Senior Director, Revenue Enablement
About The Position
Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. We are looking for a Senior Director, Revenue Enablement to set enablement strategy, build and lead the team, and own the connection between enablement investment and revenue outcomes. Reporting to the Vice President of Sales Strategy & Operations, this leader is accountable for how quickly Five9 sellers become productive, how consistently they execute, and how well they carry the company’s AI story into the field. This is a build-and-lead role. The Senior Director directly leads onboarding and leadership development, plus a team of enablement specialists across product, sales execution, AI, partner sales, manager development, and adult learning design. They will scale the function across AMER and International while leaving room for the regional customization that global selling actually requires. The right candidate treats enablement as a revenue function, not a training function. They partner with Sales Leadership, Sales Operations, Product, Marketing, and Channel, and the organizations they lead, to align capability building with go-to-market priorities — and they can defend the investment case in front of executive leadership with evidence rather than activity counts.
Requirements
- 10+ years of experience in sales and/or revenue enablement.
- 5+ years leading and developing teams.
- Track record building or significantly scaling an enablement function.
- Demonstrated ability to tie enablement work to revenue outcomes, not activity metrics.
- Deep understanding of B2B SaaS sales process, methodology, and deal management.
- Experience designing an enablement technology stack.
- Strong executive presence and proven ability to influence senior stakeholders.
- Bachelor’s degree or equivalent experience.
Nice To Haves
- Experience in contact center, CCaaS, UCaaS, or adjacent technology industries.
- Experience enabling sales teams on AI products and AI-assisted selling workflows.
- Hands-on proficiency with modern AI tools and a clear point of view on their application to enablement work — including practical experience using AI to accelerate content development, program design, and team productivity.
- Background supporting global, multi-region sales organizations in sales operations, or a closely related field.
- Familiarity with revenue enablement platforms such as Highspot or Seismic, and conversation intelligence such as Gong.
- Experience with Salesforce and sales analytics.
Responsibilities
- Own and communicate a multi-year revenue enablement strategy — tied directly to Five9 growth objectives and sales priorities.
- Establish the measurement model for enablement — connecting enablement activation to business results such as ramp time, certifications, demo readiness, and pipeline build.
- Present enablement performance, capability gaps, and investment cases to executive leadership — with a clear line from spend to outcome.
- Drive onboarding programs that measurably reduce time to first deal and time to full productivity.
- Own enablement activation at annual company kick-off — the single largest moment for setting seller focus and capability for the year.
- Set the strategy for enabling sellers to use AI in their daily workflow — so the field works faster and prepares better, not just differently.
- Equip sellers to sell Five9 AI solutions — building the fluency and confidence to carry the Genius AI story into enterprise conversations.
- Partner across Sales Leadership, Sales Operations, Product, Marketing, and Channel — aligning enablement with go-to-market priorities rather than running alongside them.
- Scale enablement consistently across AMER and International — holding a common standard while allowing for regional customization.
- Manage the enablement budget and vendor relationships — making deliberate trade-offs about where the function invests.
- Collaborate on the enablement technology stack — including the revenue enablement platform, LMS, conversation intelligence, and practice and roleplay tooling.
- Build, hire, coach, and develop a high-performing enablement team across seven functional areas.
- Directly lead onboarding and leadership development — setting the standard the rest of the function works to.
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
- 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
- 12 weeks paid parental leave.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
