Senior Manager, Strategic Initiatives

Senior Manager, Strategic Initiatives

Chicago, Illinois, United States

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, Strategic Initiatives to join our Product Operations team and lead the charge in identifying and launching our next growth horizons. This is a high-octane, "General Manager" style opportunity to build new business lines from scratch—connecting our 10M+ flexible workers ("Pros") with new industries and service categories. You will be tasked with parachuting into highly ambiguous, high-impact expansion initiatives to ignite the marketplace flywheel, prove unit economics, and transition new bets from "0 to 1."

Who You Are

• Founder Mindset & Bias for Action: You have a "get-it-done" attitude and are willing to do whatever it takes to launch a category—whether that's manually matching shifts, cold-calling early partners, or testing ground-level operational processes. You don't wait for permission or perfect data; you deliver results.
• Strategic & Curious: You think big-picture while staying fiercely grounded in data and execution. You are comfortable with fast iteration, navigating complex requirements, and solving unstructured problems in a rapidly evolving marketplace.
• Multi-disciplinary Executor: 6+ years in finance, operations, consulting, or high-growth startup environments. You have a proven track record of owning chaotic, ground-level execution and turning early momentum into sustainable success.
• Technical & Analytical Depth: You have a technical toolkit fueled by AI, using data to unearth new insights, build business cases, and measure the success of your pilots without needing a roadmap.
• Strong Communicator & Evangelist: Able to represent Instawork externally to new partners and internally as a driver of cross-functional alignment. You can turn operational friction into scalable processes and influence senior stakeholders.

What You'll Do

• Build the Playbook (0 to 1): Take new initiatives from a blank sheet to a functioning business. You will lead the ideation and incubation of new growth vectors, hacking together initial supply and demand until the project gains traction and can stand on its own.
• Strategic Execution & Category Launch: Define and implement Instawork's strategy for entering new service lines and verticals. You will be the internal owner responsible for identifying where we should "parachute" next and how we win in those markets.
• Partnership Development: Build and grow relationships with early-adopter brands and agencies in new categories. Deeply understand partner pain points to ensure Instawork can support their specific labor and data needs.
• Market & Data Analysis: Perform deep-dive research into new industry trends and competitive landscapes. Leverage data to anticipate needs and ensure our product and operations can seamlessly support massive, fluctuating workforce requirements.
• Cross-Functional Leadership: Work closely with Sales, Marketing, Product, and Operations to move aggressively and iterate on the fly. You will act as the "connective tissue" that turns frontline learnings into scalable, automated processes.

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.

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

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