Regional Sales Manager

Regional Sales ManagerChicago, Illinois, United States; San Francisco, California, United StatesInstawork 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.At Instawork, we're a full staffing platform suite that allows businesses to connect with professionals in a modern, robust way. Our labor marketplace connects over 10M professionals to top Hospitality and Logistics companies across North America, and we're looking for top talent to help us scale. We have an immediate opening for a Sales Manager with a proven track record of success to join our rapidly growing team. Reporting to the Sales Director, this role is a critical member of the sales leadership team, responsible for coaching reps through every stage of the outbound sales process, including prospecting, qualification, and pipeline building, while using data to spot gaps and drive the fixes that close them. This is a results-driven position built for someone who can build and manage remote software sales teams, and who is as comfortable in a rep's deal review as they are in a pipeline dashboard.What You'll Do & Who You AreCoach reps through the full outbound sales cycle (prospecting, qualifying, and building pipeline), with 2+ years of experience building and managing high-performing remote software sales teamsRead the data and act on it: monitor pipeline, activity, and conversion metrics to spot gaps, then design and execute the coaching, process, or enablement changes that close themBring 5+ years of quota-exceeding experience selling mid-enterprise deals, with a track record of overachievement and hitting sales targetsSupport deals directly as senior air cover, managing multiple stakeholder deal cycles and helping the team navigate complex organizations and negotiationsOnboard and ramp new Account Executives, accelerating their time to productivityForecast accurately and represent your business clearly to the executive teamPartner cross-functionally with Marketing, Operations, Product, and Engineering to develop and execute initiatives that support the sales orgKnow the Instawork platform deeply enough to coach reps on value proposition, positioning, and strategyOwn and evolve the sales playbook, driving adoption across your teamDevelop future sales leaders and share learnings and best practices across the companyScale the organization sustainably as the team growsYou're a self-starter who's passionate about coaching, mentorship, and team management, motivated by helping people grow, self-aware, and high in emotional intelligence. You learn fast, establish credibility quickly, and thrive in a high-growth, rapidly changing marketplace. You're excited to build a career at a startup disrupting the gig economy, and you're committed to developing a deep understanding of Instawork's mission, values, and product.Nice to HavesExperience leading outbound/inside sales teamsA track record of thriving in fast-paced environmentsA background in cultures that prioritize learning and developmentFor CA or IL-Based ApplicantsThe base salary for this position is $133,000 base, with an OTE of $223,000 (uncapped sales incentive pay)This position is eligible for equity in the form of stock optionsThis position is eligible for Instawork benefits, including:A variety of medical, dental, and vision plans with coverage beginning on the date of hireFlexible paid time offAt least 8 paid company holidays annuallyPhone stipendCommuter stipendSupplemental pay on qualified leavesEmployee health savings account (HSA) contributionFlexible spending plans401K planPerkspot: discount program through LumityOur ValuesEmpathy, Trust & Candor We put ourselves in the shoes of our colleagues and customers and don't shy away from uncomfortable conversations, instead building trust through honest and direct feedback.Bias for Action We practice high-velocity decision-making, clear-eyed that we often operate with incomplete information. Growing quickly means it's OK to be wrong, so long as we learn from our mistakes and course correct!Always Be Learning We're a curious bunch, and with AI transforming our workplace we encourage everyone to learn from each other, compounding our knowledge and experience to help us change an entire industry.Act Like an Owner We work long, hard, and smart, building products that delight our users and drive growth. Your ability to impact Instawork is limited only by your courage and conviction, not your job description.About InstaworkFounded in 2015, Instawork is the nation's leading online labor marketplace for food services, hospitality, light industry, and logistics, connecting more than 7M skilled workers with local restaurants, hotels, warehouses, stadiums, and more. Our AI-powered platform serves thousands of businesses across more than 50 major markets in the United States and Canada. We're not just helping fill shifts, we're supporting local economies—and we're just getting started!Instawork has been featured by CBS News, The Wall Street Journal, The Washington Post, and the Associated Press. Forbes included us on their Next Billion Dollar Startups list; RetailTech Breakthrough named us Workforce Hiring Solution of the Year for 2025; and Inc. 5000 recognized us as one of the country's top 10% fastest-growing companies two years in a row. But what matters most is our impact. We're solving real problems for real people, and we're doing it at scale.Join our team to help us build something that matters! We're looking for superstars who want to help us shape the future of work. With hubs in San Francisco, Bangalore, and Chicago, city offices in New York, Phoenix, and Singapore, we're back to working together in-person five days a week because we believe the best ideas happen when great people collaborate face-to-face. We also value diverse perspectives and encourage applications from candidates of all backgrounds. Ready to make an impact? Learn more at Privacy Policy