Senior Account Executive

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works. 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 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 p