Sales Development Representative, Retail

About the role

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.

Responsibilities

• 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
• Arc Instawork's value proposition crisply and confidently across cold calls, emails, and LinkedIn

Requirements

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