Senior Manager, Sales Onboarding & Leadership Development

About the role

Five9 is seeking a Senior Manager to own global sales onboarding and leadership development, a role that sits at the intersection of program design, people leadership, and data-driven execution. The hire will own the complete end-to-end onboarding experience for sellers across AMER and International markets, ensuring new talent converts into high performers efficiently and consistently. This position carries a dual mandate of accelerating time to productivity for new hires while building the leadership capability that sustains long-term team performance. The role owner will design, deliver, and refine role-specific paths for New Logo and Expansion Account Executives, Business Development, and Technical Sellers while owning the metrics that prove program effectiveness. They will also design and deliver leadership development programming for frontline managers and senior sales leaders, providing direct coaching to both new hires and established sales leaders on skill development and performance. This is the only people leadership role on the enablement team, requiring fluency in managing facilitators, coordinators, and cross-regional stakeholders to maintain program integrity. The successful candidate will be equally credible facilitating a room of senior sales leaders and coaching a seller in their first ninety days, balancing strategic program oversight with hands-on development.

Key facts

What you'll do

Own the design, delivery, and continuous improvement of global sales onboarding programs across AMER and International regions.

Set and track ramp metrics including pipeline build, time to first deal, time to full productivity, and new hire attainment against plan to measure program effectiveness.

Build and maintain role-specific onboarding paths for Account Executives, Sales Development Representatives, and Technical Sellers to ensure relevance and scalability.

Design and deliver leadership development programming for frontline managers and senior sales leaders that aligns with company goals and sales motion evolution.

Facilitate live and virtual training sessions, workshops, and manager cohorts across multiple time zones while maintaining high engagement and participation.

Provide direct coaching to new hires and sales leaders on skill development and performance, translating enablement frameworks into actionable behaviors.

Manage onboarding logistics including scheduling, facilitator coordination, and cross-region communication to ensure seamless program execution.

Own onboarding content within the revenue enablement platform and Learning Management System, partnering with Learning Design on structure, quality, and content currency.

Report on onboarding effectiveness and leadership program impact to Sales and enablement leadership using data to drive decisions and improvements.

Partner with Sales leadership, HR, and Talent Acquisition on hiring forecasts and onboarding capacity to align program design with business needs and growth plans.

Defend ramp data to Sales and enablement leadership, explaining variances, highlighting trends, and recommending corrective actions to stakeholders.

Lead a small team of facilitators and coordinators, providing guidance, feedback, and development opportunities to ensure consistent program delivery.

Champion the adoption of onboarding content and learning experiences inside Five9's revenue enablement platform, ensuring alignment with sales methodology and process updates.

Balance strategic oversight with hands-on involvement, demonstrating comfort coaching at both individual contributor and manager levels across diverse cultural and time zone contexts.

Act as the primary owner for sales onboarding and leadership development, driving accountability for program outcomes and continuous evolution of the experience.

Requirements

7+ years of experience in sales enablement, onboarding, or leadership development is required for this role.

Demonstrated experience building onboarding programs and measuring ramp outcomes is a non-negotiable standard for this position.

Strong facilitation skills must be evidenced by a track record of delivering live and virtual training effectively across diverse audiences.

Coaching experience with sellers and sales managers is essential, showing the ability to develop skills and improve performance through targeted guidance.

Proven ability to run a program that works across time zones and regions while maintaining quality, consistency, and engagement.

Experience defending ramp data and program results to Sales and enablement leadership is required for success in this position.

Ability to lead the small team of facilitators and coordinators who keep onboarding logistics running smoothly across regions.

Comfort with ambiguity and fast-paced environments is mandatory, given the evolving needs of sales execution and leadership development.

Nice to have

Experience with cloud contact center technology and familiarity with Five9's product suite would be advantageous for this role.

Background in managing Learning Management System and revenue enablement platform content strategy is preferred.

Prior experience working in a SaaS environment and managing quota-carrying sales teams is highly valued.

Practical notes

This is a full-time position based in San Francisco, California, with hybrid work expectations.

Travel is not expected as part of this role, though flexibility to support global teams across time zones may be required.

Candidates must be authorized to work in the United States without sponsorship at this time.