Senior Account Executive

The future of hourly work has arrived, and we are looking for a top-performing Senior Account Executive to help lead the charge. Instawork is the #1 marketplace connecting businesses with skilled hourly workers, with 10M+ workers across 40+ markets in North America. Backed by Benchmark, Greylock, and other world-class investors, we are reinventing how businesses hire, and we are just getting started.

This is your chance to sell a product that genuinely changes lives. Our AI-powered platform creates real economic opportunity for workers while solving one of the most pressing challenges businesses face: reliable, on-demand staffing. You will be selling into an expansive and exciting total addressable market, including Major Sports Stadiums, E-commerce brands, major universities, AI companies, and beyond.

This is a high-impact role for a hunter who thrives on competition, loves to win, and wants to be part of something that matters. You will report to a Sales Manager and play a critical role in driving Instawork’s next phase of growth, on-site 5 days per week in our downtown Chicago office.

Who You Are

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

What You’ll Do

• 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
• Career Growth: We promote from within. From day one, you'll see the AE promotion path laid out, typically with 12-month success intervals

For IL-based applicants

• The base salary for this position is $80,000, with an eligible OTE for a total of $160,000, and uncapped earning potential
• 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