Commonwealth Executive and Leadership Team

July, 2026

Leadership Overview

Commonwealth has 9 executives leading key functions including strategy, operations, technology, finance, compliance, and advisor support.

Driven by a commitment to advisor success, Commonwealth empowers independent financial advisors with comprehensive business solutions, fostering growth and operational efficiency through flexible affiliation and personalized development.

Leadership Roles at Commonwealth

  • Milestone Investment Management Llc Chief Executive Officer & Founder - Michael Stone
  • Principal, Chief Executive Officer - Matthew Ramer
  • Chief Financial Officer - Heather Stein
  • Senior Vice President, Chief Financial Officer - Jonathan Cleasby
  • Chief Operating Officer - Vernessa Christie
  • President & Chief Operating Officer - Trap Kloman
  • Advisor, Chief Compliance Officer, Financial Advisor, Investment Advisor Representative, President - Justin Brillhart
  • Chief Technology Officer - Thavachelvan Kanaganathan
  • Vice President & Chief of Staff - Erin Rainwater
  • Michael Stone - Milestone Investment Management Llc Chief Executive Officer & Founder

    Michael Stone, the Milestone Investment Management Llc Chief Executive Officer & Founder at Commonwealth, architects the strategic vision for Milestone Investment Management Llc, driving its core business objectives. Stone's leadership focuses on establishing robust investment strategies and fostering a culture of innovation within the organization. This role involves direct oversight of all investment-related activities, ensuring alignment with market dynamics and client needs. The founder's perspective informs long-term planning, guiding the firm's expansion and market positioning. Michael Stone's dedication to entrepreneurial principles shapes the operational framework, emphasizing sustainable growth and financial prudence. The executive's influence extends to cultivating key partnerships and identifying new avenues for business development, solidifying the firm's competitive edge in the financial sector.

    Matthew Ramer - Principal, Chief Executive Officer

    Matthew Ramer, the Principal, Chief Executive Officer at Commonwealth, directs the overarching corporate strategy and operational execution. Ramer's leadership ensures the firm's mission to support independent financial advisors is consistently met through innovative business solutions and technology tools. This executive oversees the integration of flexible affiliation options and compliance frameworks, directly impacting advisor practice growth and efficiency. By championing a collaborative, advisor-focused approach, Matthew Ramer enhances client service delivery and operational streamlining across the network. The Chief Executive Officer's strategic initiatives are crucial for maintaining Commonwealth's market position and driving its commitment to advisor independence. Ramer's focus on personalized development programs supports advisor success and practice expansion.

    Heather Stein - Chief Financial Officer

    Heather Stein, the Chief Financial Officer at Commonwealth, directs the company's financial planning, analysis, and fiscal management. Stein oversees all aspects of financial operations, ensuring robust capital allocation and profitability for the firm and its affiliated advisors. This executive manages budgeting, forecasting, and financial reporting, providing critical insights that support strategic decision-making and sustainable growth. The Chief Financial Officer's responsibilities include optimizing financial performance, managing risk, and ensuring compliance with all financial regulations. Heather Stein's expertise is vital in maintaining the financial health of Commonwealth, enabling the firm to offer flexible affiliation options and integrated investment solutions. The executive's focus on financial integrity underpins the advisor-focused approach and commitment to practice growth.

    Jonathan Cleasby - Senior Vice President, Chief Financial Officer

    Jonathan Cleasby, the Senior Vice President, Chief Financial Officer at Commonwealth, manages the financial health and strategic fiscal planning for the organization. Cleasby oversees financial reporting, budgeting, and investment analysis, ensuring robust financial controls and compliance with industry standards. This executive's role involves optimizing financial performance and resource allocation to support the firm's growth objectives and its commitment to independent financial advisors. The Senior Vice President, Chief Financial Officer plays a key part in developing financial strategies that enhance practice growth and operational efficiency for affiliated advisors. Jonathan Cleasby's expertise guides the firm's financial operations, supporting flexible affiliation options and integrated solutions. The executive's focus ensures financial stability and supports the advisor-focused approach.
    Jonathan Cleasby

    Vernessa Christie - Chief Operating Officer

    Vernessa Christie, the Chief Operating Officer at Commonwealth, drives operational excellence and streamlines business processes across the organization. Christie oversees the day-to-day management of operations, ensuring the efficient delivery of business solutions and technology tools to independent financial advisors. This executive's purview includes enhancing practice growth and operational efficiency, focusing on the seamless integration of compliance and investment solutions. The Chief Operating Officer champions the advisor-focused approach, ensuring personalized development programs and flexible affiliation options meet advisor needs. Vernessa Christie's leadership is instrumental in optimizing advisor operations, enhancing client service, and supporting the pursuit of independence. The executive's commitment to operational efficiency underpins Commonwealth's collaborative environment.

    Trap Kloman - President & Chief Operating Officer

    Trap Kloman, the President & Chief Operating Officer at Commonwealth, directs the firm's operational strategy and execution, driving efficiency and growth. Kloman oversees the delivery of comprehensive business solutions and technology tools, ensuring independent financial advisors receive optimal support for their practices. This executive leads initiatives to enhance operational efficiency, streamline compliance, and integrate investment solutions, directly impacting advisor success. The President & Chief Operating Officer champions the firm's commitment to flexible affiliation options and personalized development programs, fostering advisor independence. Trap Kloman's leadership ensures the collaborative and advisor-focused approach remains central to Commonwealth's operations, enhancing client service and practice management. The executive's focus is on scalable operational frameworks.

    Justin Brillhart - Advisor, Chief Compliance Officer, Financial Advisor, Investment Advisor Representative, President

    Justin Brillhart, the Advisor, Chief Compliance Officer, Financial Advisor, Investment Advisor Representative, President at Commonwealth, ensures the integrity and adherence to regulatory standards across all firm operations. Brillhart oversees the development and implementation of robust compliance frameworks, safeguarding the firm and its affiliated advisors. This executive's multifaceted role includes providing expert financial advice and managing investment strategies, directly supporting advisor practice growth and efficiency. The President's leadership ensures that Commonwealth's flexible affiliation options and integrated solutions meet stringent compliance requirements. Justin Brillhart's dedication to regulatory excellence and client advocacy reinforces the firm's commitment to an advisor-focused approach. The executive's focus is on maintaining the highest standards of fiduciary responsibility and operational compliance.

    Thavachelvan Kanaganathan - Chief Technology Officer

    Thavachelvan Kanaganathan, the Chief Technology Officer at Commonwealth, architects the firm's technology roadmap and digital transformation initiatives. Kanaganathan oversees the development and implementation of advanced technology tools designed to enhance practice growth and operational efficiency for independent financial advisors. This leadership role involves managing the firm's IT infrastructure, cybersecurity protocols, and the integration of cutting-edge solutions that support advisor independence. The Chief Technology Officer ensures that technology investments directly align with Commonwealth's mission to provide seamless business solutions and personalized development programs. Thavachelvan Kanaganathan's strategic direction in technology empowers advisors to streamline operations, elevate client service, and maintain a competitive edge in the evolving financial landscape. The executive's focus is on scalable, secure, and user-friendly technological platforms.

    Erin Rainwater - Vice President & Chief of Staff

    Erin Rainwater, the Vice President & Chief of Staff at Commonwealth, provides strategic support and operational coordination across key executive initiatives. Rainwater works closely with leadership to drive the implementation of business solutions and technology tools that enhance advisor practice growth and efficiency. This role involves facilitating communication between departments, managing special projects, and ensuring alignment with the firm's overall mission. The Vice President & Chief of Staff plays a crucial part in refining the flexible affiliation options and personalized development programs offered to advisors. Erin Rainwater's efforts contribute to streamlining operations, enhancing client service, and fostering the collaborative, advisor-focused approach that defines Commonwealth. The executive's focus is on strategic execution and organizational effectiveness.

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    Frequently Asked Questions Regarding Commonwealth Top Executives and Leadership Team

    Who leads Commonwealth?
    Commonwealth is led by Michael Stone (Milestone Investment Management Llc Chief Executive Officer & Founder), along with executives such as Matthew Ramer (Principal, Chief Executive Officer) and Heather Stein (Chief Financial Officer).
    Who is part of Commonwealth’s executive team?
    The executive team of Commonwealth includes leaders such as Michael Stone (Milestone Investment Management Llc Chief Executive Officer & Founder), Matthew Ramer (Principal, Chief Executive Officer), Heather Stein (Chief Financial Officer) and other senior executives.
    How many executives does Commonwealth have?
    Commonwealth has 9 executives leading key business areas.
    What roles are included in Commonwealth’s leadership team?
    The leadership team of Commonwealth includes roles such as Milestone Investment Management Llc Chief Executive Officer & Founder, Principal, Chief Executive Officer, Chief Financial Officer, Senior Vice President, Chief Financial Officer, Chief Operating Officer.