1.1 Stage 1: Startup Phase (0-50 employees, <$5M ARR)
Foundation Building : At this stage, you need scrappy generalists who can establish your education program from scratch.
Your First Hire: The Education Enthusiast
Role: Customer Education Lead (Individual Contributor)
Reports to: Founders, Head of Customer Support
This versatile professional wears multiple hats - creating content, choosing tools, and setting up basic processes. They're your education program's founder.
Key responsibilities:
- Create initial help documentation
- Record basic product videos
- Set up knowledge base
- Handle all education requests
- Establish content standards
What to look for:
- Self-starter mentality
- Basic video/writing skills
- Product knowledge
- Technical aptitude
- Customer empathy
Budget allocation: 5-10% of customer success budget
Tools needed: Video editing or Screen Recording Tool, Knowledge base
When you're small, you're probably going to create either documents or videos. But the problem that you run into is if you create just documents, you're going to have people complain that you don't have video. And if you give someone a video, they're going to complain they don't have the text.
2.1 Stage 2: Growth Phase (50-200 employees, $5M-$20M ARR)
Specialization & Scale : Time to build a dedicated team with specialized skills.
Core Team Structure
Customer Education Manager
Reports to: Director of Customer Success
Owns strategy, metrics, and team growth. Transitions from creating content to managing the program.
Key responsibilities:
- Develop education strategy
- Manage team and budget
- Track program metrics
- Build stakeholder relationships
- Plan content roadmap
Learning Experience Designer (1-2)
Creates structured learning experiences and applies instructional design principles.
Key responsibilities:
- Design learning paths
- Develop course curricula
- Create assessments
- Apply learning science
- Measure outcomes
Content Producer
Handles day-to-day content creation across formats.
Key responsibilities:
- Produce videos and articles
- Maintain help center
- Update post-release content
- Manage tools and assets
- Ensure brand consistency
It's different for every business so at one company I started off with purely instructional designers... at Outreach it was completely opposite.
Budget allocation: 15-20% of customer success budget
Advanced tools: LMS, professional video tools, analytics
3.1 Stage 3: Scale Phase (200-1,000 employees, $20M-$100M ARR)
Revenue Generation & Efficiency : Customer education becomes a profit center with specialized roles.
Leadership Structure
Director of Customer Education
Reports to: VP Customer Success or Chief Customer Officer
Drives education as a business function with revenue targets.
Key responsibilities:
- P&L ownership
- Strategic planning
- Executive alignment
- Revenue generation
- Team scaling
Specialized Teams
Content Team (3-5 people):
- Senior Instructional Designer
- Video Production Specialist
- Technical Writer
- Localization Coordinator
- Visual Designer
Program Management (2-3 people):
- Education Program Manager
- Certification Manager
- Partner Training Lead
Training Delivery (2-4 people):
- Live Training Specialists
- Webinar Coordinators
- Workshop Facilitators
My team right now is eight people and it is going to increase slightly this year, probably two more people... I have my learning experience designers who create the e-learning... And then I have my trainers who deliver the training.
Budget allocation: Standalone budget with revenue targets
Enterprise tools: Advanced LMS, video platform, certification system
Hiring Best Practices
Look Beyond Traditional Backgrounds: Hire people who can bridge education and customer success, not just traditional teachers.
If they do come from academics, you have to be able to really convert and understand customers... I'm always looking for people who understand Mayer's principles of multimedia.
Consider Remote-First: Most customer education roles can be remote, expanding your talent pool significantly.
Build Career Paths: Create clear progression from individual contributor to leadership roles to retain talent.
Red Flags When Hiring
- Lack of technical curiosity
- Resistance to rapid change
- Poor cross-functional skills
- No experience with metrics
- Inability to simplify complex topics
Common Pitfalls to Avoid
Hiring too specialized too early: Start with generalists who can adapt
Underinvesting in tools: Good tools multiply team productivity
Isolation from other teams: Education must be integrated across the organization
Neglecting measurement: Data drives budget and headcount decisions
Ignoring career development: Top talent needs growth opportunities
