📣Postmark has been acquired by ActiveCampaign

​Sketch, Write, Talk

With three products and one more evolution of a product on the way, I’ve never been more busy. Overwhelmed is probably a better word. Natalie and I constantly discuss ways to focus on what is important to the company, our products, and our team. During a single day I might be working with systems on an outage, planning a new iteration for our products, helping steer a decision on a feature, or interviewing someone for a new position on the team. It’s clear I need to get better at delegation and that we need more people on the team.

At the same time, when so much is going on, it’s extremely hard to stop and think about what will have the most impact. It’s hard to find time for focused work in general. I had to figure out what I can do that will affect growth or improve our products the most.

To make this more manageable, I’ve come up with three main areas where I’d like to focus. I’ll still do everything in between, but by breaking it down I can easily pick my head up and question if I missed the mark.


The first area I want to focus on is paper sketching. I’m far from a designer, but over the years I’ve always been the one to help the team get past that blank page state. With our next product in the works, it’s extremely hard to start fresh with a new layout, new navigation, new labels and a new information architecture. The last time we did this was almost five years ago with Postmark, so we are definitely out of practice. I usually just sketch some screens on paper and send it along. The end result is rarely what I sketched, but it’s enough to help generate opionions and direction for a feature, product, or layout. I’ve been doing more of this recently and not only has it helped push things along, I also realized how much I missed it.

A high level sketch can also bring clarity. As the product owner/founder, it’s important that the team can get a clear picture of the vision I have for the product. We all collaborate on the end result, but the more clear I can be about my own vision, the easier it is to discuss and collaborate on concepts. I could write specs for every single feature, define personas, and put together a navigation hierarchy, but a single sketch could represent all of that at once. The more clarity we have around ideas and concepts, the faster we can make decisions.

Once a week, I’d love to sketch something relevant to our current work, even if it will not be used or implemented.


Writing is similar to sketching for me. In all of the multi-tasking I do, writing is freedom from the back and forth, the commotion, and the chaos. It’s a bit therapeutic, and it helps me refine my opinions and reasoning for what we do every day. The nice part is that we have so many opportunities for writing at Wildbit. It could be a post like this, a new guide for DeployBot, content as part of a user experience, or even an internal process document that helps improve our productivity and communication as a team.

Writing is extremely important in every aspect of our work, and it’s even more important for me to keep up that practice. While I do write every day, I want to make sure I write something thoughtful or permanent once per week. It should be something that we use in our team as a reference, a guide or instructions that our customers read to improve their use of our products, or a real experience I’ve had running Wildbit that might inspire or help others in the same position. Whatever it is that I write, it needs to be a resource, not just something that can be thrown away or forgotten.


My default behavior is to solve problems on my own. I tend to prefer closing a door and thinking about problems rather than discussing as a team. I see the value in collaboration, but I am just not as good at thinking and problem solving with a group. This is possibly what was so attractive with running hosted products. I can run a product from anywhere in the world and only talk to customers via email or chat.

Obviously, this is a terrible strategy, and it’s only become apparent recently. In Postmark we have some really large accounts, some who spend 10’s of thousands per year with us. It’s quite a change from Beanstalk or DeployBot, where you can barely exceed $200 per month. A year ago we noticed more of these type of accounts, and I decided to get on the phone to help with integration, questions, and support. I was stunned by the useful feedback and ideas that came out of a single phone call or demo. We’ve opened up phone conversations even more on the customer success side. It’s helped us not only bring great feedback to the product team, but has helped us refine our messaging and focus based on why customers value our products and how they perceive them.

It’s interesting to hear I am not alone on this. I really enjoy the Work in Progress podcast, and just recently Jason Fried was mentioning how doing demos of your product could be one of the most important things you can do for product development. I could not agree more. So, with this in mind, my third focus is to make sure talking to customers on the phone is a priority each week.

I was talking with Natalie recently about these three focus areas. While it sounded like a good idea when I talked to her, I felt that making it public will help me stick to my plan even more. Wish me luck!