Kyle Whittle

Professional Experience

2025

Associate Director, Customer Knowledge & Content Strategy

Entrata

Lead product education inside Professional Services. Partner with Training, Implementation, and Support to turn complex product knowledge into resources customers actually use.

• Built an AI agent pipeline in Python and GitHub with 4 specialized agents that cut standard article updates from 8 hours to 3 (62% faster across 80% of the workload) and dropped complex article drafting from 14 hours to 90 minutes. That's 8+ hours per cycle the team now spends on real audits instead of draft cleanup.

• Set up an AI analysis system across Cursor, Claude, ChatGPT, and Gemini that pulls signal from support tickets, release patterns, and content engagement automatically. Replaced manual analysis that used to need engineering time.

• Applied KCS methodology and content signal scoring across 3,500+ articles to set deflection KPIs. Investment decisions now have data behind them: accuracy, complexity, and ticket impact.

• Designed a release-aligned listening strategy that syncs help content, release notes, and in-app tooltips with each product release, built with Product, Training, and Support.

• Ran the full Zendesk Copenhagen to Lotus migration. Brought in AI-powered search, new taxonomy, and analytics tracking so self-service activation is finally measurable.

• Built a Jira-driven content workflow that cut turnaround time 35% and ended the recurring SME bottlenecks.

2023

Director, Customer Onboarding & Education

Canopy

Led change management for thousands of accounting and tax firms moving onto new systems. Built the teams and infrastructure to get them to value fast, then keep them there.

• Grew the onboarding and training org from 1 person to 30, running 4 CX teams across global SaaS rollouts supporting 900 to 1,000 customers per year.

• Cut average onboarding time from 3 to 4 months down to 30 to 60 days by redesigning the program around customer size and complexity.

• Contributed to a 40% churn drop in the first year after the redesign.

• Built the enablement stack from scratch: Knowledge Base, LMS, video library, and 2 certification programs. Onboarding efficiency up 30%.

• Set up a closed-loop listening system pulling CSAT and CES signals across Implementation, Training, and Support. Customer friction became trackable action items with owners.

• Deflected 45%+ of support tickets year over year through AI-driven self-service and chatbot rollout, freeing support to handle the harder calls.

• Stood up dashboards for customer proficiency, CSAT, and training effectiveness. Those feedback loops directly shaped what content we built next.

2022

Senior Manager, Customer Support

Canopy

Led support and enablement across accounting and tax markets. Built the team and knowledge systems that fed into the broader onboarding redesign.

• Recruited and developed Level 1 and Level 2 support teams across Utah and remote.

• Held 90%+ customer satisfaction during a 200% surge in support volume.

• Redesigned multi-channel process flow, cutting ticket queue depth to a third of where it started.

• Wrote 60+ internal troubleshooting guides and SOPs so new hires could ramp without weeks of shadowing.

2022

Manager, Instructional Design

Canopy

Designed customer-facing training and curriculum for a growing SaaS product. Laid the foundation for Canopy's first formal onboarding program.

• Rebuilt on-demand training from the ground up: 60+ new videos and 2 e-learning courses.

• Built and ran the customer Knowledge Base in Zendesk.

• Cut support queries 37% by moving common onboarding questions into short-form video.

2019

Operations Manager

McMaster-Carr, Cleveland, OH

Started in the customer contact center, moved into warehouse operations. Led a 25-person team handling 10,000+ daily orders.

• Redesigned workstation layout and process flow, lifting operational efficiency 25%.

• Built a predictive staffing model for peak demand, holding 97% SLA through the busy season.

• Rolled out a new inventory management system that cut order errors 15%.

• Set the staffing pattern for weekend operations so coverage stopped depending on heroics.

2014

Product Manager, CX Education

Qualtrics, Provo, UT

Ran product management for Qualtrics' post-sales education portfolio. Started as Instructional Designer, moved into PM. Built programs that drove adoption and expansion for enterprise customers globally.

• Partnered with enterprise customers to design VoC programs across NPS, CSAT, and relationship surveys. Turned platform features into customer listening infrastructure that drove retention.

• Built Qualtrics' first enterprise-wide training program for platform admins and site staff. Became the adoption playbook for global rollouts and closed the gap between configuration and real usage.

• Created a partnership offering for $1M+ accounts that reached 250,000 employees globally.

• Launched Experience Basecamp on Skilljar, an on-demand learning platform with 70+ courses on guided pathways. Generated $1.6MM in revenue over 24 months.

• Piloted an analytics curriculum across 20+ priority accounts, hitting 130% of expansion targets.

• Cut content production time 20% by coaching a 9-person team through a new content strategy.

Education

2022

Master of Business Administration

Quantic School of Business and Technology

Minor in Strategy • 4.0 GPA

2019

Master of Education in Instructional Design

University of Utah

Minor in Psychometrics • 3.9 GPA

2014

Bachelor of Science, Industrial/Organizational Psychology

Brigham Young University-Idaho

Minor in Statistics • 3.7 GPA

Qualtrics CX Certified

Anthropic AI Certifications

Team Growth & Coaching

Change Management

Cross-Functional Program Leadership

Global Training Operations

SOP Design & Process Standardization

LMS / CMS / Knowledge Base

KPI Development & Effectiveness Metrics

ADDIE & Instructional Design

AI Tools: Claude, ChatGPT, Gemini

AI Agent Pipelines (Python + GitHub)

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