As a Sales Development Representative, you'll own the critical early-stage funnel by responding to inbound interest, qualifying opportunities, and feeding warm leads to the Account Executive team. Your day-to-day involves researching prospects, crafting targeted outreach sequences, and conducting discovery calls to uncover fit and pain points. You'll become fluent in the product's capabilities and articulate why it matters to different buyer personas—from bootstrapped founders to enterprise teams. Cross-functional collaboration is built into the role: you'll gather feedback from marketing, customer success, and product teams to refine messaging and improve handoff quality. You'll maintain meticulous CRM hygiene, track activity metrics, and contribute ideas to scaling playbooks that actually work. Success means hitting activity and qualification targets, building rapport with prospects, and developing the consultative skills that define top-tier sales professionals. Expect 3 days on-site in Chicago (Tuesday–Thursday), occasional travel to events or company offsites, and a compensation package combining base salary and commission.