Senior Manager, Product Operations
Instawork · Chicago, IL
📍 Chicago, Illinois, United States💰 $160,000 - $200,000via greenhousePosted 2026-06-15
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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.
Operational Strategy: 5+ years in Product Ops, TPM, or similar, where you defined the "what" and "why" of a product strategy and then personally helped build the "how."
Nice To Have:
B.S. or M.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.
For IL based applicants:
The base salary for this position is $160,000 - $200,000
This position is eligible for equity in the form of stock options
This position is eligible for Instawork 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
Phone stipend
Commuter stipend
Supplemental pay on qualified leaves
Employee health savings accounts (HSA) contribution
Flexible spending plans
401K plan
Perkspot - discount program through Lumity
A variety of factors are considered when determining someone’s compensation including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed above.
#LI-Onsite #JG-1
Our Values
Empathy, Trust & Candor
We put ourselves in the shoes of our colleagues and customers and don’t shy away from uncomfortable conversations, instead building trust through honest and direct feedback.
Bias for Action
We practice high-velocity decision-making, clear-eyed that we often operate with incomplete information. Growing quickly means it’s OK to be wrong, so long as we learn from our mistakes and course correct!
Always Be Learning
We’re a curious bunch, and with AI transforming our workplace we encourage everyone to learn from each other, compounding our knowledge and experience to help us change an entire industry.
Act Like an Owner
We work long, hard, and smart, building products that delight our users and drive growth. Your ability to impact Instawork is limited only by your courage and conviction, not your job description.
About Instawork
Founded in 2015, Instawork is the nation’s leading online labor marketplace for food services, hospitality, light industry, and logistics, connecting more than 7M skilled workers with local restaurants, hotels, warehouses, stadiums, and more. Our AI-powered platform serves thousands of businesses across more than 50 major markets in the United States and Canada. We're not just helping fill shifts, we're supporting local economies—and we're just getting started!
Instawork has been featured by CBS News, The Wall Street Journal, The Washington Post, and the Associated Press. Forbes included us on their
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