Senior Manager, Strategic Initiatives

Instawork • Chicago, IL

8h • $160,000 - $200,000 • Onsite

About The Position

Instawork is seeking a Senior Manager, Strategic Initiatives to join their Product Operations team. This role will lead the identification and launch of new growth horizons, acting as a "General Manager" to build new business lines from scratch. The position involves connecting flexible workers with new industries and service categories, and will be responsible for ambiguous, high-impact expansion initiatives to ignite the marketplace flywheel, prove unit economics, and transition new bets from "0 to 1."

Requirements

• Founder Mindset & Bias for Action: "get-it-done" attitude, willing to do whatever it takes to launch a category (e.g., manually matching shifts, cold-calling early partners, testing ground-level operational processes). Deliver results without waiting for permission or perfect data.
• Strategic & Curious: Think big-picture while staying grounded in data and execution. 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. Proven track record of owning chaotic, ground-level execution and turning early momentum into sustainable success.
• Technical & Analytical Depth: Technical toolkit fueled by AI, using data to unearth new insights, build business cases, and measure pilot success without needing a roadmap.
• Strong Communicator & Evangelist: Able to represent Instawork externally to new partners and internally as a driver of cross-functional alignment. Can turn operational friction into scalable processes and influence senior stakeholders.

Responsibilities

• Build the Playbook (0 to 1): Take new initiatives from a blank sheet to a functioning business. 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. Be the internal owner responsible for identifying where to "parachute" next and how to 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. Act as the "connective tissue" that turns frontline learnings into scalable, automated processes.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed