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Sales Development Representative - Chicago (Hybrid) at Firstup. Location Information: United States. Connect every worker, everywhere with the right information at the right time.. Build and execute a multi-touch, multi-channel prospecting strategy (phone, email, LinkedIn, video, direct mail) targeting Director through C-suite buyers at named enterprise accounts.. Research target accounts and individual stakeholders to develop insight-led outreach, understanding their business priorities, recent initiatives, and internal communications challenges before making first contact.. Partner closely with your Account Executive to align on account strategy, prioritize opportunities, and convert booked meetings into qualified pipeline.. Collaborate with Marketing to leverage campaigns, events, and content as outreach triggers and conversation starters.. Achieve and exceed monthly and quarterly KPIs including meetings booked, pipeline generated, and connect rates.. Maintain accurate activity logging and pipeline data in Salesforce and Groove, and use data to continuously refine your approach.. Participate actively in team enablement sessions, bringing feedback from the field to sharpen the team's collective messaging and sequencing.. 1+ year of SDR, BDR, or outbound sales experience.. Demonstrated ability to self-source meetings with senior stakeholders.. Strong written and verbal communication skills — executive-ready.. Comfort with outreach platforms (Groove, SalesLoft, or equivalent).. High attention to detail in CRM hygiene and activity tracking.. Bachelor's degree or equivalent practical experience.. Experience selling into HR, Internal Communications, or HCM buyers (strongly preferred).. Familiarity with enterprise SaaS sales cycles and multi-threaded account strategies (strongly preferred).. Working knowledge of MEDDPICC, Challenger, or similar sales frameworks (strongly preferred).. Experience with Sales Navigator and intent data tools like HockeyStack (strongly preferred).. Demonstrated coachability — examples of feedback you received and applied (strongly preferred).. Pay range:. $27.50 - $31.25p/h. Excellent PTO program.. Great health benefits.. Casual and friendly environment.. Remote work.. Growth opportunities - both personally and professionally.