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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, 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.
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.
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.
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.
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.
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