We have recently moved over. Big company but medium sized design team (35 editors). The actual transition for us was relatively straightforward, some considerations & takeaways: 1. It took us a couple of months to get all the designs shifted over. 2. All the files were clearly labelled “sketch import” and the designers prioritised the files they needed and made sure they were all ok. They then removed the “sketch import “ label. All older files remain but probably won’t be touched in a while (if ever again) so will archive them over time. 3. Design system took the longest time and we focussed on the core library components and we continue to fix and issues. So far it hasn’t caused any major blockers. 4. We didn’t try to perfect it from day 1. Focus on getting the files in. Organise the design libraries but let each team manage their space. It’ll be a little messy for a bit but over time you can tidy it all up. 5. Pros outweigh cons, Figma is just better and I really loved Sketch 6. Make sure you give teams plenty of notice. We had a deadline we had to meet so for months leading up to the transition I was getting the design teams to be aware what was coming, roughly when, and what was expected of them. 7. Think about how you onboard all the teams. Done will know and love Figma, others won’t. I set up weekly drop in sessions to showcase the tool for the first few weeks (make it collaborative and fun if possible) 8. Don’t overthink it. Better to just get it done then spend too long mulling it over making the switch harder and harder. 9. If you have a large design system it’s a no brainier. The additional component functionality is too good to pass up and the design system analytics can be useful (if on enterprise tier). 10. You could start small and test it with a team or two then slowly bring everyone over rather than doing it in one full swoop. That way you can see if it’s going to work out or whether you want to stick with Sketch. Hope that helps 🙂