Sales Development Representative - Chicago (Hybrid)

Firstup is dedicated to enhancing the employee experience and serves a significant number of Fortune 100 companies. They are seeking a Sales Development Representative to create top-of-funnel pipeline for enterprise accounts, collaborating closely with Account Executives and Marketing teams to engage senior leaders in workforce engagement solutions.

Responsibilities

• 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 AE 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

Skills

• 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
• Familiarity with enterprise SaaS sales cycles and multi-threaded account strategies
• Working knowledge of MEDDPICC, Challenger, or similar sales frameworks
• Experience with Sales Navigator and intent data tools like HockeyStack
• Demonstrated coachability — examples of feedback you received and applied

Benefits

• We offer an excellent PTO program
• Great health benefits
• A casual and friendly environment
• Remote work
• A leadership team who truly believes in your growth 60 both personally and professionally

Company Overview