Senior Manager, Sales Onboarding & Leadership Development

Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. Five9 is looking for a Senior Manager to own global sales onboarding and leadership development. Reporting to the Senior Director of Revenue Enablement, this is the only people leadership role on the enablement team, and it carries a dual mandate: get new sellers productive faster and build the leadership capability that sustains performance once they get there. The role owns onboarding end to end across AMER and International — from role-specific paths for New Logo and Expansion Account Executives, Business Development and Technical Sellers, to the ramp metrics that prove the programs are working. Alongside onboarding, this leader designs and delivers leadership development programming for frontline managers and senior sales leaders and provides direct coaching to both new hires and sales leaders on skill development and performance. The right candidate is equally credible facilitating a room of senior sales leaders and coaching a seller in their first ninety days. They can run a program that works across time zones, defend ramp data to Sales and enablement leadership, and lead the small team of facilitators and coordinators who keep onboarding logistics running across regions. This role also owns the onboarding content that lives inside Five9’s revenue enablement platform and LMS, partnering with Learning Design on structure and quality, so the content stays current as the sales motion evolves. Key Responsibilities Onboarding Program Design & Ramp Measurement Own the design, delivery, and continuous improvement of global sales onboarding — across AMER and International Set and track ramp metrics — including pipeline build, time to first deal, time to full productivity, and new hire attainment against plan. Build role-specific onboarding paths — for Account Executives, Sales Development Representatives, and Technical Sellers. Leadership Development & Coaching Design and deliver leadership development programming — for frontline managers and senior sales leaders. Facilitate live and virtual training sessions, workshops, and manager cohorts — across time zones. Provide direct coaching to new hires and sales leaders — on skill development and performance. Program Operations & Content Management Manage onboarding logistics — including scheduling, facilitator coordination, and cross-region communication. Own onboarding content within the revenue enablement platform and LMS — partnering with Learning Design on structure and quality. Reporting & Cross-Functional Partnership Report on onboarding effectiveness and leadership program impact — to Sales and enablement leadership. Partner with Sales leadership, HR, and Talent Acquisition — on hiring forecasts and onboarding capacity. Candidate Requirements and Experience 7+ years of experience in sales enablement, onboarding, or leadership development is required. Demonstrated experience building onboarding programs and measuring ramp outcomes. Strong facilitation skills, with a track record delivering live and virtual training. Coaching experience with sellers and sales managers. Experience managing learning content within an LMS or revenue enablement platform. Strong analytical skills and comfort working with performance data. Experience supporting global or multi-region teams. Bachelor’s degree or equivalent experience is required. Coaching certification or formal coaching training, and experience in contact center, CCaaS, UCaaS, or adjacent technology industries are all highly recommended. Familiarity with revenue enablement platforms and conversation intellige…