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Senior Sales Training & Enablement Specialist - Account Sales

at Five9

United States (Remote)

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. 

Job Summary:


The Senior Sales Training & Enablement Specialist – Account Sales is responsible for accelerating sales effectiveness across Customer Success by developing team members in the knowledge, skills, strategies, and best practices needed to expand business in existing accounts, through cross-selling and up-selling.

In this role, you will drive transformation with account sales teams through planning, coordinating, designing, and delivering learning and development solutions. This role will primarily focus on account directors, customer success managers, and customer success leadership teams.
The ideal candidate will have a strong background in adult learning, facilitation, and learning experience design.


Location: This role is fully remote for candidates who reside at least 50 miles away from our San Francisco or San Ramon office locations. For candidates who reside within 50 miles of our San Francisco or San Ramon locations, this role will be Hybrid. 



  • Collaborates with account sales leadership to identify needs and opportunities for performance improvement.
  • Partners with account sales leadership and key stakeholders to architect and implement sales enablement programs and curriculum to enhance the knowledge and skills of account sales teams.
  • Operates as a key team member of the global Sales Excellence Team; Collaborates with the Director of Sales Excellence on key initiatives and workshops.
  • Applies learning principles, establishes learning objectives, and selects appropriate instructional methods for learning delivery.
  • Facilitates instructor-led training, virtual training, reinforcement sessions, seminars, and/or workshops. Creates an active learning experience where sales reps actively participate in the development of techniques, skills, strategies, and solutions.
  • Designs and develops program materials including case study exercises, scenarios, team exercises based on fictional accounts, role plays, etc.
  • Onboards new account directors, ensuring they have the necessary skills and knowledge to succeed in their roles; Organizes break-out sessions for account sales during Sales Bootcamp.
  • Develops role-specific learning paths in the LMS for account directors and/or customer success managers. Paths may include creating learning journeys, onboarding activities, milestones, assessments, etc.
  • Develops and implements reinforcement and sustainment plans that drive knowledge retention and behavior change.
  • Designs assessments to evaluate the attainment of desired learning outcomes and to measure knowledge/skill increase or behavioral change.
  • Builds and maintains productive relationships with key stakeholders including Customer Support, Legal, Sales Ops, Marketing, Professional Services, etc. Collaborates with cross-functional teams to align training initiatives with business objectives.
  • Develops strong knowledge of Five9 products, processes, teams, and pricing policies including approval processes.
  • Evaluates effectiveness and proposes adjustments to sales enablement programs to improve performance and ensure objectives are met.

Required Qualifications:

  • Bachelor's Degree from a 4-year college or university.
  • 5-7 years of formal Learning & Development (L&D) experience, Facilitation experience or equivalent combination of experience.
  • 2+ years of experience in Learning Experience Design, Learning Solutions Architect, Instructional Design or similar.
  • Solid understanding of Adult Learning Principles and how to apply principles to the design of learning experiences.
  • Strong facilitation and presentation skills, with the ability to effectively convey complex concepts in a simple, easy to understand manner.
  • Extensive knowledge of modern training approaches including blended learning, workshops, self-paced online learning, virtual ILT, & experiential learning methods.
  • Experience with learning management systems (LMS) and other learning technology.
  • Ability to establish and maintain strong relationships with stakeholders.
  • Demonstrated ability to work independently and with little direction – and comfortable asking for help when needed.
  • Ability to travel as needed.

Preferred Qualifications:

  • Proven experience in sales training and enablement
  • Background in account sales, account management, or customer success
  • Strong understanding of key sales processes, especially cross-selling and up-selling processes.
  • Proven work experience in tech, CCaaS, or SaaS sales environments
  • Working knowledge of contact centers

#LI-CM1 #LI-Remote


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.
$87,400$163,700 USD

Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills.  The more inclusive we are, the better we are.  Five9 is an equal opportunity employer. 

Our headquarters are located in the San Francisco Bay Area with global hubs in the United Kingdom, Germany, Philippines, Portugal, and Australia. 

View our privacy policy, including our privacy notice to California residents here:  

Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.


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