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Instawork

Enterprise Account Executive

Instawork, Chicago, Illinois, United States, 60290

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Enterprise Account Executive Instawork’s vision is to create economic opportunities for local businesses and skilled hourly workers in communities around the world. With an AI‑first approach, we’re supercharging the leading online labor marketplace and looking for exceptional talent to help us build the future of hourly work.

Who You Are

5+ years of enterprise sales experience, leading end‑to‑end sales cycles—from initial discovery, executive alignment, and contract negotiation—ensuring a seamless transition to onboarding and implementation.

Proven track record of closing complex, high‑value deals ($200K+) over extended sales cycles (6–12 months).

Deep experience with multi‑threaded sales strategies and developing relationships across various departments and leadership levels.

Strong executive presence with exceptional communication, negotiation, and presentation skills.

Self‑starter mentality with the ability to work autonomously and adapt quickly in a fast‑paced, high‑growth environment.

Proficiency with CRM tools (e.g., Salesforce) for pipeline management, forecasting, and sales reporting.

Bachelor’s degree in Business, Marketing, or a related field is preferred but not required.

What You’ll Do

Identify, engage, and win enterprise‑level clients through a multi‑threaded prospecting approach, building relationships across multiple functions and levels within target organizations.

Build and manage a robust pipeline of qualified opportunities through proactive outreach, targeted research, and industry networking.

Lead end‑to‑end sales cycles—from initial discovery, executive alignment, and contract negotiation—ensuring a seamless transition to onboarding and implementation.

Engage C‑suite and senior decision‑makers with a consultative sales approach focused on solving critical workforce challenges.

Consistently achieve or exceed quarterly and annual revenue targets aligned to a $200K+ average deal size, averaging 10 net‑new logos per year.

Foster long‑term client relationships post‑sale, identifying opportunities for expansion and continued partnership.

Travel expectations: 40% annually (on‑site client visits, tradeshows, conferences, events).

Compensation and Benefits

Base salary: $110,000. Eligible OTE for a total of $230k, uncapped commissions.

Equity: Eligible for stock options.

Benefits: Medical, dental and vision plans; flexible paid time off; at least 8 paid company holidays; phone stipend; commuter stipend; supplemental pay on qualified leaves; HSA contribution; flexible spending plans; 401K; Perkspot discount program.

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.

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

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