What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)
Mar 6, 2025
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Eeke de Milliano, Head of Global Product at Stripe, shares her vast experience from roles at Retool and Constellate. She discusses the daunting challenges of executive hiring, pinpointing red flags and key qualities to look for in candidates. Eeke emphasizes the importance of aligning a new leader's vision with company values and offers practical advice for successful hiring. She also explores how introspection and understanding one's strengths can streamline the process, alongside valuable lessons learned from transitions between startups and established companies.
Successful executive hiring starts with understanding the organization's specific leadership needs and introspective clarity on values.
Choosing between internal promotions and external candidates requires assessing domain knowledge, cultural fit, and the adaptation potential of hires.
Cohesive executive teams prioritize complementarity, cultural alignment, and collaboration to drive organizational success and retention.
Deep dives
The Importance of Introspection in Hiring
To improve executive hiring, organizations must prioritize introspection before candidate sourcing. Failure often stems from jumping straight into the hiring process without understanding the specific leadership needs of the company. Leaders should clarify their values and what the team requires at that moment, making introspective work essential for successful recruitment. This foundational step ensures that when candidates are evaluated, they align with the desired future vision of the company.
The Risks of External versus Internal Hiring
When hiring executives, organizations face a choice between promoting from within or bringing in external talent, each with its own risks and benefits. Internal hires possess valuable domain knowledge and cultural fit, though they may require skill development in specific areas. Conversely, external candidates bring fresh perspectives but come with cultural integration risks. Assessing the right approach involves understanding whether the organization should build skills internally or buy them externally.
Recognizing Leadership Potential
Noting the difference between internal promotions and external hires, it's crucial to evaluate future potential rather than current capability. Promoting leaders who are stretching up often leads to enhanced performance, while those stretching down can feel unchallenged, leading to disengagement. The challenge is to identify which candidates possess the humility to grow into their roles even if they come from larger, established companies. Finding the right balance between recognizing potential and ensuring capability is key to enhancing team performance.
The Consequences of Poor Executive Selection
Poor hiring decisions for executives can have detrimental effects on both organization culture and employee retention. A bad hire can undermine trust in leadership, leading to turnover of other valuable employees. The stakes are much higher with executives compared to other roles, making it crucial to get the selection right. Founders and leaders should approach this with an understanding of the long-term impacts and work diligently to avoid common pitfalls in the hiring process.
Evaluating Executive Fit Within the Organization
Successful executive hires depend significantly on understanding how candidates will fit within the existing leadership team. Complementarity among executives leads to a strong, cohesive team that can effectively drive the organization forward. Each executive should not only fulfill their unique roles but also contribute positively to the team's dynamic. Thus, assessing cultural fit, alignment of values, and the potential for collaboration among executives is vital for sustained success.
Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.
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In today’s episode, we discuss:
Eeke’s wealth of experience as an executive leader
The challenges companies face when hiring new executives
Common hiring red flags and pitfalls
Practical advice for measuring success
Why learning your strengths is an underrated piece of the process