Enterprise Account Executive

Instawork•Chicago, IL

10d•$110,000•Onsite

About The Position

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'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.

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.

Nice To Haves

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

Responsibilities

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.

Benefits

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