Five9 Inc

Senior Manager, Sales Onboarding & Leadership Development

Five9 Inc$96K — $283K *
Business Services
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7+ years in sales enablement, onboarding, or leadership development
  • Proven track record in designing onboarding programs and analyzing ramp outcomes
  • Strong facilitation skills, both in-person and virtual
  • Experience coaching sellers and sales managers
  • Proficient in managing learning content within an LMS
  • Excellent analytical skills for performance data assessment
  • Experience with global or multi-region team support
  • Bachelor's degree or equivalent experience required
  • Coaching certification or training preferred, with familiarity in CCaaS or UCaaS industries further recommended
  • Knowledge of revenue enablement platforms and sales reporting tools, including AI applications.

Responsibilities

  • Design and continuously improve global sales onboarding programs across AMER and International
  • Set and track ramp metrics for new hires, including pipeline build and productivity timelines
  • Create role-specific onboarding paths for various sales roles
  • Develop and facilitate leadership development programs for managers and senior leaders
  • Conduct live and virtual training sessions and workshops effectively across time zones
  • Offer direct coaching to new hires and sales leaders focusing on skill and performance development
  • Manage logistics for onboarding, including scheduling and facilitator coordination
  • Maintain onboarding content quality and organization within the revenue enablement platform

Benefits

  • Comprehensive health, dental, and vision coverage with 100% of employee costs covered
  • Innovative mental health support platform for therapy and self-care resources
  • Generous employee stock purchase plan
  • Paid Time Off, company holidays, and paid volunteer hours
  • 12 weeks of paid parental leave
  • 401k saving plan with employer matching
Full Job Description
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 intelligence tooling, experience with Salesforce and sales performance reporting, and hands-on proficiency with AI tools - with a point of view on how they can accelerate onboarding content design and ramp analysis - are all highly recommended.


Work Location: This role is hybrid. 3 days a week (T, W, TH) in our San Ramon office is required.

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:
  • 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. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 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 and 12 weeks paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.

The US base salary range for this role is below.

$96,200-$283,600 USD

Work Location: This role is hybrid. 3 days a week (T, W, TH) in our San Francisco office is required.

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:
  • 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. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 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 and 12 weeks paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.

The US base salary range for this role is below.

$96,200-$283,600 USD

Work Location: This role is hybrid. 3 days a week (T, W, TH) in our Dallas office is required.

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:
  • 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. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 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 and 12 weeks paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.

The US base salary range for this role is below.

$96,200-$283,600 USD

About Five9 Inc

Five9 is a leading provider of cloud contact center software for the digital enterprise, bringing the power of cloud innovation to customers and facilitating more than three billion customer interactions annually. The company was founded in 2001 and has since become a trusted partner to thousands of customers worldwide, including some of the largest and most well-known brands. Five9's cloud-based software enables businesses to create exceptional customer experiences, improve agent productivity, and increase operational efficiency. The company is committed to delivering innovative solutions that help businesses transform their customer service operations and drive growth.
Learn more about Five9 Inc
Size
2,138 employees
Market Cap
$4.6 billion
Industry
Net Income
-$42.1 million
Founded
2001
5 Year Trend
+30.3%
Revenue
$434.9 million
NASDAQ

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