Director - Sales Development (Outbound, US SMB)

Job Description About Rippling Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system. Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365all within 90 seconds. Based in San Francisco, CA, Rippling has raised $1.4B+ from the world's top investorsincluding Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrockand was named one of America's best startup employers by Forbes. We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses. About The Role As our Director, Outbound Sales Development, you will be the driving force behind Rippling's proprietary pipeline generation engine. You will lead, coach, and scale a team of high-performing Outbound SDR Managers and Outbound SDRs, focusing relentlessly on competitive execution and maximizing qualified pipeline sourced through strategic cold outreach. Your leadership will directly impact the acceleration of the entire sales cycle, ensuring that our Account Executives (AEs) have a consistent and high-quality flow of opportunities to crush revenue goals. This position reports into the VP Sales, India Note: - This role is requires you to work in Eastern Standard Timezone (EST) - This is a hybrid role requiring to work from office 3 days a week (Mon, Tue, Thur) What You Will Do Strategy & Execution - This role requires a leader who is comfortable owning the entire top-of-funnel outbound strategy and optimizing conversion metrics at every stage. The ideal candidate will have a strong background in sales development leadership, a passion for coaching and developing talent, and a proven ability to deliver results in a fast-paced, change oriented environment. - Own Outbound Pipeline Generation: Define and execute a comprehensive outbound strategy to achieve and exceed all monthly Sales Qualified Lead (SQL) and pipeline generation targets. - Drive Competitive Positioning: Implement training and processes that enable SDRs to effectively pitch against market incumbents (e.g., ADP, Paychex, Gusto), focusing on differentiating Rippling's integrated platform value. - Optimize Outbound Cadences: Continuously review cold calls, outbound emails and optimize sequences, talk tracks, and social selling strategies to maximize connection rates and demo conversions from cold leads. - Forecasting & Reporting: Accurately forecast outbound-sourced pipeline contribution, providing clear, data-driven reporting on team and individual performance, conversion rates, and pipeline health (e.g., lead velocity rate). - Territory & Account Strategy: Collaborate with Sales leadership to define optimal territory carving, account assignment, and Account-Based Sales strategies to ensure maximum market coverage and lead quality for the AE teams. - Assist in recruiting, staffing and training to grow and maintain a sales team to ensure predictable territory coverage. What You Will Need Leadership & Coaching - Scale & Coaching Expertise: Manage, coach, hire, and scale a team of O-SDR Managers, providing continuous development focused on foundational sales skills (active listening, objection handling, discovery). - Performance Culture: Instill a high-performance culture defined by competitive stamina, consistency, and discipline in daily prospecting activities (calls, emails, social outreach). - Cross-Functional Alignment: Serve as the key liaison between the Outbound SDR team, Sales Enablement, and Marketing to ensure content and messaging are leveraged effectively in the market. - Technology Mastery: Expertly leverage sales engagement platforms (e.g., Outreach, Salesloft), CRM (Salesforce), and analytics tools to enforce best practices and identify coaching opportunities. Qualifications - 5+ years of experience in Sales Development leadership roles, with at least 2 years in a 2nd-line leadership position managing SDR Managers. - Proven track record of scaling and consistently hitting outbound pipeline targets in a B2B SaaS environment known for high velocity and high growth. - Expertise in Outbound methodologies, including cold calling strategies, advanced sequencing, and objection handling for early-stage conversations. - Deep understanding of competitive sales motions and the ability to train teams to successfully pitch against established market incumbents. - Resourceful, data-driven leader with the ability to build and enforce repeatable processes. - Strong communication skills with a proven ability to lead and motivate teams Additional Information Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email [Confidential Information] Rippling highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role. - Commission is not guaranteed