Woah, this is fascinating. I'm on the other end of the spectrum! I've been in agency world for the last 5 years and not been able to break into Senior role in Product Design. I'm also a jack-of-all-trades/generalist in my skillset so I empathize with you!

I've worked up the ladder from Junior Art Director to Senior Interactive Art Director, all in agency land. It has been a fascinating and wonderful ride, with a lot of good learnings along the way.

When it comes to your portfolio. the key thing for agencies is your understanding of client relationships and client work in general. Concepting and selling your concept work is highly valued from a work perspective—how strong is your idea? How interesting or captivating is it? Does it sell while being memorable and showstopping?

I'd focus on showcasing through a client lens the projects that you work on. For instance, imagine if your client was ACME and you created a mobile app to crowdsource bicycle sharing. You'd say all the same things you'd say in a typical Product Designer portfolio, except frame the story as "client's problem" and "our solution to client's problem" along with things you learned along the way.

Other things that help with breaking into agencies include: —Showcasing your collaboration skills with copy, editorial, project management, strategy, data, and account —Showcase your thinking with a design process that you embody, from start to finish —Apply to jobs via LinkedIn, through 2nd and 3rd degree connections and their related companies. Networking and relationships help you break in much quicker to a role. (If you are interested in a NY or DC role, lmk and I'd love to help out.)

All in all, best of luck and God speed :) Feel free to send any other questions you have.