Barry Shields

Professional Summary

Enterprise SaaS enablement leader driving global onboarding and everboarding programs that cut ramp time, increase sales readiness, and deliver measurable revenue outcomes. Expert at embedding advanced methodologies (Challenger™, Command of the Message, MEDDICC) and leveraging AI tools (NotebookLM, Perplexity, LibreChat agents) to personalize learning and scale sales productivity.

$493.9M

Pipeline Impact

72%

Win Rate

Larger Deal Sizes

250+

Hires Ramped

Professional Experience

Shopify

Ottawa, Canada (Remote) Nov 2024 – Present

Head of Global Support Enablement (Jul 2025 – Present)

Currently leading the transformation of global support enablement, aligning onboarding, process adoption, and knowledge systems to CX and operational KPIs.

Support Enablement Operating Model: Designed and operationalized three-pillar framework

Craft Success: Vision alignment, AI-powered learning journeys, curated content governance

Facilitation & Coaching: AI-driven feedback, readiness scorecards, leadership development

Rhythm of Enablement: "Figure it out" service model, AI agents, practice labs, digital literacy

Driving FCR, time-to-ramp, and CSAT improvements across 2,000+ global support professionals

Head of Global Sales Onboarding & Process Enablement (Nov 2024 – Jul 2025)

Accelerated ramp for 250+ hires in 7 months

Boosted readiness with AI-powered personalization

Saved 6+ hours weekly through automation

82% readiness scores, 88% recommendation rate

Elastic

Mountain View, CA 2021 – 2024

Senior Director, Sales Enablement

-66% CSM Ramp Reduction

-23% AE Ramp Reduction

+27% Engagement Increase

Built Elastic's global enablement function across sales, success, and partner teams. Delivered $493.9M pipeline impact via deal labs, coaching, and AI-enabled programs.

Avalara

Durham, NC 2019 – 2021

Director, Customer Experience Training & Enablement

-11% Case Resolution Time

-78% Tier 3 Escalations

+17% Agent Perception

Implemented scenario-based training that dramatically improved customer experience metrics and reduced escalations.

Charter Communications (Spectrum)

Charlotte, NC 2017 – 2019

Director, Learning Experience for Sales & Services

30,000+ Agents Trained

$630K Annual Savings

+10% FCR Improvement

Delivered Spectrum Mobile launch training in under 9 months with 6 curricula, 20+ e-learnings, and 12 simulations.

Cisco Systems

Charlotte, NC 2006 – 2017

Multiple Leadership Roles, Learning & Development

10,000+ Leaders Developed

$700M Revenue Impact

$400K Annual Savings

Directed development for 10,000+ leaders, including Cisco's first immersive 3D learning program. Delivered significant cost savings and revenue impact through knowledge management initiatives.

Professional Summary

Core Expertise

Strategy & Leadership

Sales & Product

AI & Technology

Platforms & Tools