Sales Development Representative, Outbound (Hybrid - CHI)

Rippling • Chicago, IL

24d • $99,992 - $99,992 • Hybrid

About The Position

This is a high-activity, outbound Sales Development role focused on creating sales pipeline by researching target accounts, reaching prospects through phone, email, LinkedIn, and other channels, and booking qualified meetings for Account Executives. It is a top-of-funnel position, not an inbound or full-cycle sales role, suited to someone energized by prospecting, quick feedback, daily activity goals, and a team environment where performance is visible and celebrated.

The role offers the opportunity to learn Rippling’s platform and understand customers’ operational pain points while building core prospecting, discovery, objection-handling, and territory-management skills for a longer-term sales career. Successful SDRs typically develop these skills in-seat before pursuing further sales opportunities.

This is a hybrid role requiring three days per week in the Chicago office. The first 30 days focus on onboarding, product knowledge, sales methodology, tools, messaging, and customer understanding. In the second month, the employee begins live prospecting, building activity consistency, and working toward partial quota expectations. By the third month, the employee is expected to meet full ramp expectations, manage daily outbound activity, book qualified meetings, and demonstrate improvement through coaching and repetition. Longer term, career paths may include Account Executive, SDR leadership, or another go-to-market role.

Compensation is competitive on-target earnings comprising base salary and commission, with a 70/30 base-to-variable split for US-based employees. Commission is not guaranteed. Final offers may vary based on professional background, experience, and location.

Requirements

• BA/BS degree or equivalent work experience.
• High sense of urgency and genuine interest in a sales career.
• Strong communication skills, especially over the phone and in concise written outreach.
• Coachability and ability to apply feedback quickly and improve.
• Curiosity and initiative, including seeking context and ways to improve.
• Resilience and consistency in a high-activity prospecting environment.
• Comfort working toward measurable goals in a competitive, team-oriented setting.
• Ability to collaborate cross-functionally with sales, marketing, and other teams.

Nice To Haves

• Prior sales, customer-facing, athletics, or competitive team experience is helpful but not required.

Responsibilities

• Research target companies, personas, business triggers, and operational pain points to identify high-quality prospecting opportunities.
• Prospect into target accounts using phone, email, LinkedIn, and sales engagement tools.
• Own a high-volume outbound motion, including daily call blocks, email follow-ups, account research, and multi-touch sequences.
• Work toward daily and weekly activity expectations, including roughly 80–100 calls and 40–50 emails per day, depending on territory priorities and team guidance.
• Qualify prospects using defined criteria and schedule high-quality meetings for Account Executives.
• Partner with Account Executives on territory strategy, account prioritization, messaging, and follow-ups.
• Participate in weekly enablement sessions, team call reviews, and manager coaching; apply feedback to improve messaging, objection handling, and prospecting effectiveness.
• Maintain accurate records in Salesforce and keep outreach, account, and prospect data clean.
• Use Salesforce, Outreach, LinkedIn Sales Navigator, ZoomInfo, Apollo, and dialer technology to execute efficiently.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level