Culture includes tools, so selecting our tools is more than matching feature lists. They need to support our style of work or encourage us to change in ways we appreciate. We must accommodate some bad design, but need to avoid too much frustration or, worse, tainting our environment with anti-inspiration.
Of course, costs are also a concern. At our scale, we’re not small enough to shrug off per-user charges, because I don’t want to add to the “one more seat" financial impact of every individual hire. But we’re also not so big that we can absorb typical corporate IT inefficiency with “enterprise” plans. Many lean-era startups use pricing models that seem aimed at freelancers or 50-person companies, creating a gap for small teams that need just a little scale.
So, as a form of advice for others in similar situations, here are some of the tools we’re happy enough to pay for:
Adobe Creative Cloud is really still Creative Suite for our purposes; we depend heavily on Illustrator and InDesign. Their cloud services don’t fit us, because we can’t lock into only Adobe for everything, and their team features are not that strong anyway.
Slack is pretty integral to our workflow. It’s easy to imagine replacing it with another IRC clone with GIFs, but we would be crippled without chatrooms.
Dropbox means we don’t have to maintain servers or backups. Though we do have an on-site NAS syncing with it, just in case.
Github brings peace of mind but understanding git is still hard, even for the technically savvy. The new Github desktop app is, unfortunately, a step backwards in abstracting the complexity for users, but there is no better way for us to manage our code projects.2
Some we use but don’t feel very committed to include G Suite for email and calendaring, Harvest for time tracking, Recruitee for job applications, iCloud for sharing notes, Heroku for hosting web apps, and AWS for hosting static sites.