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Five9

Enablement Specialist, Sales Execution

Five9 · San Francisco, CA (Hybrid)

Posted 28 days ago

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.

Our read on this posting3.6out of 5
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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