CTO

Stumbling into chaos

The new director of engineering at a startup had to jump in on day one when the team had just done a re-org and re-oriented the product roadmap. He met with the CTO and engineering leads to understand why the new structure had been put in place, then worked with the product managers to focus on pieces they had high certainty of needing. He also added weekly planning meetings for each product team and daily standups to create structure and accountability. Through retros and feedback, he tailored these initial short-term fixes to their needs. He learned that plans often go awry and we have to adapt, look for short-term engineering work when long-term plans change, and creating a predictable process cadence can help create stability.

Scaling To The Extreme

Plixi, a company that allowed people to put photos on Twitter, experienced outages on their web servers due to high traffic. After a period of investigation, they discovered the problem was due to disk reads locking up. With the help of Rackspace and Fusion-io, they were able to install four servers with the fastest hard-drives in the world, which solved the problem. The lesson learned was that it was important for the CTO to understand the whole stack and collaborate with vendors to find a solution.

How I Moved Away From A Flat Organizational Structure

When the CTO of Narrative Science took over, the company was flat-structured with 14 engineers and 40 employees in total. To prepare for growth, the CTO implemented a QA and DevOps team, created a career ladder with five levels, and set up a program to hire recent graduates. He also had to explain the reasoning behind the changes to the existing organization and train people in having difficult conversations. He learned that it is important to make sure the requirements for each level are clear and that he should deliver on any promises made to employees.

Creating Focused Paths for Growth

In response to feedback from team members, the organization created three paths for career growth: a technical lead path, an architect path, and a manager path. This was supported by the TILES framework and a strategy document, as well as an engineering health framework. The implementation of these paths was adjusted to provide a softer transition for those crossing over to a manager role, and to separate tech leads from HR duties.

The Ambiguous Role of a CTO

The role of a CTO is often difficult to understand, as it can involve managing people, technology, or customers. It is important to understand the distinct approach to the role that is context-dependent and varies from company to company. It is possible to be good at all three, but it is impossible to be great. It is important to find an alignment between what you like and what you are good at, and to hire people to fill in the other positions or allocate those responsibilities to other managers. Introspection and understanding what kind of CTO you are/should be is key, and multitasking is never a good idea.

The Approach of Not Stopping for a Massive Rewrite

This article outlines the steps taken by a company to keep innovating and upgrading their product over the past 14 years. They started off with a basic appointment screen built in Delphi and on-premise, and then moved to the cloud with Memento 7. They also had two big overhauls of Memento 7, a look and feel facelift and an infrastructure overhaul. They are now working on Phorest Web, which is built with Ember.js and has an embedded web browser. The article also discusses the common problems with scaling product and the approach taken to avoid having to build a Phorest Web 2 in a few years.