Hiring the right product leader is one of the most critical decisions a CEO can make.
This role is essential in bridging the gap between business strategy and product execution. The best product leaders drive innovation, champion the customer, and lead teams to create impactful solutions.
However, when it comes to product leader hiring, finding the perfect fit goes beyond scanning resumes—it requires understanding the nuances of what makes a successful partnership between the CEO and their product leader.
To shed light on this topic, we asked experienced product leaders to share their top advice for CEOs embarking on this important hiring journey.
Here are their insights:
There are a few signals that it might be time for a founder to bring in a startup CPO. You might notice the product development process getting increasingly complex or struggling to prioritize features and manage everyone’s expectations. You may realize you need more sophisticated metrics and analytics to really understand your product’s performance. Or you’re facing challenges in aligning your product strategy with your overall business goals. When these issues start popping up, it’s often a sign that it’s time to bring in some specialized product leadership.
A typical example of this evolution for emerging product organizations is looking at their product roadmap. The question founders often need to ask themselves is – Is my product roadmap just a list of to-do items? Or is it an articulated way to map out the steps to take your product and company vision through to day-to-day execution? A skilled CPO can help transform that to-do list into a strategic roadmap that aligns with your company’s vision and goals.
Jason Dea
Venture Chief Product Officer, Koru
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Think about what you need to complement your skills, especially if you are still a very small team. It’s crucial to identify the gaps in your expertise and find someone who can fill those gaps.
For example, suppose you have a founder team with one ‘business’ brain and one passionate ‘technologist.’ In that case, you might need someone to mediate their conversations and translate their shared vision into reality.
Different profiles of product leaders could be a fit, depending on your founding team and the complexity of your product:
- Visionary Leader: If you are still unclear on key aspects of the product (target market, form factor, pricing, positioning, etc.), look for someone who can lead on that vision component and drive you through to product-market fit. This type of leader excels at setting a clear direction and inspiring the team to achieve it.
- Practice Leader: If you need someone to organize your product practice, find a leader who is experienced in the day-to-day realities of product management and has worked in various contexts or businesses. This person should be able to bring processes, routines, and discipline to your teams.
- Technical Leader: If you have a highly technical product, it might be pragmatic to hire someone with industry or technical experience alongside their product management skills. This ensures they can understand the product and the needs of the target market well enough to drive decision-making.
Breanne Hargreaves
VP Growth & Product Commercialization, Eugeria
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When looking for a content product management leader, domain expertise is critical. Seek strategic thinkers who understand the content ecosystem. Look for data-driven decision-makers who balance immediate wins with long-term growth. Prioritize cross-platform expertise. Creativity, adaptability, and collaboration skills are what separate excellent product content leaders from the rest. Ask for evidence of each.
Michelle Kempner
Product Leader, Reddit
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A VP of Product Platforms is essentially a Product Manager, so candidates for this niche position can be assessed according to your standard PM rubric; however, there are three key areas where they should shine:
- Prioritization: Everybody in product needs to prioritize, but platform leaders need the wisdom of King Solomon to do it effectively. The VP of Product Platforms does not prioritize the customer alone; rather, they arbitrate between features and services requested by customers, regulators, and their peers within the product organization. To get a better understanding of this skill set, ask candidates to share examples of how they’ve tackled challenging trade-offs and how they typically frame those discussions with their peers and/or their teams.
- Tech Literacy: Product Platform leaders serve as a translation layer between the strategic priorities of the business and the technical and architectural implementation of those priorities. Can the candidate make a case for implementing a new technology or addressing specific technical debt in the context of how it benefits the business? Are they conversant in implementing and optimizing broad business functions that apply to any SaaS business? (e.g., billing, security, notifications, search, information architecture, design systems, etc.)
- Emotional Intelligence: Managing a product platform upon which one or many products and revenue lines depend is always an exercise in effective change management with a substantial side of influencing without authority. Potential candidates should be able to articulate their approach to change management with examples and outcomes.
Alianna Inzana
Former Vice President of Product, WeTransfer
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When evaluating product leaders for a global organization, look for ones with these three critical dimensions:
- Scale is a dimension most CEOs understand but overlook. At Meta, we were building experiences for billions of users. Ensuring that the product creates value for millions of users and does not degrade the experience for non-users is an art. A product leader from such a background understands how to handle combinations of user segments and markets, complex infrastructure, and leading through influence across many layers to make outcomes possible. These leaders bring a level of craft that will up-level your products and deliver finesse.
- Adaptability is another dimension often overlooked. Product leaders at global organizations are “swiss-army knives” at problem-solving across various domains and can understand a new domain quickly. Most CEOs look for product leaders with a deep understanding of their industry and miss out on bringing a fresh perspective to a product team that potentially already has domain experts.
- The most important dimension beyond these is being a culture fit. Global experiences often bring a diverse perspective with the ability to balance global insights with local relevance, ensuring that the strategies resonate across different markets. These leaders have seen beyond the corner you are yet to discover and can help you navigate those corners while leveling up your culture for the next stage of the company’s growth.
Tapan Kamdar
Senior Director of Product Management (Generative AI, Search & Productivity), Mozilla
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To help sell and an opportunity, make sure to provide prospective product leaders with clarity on these crucial aspects:
- Understanding the company’s long-term vision and current strategic objectives to ensure alignment with their own professional goals.
- Insight into team dynamics, collaboration, and leadership style, particularly from the CEO will help them assess the level of support for innovation and risk-taking that’s available.
- Knowledge of the product roadmap, challenges, market position, and competition allows them to gauge the potential impact they can make by joining the organization.
- Assessing company culture and values is paramount for cultural fit and long-term satisfaction. This factor is becoming more critical as they decide where to work.
A comprehensive overview of these elements during the interview process ensures that both the product leader and the CEO can make informed decisions about the alignment of the opportunity with their respective objectives.
Jillian Maloney
Co-Founder, Productive Minds LLC (Former Head of Product)
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The advice would be different for each part of a tech company’s lifecycle, from ideation to startup to expansion and scale-up to maturity and growth.
Ideation to Startup: Partner with a product leader who is bold, passionate, and informed, someone who can hustle and sell the vision as much as the CEO. As you look for investment, you need your product team to test the hypothesis to see if there is a distinct need you have solved and that the designed approach is clearly differentiated. CEOs will need a very compelling product leader to partner with so they can focus on the “sizzle,” while the product leader focuses on the “steak,” and engineering can focus on the tech.
Expand and Scale: A product leader with experience designing and developing a defined product management process is critical because it allows the organization to validate its market position, define and quantify the opportunity, and make product choices that meet those needs in a unique and differentiated manner. The process also acts as the catalyst to shift the company to be more customer-centric and product-orientated. Shifting from being technology-led to more customer-led is a significant change in how an organization operates and requires a leader who understands how to make that shift.
This stage can be very personal to a CEO/founder, so I advise those CEOs to ensure that the person you hire is someone you trust. It is also crucial that the company’s values are clear so that the product leader can align with those values. With that trust, CEOs should be more comfortable being challenged and making critical product choices and investments regarding where the product needs to go. Having the courage to pivot to a place with the greatest opportunity will require tough choices, and with investors breathing down your neck, you need a confident product leader who understands what it takes to move the product to a place of more sustained growth.
Maturity and Sustained Growth: There is success when a product leader can leverage the product management process with a more data-driven approach to understand customer needs, market opportunities, and market fit. With that foundation, aligning the organization and prioritizing the right customers with the right features and experience becomes easier.
Adrian Borys
Director, Customer Strategy and Design Leader, Slalom
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There is empathy with any Founder who is considering bringing on a product leader. That empathy is rooted not in the difficult task of building out your leadership team but in the far more daunting challenge of empowering someone else to take the reins on product decisions—something that the Founder has undoubtedly owned since the company’s inception. As you embark on this journey, here are some considerations for each stage of the hiring process:
Before Hiring: Before you commit to hiring a VP Product, ask yourself whether you are ready for the transition from personal ownership to collaborative leadership. Ensure you’re ready and able to set up an incoming product leader for success.
During Hiring: There is no typical product leader profile. Generalists, by nature, most product leaders will have the mental agility to succeed in the face of a variety of challenges. Don’t consider a product leader’s skills and experience in isolation. Carefully gauge a product leader’s strengths relative to your broader leadership team and assess how their collaboration will empower the organization to reach new heights.
After Hiring: Providing the product leader with the freedom to explore new perspectives is imperative – remember, you did say you were ready to hand over the reins. Now, more than ever, focus on articulating a clear vision and desired outcomes. Provide your new product leader with the space for innovation to think differently about people, processes, and the product itself. In parallel, measure outcomes to ensure seamless integration of the product leader’s expertise into the company’s overall vision.
Kate McLauchlin
Former Head of Product, Daisy Intelligence
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A standout trait among early Founders is their resilience in the face of failure. This ability to rebound sets them apart from other employees who may be less tolerant of pivots. When Founders bring on their next product leader, they essentially outsource this innate resilience and recovery capacity.
For first-time Founders, it’s crucial to assess how a potential product executive has navigated and improved decision-making during career setbacks. To borrow from Mike Tyson, “We all have a plan until we get punched in the face.” Founders should establish their own expectations for a rebound or bounce-back Key Performance Indicator (KPI), as they will subconsciously measure their executives against such a metric. Understanding how a prospective leader rebounds from challenges should be a top priority in the hiring process.
While conventional hiring practices focus on challenges and learning experiences, it’s equally vital to delve into the recovery process from failure. Instead of fixating on defining a failure situation, engage in the specifics of the CPO’s recovery process. This sheds light on their approach – whether it’s reactive, defensive, blaming, systematic, reflective, or transparent.
Curiosity about the candidate’s emergence from failure is crucial. Pay attention to how they discuss it – does it come across as arrogant or humble, a gloss-over, or an appreciation of the experience? The ability to fail fast and learn aligns with agile methodologies, but founders need to assess if this extends beyond product processes and into the character of their product leader.
Michael Park
VP of Product & Project Management, Buffini & Company
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Look for individuals with sharp business acumen and those with the demonstrated ability to immerse themselves in the market to understand its intricacies and nuances. Someone who has shown they can develop deep relationships with customers. These characteristics are so crucial because whoever you hire will need to either have those relationships or be able to build them in order to understand why anyone should buy your product.
Amit Kumar
Head of Product Marketing, Gooten
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When looking to hire a VP Product Operations, think of them more like your Chief of Staff in pursuit of operational excellence focused on product outcomes. Is the candidate talking about strategy and outcomes? A product operations leader is a highly specialized product leader where the whole product discipline is the product. Success is when product management has everything they need to do their job, and everyone else has what they need from product management to collectively work towards the strategy.
The key to success is making sure that your principles and values of product management are aligned. This person is going to be doing a lot of organization-wide alignment and buy-in work on your behalf. If you don’t believe in Product Owners, and they do, they are going to build the wrong team structure. If you want fully complete PRDs before engaging development and they subscribe to Teresa Torres’s product trio principle, this is not going to work well.
The hardest part of product operations is organization-wide change leadership. This skill is non-negotiable. If you are spinning up a new product operations discipline, previous 0-1 experience goes a long way, focused more around larger pieces of change. If you’re looking at more slow and steady growth, the organization is likely stable enough to track metrics around the impact of product ops. Generally, these product ops people come from larger and more established companies and focus more around continuous improvements.
A great product operations person inspires the whole organization to do better. Look for that spark. What kind of questions are they asking, and is it leading you to think about deeper problems? Do you feel the urge to divulge more about your feelings than you normally do? Tackling deep systemic problems requires these abilities. It’s never about specific frameworks but the discovery and implementation of great ways of working that fit your product, market, and organization.
May Wong
Freelance Product Operations & Vice Chair of the Board for Open Digital Literacy and Access Network (ODLAN)
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These seasoned product leaders emphasize the importance of finding a candidate who aligns with your company’s vision, excels in execution, and possesses the ability to adapt as your business evolves.
As a CEO/Founder, hiring a product leader is an investment in your company’s future—it’s worth taking the time to identify someone who brings both strategic clarity and the capability to deliver results. When approached thoughtfully, this hire can be a game-changer for your organization.
Struggling to find the right product leader for your organization? Book a call to learn more about the current product leader hiring market and how we can help to find the perfect fit.