Work with Caroline

Custom Executive Coaching
One-on-one executive coaching tailored to your goals and challenges. Whether you're navigating a leadership transition, managing complex team dynamics, feeling stuck or burned out, or considering your next career move, I'll bring firsthand executive experience and direct, thoughtful coaching.
$2,120.40

Executive Coaching — Getting Started Package
Starting at
$1,325.25

Complete 6 Month Executive Coaching Engagement (360 Analysis Included)
$15,000
About
Caroline also coaches for General Management and Leadership Coaching. View all.
Caroline’s free events
Live interactive sessions you can join for free.

Caroline’s Executive Coaching Qualifications
Coaches professionally
Experience level: Vice President
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.
Caroline can help with:
Communication Skills
Decision Making
Leadership Development
Strategic Planning
Succession Planning
Team Management
Why do I coach?
Throughout my career, I've been fortunate to work with people who challenged my thinking, asked questions I hadn't considered, and helped me see situations differently. Some of the most valuable conversations I've had weren't with people who gave me answers. They were with people who helped me arrive at better answers myself. As a leader, I found that one of the most rewarding parts of my work was helping other people develop their judgment, navigate difficult situations, and grow into responsibilities they weren't always sure they were ready for. That interest eventually led me to formal coaching training at Georgetown University and to founding my own coaching practice. What I enjoy most about coaching is getting beneath the surface of a challenge. Often, the problem someone initially brings to a session isn't the most important thing we end up discussing. A well-timed question, a different interpretation, or an assumption worth challenging can fundamentally change how someone sees a situation. I love being part of those conversations and helping people recognize possibilities they might not have seen on their own.
Work Experience

Founder and Executive Coach
Swell Point Partners
April 2026 - Present
Swell Point Partners is an executive coaching practice for leaders and professionals facing consequential decisions, new challenges, and situations where the right answer isn't obvious. I help clients step back from the immediate problem, examine their assumptions and patterns, and get clearer about what they want and how they want to move forward.
Vice President of Operations
Fundrise
February 2022 - June 2025
Hiring Manager
Led a 60-person real estate investment management business unit at Fundrise, a technology-driven vertically integrated investment platform, with responsibility for business operations, financial performance, strategic planning, and organizational leadership.
Senior Director of Operations, Real Estate Investment Management
Fundrise
March 2021 - February 2022
Hiring Manager
Built and scaled the business operations and people operations functions within Fundrise's real estate investment management business. Hired functional leaders and partnered with them to establish portfolio management, real estate legal, real estate accounting, and capital markets capabilities. Led the hiring efforts that added more than 50 employees across the organization.

Senior Consultant, Strategy and Operations
Deloitte
March 2017 - June 2018

Naval Aviator
US Navy
December 2006 - December 2016
Education

Kellogg School of Management (Northwestern)
MBA, General Management
2018 - 2020

University of North Carolina at Chapel Hill
Bachelor of Arts
5.0 average review
9 reviews
Overall rating
Caroline has helped Leland clients get into Nuveen

Custom Executive Coaching
One-on-one executive coaching tailored to your goals and challenges. Whether you're navigating a leadership transition, managing complex team dynamics, feeling stuck or burned out, or considering your next career move, I'll bring firsthand executive experience and direct, thoughtful coaching.
$2,120.40

Executive Coaching — Getting Started Package
Starting at
$1,325.25

Complete 6 Month Executive Coaching Engagement (360 Analysis Included)
$15,000
Caroline also coaches for General Management and Leadership Coaching. View all.

