Sales Development Representative, Outbound (Hybrid - CHI)

The Sales Development Representative, Outbound (Hybrid - CHI) at Rippling is a high‑velocity, pipeline‑building role that sits at the front line of our rapid growth in the HR‑tech space. In this position you will research, prospect, and engage mid‑market organizations across the Chicago, IL region, turning cold leads into qualified opportunities that fuel our revenue engine. Your outreach directly influences how quickly businesses adopt Rippling’s unified payroll, benefits, and HR platform, accelerating digital transformation for thousands of employees. As a key member of the outbound sales team, you will gain deep exposure to enterprise sales cycles, data‑driven prospecting, and strategic territory management—providing a fast‑track path to Account Executive or Sales Manager roles within a company that’s redefining the future of work.

You will:
- Conduct high‑volume outbound outreach (calls, emails, LinkedIn) to identify and qualify prospects in targeted verticals such as athletics, voter outreach organizations, and fast‑growing tech firms.
- Leverage advanced prospecting tools and data analytics to map territory, prioritize accounts, and personalize messaging that resonates with decision‑makers.
- Execute rigorous discovery conversations to uncover pain points around onboarding, compliance, and employee engagement, then hand‑off qualified opportunities to the sales closing team.
- Collaborate daily with Marketing, Customer Success, and Product to share market insights, refine outreach scripts, and align on go‑to‑market strategies.
- Track and report key performance metrics (connect rates, meetings set, pipeline value) in Salesforce, continuously iterating to exceed quarterly targets.
- Participate in weekly sales huddles, role‑plays, and training sessions to sharpen objection handling, negotiation, and consultative selling skills.
- Represent Rippling at industry events and community gatherings, building brand awareness and fostering relationships within the Chicago ecosystem.

Joining Rippling means becoming part of a purpose‑driven culture that values curiosity, impact, and inclusive teamwork. We champion professional growth with structured mentorship, internal mobility, and access to cutting‑edge sales technology that keeps you ahead of industry trends. Our hybrid model offers the flexibility to work from our modern Chicago office while maintaining remote productivity, and our benefits package supports holistic well‑being—from comprehensive health plans to generous PTO and equity participation. As a Sales Development Representative, Outbound (Hybrid - CHI), you will play a pivotal role in scaling a market‑leading platform, gaining the experience and visibility to accelerate your career in tech sales while helping organizations streamline their people operations.