Sales Development Representative - Chicago (Hybrid)

Firstup•Chicago, IL

7d•$28 - $31•Hybrid

About The Position

The SDR role at Firstup sits at the intersection of Sales and Marketing. You'll own top-of-funnel pipeline creation for a set of named enterprise accounts, working in close partnership with an Account Executive and aligned Marketing support. Your primary buyers are CHROs, VPs of Internal Communications, and Directors of Employee Experience — senior leaders who control meaningful budget and are actively looking for solutions to workforce engagement challenges. Success here requires business acumen, intellectual curiosity, and the ability to build credibility with executives through relevance and insight — not persistence alone.

Requirements

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

Nice To Haves

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

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.