alphalist Blog

Landing Your Ideal CTO Role in 2023: Navigating the Job Market and Finding the Right Fit


The job market for CTOs in 2023 has undergone some significant changes, with funding becoming less abundant and location playing an increasingly important role in finding a new role.  Will Larson recently spoke on the alphalist CTO podcast about his experience navigating this landscape and finding his next CTO role. Using the podcast as a abse, in this blog post,we’ll share insights and strategies to help you find the perfect opportunity that aligns with your skills and interests.

Table of Contents
  • Location
  • The Ideal Company Stage
  • The Right Domain for You
  • Cultural Fit
  • Red Flags

Location Matters in the CTO Job Market

Will’s experience and conversations with executive recruiters have shown that it's again much easier to find CTO positions in major tech hubs like Francisco and New York City versus other places. This shift emphasizes the importance of considering location when searching for your next role

The Challenges of Company Stage: Series A, B, and Beyond

The current market for CTOs in late-stage Series A or Series B companies is challenging due to a decrease in the number of companies reaching Series B funding rounds. So if like the challenge of being a CTO in a late-stage Series A or Series B company - think again. 

Many companies are running out of money or scaling back their growth, making it crucial for CTO candidates to consider the financial stability and growth potential of potential employers. Taking a job with a limited runway can be risky for both the company and the executive, as hiring an expensive exec when you only have six months of runway is painful and high-risk. Additionally, the job may not be the right fit if the company scales down drastically, which requires a different set of skills and expertise.

The slow market also affects companies that relied on funding for growth, resulting in fewer job opportunities and a lower focus on hiring senior talent. This trend forces CTO candidates to consider the compensation and long-term growth potential of companies they're considering. As desperate companies may offer better salaries, executives must weigh the risks of accepting a position with a company that may not exist in six months or may significantly downsize. Overall, the challenging market requires CTO candidates to approach their job search with a strategic mindset and a deep understanding of the companies they're considering.

Understanding the Domain and Challenge Level

When considering a new role, it's crucial to understand both the organizational and technical domains. This includes evaluating the company's culture, team dynamics, and any friction points that exist. Additionally, assessing the technical challenges and product complexity can help determine if the role aligns with your skills and interests. Some products require high levels of precision and correctness (like Stripe), while others demand scalability and high-volume handling (like Uber). Understanding your own interests and strengths can help you find a position that aligns with your expertise and passions.

Ensuring a Cultural Fit

Don't just rely on a company's stated cultural values. Often, the stated company culture is about what they would like it to be and not what it actually is.  Dig deeper by speaking with non-executive employees to get a true sense of the work environment to get a real sense of the company culture, as executive-level employees may present an overly polished or idealized version of the work environment and success in any organization.

Identifying Red Flags in Potential Roles

Most companies hiring an executive have some underlying issues that need to be addressed. Being aware of these issues can help you make informed decisions about whether a role is right for you. If a company seems too perfect, it may be a red flag, as it could indicate a lack of transparency. Instead, focus on companies that openly share their challenges, as this demonstrates a commitment to growth and improvement.


Finding the right CTO role in 2023 requires navigating a shifting job market and carefully evaluating potential opportunities. By considering location, company stage, domain challenges, and cultural fit, you can increase your chances of finding a role that aligns with your skills, interests, and values.

Will Larson

Will Larson

CTO @ Carta

Will Larson has been a software engineering leader at Calm, Stripe, Uber, and Digg. He is the author of An Elegant Puzzle and Staff Engineer. Before moving to San Francisco, he grew up in North Carolina, and studied Computer Science at Centre College in Kentucky.