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Enterprise Account Executive

Chicago, Illinois, United States

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. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and more, we want you to help us continue to scale quickly and make an even greater impact.

We're looking for passionate, driven, and highly motivated sales professionals to help us scale our enterprise partnerships and continue our rapid growth across the U.S. As an Enterprise Account Executive, you will be responsible for acquiring key enterprise accounts and forming channel partnerships. You will work closely with mid-market and enterprise businesses to understand their staffing needs and provide tailored solutions that meet their workforce requirements. This role requires a strategic thinker with a passion for building lasting business relationships and a strong ability to close deals.

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.
    Stay informed on industry trends, market dynamics, and Instawork’s evolving value proposition to position our solutions effectively.
  • Travel expectations: 40% annually (on-site client visits, tradeshows, conferences, events)

For IL-based applicants:

  • The base salary for this position is $110,000, eligible OTE for a total of $230k, and uncapped commissions
  • 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.

#LI-OnSite 

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 www.instawork.com/about.

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