Senior Manager, Sales Onboarding & Leadership Development
About The Position
Five9 is seeking a Senior Manager to lead global sales onboarding and leadership development. This role, reporting to the Senior Director of Revenue Enablement, is the sole people leadership position within the enablement team. It has a dual focus: accelerating the productivity of new sellers and cultivating the leadership capabilities necessary for sustained performance. The position is responsible for end-to-end onboarding across AMER and International, encompassing role-specific paths for various sales roles (New Logo and Expansion Account Executives, Business Development, and Technical Sellers) and defining ramp metrics to evaluate program effectiveness. In addition to onboarding, this leader will design and implement leadership development programs for frontline managers and senior sales leaders, and provide direct coaching to both new hires and sales leaders on skill development and performance. The ideal candidate will be adept at facilitating sessions with senior sales leaders and coaching new hires, managing programs across time zones, presenting ramp data to Sales and enablement leadership, and leading a team of facilitators and coordinators responsible for onboarding logistics. This role also involves managing onboarding content within Five9’s revenue enablement platform and LMS, collaborating with Learning Design on structure and quality to ensure content remains current with evolving sales motions.
Requirements
- 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.
Nice To Haves
- Coaching certification or formal coaching training
- Experience in contact center, CCaaS, UCaaS, or adjacent technology industries
- Familiarity with revenue enablement platforms and conversation intelligence tooling
- Experience with Salesforce and sales performance reporting
- Hands-on proficiency with AI tools — with a point of view on how they can accelerate onboarding content design and ramp analysis
Responsibilities
- 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.
- 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.
- 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.
- 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.
Benefits
- Health, dental, and vision coverage, beginning on the first day of employment.
- Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost.
- Short & Long-Term Disability
- Basic Life Insurance
- 401k saving plan with employer matching.
- Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
- Generous employee stock purchase plan.
- Paid Time Off
- Company paid holidays
- Paid volunteer hours
- 12 weeks paid parental leave.
- Annual performance bonus
- Stock
- Other applicable incentive compensation plans
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What This Job Offers
Job Type
Full-time
Career Level
Manager
