Director of Training

About the Role

We're looking for a Director of Training to build and lead our comprehensive training strategy and execution across customers and internal teams. You'll be the go-to expert ensuring our global workforce and customers can maximize the value of our maritime AI solutions.

You'll be diving deep into maritime domain expertise and product knowledge to create world-class training experiences that scale globally.

Reports to: VP Business Services

What You'll Own

Training development

• Build ongoing product and solutions training curricula to keep customers and internal teams current with our evolving AI solutions
• Manage certification programs and compliance training requirements
• Create maritime domain training for non-maritime team members
• Develop and adjust to role-specific training tracks (customer success, support, sales etc.)

External Customer Training

• Lead customer education strategy from onboarding through advanced use cases
• Build scalable training programs for our diverse global customer base
• Create self-service training resources and knowledge bases
• Design certification programs for customer power users
• Deliver executive-level training sessions and workshops

Strategic Training Operations

• Partner with Product, R&D, Product Marketing and Customer Success to stay ahead of feature releases
• Build training analytics and success metrics to measure program effectiveness
• Manage training technology stack and platforms - use advanced AI tools
• Scale training delivery across multiple time zones and languages

What You Bring

Must-Haves

• Experience in training/education roles, preferably in B2B SaaS environments
• Deep maritime industry knowledge and understanding of maritime operations and challenges - Huge advantage
• Direct experience with Windward products and maritime AI solutions - Huge advantage
• Experience with global, distributed teams and customers
• Strong presentation and facilitation skills for both technical and executive audiences
• Proven track record building training programs from scratch
• Background in developing training materials for global enterprise customers
• Experience in fast-growing SaaS companies with complex technical products
• Maritime certifications or professional maritime background
• Instructional design certifications or formal training methodology experience
• Knowledge in new AI based training tools and LMS’s
• Manage and conduct train the trainer
• Travel abroad to customers and Windward’s offices

Nice to Have

• Experience with training platforms and learning management systems
• Multilingual capabilities for global customer base
• Technical background to understand AI/ML concepts
• Previous experience in customer-facing roles

Why You'll Love This Role

• Shape the training strategy for a cutting-edge maritime AI company
• Work with customers solving real-world maritime challenges
• Build programs that directly impact product adoption and customer success
• Join a global team of maritime and AI experts
• Opportunity to become the training authority in the maritime AI space