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Description
This package is built for executives, founders, and rising leaders looking to elevate their impact, sharpen their strategy, and lead with clarity. Whether you're navigating a new role, preparing for expanded responsibility, or seeking to level up your leadership, this personalized coaching experience helps you unlock growth and drive results. Available in 5- or 10-hour increments, you’ll work 1-on-1 with an experienced executive coach to focus on the areas most relevant to you—from managing complex teams to refining your leadership presence. Every session is tailored to your goals, challenges, and leadership context. Common coaching activities include: - 360 Analysis: Gather feedback from your direct reports, investors, peers, and others to paint a clear picture of your strengths and weaknesses - Vision & Strategy: Set a clear direction and align teams around mission-critical objectives. - High-Stakes Decision-Making: Gain tools to lead confidently through ambiguity and change. - Leadership Style & Presence: Develop greater self-awareness and adapt your style to lead more effectively across contexts. - Stakeholder Management: Navigate board relationships, cross-functional influence, and internal politics with credibility and poise. - Team Performance & Culture: Build high-trust, high-output teams and foster a culture of accountability. - Situational Leadership Coaching: Work through real-time leadership challenges with a trusted thought partner. - Executive Career Planning: Clarify your long-term goals and position yourself for growth, transition, or promotion. This package is ideal for leaders who want structured yet flexible support to accelerate their personal and professional development. With expert guidance, you'll move forward with greater confidence, clarity, and impact.
What you'll get from this package
Strengthened decision-making and executive leadership skills
Gained insight into your strengths and growth areas
Developed a tailored growth plan to guide your journey
Built confidence to lead and motivate high-performing teams
Additional details
Coaching delivered via live sessions and .
Services included:
Decision Making
Strategy
Communication Skills
Strategic Planning
Board Relations
Team Management
Leadership Development
Succession Planning
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
More packages from Caroline
Custom hourly · $279/hr
Get help with Decision Making, Communication Skills, and .
Caroline also coaches for General Management and Leadership Coaching. View all.

Offered by Caroline P.
Joined October 2026
5.0
Former Tech VP & Navy Pilot | Executive Leadership Coach
I bring nearly 20 years of leadership and management experience across the technology sector and U.S. Navy, along with an MBA from the Kellogg School of Management. In 2026 I completed Georgetown University's Leadership Coaching Executive Certificate Program, an ICF-accredited coach training program. Most recently, I served as VP of Operations at Fundrise, where I led a 60-person business unit with responsibility for business operations, financial performance, strategic planning, and organizational leadership. Previously, I served as a U.S. Navy pilot and Flag Aide to two admirals. My career experiences have given me firsthand exposure to the demands of leadership, from managing teams and navigating organizational change to making difficult decisions and balancing competing priorities. My coaching provides a space for leaders to step away from the day-to-day demands of their roles and examine the challenges they're facing from a different perspective. My approach is thoughtful, direct, and grounded in genuine curiosity. Through pointed questions and honest reflection, I help clients recognize patterns, challenge assumptions, better understand the dynamics at play, and make more intentional choices about how they lead.
Starting at $1,325.25
5h+ of coaching