Navigating the Hiring Journey: Expert Advice for Founders Hiring a Head of Product

In the fast-paced world of startups, the decision to bring on a Chief Product Officer (CPO) or Vice President of Product (VP Product) is a pivotal moment for Founders seeking to propel their company forward. Drawing on the wisdom of seasoned professionals, we recently reached out to product leaders across North America to gather valuable insights. 

In this feature, we highlight the expertise of Rosalee Gordon, a CPO-turned Executive and Leadership Coach with over 25 years of product experience. Rosalee's journey through the product landscape has provided her with a unique perspective on the evolution of product as both a function and a practice. She also serves as an Executive Director of APMConnect, a non-profit Canadian initiative dedicated to fostering thriving and diverse product communities. 

Here, Rosalee shares her insights for first-time Founders aspiring to hire their inaugural product leader.

1. Establish initial product-market fit

Before diving into the hiring process for a CPO or VP Product, Founders must ensure their product has achieved initial product-market fit. Rosalee emphasizes that the founding team, armed with deep market expertise and intuition combined with a product mindset, is usually best equipped to reach this milestone most efficiently. Once initial product-market fit is achieved, Founders can consider bringing in a full-time product leader to drive growth and the expansion of product-market fit. 

2. Consider the composition of your current leadership team

When companies hire their first Head of Product, they often need that person to lead in other areas for a period of months or even a year while they build out the whole leadership team. Do you need your Head of Product to also lead Engineering? Marketing? Growth? Operations? Hire someone with a broader view who can take on an expanded portfolio for a time.

3. Consider the specific challenges ahead for your company

Are you looking to enter a new vertical? Enter a new geography? Launch a second product? Turn around a flagging business? Evolve your business model from SaaS to Marketplace? There is no one-size-fits-all product executive. Be specific about what you need next and look for someone who has experienced that in a previous role. 

4.  Prepare for a transition in product leadership

Founders accustomed to making hands-on decisions about features and designs may find it challenging to transition product leadership. Rosalee advises Founders to recognize that a Head of Product will not thrive in an environment where the Founder remains involved in the day-to-day of product-related decisions. Prepare to elevate your thinking about your product to a business strategy level.

Your new Head of Product will rely on you for your insight on market needs (rather than solutions), and clarity about your company’s vision, strategy, goals, and top-level success metrics. In return, expect your new Head of Product to clearly align product initiatives to these business goals and clearly communicate progress, metrics, and learnings. Have open conversations about what the evolving structure will look like. Navigating this dynamic can be challenging but is crucial for the company's success. 

5. Consider supporting your new hire with coaching

There is very little formal training for product executives, and many in the role are doing it for the first time. Industry stats show that many CPOs stay in the role for only two years, and choose not to repeat the experience a second time. As an Executive Coach to Product Executives, Rosalee is passionate about equipping and empowering product leaders to thrive in highly impactful and rewarding careers that take their company forward to new heights.

The journey to hiring a CPO or VP of Product is a significant milestone for any startup Founder. Ensuring that both the product and leadership team are prepared for what this hire will mean for the business is the best way to ensure hiring and future product success.  

Are you a Founder feeling unsure how to tackle this critical hire? Connect with us today to learn more about the current product market conditions, competitive compensation packages, and effective strategies for pitching the position to attract the right product leaders.