Senior Manager, Sales Onboarding & Leadership Development

Five9•San Francisco, CA

1d•$96,200 - $283,600•Hybrid

About The Position

Five9 is a leading provider of cloud contact center software. This role is responsible for global sales onboarding and leadership development. The primary goals are to accelerate the productivity of new sellers and build the leadership capabilities necessary for sustained performance. The role involves end-to-end ownership of onboarding programs for various sales roles across AMER and International, including setting and tracking ramp metrics. Additionally, the role designs and delivers leadership development programs for frontline managers and senior sales leaders, and provides direct coaching to both new hires and sales leaders. The ideal candidate can effectively engage with senior sales leaders, coach new hires, manage programs across time zones, analyze ramp data, and lead a team of facilitators and coordinators. This position also manages onboarding content within the revenue enablement platform and LMS, collaborating with Learning Design for quality and currency.

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