CTO.berlin Articles

Dear CEO, Never Hire Two Tech Executives At Once

As the CEO of a burgeoning startup, you face a myriad of decisions that can profoundly affect the future of your enterprise. One such critical choice is whether to hire tech executives and specifically, if you should bring on two simultaneously. With fresh funds from investors and the directive to scale, it's tempting to rapidly in-house your tech team with top-tier leadership. However, this seemingly efficient strategy can be fraught with unforeseen challenges.

A Tale from the Trenches

Recently, I stumbled upon two job descriptions from the same company: one for a CTO and another for a VP of Engineering. This dual listing made me reflect deeply. How could anyone expect these two roles, so crucial and complex, to be filled simultaneously and work harmoniously? It brought to light the complexities and potential pitfalls of hiring multiple tech executives simultaneously and set the stage for a deeper exploration into this topic.

The Allure and the Trap

Hiring a visionary, hands-on CTO alongside another executive focused on people and processes seems like the ideal blend. In theory, it promises rapid development and efficient management. However, the reality is more complex. People come with unique and varied skills, talents, and visions. Finding two individuals who not only excel in their respective roles but also complement each other almost perfectly is exceptionally challenging.

The Yin and Yang

Every CEO, especially when freshly equipped with substantial funding, might feel the urge to expedite problems away with financial solutions. This mindset often leads to ambitious yet impractical job postings, like simultaneously seeking a CTO and a VP of Engineering. The inclination to "throw money at the problem" and quickly fill these top positions is understandable but misguided. The issue isn't just about the risk of having leaders pull the company in different directions; it's about the redundancy of overlapping skills and visions.
In reality, while you may succeed in hiring two top executives swiftly, it's not always the wisest move. The nuanced understanding of where a company needs to head technologically, and the specific talents required to get there, lies predominantly with the CTO. They are best positioned to know their strengths, the areas they wish to directly influence, and where they need complementary skills. This self-awareness and strategic insight make the CTO the ideal person to define and recruit for any subsequent leadership roles, like a VP of Engineering.
The yin and yang of executive leadership can't be artificially assembled; it must be organically designed by someone deeply embedded in the company's technological vision—typically the CTO. Hiring for a role that closely interacts and overlaps with the CTO, such as a VP of Engineering, should therefore be a decision influenced and led by the CTO. This ensures that the two roles are complementary, not duplicative, propelling the company forward in a unified direction.

A Step-wise Approach to Leadership Building

A more measured, phased approach is advisable. Start by hiring a singular CTO. This person should be the anchor of your technological aspirations, embodying the company ethos and understanding the strategic direction of the business. Once settled, they can identify and recruit a partner who complements their skills and leadership style.

The Reflection and Hiring Paradigm

For this approach to work, reflection is crucial. The CTO must understand their strengths and the support they need. This self-awareness will guide them in identifying the right kind of partner. They should also lead the hiring process for their team, ensuring commitment to crafting a cohesive unit.

Actionable Points for CEOs

  • Methodical Hiring: Avoid the urge to fill positions quickly. Focus on finding the right CTO who aligns with your company's culture and vision. This might take time, but the right fit is worth the wait.
  • Encourage and Enable Reflection: Your tech leader should regularly assess their strengths, weaknesses, and the type of support they need. Facilitate this by providing resources for professional development and self-assessment.
  • Clearly Define Roles and Expectations: The CEO and the CTO should clearly understand their respective roles and how they interplay with each other. This clarity will prevent overlap and conflict.
  • Establish a Transparent Communication Channel: Regular, clear communication between you and your tech leader is vital. It ensures that expectations are understood and any issues are addressed promptly.
  • Foster a Culture of Ownership and Accountability: Encourage your CTO to take ownership of their team and the products they are building. This sense of responsibility will drive them to seek out the best people and get the best out of them.
  • Monitor and Mentor, Don't Micromanage: Provide guidance and support without stifling creativity and innovation. Trust your CTO's expertise while ensuring they align with the broader company vision.


As you navigate the complex journey of scaling your startup, remember that the composition of your leadership team is paramount. The urge to quickly assemble a robust team, especially when backed by substantial funding, is understandable. Yet, as tempting as it may be to "throw money at the problem," hastily hiring multiple top executives is not the solution.
The key lies in understanding that while you may be able to hire two executives rapidly, it’s not just about filling seats or having a diverse skill set. It’s about creating a harmonious and efficient leadership dynamic. This starts with a solid foundation—a visionary CTO who deeply understands the technological and strategic needs of your company. Empower this individual to lead the charge in building their team, including the decision to hire a VP of Engineering or similar role. Their intimate knowledge of the company's technological direction, their own skills, and the gaps they need to fill make them uniquely qualified to design the tech leadership team.
By adopting a more measured and CTO-led approach to expanding your executive team, you avoid the pitfalls of overlapping roles and conflicting visions. Instead, you cultivate a leadership synergy that is not only aligned with your startup's goals but is also capable of propelling your company toward sustainable growth and innovation. The right CTO will not just fill a role but will be instrumental in crafting a cohesive, dynamic, and forward-thinking tech team that is the real driving force behind your company's success.