Enablement Specialist, Sales Execution

Five9

1d • $65,100 - $181,400 • Hybrid

About The Position

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. Five9 is looking for a Sales Enablement Specialist to own sales execution enablement across all regions and segments of the business. This is an individual contributor role reporting to the Senior Director of Revenue Enablement. You will work collaboratively to build the playbooks, training, and tools that drive consistent selling behavior, healthier pipeline, and better win rates — from discovery and qualification through proposal, negotiation, and close. That includes competitive enablement like battle cards and objection handling, deal planning and forecast inspection frameworks, and the coaching guides that give sales managers a consistent way to develop their own teams. The right candidate has been close enough to a sales cycle to know what a seller actually reaches for mid-deal, and disciplined enough to prove a playbook is working with process adherence data, not course-completion counts. They are equally comfortable facilitating a training session and pulling a report on how enablement participation relates to win rate, deal size, and cycle time. This role uses conversation intelligence data to find where coaching will move outcomes, not just where it’s easiest to deliver — targeting the specific skill gaps that separate a stalled deal from a closed one.

Requirements

• 5+ years of experience in sales enablement, sales training, or quota-carrying sales is required.
• 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.
• Bachelor’s degree or equivalent experience is required.

Nice To Haves

• Experience in contact center, CCaaS, UCaaS, or adjacent technology industries, and prior experience as a seller or sales manager, are highly recommended.
• Experience with conversation intelligence platforms such as Gong, and with practice and roleplay tooling such as Mindtickle or Second Nature, is highly recommended.
• Experience supporting multiple sales segments or regions, and hands-on proficiency with AI tools — with a point of view on how they can accelerate playbook creation, coaching targeting, and content development — is highly recommended.

Responsibilities

• Build and maintain sales playbooks — covering discovery, qualification, proposal, negotiation, and close.
• Deliver training on Five9’s sales process, methodology, and selling best practices — across segments.
• Facilitate live and virtual training sessions — for sellers across regions.
• Measure methodology adoption through process adherence — not course completion.
• Build tools and frameworks for deal planning, opportunity inspection, and forecast discipline.
• Own competitive enablement — including battle cards, objection handling, and positioning content.
• Equip sales managers with coaching guides and inspection frameworks — for their teams.
• Use conversation intelligence data to identify skill gaps — and target coaching where it will move outcomes.
• Analyze the relationship between enablement participation and win rate, deal size, and cycle time.
• Partner with Sales Operations — on process design, CRM configuration, and performance reporting.

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, 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: Associate degree