Senior Manager, Product Operations

Senior Manager, Product Operations at Instawork leads an agent-first interface, prototypes AI powered workflows, and bridges strategic objectives with hands-on technical delivery. This onsite role is based in Chicago, IL, with a salary range of USD 160,000 to 200,000 per year.

Responsibilities

• Design and deploy an Agent-First Interface that actively manages user tasks, transforming passive browsing into a hands-free, autonomous experience where the app does the work for users.
• Prototype and implement intelligent systems to handle complex marketplace reasoning, including liquidity balancing, preference matching, and real-time negotiation to keep the market responsive.
• Serve as the technical bridge translating high level business goals into functional AI prototypes and automated pipelines that you build, test, and validate.
• Apply programmatic analysis to identify friction points in the user journey and deploy self-healing layers to fix issues in real time.

Requirements

• Technical & Engineering Fluency: 2+ years of engineering experience (or equivalent proficiency) with the ability to write code in Python or TypeScript and to 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. Knowledge of the difference between a prompt and a pipeline, and experience building both.
• Operational Strategy: 5+ years in Product Operations, TPM, or similar roles, where you defined the what and why of a product strategy and directly contributed to building the how.

Technologies

• Python
• TypeScript
• Cursor
• Replit

Benefits

• A variety of medical, dental, and vision plans with coverage starting 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
• Health savings account (HSA) contribution
• Flexible spending plans
• 401K plan
• Perkspot - discount program through Lumity

For Illinois 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

Our Values

• Empathy, Trust & Candor: We consider colleagues and customers, embracing honest feedback to build trust.
• Bias for Action: We move quickly with the understanding that learning from mistakes is part of growth.
• Always Be Learning: We encourage continuous learning as AI transforms the workplace and industry.
• Act Like an Owner: We contribute long, hard, and smart work to deliver delightful products and drive growth.

About Instawork

Founded in 2015, Instawork is a national online labor marketplace connecting skilled workers with restaurants, hotels, warehouses, and more across the United States and Canada. Our AI powered platform serves businesses in over 50 markets, supporting local economies beyond simply filling shifts. We have received coverage from CBS News, The Wall Street Journal, The Washington Post, and the Associated Press, and have been recognized by Forbes as a Next Billion Dollar Startup, RetailTech Breakthrough as Workforce Hiring Solution of the Year for 2025, and Inc. 5000 as a fast growing company two years running. Our teams operate from hubs in San Francisco, Bangalore, and Chicago, with offices in New York, Phoenix, and Singapore, and we value diverse perspectives across backgrounds.

Learn more at www.instawork.com/about.