Dear Chris and Boom team —

I’d love to be your new Principal Communication Designer—and here’s why I think you’ll love to have me:

First: I’m a strong, creative leader comfortable being a voice for design while advocating for the interests of others, too—someone you can trust with taste, execution, and mentorship.

I empower and protect my team. At Twilio, I turned the Creative team from a neglected service org.—one that made logos bigger and reacted to last-minute requests for image assets—into a valued partner built on trust, service, and integrity. While there, I improved cross-functional effectiveness with tiered SLAs, streamlined brief templates, and launched self-serve solutions; all of it increasing the number of projects we support by 466% with no increase to fixed costs.

Second: I’m a clear communicator and one who can quickly identify the right blend of speed to execution, keeping costs down, and maximizing quality no matter the brief or audience.

I’ve made it all: presentations for (and to) C-levels, web design systems that increased page performance by 80%, multi-channel global campaigns delivering $2.3M in attributed revenue, visual identity governance for teams of 70+ designers, event designs for 10,000 attendees, print production that automated 3,000 sticker sheets with variable data, and stadium animations for 20,881 Chicago Bulls fans. Recently, I led 8 designers across 15 campaigns per month and 3 web pages per week, collaborating with developers, analysts, program managers, and content writers.

What’s more, I help everyone breathe the brand. I care about integrity and how it anchors successful teams. To me, unsung work is the strongest proof of integrity; by distilling company values into actionable design-specific quality standards, to asking the right questions along the way, to robust internal documentation. Even when these might never go to market, I’m rigorous in my principles and I help get everyone on the same page about where the bar is so that we can celebrate when we cross it and make changes when we don’t.

Thanks for reading. Hopefully this gives you a sense of who I am, what’s important to me, and how we could make the world dramatically more accessible.

Sincerely,
— Sky MacFadyen

While this cover letter does highlight my impact as a designer, it is important to also convey my love for aviation. My father’s career in the industry had a large influence. Beyond having KDEN ATC or a MSFS Stream on in the background, like one might the FM Radio, I follow advancements in private and commercial avionics and am slowly pursuing my PPL.