This report draws from direct engagement with leaders throughout the spring 2026 LEAP Flagship experience and offers a grounded, qualitative view of how today’s marketing leaders are navigating the complexities of leadership in real-time.
The cohort was comprised of 40+ senior marketing and growth leaders and 9 CMO and C-suite mentors, spanning 7 sitting CMOs, CEOs, and Chief Growth Officers, 27 VP and SVP-level leaders, and 7 Directors stepping into broader enterprise scope. Most bring 15–20+ years of experience across global enterprises, high-growth companies, with representation across the U.S., Europe, Canada, Asia, Latin America, and the Middle East.
They operate inside complex, matrixed organizations, responsible for driving growth, transformation, and performance while expanding their impact at an enterprise level.
These are leaders already operating at a high level—yet being pushed to expand into enterprise leadership, lead through constant change, influence at scale, and carry growing pressure, all while rethinking their role, impact, and direction in real time.
Across these perspectives, six consistent leadership realities emerged:
Enterprise roles are expanding faster than they’re being defined
Performance is increasingly driven by influence, not just execution
Scaling impact through others is the hardest transition
Constant, layered change is now the baseline
Alignment, purpose, and long-term direction are being reassessed
The pressure is intensifying—and often invisible
Here is what leaders are feeling, where they’re needing more support, and what it means for organizations. These patterns point to a broader shift—not just in how leaders operate, but in how organizations need to think about talent development at the senior level.
Leaders are being asked to operate at an enterprise level—often before they’ve had the space or support to fully redefine how they lead. Scope is expanding faster than leadership models, leaving many to figure it out in real time.
“I want to shift people’s perception of me from a strong workhorse to a true leader.”
“I’m at a pivotal point in my career and trying to define what that next step really looks like.”
“My greatest priority is to gain clarity on how I show up differently at this level.”
“I’m being asked to operate more broadly, but I’m still figuring out what that actually means in practice.”
This is the most dominant theme across all inputs. Career growth, transitions, and leadership identity evolution appear more than any other topic in mentorship conversations. Leaders are navigating promotions, expanded scope, and key inflection points where expectations have shifted significantly. One mentor reported “Many of these leaders are already operating at the next level—they just haven’t had the space to fully define it.” Another shared “our conversations focused on how to step back from execution and lead with perspective and judgment.”
This is where leadership trajectories accelerate—or stall. Without clarity, leaders often default to execution, when the role now requires prioritization, perspective, and enterprise-level judgment. What’s often missing is not capability, but the space to step back and intentionally redefine how they lead at this level.
As leaders move into broader roles, success is increasingly tied to how they communicate, align, and influence—not just what they deliver.
“I want to be sharper in the room and land my message more clearly.”
“I want to show up with a more confident point of view, especially with senior stakeholders.” “I know I have the thinking—I want to communicate it in a way that actually drives decisions.” “I want to influence outcomes more effectively, not just contribute to them.”
Executive presence, influence, and strategic visibility are among the most frequently discussed development areas. Leaders are focused on translating complex thinking into clear, compelling narratives and becoming more effective in high-stakes settings.
At this level, ideas alone are not enough. Leaders who cannot clearly articulate their thinking or influence direction risk being under-leveraged, regardless of capability. As one mentor put it, “Leaders at this level are not struggling with ideas—they’re working on how to frame and land those ideas.” Another mentor added, “A lot of the work is around clarity, presence, and helping others understand what matters most.” This is increasingly a talent development gap, not just a performance gap.
Leaders are expected to deliver through teams at scale while maintaining performance, culture, and clarity. This requires a shift from owning work to enabling others to succeed.
“Leading and building high-performing teams at scale is my biggest focus right now.”
“I’m working on how to create accountability without losing engagement.”
“I need to delegate more, but still feel responsible for the outcomes.”
“I’m trying to raise the bar while bringing the team along with me.”
Leaders are actively working through team development, delegation, org design, succession planning, and how to build stronger leadership benches. One mentor shared, “Many leaders are still operating as the best individual contributor on their team.” Another shared, “Building a strong leadership bench is a consistent focus across conversations.”
This is where talent development either scales or breaks. If leaders aren’t equipped to lead through others, organizations stall at the exact moment they need leverage. Many leaders remain too close to execution, limiting both team growth and their own ability to operate at a broader level. Creating impact through others requires a different mindset and operating model.
Leaders are operating in environments where transformation is continuous. They are expected to drive change while also creating stability for their teams.
“Re-org, workforce reduction, AI transformation… it’s all happening at once.”
“I’m leading through change while also trying to stay ahead of what’s coming next.”
“The pace of change feels constant—it’s not one moment, it’s ongoing.”
“I’m expected to create clarity even when things aren’t fully clear yet.”
Mentors repeatedly pointed to the fact that leaders are not dealing with change in isolated moments, but across multiple fronts at once. As one mentor noted, “Leaders are navigating multiple layers of change simultaneously, not sequentially.”
This layering of change is creating a second tension—between the need to move quickly and the responsibility to maintain stability within teams. “There’s a real tension between moving fast and helping teams stay grounded,” one mentor observed. AI is compounding this dynamic.
Leaders are expected to create clarity for others while often operating without the space to fully process and align themselves. The tension between speed and stability is intensifying—requiring them to drive progress while keeping teams focused and aligned. As AI and ongoing disruption compress timelines and raise expectations, leading through ambiguity is no longer situational—it is a core requirement of the role.
As leaders progress, questions of alignment, fulfillment, and long-term direction become more visible.
“I want to reconnect my leadership decisions to my values.”
“I’m thinking more intentionally about what I want from the next phase of my career.”
“I’m evaluating whether what I’m doing aligns with what matters most to me.”
“I’m starting to think differently about fulfillment—not just success.”
Purpose and values surface consistently in mentorship conversations, especially during periods of transition and pressure. Leaders are not just thinking about what’s next—they’re reassessing how their roles align with what matters most.
As one mentor noted, “These conversations often shift from performance to purpose.”
Another observed, “Leaders are asking deeper questions about alignment, not just advancement.”
Alignment is increasingly tied to engagement and retention at this level. As roles evolve and pressure increases, leaders who lack clarity on direction or purpose are more likely to disengage or start looking elsewhere.
Leaders are carrying sustained pressure while also supporting their teams through it. Much of this pressure is not openly discussed.
“These roles can feel isolating and lonely.”
“I’m carrying pressure from all sides—team, leadership, business.”
“Tackling burnout and disengagement on the team while managing my own energy.” “I have to show up with confidence even when I’m still figuring things out.”
Resilience, confidence, and operating under pressure surface consistently across mentorship conversations. Leaders are managing burnout, navigating uncertainty, and maintaining performance—often without signaling the strain. As one mentor shared, “There is a level of pressure here that isn’t always visible on the surface.” Another noted, “Many leaders are managing a lot internally while continuing to perform externally.”
Much of this pressure is compounded by a lack of environments where leaders can pause, reflect, and reset how they operate. Without that space, the risk is not just burnout—but diminished clarity, decision-making, and long-term effectiveness.
Leaders today are not lacking awareness or ambition. They know where they want to grow. They are actively seeking ways to improve how they lead. What’s often missing is the space—and the conditions—to think, test, and evolve how they show up and how they drive impact for themselves, their teams and their organizations.
Leadership experiences like LEAP Flagship and LEAP Essentials are designed to close that gap—creating space not only to think and reset, but to connect with peers across industries, expand perspective beyond their own organizations, and realize they’re not navigating these challenges alone. What participants have to say about their experience:
3 MOVES EVERY CMO AND TALENT LEADER SHOULD MAKE NOW
Align and proactively communicate expectations around enterprise leadership—and build them into how you assess and develop talent. i.e.
Prioritize clarity, presence, and decision-making—and create real opportunities for leaders to practice and be seen.
Employ talent development grounded in application, perspective, and real-world context. Partner with organizations like Virtuosi League that lift leaders out of the day-to-day and beyond organizational silos to drive lasting shifts in how they lead.