Resume

Jeremy Gleason

Learning & Enablement Leader  ·  Instructional Design  ·  AI-Enabled Training

Summary

Instructional design and enablement leader with over a decade of experience building learning functions from the ground up, managing cross-functional teams, and turning complex software into training that thousands of learners actually use, across K–12, higher education, and enterprise SaaS. Founded a content development department from zero, led teams of designers and technical writers as final quality authority, managed six-figure technology decisions, and now applies hands-on AI fluency to modernize how learning content gets built. Seeking a manager or senior individual contributor role where deep instructional expertise and a track record of ownership drive measurable business outcomes.

Career Highlights

  • Founded a department from zero. Built Dealertrack's entire content development function from scratch, establishing governance, intake workflows, content and visual standards, and the foundational tech stack (Docebo, Captivate, Adobe Suite).
  • Led teams and owned quality. Managed five instructional designers at Dealertrack and later led a cross-functional team of designers and technical writers at Visual Lease as the final quality authority for all instructional content.
  • Delivered six figures of value on budget. Allocated a $100K budget to source and implement an enterprise LMS, completing the project roughly $40K under budget while administering the platform for over 1,500 global learners.
  • Built measurable program outcomes. Launched a partner certification program that cut onboarding time 30%, designed state DMV-mandated certification programs with real compliance stakes nationwide, and implemented SOPs that reduced content creation time 30%.
  • AI-powered content workflow. Built an AI-powered content workflow, using AI across discovery and scriptwriting, that moves projects into production faster and increased development speed 10–15%. Uses Claude and enterprise AI tools daily, has built working applications on AI, and is writing a book on AI's practical role in L&D.

Professional Experience

Senior Instructional Designer

04/2025 – Present

Juniper Square • Remote

  • Own a 100-course internal learning portfolio in Skilljar, maintaining technical accuracy across Customer Success and Education teams.
  • Built an AI-powered content workflow using AI across discovery and scriptwriting, moving projects into production faster and increasing development speed 10–15%.
  • Manage the full content production lifecycle from research and scripting through publishing, coordinating content standards across two stakeholder organizations.

Lead Instructional Designer

08/2022 – 04/2025

Visual Lease • Remote

  • Team leadership and quality ownership. Led a cross-functional team of instructional designers and technical writers, serving as the final QC authority for all instructional content leaving the department.
  • Partner certification program. Designed and launched a partner certification program from scratch, cutting partner onboarding time 30%.
  • Data-driven program design. Analyzed Customer Success and product usage data to find where users got stuck, built a Pendo Resource Center that reduced How-To support call volume 10%.
  • Platform administration. Owned implementation and daily operations of Cornerstone LMS and a WordPress learning hub.
  • Stakeholder alignment. Partnered with SMEs and executive stakeholders to align product training with international business goals, and directed monthly release-note production with the technical writing team.

Manager, Instructional Design

12/2021 – 08/2022

Dealertrack Technologies • Remote

  • Team management. Formally managed a team of five instructional designers, owning capacity planning, workload distribution, and deadline accountability across all active projects.
  • Coaching and efficiency. Mentored and technically coached new hires onto SOPs, and implemented new SOPs that reduced training content creation time 30%.
  • Strategic roadmapping. Built 3, 6, and 12-month client education roadmaps aligned to major software release cycles.
  • Recognition. Awarded Employee of the Quarter four consecutive quarters for leadership and project management.

Instructional Designer II

08/2018 – 12/2021

Dealertrack Technologies • Remote

  • Department architecture. Built Dealertrack's content development function from zero: governance, intake workflows, content and visual standards, SOPs, and the foundational tech stack (Docebo, Captivate, Adobe Suite, Reaper DAW).
  • Global LMS administration. Administered Docebo LMS serving over 1,500 global learners across international markets: user accounts, curriculum assignments, compliance tracking, and reporting.
  • Compliance certification programs. Designed state DMV-mandated certification programs required for dealerships nationwide to legally operate, managing program governance, exam delivery, and renewal cycles.
  • LMS procurement. Led end-to-end evaluation and procurement of the company's first LMS against a $100K budget, coming in roughly $40K under and overseeing full deployment.

Software Trainer II

09/2014 – 08/2018

Dealertrack Technologies • Remote

  • Managed software implementations and client relationships across the NC territory, including onboarding for executive and C-suite stakeholders, and led training for the state's largest automotive dealership. Acted as a trainer-of-trainers for new hires and large-scale installations.

Department Chair / Project Lead, Course Revision

08/2011 – 08/2016

North Carolina Virtual Public Schools • Remote (concurrent, part-time)

  • Managed and mentored a team of 10 virtual educators across daily operations, professional development, and performance. Designed and executed a full course-revision plan meeting strict state deadlines.

High School Teacher

09/2003 – 06/2012

Public School District • Various

  • Engineered a curriculum framework adopted district-wide, contributing to a measurable rise in standardized test scores. 16 years translating complex content into clear, engaging learning for diverse audiences.

Skills & Tools

Leadership & Strategy

  • Team management
  • Curriculum design
  • Project management
  • Mentoring & coaching
  • Data analysis
  • Adult learning theory
  • Stakeholder alignment

AI

  • Claude & enterprise AI tools
  • AI content workflows
  • AI-assisted scriptwriting
  • Built apps on AI

Authoring & Media

  • Articulate Storyline & Rise
  • Adobe Captivate
  • Camtasia
  • Adobe Creative Suite
  • Adobe Audition
  • Reaper DAW
  • Video editing
  • Professional voiceover

Platforms & Systems

  • Docebo
  • Cornerstone
  • Skilljar
  • Blackboard
  • Moodle
  • WordPress
  • Pendo
  • WalkMe
  • SCORM

Data & Analytics

  • PowerBI
  • Learning gap analysis
  • LMS reporting
  • Adoption & engagement metrics

Education

MBA Baker College, Flint, MI
B.A., Secondary Education SUNY Fredonia, NY