SlipstreamJobsFresh Startup & VC-Backed Jobs

Sales Development Representative, Outbound (Hybrid - CHI)

Rippling - Chicago, IL, United States - Hybrid - posted 2026-10-15

Apply on the company site

SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.

Rippling is a unified HR, IT, and Finance platform that consolidates workforce systems—payroll, expenses, benefits, computers, and third-party apps—into a single system. The company has raised $1.4B+ from top-tier investors including Kleiner Perkins, Founders Fund, and Sequoia. This is a high-activity, outbound Sales Development role focused on top-of-funnel pipeline generation. You will research target accounts and personas, identify high-quality prospecting opportunities, and reach prospects through phone, email, LinkedIn, and sales engagement tools to book qualified meetings for Account Executives. This is not an inbound or full-cycle sales role. Key responsibilities include: - Research target companies, personas, business triggers, and operational pain points - Execute high-volume outbound prospecting: roughly 80–100 calls and 40–50 emails per day - Own multi-touch sequences, account research, and daily call blocks - Qualify prospects using defined criteria and schedule meetings for Account Executives - Partner with Account Executives on territory strategy, account prioritization, and messaging - Participate in weekly enablement sessions, team call reviews, and manager coaching - Maintain accurate Salesforce records and keep prospect data clean - Leverage tools including Salesforce, Outreach, LinkedIn Sales Navigator, ZoomInfo, Apollo, and dialer technology Success milestones: Month 1 focuses on onboarding and product knowledge. Month 2 involves ramping into live prospecting and building activity consistency. By month 3, you should operate at full ramp expectations with consistent improvement through coaching. Longer-term, this role builds the foundation for career growth at Rippling—whether toward Account Executive, SDR leadership, or other go-to-market roles. Why join: You'll sell a comprehensive platform solving real operational problems (not a point solution), learn how businesses operate across HR, IT, Finance, payroll, and benefits, join a fast-paced sales environment with strong coaching and clear goals, be part of a collaborative SDR team with healthy competition and accountability, and gain exposure to expanding product areas including AI and data. The role is hybrid, requiring 3 days per week in the Chicago office. Qualifications: - BA/BS degree or equivalent work experience - High sense of urgency and genuine interest in a sales career - Strong communication skills, especially over phone and in written outreach - Coachability: ability to take feedback, apply it quickly, and improve from one call to the next - Curiosity and initiative: ask good questions, seek context, improve without waiting to be told - Resilience and consistency in high-activity prospecting environments - Comfort working toward measurable goals in competitive, team-oriented settings - Ability to collaborate cross-functionally with sales, marketing, and other teams - Prior sales, customer-facing, athletics, or competitive team experience is helpful but not required

Similar roles