Senior Director, Revenue Enablement

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. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves.

About the role

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 allowing for regional customization.

The right candidate treats enablement as a revenue function, not a training function. They partner with Sales Leadership, Sales Operations, Product, Marketing, and Channel 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.

Responsibilities

• Enablement Strategy & Measurement
  • 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.
• Onboarding & Seller Productivity
  • 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.
• AI Enablement
  • 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.
• Cross-Functional Partnership & Global Scale
  • 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.
• Budget, Vendors & Enablement Technology
  • 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.
• Team & Function Leadership
  • 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.

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.

Preferred Qualifications

• 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.

Schedule

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 requires 3 days a week (Tuesday, Wednesday, Thursday) in office.

Pay

The US base salary range for this role is $107,900—$336,200 USD. Actual compensation packages are based on several factors unique to each candidate, including skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Additionally, the total compensation package may include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Benefits

• Health, dental, and vision coverage beginning on the first day of employment. Five9 covers 100% of the employee portion and shares a high portion of the dependent cost.
• Short & Long-Term Disability, Basic Life Insurance, and a 401k savings plan with employer matching.
• Access to an innovative mental health support platform offering personalized care and resources in areas such as therapy, coaching, and self-guided mindfulness exercises for all covered employees and their dependents.
• Generous employee stock purchase plan.
• Paid Time Off, company-paid holidays, paid volunteer hours, and 12 weeks paid parental leave.