Senior Sales Enablement Specialist

Role Overview

Join Five9, a leading provider of cloud contact center software, in bringing joy to customer experience. This role is an individual contributor position that requires 5+ years of experience in sales enablement, sales training, or quota-carrying sales. The ideal candidate will have a working knowledge of B2B SaaS sales process and recognized methodologies such as MEDDIC, Challenger, or Sandler. They will work collaboratively to build playbooks, training, and tools that drive consistent selling behavior, healthier pipeline, and better win rates.

What You Will Do

Key responsibilities include building and maintaining sales playbooks, delivering training on Five9’s sales process and methodology, facilitating live and virtual training sessions, and measuring methodology adoption through process adherence. The role also involves building tools and frameworks for deal planning, opportunity inspection, and forecast discipline, as well as owning competitive enablement and equipping sales managers with coaching guides and inspection frameworks.

Why It Might Be a Fit

The right candidate will have a strong facilitation skill, experience with Salesforce or a comparable CRM, and comfort working with sales performance data. They will be disciplined enough to prove a playbook is working with process adherence data, not course-completion counts, and will be equally comfortable facilitating a training session and pulling a report on how enablement participation relates to win rate, deal size, and cycle time.

Requirements

• 5+ years of experience in sales enablement, sales training, or quota-carrying sales
• Working knowledge of B2B SaaS sales process and recognized methodologies such as MEDDIC, Challenger, or Sandler
• Experience building playbooks and sales tools that sellers actually adopt
• Strong facilitation skills
• Experience with Salesforce or a comparable CRM
• Comfort working with sales performance data

Benefits

• Health, dental, and vision coverage
• Short & Long-Term Disability
• Basic Life Insurance
• 401k saving plan with employer matching
• Access to an innovative mental health support platform
• Generous employee stock purchase plan
• Paid Time Off
• Company paid holidays
• Paid volunteer hours
• 12 weeks paid parental leave