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.

Make Hard Time Easier -- Work With a Sponsor

When the company needed to bring in a more experienced CTO, the Product Development team, including the author, had to go through a difficult transition. The author was able to recruit a technical advisor as the new CTO, and through their relationship, the author was able to learn valuable lessons about asking for and listening to feedback, challenging and disagreeing with their manager, and using what they learned to help turn their next manager into a sponsor.

Setting Clear Expectations of the Leadership Roles

The CTO of an organization faced a taxing problem of having to address the preconceived notions of what the role of CTO entails. To address this, the CTO set up expectations of what the role of CTO, VP of Engineering, and VP of Product entails, and highlighted the differences between the roles. As the organization grew, the expectations of the team evolved and three specific leadership roles were defined. This evolution has been a major growth point for the organization.

Completing a Successful Reorganization within a Well-Established Company

As CTO of a well-established organization, I was tasked with reorganizing the company to provide better cybersecurity and data security tools. I ran an audit to understand the company’s situation, implemented a platform approach, aligned job descriptions, and collaborated with leadership and teams. I also held a town hall meeting to discuss the reorganization and put in place KPIs to follow up with my team. The keys for a successful reorganization are to focus on processes, objectives, and pains, and to provide empathy during conversations.

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.

In Need of Extra Hands: Hiring Independent Contractors and External Vendors

When needing to hire additional capacity or expertise, it is important to secure the hiring budget, identify contractors or vendors, vet their quality, and be prepared on the logistical, product, and engineering side. Contracting is a good opportunity to make the right hire and it is important to ensure that the regular team knows and understands what the contractors are building.