Account Executive

Instawork • Chicago, IL

13d • Onsite

About The Position

Instawork is seeking a top-performing Account Executive to drive growth in the hourly work market. This role involves selling an AI-powered platform that connects businesses with skilled hourly workers, creating economic opportunities for professionals and solving staffing challenges for businesses. The Account Executive will target diverse industries such as Major Sports Stadiums, E-commerce brands, universities, and AI companies. This is a high-impact, competitive role focused on driving Instawork's growth, reporting to a Sales Manager, and requiring a 5-day per week on-site presence in the downtown Chicago office.

Requirements

• 2+ years of B2B sales experience with a proven, consistent track record of exceeding quota
• A relentless competitor who lives at the top of the leaderboard and will not settle for anything less
• Energized by coaching and obsessed with leveling up your craft
• A true hunter who thrives in fast-paced environments and knows how to build pipeline from scratch through outbound prospecting
• Fluent in a robust sales stack; proficiency in Salesforce, Outreach, and ZoomInfo/Sales Navigator preferred
• Sharp negotiator with experience navigating commercial and legal terms to close
• Passionate about selling a product that creates real economic opportunity and changes people’s lives
• An exceptional communicator who is compelling on the phone, polished on video, and persuasive in person

Nice To Haves

• Experience selling into large hospitality or warehousing brands is a plus

Responsibilities

• Own your territory and build high-value partnerships with top partners across Major Sports Stadiums, E-commerce brands, universities, AI companies, and more
• Drive aggressive outbound prospecting to generate your own pipeline through cold calls, targeted sequences, and creative outreach
• Reach executives and key decision makers, delivering compelling and tailored presentations that win
• Use a consultative sales approach to show prospects exactly why Instawork is the faster, smarter alternative to legacy staffing solutions
• Close new business over the phone, video, and in-person, then obsess over expanding those accounts from day one
• Negotiate commercial and legal terms with confidence to get deals across the finish line
• Deliver accurate weekly forecasts and own your number
• Collaborate with sales and operations to ensure customers experience the full power of Instawork’s platform
• Keep a sharp, healthy Salesforce pipeline and leverage our full sales stack to stay ahead

Benefits

• 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
• Equity in the form of stock options

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed