Last week, the Sudo Make Me a CTO Community gathered for an insightful discussion on a critical topic for many of us: how to get hired as a senior engineering leader, specifically for VP and CTO roles. Our conversation covered strategies for standing out, demonstrating value, and navigating the often complex hiring process for these executive positions.
Here are the key takeaways from our community discussion:
One of the most fundamental steps is to understand and articulate what makes you special professionally. This isn't about bragging, but about genuine self-awareness and understanding your unique contribution. Once you have clarity about your key strengths, you can build an entire narrative around them and how they could benefit your next employer.
Reflect and write it down: Take time to reflect on what you do best or better than most people you work with. Community members shared various strengths, from curiosity and knowledge sharing to bridging business and technology, or deep technical skills combined with people management. Set aside one hour to reflect on your answer.
Seek external validation: Ask yourself the question: "How do I know this is true?". How do you know that your self-perception is confirmed by others? Ask former senior colleagues, "What do you think I'm very good at?" or "What is one thing you think I do better than anyone else you've worked with?" This feedback provides credible evidence to either support your claims or help you discover traits you're not aware of.
Be specific, not generic: Avoid vague statements like "I'm good with tech.” While "bridging business and technology" is a common theme at senior levels, qualify it with examples or specific achievements to differentiate yourself. Frame your narrative around these unique skills, proactively bringing them up in interviews.
Remember to stay humble, and don't pretend to be good at something only because you believe that's what the other person would like to hear. Be honest with yourself and others, which includes highlighting your key strengths.
It's vital to build a robust list of the impact you've had in previous roles. This goes beyond listing responsibilities; it's about describing tangible business outcomes. As I shared last week, I recently came unprepared to a conversation where this question arose. As a consequence, I didn't make as good an impression as I would have if I had been able to give a better answer.
Take the time to sit down with yourself and list your key achievements. Here are some recommendations that we discussed in the call:
Focus on measurable results: Your impact should be quantifiable in terms of how it helped the organization, company, team, or shareholders. Examples include reducing costs, increasing revenues by a certain percentage, delivering critical projects on time, or improving the team's productivity.
Prepare for the "How": Be ready to explain not just what happened, but what specific levers you pulled and what your personal role was in achieving that result. This helps demonstrate how you operate and clarifies how you directly contributed to the success, rather than being a mere spectator.
Numbers are powerful, but not always essential: For interviews with C-levels, especially the CEO/CFO, numbers are highly effective, as they speak the language of quantifiable business results. If exact figures are hard to recall, provide ballpark indications (e.g., "double-digit growth" or "between 20-35% improvement"). For peers or engineering teams, qualitative improvements (like perceived productivity or improved team efficiency) might be more relevant.
Track Your Achievements: As one member highlighted, actively tracking impact on projects can be invaluable, as humans have notoriously bad memories. That's something you can start today. For your past achievements, dedicating an hour or two to document a handful of examples from different contexts can significantly improve your interview preparation.
Qualitative Evidence for Change Management: For process changes or cultural shifts, where direct quantitative metrics are difficult, leverage qualitative feedback. Surveys, employee feedback, or observations of how decisions changed can serve as credible evidence.
It's often hard to answer questions about the measurable impact we've had in our endeavors unless we spend time reflecting on our trajectory and writing down notes. Make sure not to overstate your contributions, and definitely do not make things up. Bonus points if you can provide references to people who could confirm the most notable ones.
For senior leadership roles, being the one who asks the most questions is often more effective than just providing answers. It demonstrates genuine interest and your ability to think holistically about the business.
Research the business: Your initial interactions should focus on understanding the company's business model, financials, growth plans, and strategy. This helps you position yourself better, as it shows you truly care about the business and are not just attracted by interesting technical problems. Equally important, it helps you determine if the company is the right fit for you, as you might not want to join a business built on weak fundamentals.
Observe the Culture and Values: Speak to as many people as possible across different roles (CEO, CFO, CPO, HR, board members, and team members) and ask similar questions. Discrepancies in answers can signal cultural dysfunction or lack of alignment. Observe how decisions are made to understand the de facto culture, asking very specific questions: What is the biggest challenge the team is facing? What have been their biggest achievements? Who has been recently promoted, and why?
Navigating Case Presentations: We all agreed in the call that case studies are often very annoying, but they're a reality for most C-level hires. If you're given a case study, treat it as if you're already on the job, as an opportunity to further understand how the company operates.
Ask Clarifying Questions: Don't stick solely to the provided brief; ask plenty of specific, clarifying questions to the business owners or interviewers. Cases often assume implicit information, sometimes even on purpose, to assess your ability to deal with partial data. This demonstrates you know how to research information beyond what you're being served.
Embrace "It Depends": Resist the urge to present a single, definitive answer. Instead, make your assumptions and trade-offs explicit (e.g., "With the information I have, I'd consider this approach, with these trade-offs…"). Pretending to know exactly what the company needs might make you sound like the person with a hammer looking for nails.
Propose Scenarios: Presenting multiple scenarios, outlining their benefits and drawbacks, demonstrates your ability to reason about complex problems, rather than just finding a "right" answer. It shows that you're able to reason openly about the merits and drawbacks of different approaches, without dogmatic or emotional attachment to any particular solution.
Your first day on the job will be full of new information. There is no need to add a bunch of surprises on how the business operates to that list.
Some community members asked a very valid question: how do you even find those roles? Indeed, finding a CTO or VP role differs significantly from other engineering positions in many ways.
Internal growth is often the first step: it's generally harder to land a first-time CTO role as an external hire, unless the hiring company is willing to take a high-risk bet, which they usually don't do. Proving your value and leadership capabilities within your current company often provides the initial stepping stone to a similar level elsewhere. This requires patience, as the road to the top can be a long journey.
Executive headhunters: Most senior executive roles are external hires but are managed by specialized headhunters. Frequently, "stealth searches" take place when a company needs to replace an existing CTO discreetly, so you won't see these roles advertised publicly. Such headhunters tend to search for candidates with a professional history demonstrating they've held similar roles in the past.
Network Referrals: Another effective channel for such hires is the network and referrals from peers. CEOs tend to be connected with peers with whom they frequently share tips on how to raise capital, pretend their company is at the forefront of GenAI adoption, or where to find good talent. Doing a good job wherever you are today can open a lot of doors in the future.
Direct Applications: While possible, direct applications are typically less common for these top-tier roles. When such a role is publicly posted, it often means the previous leader has already left, and the company is expanding the search due to recruitment challenges. This might or might not be a worrying sign to investigate during the process.
Startups as an Entry Point: Moving from a Director/Head of Technology role in a large corporation to a CTO position in a smaller startup is also a viable path. Many of the skills you've demonstrated in the corporate environment are relevant to the new position. The major challenge will usually be joining the executive team and putting on the business leader hat.
There isn't a single path for accessing such roles, and no shortcut either. What will work best for you will depend significantly on your past trajectory, opportunities for growth in your current company, and your willingness to take risks. Taking a deliberate and structured approach will help in any situation, and that's why I recommend you start preparing yourself for those eventual conversations.
We'll continue discussing these topics in our upcoming community calls, especially as some of the members might go through interview processes.
Find out how you could join the conversation below.
I love writing this newsletter, and I intend to keep it free forever.
If you want to support my work, you can engage with me in one of the following ways:
If you need help with your Startup, Company, or team, I can support through advisory or fractional services. Find out more on this page.
If you need personal support to overcome challenges and grow as an engineering leader, I can support you through Mentoring and Coaching. Find out more on this page.
If you are looking for continued support and the chance of joining a thriving community of like-minded people, I host a Community for engineering leaders. Find out more on this page.
If your needs fall into a different category, such as newsletter collaborations or sponsoring, please reply to this email or schedule a free call via this link.
All the content in this article was derived from the most recent session in the Sudo Make Me a CTO Community, for which I prepared all the materials.
Those sessions are recorded using Firefly as a way for people to watch the session again in the future, especially if they could not attend it. Fireflies also captures full transcripts of the session, which are also made available to members.
For this article, I've experimented with NotebookLM by feeding it with the transcript and audio recording from the session, and it helped me come up with the structure and key points you just read. While I don't use AI to generate the content for me, I found this an effective way of distilling some arguably original content into a short article.
As I've been regularly writing about AI in the past, I find it ethical to fully disclose its usage.
