Hi! I'm Lyssa...
Education Leader &
AI-Powered Learning Designer
I'm a learning and development leader who's spent the last decade building programs that scale. I've led education initiatives at LinkedIn and HubSpot, trained Fortune 500 executives and LinkedIn Top Voices, and been named to Learning's 30 Under 30. I'm a Swiss Army knife who can both lead strategy and execute: I facilitate workshops, produce videos, build courses, host podcasts and events, and shape how teams think about learning at scale.
This portfolio shows some of my favorite work. If you're building something transformative in learning, education, or AI, let's talk!
~ Lyssa Leigh Jackson
LIVE DELIVERY & Facilitation
I design learning programs and bring them to life at scale. From enterprise training to live workshops, podcasts, and conference speaking, I create experiences that span customer education, AI upskilling, and thought leadership. My focus? What actually helps people learn, apply new skills, and grow in their careers. Here are a few recent highlights:
InStruct Accelerator
Workshop Program
As a Program Manager on LinkedIn's Education team, scaled the InStruct program, LinkedIn's flagship accelerator, leading 50+ enterprise workshops for Fortune 500 companies and creating a train-the-trainer program for LinkedIn Top Voices to teach LinkedIn strategy at scale.
Podcast Creator & Host
Created and host HubSpot's first internal podcast, Spot On, upskilling employees on AI tools and applications. Covering topics from AI agent-building to workflow optimization, Spot On has achieved 10x higher engagement than typical employee initiatives.
Industry Speaking &
Thought Leadership
Speaker and published writer featured at Google's Saint John's Terminal office in NYC, Microsoft MVP Summit, universities nationwide, 20+ industry conferences, and in Business Insider on topics including AI-powered learning, customer education, and career development.
Higher Logic Academy
Built and delivered technical training curriculum for Higher Logic's marketing automation platform as sole training manager. Taught thousands of association leaders how to build behavior-based automations, design workflows, and leverage data-driven engagement strategies through live and virtual programs for 3 years.
AI Learning
Experiences & Design
I create strategic presentations and learning resources focused on AI adoption and education. From analyzing feature engagement to designing learning pathways that help users build AI literacy, I combine data-driven thinking with clear design. Here are a few examples:
(Click any cover to download the PDF or view the online version.)
On-Camera Content &
Product Education
I create both technical product walkthroughs and promotional videos that get people excited to learn.
I handle the full production process: writing scripts, filming, on-camera delivery, and editing. This end-to-end ownership means I can produce professional content quickly. My work has reached hundreds of thousands across LinkedIn's YouTube channel, HubSpot platforms, and customer education hubs.
My AI Tech Stack:
AI-Powered
Tutorials & Explainers
I create tutorial and explainer videos that turn complex product features into clear visual guides.
I'm actively experimenting with AI tools to scale content production: ElevenLabs for professional voiceovers, Hedra for lifelike animation, and platforms like VEED and Descript for efficient editing. The result? High-quality product education content I can produce quickly, helping customers learn features and solve problems on their own.
I've trained teams at:
Courses & Webinars
I've designed dozens of self-paced courses on LXP and LMS platforms like Skilljar and co-managed live webinar programs at scale. Here's what sets me apart: I love live facilitation. I've led hundreds of sessions, from classrooms with 100 people to virtual webinars with 10,000+ attendees, and co-managed webinar operations at LinkedIn across multiple time zones and seven languages, reaching hundreds of thousands of customers.
Sales Navigator Community Course
