Sales Development Representative - Chicago… at Firstup · Chicago

Summary: Firstup is an intelligent communication platform that improves employee experiences and connects workforces through meaningful communication and engagement insights. The Sales Development Representative will create top-of-funnel pipeline for named enterprise accounts by researching stakeholders, executing multi-channel prospecting, partnering with Account Executives and Marketing, and meeting sales performance KPIs.

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

Required Qualifications:
- • 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

Preferred Qualifications:
- • 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

Required Skills: Outbound Sales, Executive Communication, Groove, SalesLoft, CRM Data Management, HR, Internal Communications, or HCM Sales, Enterprise SaaS Sales, MEDDPICC, Challenger Sales Methodology, LinkedIn Sales Navigator, HockeyStack, Coachability

Benefits: An excellent PTO program, Great health benefits, A casual and friendly environment, Remote work, A leadership team who truly believes in your growth – both personally and professionally