Diana Walsh

Strategic Revenue Enablement GTM Leader | Learning and Development Professional | Global Impact Leveraging AI, Analytics, & Cross-Functional Execution

Tampa, Florida, United States

About

As a Learning & Development Revenue Enablement Leader with 15+ years of experience, I specialize in building high-impact enablement, onboarding, and learning ecosystems that align people, process, and technology to drive measurable business growth. I integrate AI, analytics, and data-driven strategy to streamline operations, enhance performance, and deliver consistent revenue outcomes across global teams. Throughout my career, I’ve partnered with cross-functional leaders to scale programs that strengthen sales excellence, improve talent readiness, and elevate customer engagement. I’m passionate about transforming organizations into agile, learning-focused cultures where innovation and performance thrive together. Key Achievements Include: ✅ Cut sales ramp-to-productivity from 6 months to 45 days through the launch of a multi-phase onboarding and certification ecosystem integrating AI-driven tools, adaptive learning, and real-time analytics that redefined enablement standards company-wide. ✅ Architected 5 end-to-end enablement departments across SaaS, manufacturing, and enterprise industries, establishing hiring frameworks, data dashboards, and coaching programs that improved workforce productivity by 40-60% and organizational collaboration by 30%. ✅ Enabled $150M+ in sales impact across multiple companies by launching cross-functional enablement programs aligned with GTM strategy, product readiness, and sales operations. ✅ Transformed internal promotion pipelines, developing and mentoring 100+ emerging leaders through leadership accelerators and succession planning programs that increased promotion rates by 40% and reduced managerial turnover by 25%. Contact me through this profile if you wish to connect.

Experience

  • Senior Director, Enablement at HHAeXchange
    2025 - 2025 · Less than a year

    • Recruited to establish the company’s first full-scale enablement function for a 1,200-employee SaaS healthcare organization, developing comprehensive strategies to accelerate readiness across sales, customer success, and operations. • Expanded new hire onboarding from a basic 2-day orientation to a 90-day integrated learning experience, embedding AI-enabled modules, role-based learning paths, and shadowing frameworks that improved engagement by 20% and reduced turnover in the first 90 days by 15%. • Designed and launched the Sales Acceleration Certification Program, reducing average time-to-first sale from 4 months to 3 weeks and time-to-full-quota attainment from 6 months to 6 weeks, driving a 75% faster ramp-to-productivity across all sales roles. • Partnered with senior leadership to build an Enablement Council aligning Sales, Product, Marketing, and Customer Success around unified messaging, product readiness, and training priorities, enhancing interdepartmental efficiency by 35%. • Created company-wide performance dashboards and learning analytics to measure adoption, proficiency, and ROI of training programs, achieving an average 10% time savings per employee through improved process design. • Developed and deployed a sales hiring and competency model that raised hiring accuracy and retention of top performers by 30%.

  • Channel Marketing, Sales Enablement at Masonite®
    2023 - 2025 · 2 yrs

    • Tasked with reimagining enablement for a Fortune 1000 manufacturer’s global partner network across North America, overseeing a 15-person field activation team supporting 3,000+ retail partner associates across Home Depot, Lowe’s, and Menards. • Launched a comprehensive Partner Enablement Ecosystem, resulting in a 25% increase in product knowledge scores and 15% growth in upsell revenue within the first 6 months of deployment. • Implemented a global KPI and analytics framework tracking adoption, performance, and ROI across training tools, increasing enablement program efficiency by 40% and tool engagement by 50%. • Built and deployed a suite of digital channel tools and micro-learning experiences, driving a 45% increase in product adoption and 30% boost in partner-generated revenue across retail networks. • Partnered directly with Product and Marketing to co-develop storytelling assets and sales enablement playbooks that strengthened field engagement and created brand consistency across global partners. • Developed training content that became the industry benchmark, inspiring replication from competitors.

  • Director, Sales Enablement at WooCommerce
    2022 - 2023 · 1 yr

    • Joined during company’s enterprise transformation to build its first-ever direct B2B sales organization, leading the design of the organizational structure, role profiles, hiring strategy, and end-to-end onboarding framework. • Built and led an internal team of enablement specialists, onboarding managers, and technical trainers to design scalable enablement programs aligned with business goals and product innovation. • Cut Time-to-First Sale by 85% through introduction of structured playbooks, adaptive onboarding paths, and competency-based training. • Partnered with Revenue and Marketing leadership to improve MQL-to-SQL conversion rates by 20% and increase overall lead volume by 25%, aligning enablement strategy directly with growth objectives. • Designed and rolled out Leadership Development and Career Pathing Programs that boosted internal promotion rates by 40% and increased overall team engagement and performance by 25%. • Collaborated on go-to-market launch readiness, achieving 30% higher adoption rates and accelerating the speed of new product integration into the sales motion.

  • Manager, Internal Training at ConnectWise
    2017 - 2022 · 5 yrs

    • Hand-selected to build ConnectWise’s first global internal training department supporting 3,500+ employees, implementing foundational frameworks for onboarding, enablement, and continuous development. • Designed and implemented multi-phase onboarding tracks that reduced new hire ramp time by 40% while increasing sales productivity by 25% within the first 90 days. • Created a Leadership Accelerator Program, identifying high-potential talent and equipping them with the tools, behavioral competencies, and business acumen to move into management, reducing promotion-related turnover by 50%. • Developed advanced technical, sales, and marketing learning pathways that improved cross-functional skill proficiency by 30% and enhanced collaboration between sales, customer success, and product marketing teams. • Led GTM readiness initiatives for product launches, improving launch success rates by 30% and reducing time-to-market by 25% through alignment of training, communications, and sales tool adoption.

  • Customer Experience and Training Manager at Target Logistics
    2015 - 2016 · 1 yr

    Oversaw nationwide training, onboarding, and service excellence initiatives across 19 U.S. locations in the oil, gas, and logistics sectors, strengthening operational consistency and workforce capability. • Launched data-driven customer experience and service training programs that improved customer satisfaction by 30%, accelerated NPS by 21 points, and standardized performance across dispersed teams. • Implemented structured onboarding and “train-the-trainer” systems that reduced employee ramp-up time by 30% while improving leadership quality, retention, and communication effectiveness in partnership with HR and operations.