Taking the pain out of time tracking and invoicing. And ensuring you look good when you ask for money.
Billings was a breath of fresh air for one of the most tedious sets of activities independent businesspeople (especially creatives) face—time tracking and invoicing. AJ, the CEO of Marketcircle, correctly recognized the pain point and as the company’s head of design I helped bring Billings from a sketchy prototype through to a multi-user and actually pretty damn good product by the time I left. It ultimately won an Apple Design Award, and before then I was invited to speak at Apple’s developer conference about the importance of great design in business software.
Billings 1 and 2 were a little rough; it wasn’t until we hit 2.5 that we kinda figured out the right flows. The number one insight that we came to—besides the need to keep things fairly simple—was that you have to look good, with no mistakes, when you ask for money. Billings comes with a variety of attractive templates that produce professional templates, and starting with version 3 made it incredibly easy to send them. In general, the guiding principle of Billings was to take care of things for people, rather than make them take care of things.
I shepherded Billings from concept to version 3, and effectively product-managed it. In the last few months, our new designer (Brandon Walkin) took over the project, taking my wireframes and early mockups through fruition, and doing the first iPhone version. Up until then I had done all the UI, most marketing materials, instructional products, invoice templates, and even the box.