Skip to main content
Caroline P.

Caroline Payne

Former Tech VP & Navy Pilot | Executive Leadership Coach

  • 18

    Likes

  • 614

    Impressions

Available Tuesday

Starting at 2:00 PM UTC

Questions?

You can start chatting with Caroline before you get started.

Work with Caroline

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

Swell Point Partners Logo

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.

Fundrise Logo

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.

Fundrise Logo

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.

Deloitte Logo

Senior Consultant, Strategy and Operations

Deloitte

March 2017 - June 2018

US Navy Logo

Naval Aviator

US Navy

December 2006 - December 2016

Education

Kellogg School of Management (Northwestern) Logo

Kellogg School of Management (Northwestern)

MBA, General Management

2018 - 2020

University of North Carolina at Chapel Hill Logo

University of North Carolina at Chapel Hill

Bachelor of Arts

5.0 average review

9 reviews


Overall rating

5
4
3
2
1

Caroline has helped Leland clients get into Nuveen


Loading reviews...