or apply directly on Five9's site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 28 days Five9's roles stay open a median of 45 days
- Reposted
- No
- Salary listed
- No 0% of Five9's roles list one
- Ghost-job risk at Five9
- high 81 stale, 4 reposted of 124 open
- Hiring momentum
- 210 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-09-17
Measured from postings appearing on and disappearing from Five9's own greenhouse board since 2026-08-03. Full hiring picture for Five9.
About this role
The Enablement Specialist, Sales Execution at Five9 is responsible for developing and implementing sales playbooks, training programs, and tools that enhance sales performance across various regions and segments. This role involves analyzing sales processes, facilitating training sessions, and using data-driven insights to identify coaching opportunities that improve win rates and deal sizes. The position requires collaboration with sales managers and operations to ensure effective execution of sales methodologies and tools.
- benefits
- 5/5
- freshness
- 4/5
- career value
- 4/5
- role clarity
- 5/5
- pay transparency
- 0/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Five9 as an employer.
What you need
- 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
Nice to have
- Experience in contact center, CCaaS, UCaaS, or adjacent technology industries
- Prior experience as a seller or sales manager
- Experience with conversation intelligence platforms such as Gong
- Experience with practice and roleplay tooling such as Mindtickle or Second Nature
- Experience supporting multiple sales segments or regions
What you get
- 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
- Short & Long-Term Disability
- Basic Life Insurance
- 401k saving plan with employer matching
- Access to an innovative mental health support platform
Worth weighing
- Hybrid work model requires 3 days a week in the San Francisco office
- No specific mention of salary negotiation flexibility beyond the stated range
- Role involves significant data analysis and process adherence measurement, which may not appeal to all candidates
Summarised from Five9's posting. Read the full original.
Listed by Five9 on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.
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