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. 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 CA-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 #LI-…