James Fleming🇺🇸
Head of Design Operations at Superhuman (formerly Grammarly)
About James Fleming
Head of Design Operations at Superhuman (formerly Grammarly)
I’m the Head of Design Operations at Superhuman, where I lead the transformation of innovative, AI-native design teams. My work spans strategy and operations leadership across product design, research, and content design for Superhuman, Grammarly, and Coda. I also work on our moonshot Design Strategy team, building large-scale, cross-product north stars, prototypes, and new opportunities for AI experiences.
Previously at Airbnb and Meta, I focused on the systems behind great design: scalable design systems, modern workflows, and team models that help designers thrive as tools and expectations evolve. I’m especially passionate about guiding teams through the shift toward AI-augmented design, redefining craft, accelerating impact, and building durable creative organizations.
Expertise
Sessions with James Fleming
- General Mentorship Session (30 min)
What mentees say
“I really enjoyed speaking with James about Design Operations. He was warm, and welcoming, and shared a wealth of knowledge about design ops. He also provided actionable recommendations for my CV that I will implement. As a career transitioner, it's always a delight to speak with people who have also transitioned careers. It gives so much hope! I plan to schedule another session with him.”
“James was very patient in understanding all my problems and gave me suggestions that could enhance my potential to be a stronger candidate. This was a very insightful conversation and I am looking forward to getting more guidance from him.”
“Great session with James! Very nice atmosphere throughout the session and a lot of valuable information.”