Rachel Weston Rowell.

Opinion
What CEOs need to know about product leadership in uncertain times

"Looking forward through 2024, early- and growth-stage companies need a product strategy that not only helps them survive, but ultimately gains and maintains a competitive edge," writes Rachel Weston Rowell, SVP Onsite Product & Technology Center of Excellence at Insight Partners

We’re in the midst of a great reset in tech. The ongoing adjustment to a challenging economic and funding environment has implications across every functional area of a startup, including the product function. Even in boom times, strong product strategy is essential for startups as it provides a roadmap for efficient resource allocation, differentiation in the market, responsiveness to changing conditions, a customer-centric approach, risk mitigation, investor confidence, and long-term sustainability.
Looking forward through 2024, early- and growth-stage companies need a product strategy that not only helps them survive, but ultimately gains and maintains a competitive edge. This requires a product leader who can drive and execute on the strategy, and in the case of more mature startups, help formulate the strategy as well. However, when and who to hire isn’t always evident.
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Rachel Weston Rowell
Rachel Weston Rowell
Rachel Weston Rowell.
(Insight Partners)
CEOs often have big ideas about product but need resources to put them into practice
CEOs of early-stage companies typically exhibit strengths in either product and technology or go-to-market (GTM). They are often the “big idea” person and have relationships that will net the first customers. In the early days of the company, the CEO also needs to play the role of generalist, typically taking on all the tasks needed to establish and run a business.
However, a time will come on a company’s ScaleUp journey when CEOs and founders must begin delegating responsibilities to others in order to focus more on the business. This is the “CEO Teeter Totter”—learning to find balance and clarifying strengths as the business scales up. This requires a clear understanding of personal strengths and interests, then filling the gaps with the best people possible for the job.
Product leaders are the key piece of the puzzle
Product leaders come in at a pivotal junction on the ScaleUp journey—where the CEO is finally ready to delegate product execution, and eventually product strategy. Whether a company is making its first product leadership hire with a maturing product leader who can grow into the CPO role, or bringing on a more experienced new hire at the CPO level, being able to work cross-functionally is critical.
One of the most important cross-functional skills that product leaders possess is maintaining open lines of communication. Product leaders should provide regular updates to the CEO and appropriate internal and external stakeholders on the product’s progress, key milestones, and any challenges or opportunities. They should also collaborate with the broader executive team to help shape and align to marketing, sales, GTM and other strategies where the product is at the heart.
A method to the product leader hiring madness
As a startup is approaching the ScaleUp phase, typically on the cusp of product-market fit, the time is right to scale functional teams. These “first teams” roll into a member of the executive team and represent the first shift away from a group of generalists to more specialized teams across product, sales and business. For the product function at this stage, it’s often better to invest in an experienced product manager who can guide product and design instead of a senior product leader.
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First team chart
First team chart
First teams chart.
(Insight Partners)
Once the first teams have helped the company settle into the ScaleUp stage, it’s time to build the first organizations. This is a pivotal moment because it signals that the CEO and CTO are ready to delegate product strategy deployment to a Head of Product. The Head of Product is not yet taking on full ownership of product strategy formulation; the ideal candidate is a collaborative product leader that can help facilitate the executive and product teams into a product strategy deployment framework that helps them take the strategy, make decisions, and drive forward.
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First organizations
First organizations
First organizations chart.
(Insight Partners)
As shown in the graphic above, the Head of Product is generally not a C-level hire. Hiring someone too senior at this stage can create confusion and a lack of alignment with the CEO/CTO over ownership of strategy formulation. It’s better to look for a candidate who is excited to focus on strategy deployment and ensure consistent execution against the roadmap. Great hires have the leadership experience and career maturity to eventually grow into the CPO role.
What to look for in a CPO
As organizations mature into the ScaleUp stage, the executive team assesses the need for a focused leader who the CEO can trust with product strategy formulation. Hiring a CPO shifts ownership of both product strategy formulation and deployment from the CEO/CTO to the CPO, who executes it through the product team.
A great CPO candidate will have a strong framework for driving strategy deployment while also being in the driver’s seat for formulation, including regularly engaging stakeholders in forming and refining the strategy. However, they are the decision maker and driver of the process, so CEOs must be careful not to hire someone too junior who would need constant guidance from the CEO or CTO.
There are many reasons to be optimistic about the new year, and it’s also important to be aware of the valleys, swamps and obstacles that can keep a business from reaching its potential. By understanding the product function’s role in propelling all functional areas of a startup forward, and by being able to identify the critical junctures at which to hire a product leader who can run with a winning product strategy, CEOs will unlock a stronger, faster, and more efficient business that is primed for long-term success.
Rachel Weston Rowell is SVP Onsite Product & Technology Center of Excellence at Insight Partners