the difference between a prompt and a pipeline, and you know how to build both.
Nice To Have
S. S. in Computer Science or Engineering.
A personal portfolio of AI projects that solve real-life problems. Experience fine-tuning models for specific business or customer-facing use cases.
Benefits
, including: A variety of medical, dental, and vision plans with coverage beginning on the date of hire Flexible paid time off At least 8 paid company holidays annually Phon