Why I built Letterbatch

On the Wednesday before Thanksgiving, I was under a dryer at the hair salon, barely able to hear a Teams call about letters that had to go out that night.

The office would be closed on Thanksgiving and Black Friday. Everyone should have been stuffing turkeys. We were troubleshooting VBA.

I had already prepared the letters and left my colleague with the Excel workbook and the VBA automation I had used for years. It ran from Excel, created an individualized email for each recipient in Outlook, and attached the documents that belonged with it.

I had run thousands of letters through that process. I thought I had handed it off.

Instead, a whole group of us stayed on the Teams call until well into the evening while my colleague tried to get it to work and I tried to help from underneath a salon dryer. I could barely hear them. They could not see what I was describing. The letters still had to go out.

That was when I learned that we did not have a transferable process. We had a process I knew how to rescue.

Nobody wants to learn how to troubleshoot VBA in order to send a set of letters in 2026. More importantly, an organization should not need one particular person available every time the automation encounters something unexpected.

The work underneath the letter

The process became harder to sustain as the software around it changed. An automation that had once handled large batches became temperamental and could manage only a few letters at a time in my environment.

In its April 2026 feature comparison, Microsoft lists VBA macros and the Outlook Object Model as unsupported in new Outlook for Windows. That does not explain every problem I experienced, but it does make the larger weakness plain: when critical work depends on a workaround built around another company’s software, the workaround can change underneath you.

The platform changed. The responsibility did not. The letters still had to be right.

This is the kind of work that is often labeled administrative because the final output looks simple. Someone receives an email and an attachment. What they do not see is the work required to connect the right data to the right recipient, create the correct document, match the correct attachments, find missing information, review the finished package, and get it out on time.

I have spent much of my career inside that work. I have also watched it consume the time of people hired for strategic judgment because the process itself never received the same attention as the communication it produced.

I have a master’s degree in communications from Northwestern, and I have always cared about communication as both meaning and craft. I love calligraphy, textured paper, wax seals, vintage stamps, and a good stamp stack. These things bring me a disproportionate amount of joy.

I also love data. I love an efficient workflow. I love taking a process that should be easy and finally making it make sense.

Those interests are not opposites. The message deserves care. So does the person responsible for preparing it.

What Letterbatch is supposed to be

I built Letterbatch to make the obvious obvious and the manual work easier.

Letterbatch is not supposed to decide what an important communication should say, replace the judgment of the person responsible for it, or send something before that person is ready. It is supposed to help people connect approved data and documents, prepare the right email or mail package for each recipient, see what is missing or ambiguous, and review the finished work before it moves into the delivery systems they already control.

The tools will keep changing. AI will change how parts of the work get done. None of that removes the need for people and organizations to communicate with each other, or the responsibility to make sure the communication is right.

Letterbatch is, quite literally, a love letter to my former colleagues.

It is for the people who know which spreadsheet is the real one. The people who can spot the attachment that does not belong. The people who inherit a macro, a deadline, and the expectation that they will somehow make the whole thing work.

I built it because I have been there. I know how much work can hide underneath a simple letter. I also know that critical communication deserves a better contingency plan than hoping I can hear you over a salon dryer.

If this is work you recognize, request an invitation to Letterbatch. I would love to learn what you are preparing.