Enterprise Account Executive - Light Industrial

Instawork; Chicago (IL); On-site; USD 110,000 - 130,000; Full time

Benefits offered by this job

Medical, dental, and vision plans

Flexible paid time off

Phone stipend

401K plan

Job summary

Instawork is looking for an experienced Enterprise Account Executive in Chicago to lead enterprise sales efforts across warehousing and logistics. The role involves engaging key enterprise clients and orchestrating the sales process from prospecting to closing deals worth over $200K.

Successful candidates will have extensive experience in sales, exceptional negotiation skills, and will be rewarded with a competitive salary of $110,000 – $130,000, potential equity, and various benefits including flexible paid leave and 401K plan.

Qualifications

• 5+ years of enterprise sales experience with end-to-end cycles.
• Strong track record of closing high-value deals ($200K+) over extended sales cycles.
• Self-starter mentality in fast-paced environments.

Responsibilities

• Identify and acquire enterprise-level clients through multi-threaded prospecting.
• Manage end-to-end sales processes ensuring smooth onboarding.
• Engage senior decision-makers with consultative sales approaches.

Skills

Enterprise sales experience

Negotiation skills

Communication skills

CRM proficiency

Relationship building

Education

Bachelor’s degree in Business, Marketing, or related field

Tools

Salesforce

Job description

Instawork is looking for exceptional talent to reimagine the way the world works and help us expand our enterprise partnerships across the U.S. As an Enterprise Account Executive, you will acquire key enterprise accounts and establish channel partnerships within the warehousing, logistics, supply chain, and third‑party logistics (3PL) sectors.

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 experience with light industrial enterprises, specifically those in supply chain, warehousing, distribution, or third‑party logistics (3PL).
• 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.
• Manage end‑to‑end sales processes from cold outreach and discovery to executive alignment and contract negotiation—ensuring a smooth 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: Approximately 20–40% annually, fluctuating based on conference season and client/partner visit cadence.

For IL‑based applicants

• The base salary for this position is $110,000 – $130,000 eligible OTE for a total of $230k – $250k 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