Sales Development Representative, Retail

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. We have an immediate opening for a Sales Development Representative, with a proven track record of success to join our rapidly growing team. Reporting directly to the GM of Instawork Retail, this role serves as a critical member of the sales team and is responsible for driving top-of-the-funnel lead generation for Instawork’s retail team. This role requires prior sales development or business development experience. This is a results-driven position that requires you to consistently achieve a monthly quota of qualified opportunities. Who You Are A hunter mindset — you're energized by outbound, not drained by it Genuine curiosity about AI tools and a track record of using them to work smarter Experience building or managing automated outbound workflows (Clay, Apollo, Outreach, or similar) High call volume comfort – you don't shy away from 50+ dials a day Strong written and verbal communication; you can personalize at scale without sounding robotic Salesforce proficiency or ability to get up to speed fast Ability to qualify quickly and hand off cleanly What You’ll Do Make a high volume of cold calls daily — this is a hunting role, and the phone is your primary weapon Build, test, and iterate AI-powered outbound workflows (email sequences, call scripts, enrichment pipelines) using tools like Clay, Apollo, and AI writing assistants Own top-of-funnel lead generation for Instawork's retail vertical, from prospecting through qualified handoff Use AI tools to research accounts, personalize outreach at scale, and identify high-propensity targets before the first dial Pre-qualify prospects on business size, hiring volume, and seasonal workforce needs Partner with Account Executives to sharpen targeting strategies and prioritize accounts Maintain clean, real-time CRM hygiene in Salesforce — every call, every touch, every next step logged Consistently hit and exceed monthly quotas for qualified opportunities Articulate Instawork's value proposition crisply and confidently across cold calls, emails, and LinkedIn For CA Based Applicants: The base salary for this position is $70,304 + uncapped sales incentive pay. 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 A variety of factors are considered when determining someone’s compensation including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed above. #LI-Onsite Our Values Empathy, 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, bu