Note: The job is a remote job and is open to candidates in USA. Five9 is a provider of cloud contact center software that is seeking an Enablement Specialist, Sales Execution. The role owns sales execution enablement across regions and business segments by developing playbooks, delivering training, supporting competitive enablement, and using performance data and conversation intelligence to improve selling outcomes.
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
Skills
- 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
- Work Location: This role is fully remote for candidates who reside outside the 30 mile radius of one of our offices
- For candidates who reside within a 30 mile radius of one of our offices, this role is Hybrid and would require 3 days a week (T, W, TH) in office
- 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
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.
- Fully remote work for candidates who reside outside the 30 mile radius of one of our offices.
- Hybrid work requiring 3 days a week (T, W, TH) in office for candidates who reside within a 30 mile radius of one of our offices.
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