Enterprise Account Executive Job at Instawork (Chicago)

Job Description

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. 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.

Job Responsibility

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)

Requirements

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 we offer

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
This position is eligible for equity in the form of stock options

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Enterprise Account Executive

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