Senior Manager, Product Operations

Instawork; Chicago (IL); On-site; USD 160,000 - 200,000; Full time

Benefits offered by this job

Health plans

Equity

Stock options

Flexible PTO

Phone stipend

Commuter stipend

HSA contribution

401K plan

Job summary

Instawork is seeking a Senior Manager of Product Operations to transition our marketplace to an agent-first world. You will prototype agentic workflows, bridge business goals to AI pipelines, and lead data-driven improvements that reduce user friction on the platform.

You’ll be hands-on, building an initial agentic workflow and translating strategy into tangible AI prototypes. The role requires strong engineering fluency, applied AI experience, and a track record in product operations leadership.

Qualifications

• Technical & engineering fluency with ability to write code.
• Applied AI experience building agents or automated workflows.
• 5+ years in Product Ops, TPM, or similar to define strategy and execute.

Responsibilities

• Build the Agent-First Interface with agentic workflows.
• Prototype intelligent systems for complex marketplace tasks.
• Translate business objectives into AI prototypes and pipelines.
• Use data analysis to improve the user journey in real-time.

Skills

Programming (Python/TypeScript)

AI agent prototyping

Operations leadership

Technical writing & specs

Education

B.S. or M.S. in Computer Science or Engineering

Tools

Cursor / Replit IDEs

Job description

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 Next Billion Dollar Startups list; RetailTech Breakthrough named us Workforce Hiring Solution of the Year for 2025; and Inc. 5000 recognized us as one of the country’s top 10% fastest-growing companies two years in a row. But what matters most is our impact. We’re solving real problems for real people, and we’re doing it at scale.

Join our team to help us build something that matters! We’re looking for superstars who want to help us shape the future of work. With hubs in San Francisco, Bangalore, and Chicago, city offices in New York, Phoenix, and Singapore, we’re back to working together in-person five days a week because we believe the best ideas happen when great people collaborate face-to-face. We also value diverse perspectives and encourage applications from candidates of all backgrounds.

Ready to make an impact? Learn more at www.instawork.com/about.

Personnel Privacy Policy