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.

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Liz Rodriguez

Senior Director of Software Engineering at TopQuadrant

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.

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Andrew First

Co-founder & CTO at Plannery

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.

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Brice Lagroy de Croutte

VP of Engineering at AB Tasty

Creating Impact as One of the First Hires in a Startup

This article recounts the experience of joining a startup as the seventh employee and becoming a VP of engineering. It highlights the importance of self-awareness and adaptability when joining a startup, as well as the benefits of understanding the inner workings of a company. It also emphasizes the importance of being financially responsible when considering a startup job.

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Dale Bruce Hopkins

CTO at Vendasta

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.

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Damian Schenkelman

Principal Engineer at Auth0

Achieving Alignment and Efficiency Through a Technical Strategy

A fast-growing company was facing a lack of clarity and confusion about future decisions, leading to inefficiency. To solve this problem, a technical strategy was developed that detailed what should and shouldn't be done to be successful in the long run. This involved reaching out to different people to better understand the reasons behind slow decision-making, tailoring presentations to suit two different audiences, and establishing a process for teams and a "design and architecture" group to collaborate on designs. Lessons learned included the importance of securing buy-in before decision-making meetings, reviewing past decisions, customizing content for different audiences, and documenting decisions and guidelines.

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James Lloyd

Co-Founder/CTO at Redox

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.

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Shyam Sundar

VP Engineering at Stord

From Putting Out Fires To Preventing Them

VP of Engineering at Le Tote faced operational issues and was paged in the middle of the night. To reduce the number of issues, metrics were measured and integrated with the system to provide visibility and move from reactive to proactive work. This helped to drive change and showed the importance of reducing friction to embrace change.

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