Training Specialist V

Swoon is seeking an experienced Instructional Designer to support a large-scale enterprise AI transformation. This role is ideal for someone who is passionate about AI, enjoys creating engaging learning experiences, and thrives in a fast-paced environment where innovation and adaptability are key.

You'll partner with cross-functional teams to develop learning solutions that help employees confidently adopt AI technologies and new ways of working.

Responsibilities

• Design and develop engaging instructor-led training, eLearning courses, microlearning, videos, job aids, walkthroughs, and knowledge articles.
• Create learning experiences that support enterprise AI initiatives and technology adoption, including AI tools such as Microsoft Copilot.
• Partner with IT, HR, Change Management, Communications, and business leaders to identify learning needs and translate complex concepts into impactful training.
• Apply instructional design and adult learning principles to create learner-focused content that drives adoption and behavior change.
• Develop scalable, just-in-time learning resources that support employees in the flow of work.
• Measure learning effectiveness through learner feedback and adoption metrics, using insights to continuously improve training programs.
• Manage multiple projects while adapting to evolving priorities in a fast-paced environment.

Qualifications

Required

• 3+ years of instructional design or learning & development experience.
• Hands-on experience creating enterprise learning solutions for AI technologies or other emerging technologies.
• Strong understanding of AI tools, preferably Microsoft Copilot.
• Advanced experience with Articulate Rise/360.
• Experience creating microlearning, video-based learning, and interactive digital content.
• Experience with multimedia and rapid authoring tools such as Vyond, Synthesia, or 7Taps.
• Strong project management, communication, and stakeholder management skills.
• Ability to manage multiple priorities and work effectively in a rapidly changing environment.

Preferred

• Experience supporting enterprise technology or digital transformation initiatives.
• Familiarity with change management and technology adoption strategies.
• Experience facilitating learning sessions for large employee audiences.
• Experience working in agile or phased deployment environments.

Position Details

• Location: Hybrid – Chicago, IL
• Duration: 6-month contract with the possibility of extension
• Pay: $40–44/hour

If you're passionate about AI, learning, and helping organizations adopt emerging technologies, we'd love to hear from you!

At Swoon, we believe the future is built by great teams working on the technologies that keep the world running. That’s why we focus on more than just filling roles. We help companies build the right teams at the right time – teams that move big ideas forward.

Across the US and Canada, leading organizations trust us to leverage our expertise to help them build, secure, and scale the technologies that are shaping tomorrow. The result isn’t just successful hires. It’s a hiring journey that’s as rewarding as the outcome: teams that thrive, cultures that grow stronger, and results that exceed expectations.

Because at the end of the day, we exist to help companies and people achieve their boldest ambitions.