Senior Account Executive

InstaworkChicago, IL
Onsite

About The Position

Instawork is seeking a top-performing Senior Account Executive to drive growth in the hourly workforce 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 companies. The position offers a high-impact opportunity to work with diverse clients such as Major Sports Stadiums, E-commerce brands, universities, and AI companies. The Senior Account Executive will be responsible for owning a territory, building partnerships, driving outbound prospecting, and closing new business. This is a competitive, hunter-focused role for someone passionate about making a difference in people's lives and contributing to Instawork's growth.

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
  • Eligible for equity in the form of stock options
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