2025 Product Strategy at Risk? These 4 Leadership & Skills Gaps Could Be Why

Leadership and skills gaps… Even the most mature organizations and the best of teams have them. According to Hunt Club’s recent market survey, 48% of executive respondents shared that they are struggling to find the right talent with the right skills.

As companies set ambitious transformation goals for 2025, they can no longer afford to “make do” with existing leadership. To achieve business transformation and drive true impact, organizations must evaluate their leaders—rigorously. 

Are these leaders equipped to close critical talent gaps and drive forward-thinking strategies that fuel growth, or will they be the roadblocks that stall progress?

Product teams, in particular, are expected to be at the forefront of change. 

According to the same survey, product teams are the #1 department organizations/leaders foresee changing the most (related to budget, structure, headcount, and increases in compensation) in order to drive effective transformation in the next year. This underscores the vital role product leaders play in an organization’s ability to innovate and transform.

That’s why we spoke to David Jesse, an executive with over 20 years of product leadership experience at companies like DoorDash, eBay, and Groupon, to understand how top product organizations can meet these evolving demands and mind the gap. Jesse brings deep insight into the qualities that separate product leaders who merely “make do” from those who truly “make exceptional” happen.

“Success hinges on having the right talent – people who thrive with higher ownership and responsibility. We need this mindset across product, design, engineering, and data science.

Both hiring and coaching are critical to address capability gaps in the first place. A strong leader with good support improves the impact of your entire technology department.

David Jesse

David Jesse Shares 4 Product and Engineering Leadership & Skills Gaps To Address Now

1. The AI Leadership Gap Is Bigger Than You Think

The Gap, According to Jesse: “Product and engineering teams are experiencing the most dramatic transformation I've seen in my career, driven by AI's unprecedented rate of advancement.

The most successful teams I'm seeing are exploring how to embed AI across their workflow – from requirements gathering to testing to deployment. This requires a significant mindset shift: teams must become perpetual learners, constantly evaluating new capabilities while maintaining product quality and security. 

What worked six months ago might be outdated today, creating both opportunities and challenges for team structure and skill development.

Looking ahead, I expect we'll see dramatic evolution in how product teams are organized and staffed. The highest-performing teams will be those that can rapidly experiment with AI capabilities while maintaining strong focus on customer outcomes.”

What This Means for Finding the Right Talent: As AI reshapes the skills required for success, companies can’t afford to bring on leaders who are just “adept.” They need leaders who understand AI’s potential, and have the vision to restructure teams and workflows to capture its full value.

In short, finding talent that is both technically skilled and strategically agile has become an urgent priority—and a critical challenge—for organizations preparing to compete in an AI-driven future.

2. When “Scaling” Becomes a Buzzword, It Just Widens the Gap

The Gap, According to Jesse: “While early success often comes from founder-driven, unscalable approaches, growth demands leaders who have successfully navigated this transition before. The ideal product executives are battle-tested leaders who understand how to preserve entrepreneurial spirit while building repeatable processes that scale.

They have the judgment to know when to add structure without suffocating innovation. We hear the word ‘scale’ all the time, but finding folks who have truly done it, and done it well, isn’t an everyday occurrence.”

What This Means for Finding the Right Talent: Identifying leaders who have actually mastered the art of scaling is rare. And companies can’t rely on promises of scaling expertise alone—they need leaders who have lived it and thrived through it, and can do it all over again. 

This means seeking out executives with a proven track record of not only scaling teams, but budgets and operations—leaders who understand the complexities of growth at the exact level you need.

Easy, right?

3. The Need For Disciplined Execution Balanced With Strategic Thinking

The Gap, According to Jesse: “Growth-stage companies need leaders who can translate founding vision into systematic principles that guide broader teams. This requires a fundamental shift from building for early adopters to serving mainstream markets.

Without this discipline, products become bloated and teams lose focus on what drove initial success.”

What This Means for Finding the Right Talent: Without this skill set, product teams can easily lose focus, overcomplicate offerings, or fail to prioritize effectively, which can derail growth and hinder the ability to serve mainstream markets. 

The challenge is finding product leaders who can actually navigate this transition and drive disciplined execution without sacrificing the entrepreneurial spirit that made the company’s product successful in the first place. 

4. Communication Skills Aren’t Always a Given

The Gap, According to Jesse: “Many growth-stage teams underestimate how critical alignment and communication becomes at scale. 

The best product leaders excel at maintaining this during rapid change, ensuring teams stay coordinated without depending on the founder's direct involvement. They build communication frameworks that scale with the organization.”

What This Means for Finding the Right Talent: Communication and alignment should be tablestakes… Right? As Jesse emphasizes, this isn’t always a given and can be one of the first things to get underestimated or slip through the cracks. 

In the rush to scale, teams often prioritize execution over the systems that keep everyone aligned, resulting in breakdowns in coordination and loss of focus. The assumption that communication will "just happen" as teams grow can lead to missed opportunities, confusion, and ultimately slower decision-making.

Minding the Gap: The Non-Negotiable Skills & Qualities Product Leaders Need To Have

Minding the gap is easier said than done. It’s a long-term game with lots of nuances, complex candidate sourcing, and rigorous looks into the darker parts of your team.

TLDR: It’s not a quick fix, but there are distinct qualities you can start to look for. 

When evaluating executive leaders, Jesse shares three quick differentiators that drive company-wide impact. 

1. Exceptional team building. This is not just hiring talent, but orchestrating teams that consistently exceed expectations. The best executives create environments where strong values and clear operating models enable their teams to tackle seemingly impossible challenges.
2. Strategic vision coupled with execution clarity. Great executives don't just set ambitious goals; they articulate compelling paths to achieve them. This combination of aspiration and pragmatism energizes organizations and transforms skeptics into believers.
3. Relentless outcome orientation. While many executives talk about results, the best ones build systems that reliably deliver value to customers and sustainable impact for the business. They're masterful at connecting daily work to meaningful outcomes.
   
   

Now, What Makes a Product Leader Exceptional?

According to Jesse, exceptional product leadership operates across three critical dimensions: impact, inputs, and influence.

• Impact represents the ultimate measure – the tangible value delivered through the team's collective outcomes.

• Inputs are about creating the conditions for success. This includes articulating compelling visions, setting ambitious but achievable goals, hiring and developing exceptional talent, and establishing high standards that become part of the team's DNA. 

• Influence extends beyond direct authority – it's about building trust and alignment across the organization. 

A Final Word of Wisdom From Product Executive David Jesse

"Since a product organization is a reflection of its leader, leaders should exhibit the qualities that make a successful product manager: customer-focused, data-driven, strong product sense, close to the details, a team player, and results-oriented.

What the leader focuses on will translate into what their team prioritizes. If they lack any of these things, it’s likely that their team won’t value or demonstrate them, either."

Address Leadership & Skills Gaps With the Help of Experts Like David Jesse

David Jesse is a leading product executive in the Hunt Club ExpertAccess Program, which puts first-string operators in your back pocket for all things talent, so you can hire better, smarter, and faster.