Customer Training Lead

Customer Training Lead

Location: Chicago, IL (Relocation assistance available for candidates open to moving to Chicago.)

At project
44,
we believe in better. We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world. With our Decision Intelligence Platform, Movement, we’re redefining how global supply chains operate. By transforming fragmented logistics data into real‑time, AI‑powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently.

Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next‑gen applications that keep businesses moving forward.

Headquartered in Chicago, IL, with a 2nd HQ in Bengaluru, India, we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose. If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high‑performance team – we should talk.

We are seeking a Customer Training Lead who will empower our customers to maximize efficiencies and scale their use of our products. This role sits at the intersection of training, technology, and customer success—focused on creating impactful learning experiences that drive product adoption, efficiency, and long‑term value.

The ideal candidate will combine strong technical and analytical expertise with customer‑centric thinking and people skills. They will leverage AI‑powered tools to design, iterate, and deliver training content, while also applying behavioral nudges to guide customers toward best practices. Collaboration will be central to success in this role, as the Customer Training Lead will work closely with Product, Customer Success, and other cross‑functional teams to ensure training programs align with customer needs and company goals.

• Design and deliver customer training programs that maximize efficiency and product adoption.
• Leverage AI tools to create, refine, and scale content (guides, tutorials, workshops, self‑service modules).
• Incorporate behavioral nudges and adoption strategies to encourage best practices and long‑term product usage.
• Collaborate with Product, Customer Success, and cross‑functional stakeholders to align training with evolving customer needs.
• Analyze training effectiveness using data and feedback, continuously iterating to improve customer outcomes.
• Act as a trusted advisor for customers, ensuring they have the knowledge and confidence to scale their use of our platform.
• Stay ahead of industry trends in AI, training methodologies, and customer education to bring innovative approaches to the role.

• 8+ years of experience in customer training or enablement roles.
• Strong analytics and technical skills with the ability to translate data into actionable insights.
• Demonstrated success in building and scaling customer‑facing content or programs.
• Strong cross‑functional collaboration skills and ability to partner effectively with Product, Customer Success, and other internal teams.
• Excellent communication and facilitation skills, with a customer‑first mindset.
• Prior experience with Learning Management Systems (examples include Moodle, Canvas, Blackboard, Talent
  
  LMS, Docebo, etc.).
• Familiarity with AI‑driven tools for content creation, iteration, and delivery.
• In‑office Commitment:
  Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on‑site, in our beautiful headquarters four days a week. Together, we’re building something extraordinary—learn, grow, and thrive in our fast‑paced, transformative environment.
• Relocation offered:
  We’re proud to call Chicago home—a walkable downtown, amazing food, and a team that makes big ideas move fast. And we’re ready to help you make it yours, project
  44 offers relocation assistance for team members joining us from outside the area.

• Experience in SaaS or…