Senior Account Executive

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. 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.

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

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; 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 have

Proficiency in Salesforce, Outreach, and ZoomInfo/Sales Navigator; Experience selling into large hospitality or warehousing brands

Benefits

Equity in the form of stock options; 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; Career Growth: We promote from within