Sales Development Representative - Chicago (Hybrid)

Who We Are At Firstup, our mission is to improve the employee experience at every moment that matters, large and small. As the communication pipeline for the world's workforce, we now serve 40 of the Fortune 100 companies, reaching and connecting more than 17 million employees daily. Our employees are experts in the employee experience, workforce communications and technology. Joining Firstup means joining a movement to make work better for every worker. As the world’s first intelligent communication platform, Firstup meaningfully engages employees at every moment from hire to retire, and delivers engagement insights to help companies support, promote and retain their talent. Our movement has taken root and is evident in our world-class customer base. Now we need your help. Ready to make a difference in the world? 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. 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 Strongly Preferred 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 Who Thrives Here The SDRs who excel at Firstup share a specific profile. They are: Insight-driven, not script-dependent. They do real research before reaching out and lead with business relevance — not feature lists. Resilient and process-oriented. They understand that pipeline is built through consistent, disciplined execution, and they don't abandon what's working. Growth-obsessed. They actively seek coaching, ask thoughtful questions in team sessions, and view feedback as currency. Collaborative by default. They think of their AE as a partner, not just a handoff point, and take accountability for the quality of meetings they book — not just the quantity. Ambitious with a long-term orientation. They want to build a career in enterprise sales and understand that the SDR seat is the foundation, not the ceiling. Firstup expects the base salary for this role to be an hourly rate between $27.50-$31.25. The starting rate of pay may vary based on factors including, but not limited to, position offered, location, education, training, and/or experience. Why Firstup? Because you care - about people, the work you do, and the connections you make. Work is such a large part of life; it only makes sense to make it awesome. If you want to engage brilliant minds in a high-growth and inclusive environment where ideas are rewarded regardless of who they come from, join us. This is a rapidly changing space so if you thrive on ambiguity, are hungry for a challenge, and have the guts to speak your mind, you could be a perfect fit. We offer an excellent PTO program, great health benefits, a casual and friendly environment, remote work, and a leadership team who truly believes in your growth – both personally and professionally. Firstup is committed to providing equal employment opportunities to all applicants for employment and to all employees, without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, protected disability, veteran status, or any other protected status in accordance with applicable federal, state or local laws. #LI-TM1 #LI-Remote