8x8 · 1 day ago
Director, Sales Enablement & AI Transformation
United States
Full-time
Remote
Director/Executive
7+ years exp8x8 is a company that connects customers and teams globally, empowering CX leaders with performance and insights. The Director of Sales Enablement & AI Transformation will lead the transformation of the sales organization through AI-powered enablement and operational excellence, managing a high-performing team and ensuring sales teams have the necessary resources to succeed.
Information TechnologySaaSSoftwareTelecommunicationsVirtual RealityVoIP
Responsibilities
Architect and execute an aggressive enablement transformation roadmap that delivers rapid, measurable improvements in sales productivity and win rates
Drive organizational change through data-driven prioritization, ruthlessly focusing resources on high-impact initiatives while deprioritizing noise
Lead cross-functional alignment to ensure Sales, Marketing, Operations, Product, and Leadership are synchronized on enablement priorities and business outcomes
Manage a results-oriented enablement team, fostering a culture of accountability, experimentation, and continuous improvement
Partner with Revenue Operations to align CRM standards, pipeline inspection processes, and forecast accuracy improvement initiatives
Define role-specific performance standards using competency mapping and behavioral assessment methodologies that correlate with customer satisfaction and revenue generation
Partner with external consultancies and leverage proven assessment tools to establish evidence-based performance frameworks
Implement consultative selling methodologies that transform product-centric interactions into customer-centric, outcome-focused conversations
Create measurable competencies and behavioral standards that enable scalable excellence across all GTM roles
Build standardized qualification criteria and pipeline advancement frameworks that improve forecast accuracy
Champion the adoption of AI technologies across the sales organization from conversational intelligence and coaching tools to adaptive learning platforms and content generation
Deploy conversation intelligence platforms to analyze winning customer interactions and extract behavioral patterns that drive revenue outcomes
Design and deploy AI-enabled enablement solutions that personalize training, automate content delivery, and provide real-time coaching at scale
Enable sellers to leverage AI tools effectively in their daily workflows, driving productivity gains and competitive advantage
Create AI-powered simulation and roleplay environments that provide stress-tested experiential learning at scale
Continuously evaluate emerging AI technologies and methodologies, rapidly piloting and scaling solutions that demonstrate clear ROI
Own end-to-end design and delivery of onboarding, ongoing training, and performance development programs that compress ramp time and accelerate productivity
Implement intelligent content systems that deliver the right playbooks, talk tracks, and competitive intelligence to the right sellers at the right moment
Build AI-powered content generation capabilities that enable 'segment of one' customer narratives and personalized engagement strategies
Partner directly with Sales Leadership to identify skill gaps and deploy targeted interventions that drive immediate performance improvements
Create simulation-based training and AI role-play experiences that prepare sellers for complex customer conversations
Transform training content from product-focused presentations to customer-centric narratives that teach pain point identification and consultative selling
Own planning and execution of the annual Sales Kickoff, ensuring alignment of training, motivation, and strategic messaging across 200+ GTM team members
Lead New Product Introduction (NPI) processes, coordinating cross-functional launch readiness between Product, Marketing, Sales, and Customer Success
Develop competitive positioning frameworks and battle cards that differentiate based on business outcomes rather than feature comparisons
Create launch enablement programs that ensure GTM teams can effectively sell, implement, and support new offerings from day one
Design post-event measurement frameworks that track SKO impact on performance and NPI adoption rates
Establish clear success metrics tied directly to revenue outcomes, pipeline generation, and sales efficiency
Partner with Revenue Operations to build dashboards and reporting infrastructure that provide visibility into program effectiveness and adoption rates
Conduct rigorous analysis of performance data to identify trends, surface insights, and inform continuous optimization
Leverage conversation intelligence analytics to provide personalized coaching recommendations based on actual customer interactions
Drive accountability through transparent measurement and regular business reviews with stakeholders
Create feedback loops that continuously improve standards, enablement content, and evaluation methodologies
Qualification
Required
7+ years in sales enablement, revenue operations, or sales leadership roles, with at least 3 years leading teams through significant transformation
Proven track record driving transformative enablement in complex, fast-paced B2B SaaS organizations undergoing change
Deep expertise implementing and enabling AI-powered tools for learning, coaching, content delivery, and sales performance; not just awareness, but hands-on experience deploying these technologies at scale
Proven experience implementing consultative selling methodologies (MEDDIC, Challenger, Value Selling, Solution Selling, or similar) that drive measurable behavior change
Hands-on experience with conversation intelligence platforms (Chorus, Gong, or similar) for coaching, performance improvement, and extracting winning behaviors
Track record planning and executing large-scale sales kickoffs (200+ attendees) that drive measurable performance improvement
Experience leading New Product Introduction (NPI) enablement and cross-functional launch coordination
Demonstrated ability to manage competing priorities and make decisive trade-offs to focus teams on what matters most
Strong operator mentality with the ability to move seamlessly between strategic planning and tactical execution
Exceptional cross-functional collaboration skills with the ability to influence without authority and build consensus across diverse stakeholder groups
Self-starter with entrepreneurial instincts, comfortable with ambiguity, able to define problems and architect solutions independently
Track record of building and leading high-performing teams in results-driven cultures
Strong analytical capabilities with experience using data to drive decision-making and measure impact
Excellent communication and executive presence, able to distill complexity into clear narratives and action plans
Preferred
Experience with competency mapping and behavioral assessment frameworks
Background in revenue operations or sales analytics
Familiarity with experiential learning design and simulation-based training methodologies
Experience building AI automation workflows for sales activities and customer engagement
Knowledge of communications technology, UCaaS, CCaaS, or CPaaS markets
Experience with content management systems and intelligent content delivery platforms
Certification in recognized sales methodologies or instructional design
Benefits
Discretionary merit increases
Bonus and/or stock
Sales variable compensation incentives
Company
8x8
8x8 offers secure and reliable cloud-based, enterprise-class business phone systems, unified communications, and contact center solutions.
1001-5000 employees
H1B Sponsorship
8x8 has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (11)
2024 (4)
2023 (11)
2022 (22)
2021 (20)
2020 (30)
Funding
Current Stage
Public CompanyTotal Funding
$453.07M2024-07-15Post Ipo Debt· $200M
2022-01-18Post Ipo Equity· $121.87M
2017-12-08IPO
Leadership Team
David Sipes
Chief Executive Officer
Samuel Wilson
Chief Executive Officer
Recent News
2026-01-21
MarketScreener
2026-01-07
Company data provided by crunchbase