Work with Caroline
The Difficult Conversation: PREPARE + PRACTICE (Option to Add Role Play)
A focused coaching session to examine the situation, understand what's making it difficult, and prepare for the conversation ahead. Option to add a discounted second session dedicated to role-playing the conversation: test different approaches, receive feedback, and prepare for potential reactions.
Starting at
$279
Leadership Development Start-to-Finish
Starting at
$2,511
About
Caroline also coaches for General Management and Executive Coaching. View all.
Caroline’s free events
Live interactive sessions you can join for free.
Caroline’s Leadership 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 Kellogg and formal coaching training through Georgetown University's Leadership Coaching Certificate Program. As VP of Operations at Fundrise, I led a 60-person business unit, developed managers, built teams and functions, and created a leadership development program for first-time managers. Earlier in my career, I served as a Navy pilot, leading teams in demanding operational environments and working closely with senior military leadership. My coaching focuses on the challenges that arise as people take on greater responsibility, whether they're managing others for the first time, leading through other managers, or navigating difficult team dynamics. I take a thoughtful, direct approach, helping clients question assumptions, recognize patterns, and consider different ways of approaching the situations they're facing.
Caroline can help with:
AI Fundamentals
Change Management
Coaching and Mentoring
Conflict Resolution
Diversity and Inclusion
Emotional Intelligence
Ethical Leadership
Innovation and Creativity
Problem Solving
Time 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
The Difficult Conversation: PREPARE + PRACTICE (Option to Add Role Play)
A focused coaching session to examine the situation, understand what's making it difficult, and prepare for the conversation ahead. Option to add a discounted second session dedicated to role-playing the conversation: test different approaches, receive feedback, and prepare for potential reactions.
Starting at
$279
Leadership Development Start-to-Finish
Starting at
$2,511
Caroline also coaches for General Management and Executive Coaching. View all.
Caroline’s Leland+ Resources
Access expert resources from Caroline and hundreds of other coaches on Leland+
