Senior Account Executive

Instawork • Chicago, IL

9d • Onsite

About The Position

Instawork is seeking a top-performing Senior 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, addressing critical staffing challenges and creating economic opportunities. The position is based in downtown Chicago, requiring a hunter mentality, strong sales skills, and a passion for making an impact. You will report to a Sales Manager and play a key role in Instawork's expansion.

Requirements

• 3+ 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: Senior
• Education Level: No Education Listed