Commonwealth Executive and Leadership Team

August, 2026

Leadership Overview

Commonwealth has 9 executives leading key functions including investment strategy, financial oversight, operational scaling, technology development, and compliance management.

Dedicated to empowering independent financial advisors, Commonwealth delivers comprehensive business solutions and integrated technology tools that drive practice growth and operational efficiency across the wealth management landscape.

Leadership Roles at Commonwealth

  • Milestone Investment Management Llc Chief Executive Officer & Founder - Michael Stone
  • Principal, Chief Executive Officer - Matthew Ramer
  • Chief Financial Officer - Tina Reesman
  • Senior Vice President, Chief Financial Officer - Jon 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 - Thava 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, directs the overarching investment philosophy and strategic vision for the firm. By architecting high-level portfolio management frameworks, Stone ensures that independent advisors access sophisticated market insights and robust asset allocation models. This leadership role involves constant evaluation of global market trends to maintain competitive advantages for the entire advisor network. Michael Stone actively shapes the firm's commitment to excellence by fostering a culture of rigorous analytical discipline and client-centric decision-making. Through the implementation of advanced investment methodologies, Stone supports the long-term financial objectives of diverse client bases. The Chief Executive Officer & Founder maintains alignment with the broader corporate mission by prioritizing sustainable growth and risk management. Ultimately, Stone secures the firm's reputation as a premier partner for advisors seeking sophisticated investment solutions and professional development.

    Matthew Ramer - Principal, Chief Executive Officer

    Matthew Ramer, the Principal, Chief Executive Officer at Commonwealth, drives the strategic direction and long-term growth initiatives for the entire organization. Overseeing the executive leadership team, Ramer ensures that all business units remain focused on providing superior support to independent financial advisors. This role involves navigating complex market dynamics to expand the firm's reach and enhance the value proposition for partners. Matthew Ramer cultivates a collaborative environment where innovation and advisor success remain the primary objectives. By aligning corporate resources with the evolving needs of the wealth management industry, Ramer strengthens the firm's market position. The Principal, Chief Executive Officer manages high-level relationships with key stakeholders to ensure operational stability and continued expansion. Through decisive leadership, Ramer fosters an environment of independence and professional excellence, ensuring that the firm consistently delivers the tools and consulting necessary for advisors to thrive in a competitive financial landscape.

    Tina Reesman - Chief Financial Officer

    Tina Reesman, the Chief Financial Officer at Commonwealth, manages the fiscal health and capital allocation strategies that underpin the firm's operational success. By directing financial planning and analysis, Reesman ensures that resources support the firm's commitment to advisor growth and technology investment. This leadership role involves overseeing complex budgeting processes and maintaining rigorous financial controls to protect the firm's long-term stability. Tina Reesman collaborates with other executive leaders to evaluate the financial impact of new business initiatives and service expansions. Through precise fiscal management, Reesman enables the organization to scale effectively while maintaining high standards of service for independent advisors. The Chief Financial Officer monitors economic indicators to adjust financial strategies, ensuring resilience against market volatility. By optimizing capital efficiency, Reesman directly supports the firm's ability to provide competitive business solutions and consulting services to the entire advisor network.

    Jon Cleasby - Senior Vice President, Chief Financial Officer

    Jon Cleasby, the Senior Vice President, Chief Financial Officer at Commonwealth, directs the firm's financial reporting, treasury functions, and long-term capital strategy. By overseeing the financial health of the organization, Cleasby ensures that the firm maintains the resources necessary to invest in advisor-facing technology and development programs. This leadership role involves managing relationships with financial institutions and ensuring compliance with all fiscal regulations. Jon Cleasby collaborates with the executive team to assess the financial viability of new market opportunities and service expansions. Through rigorous financial oversight, Cleasby supports the firm's ability to provide stable and reliable business solutions to independent advisors. The Senior Vice President, Chief Financial Officer monitors performance metrics to drive profitability and operational efficiency across all departments. By maintaining a strong balance sheet, Cleasby enables the firm to pursue its mission of supporting advisor independence and practice growth through consistent investment and strategic planning.
    Jon Cleasby

    Vernessa Christie - Chief Operating Officer

    Vernessa Christie, the Chief Operating Officer at Commonwealth, executes the daily operational strategies that streamline business processes for independent financial advisors. By overseeing internal infrastructure and service delivery, Christie ensures that advisors receive seamless support for their practice management needs. This role involves optimizing workflows and integrating technology tools to enhance overall efficiency across the firm's service platforms. Vernessa Christie leads cross-functional teams to implement operational improvements that directly impact client service quality and advisor productivity. Through the management of complex operational systems, Christie maintains the firm's high standards for reliability and performance. The Chief Operating Officer coordinates with other C-suite leaders to align operational capacity with the firm's strategic growth objectives. By focusing on scalable processes, Christie enables the organization to support a growing network of advisors while maintaining a personalized, advisor-focused approach to wealth management.

    Trap Kloman - President & Chief Operating Officer

    Trap Kloman, the President & Chief Operating Officer at Commonwealth, leads the firm's day-to-day business operations and executes the strategic vision for advisor support services. By overseeing the integration of consulting, compliance, and business solutions, Kloman ensures that the firm delivers a cohesive and high-value experience for independent advisors. This role involves managing the firm's operational scale to accommodate growth while maintaining the personalized service that defines the organization. Trap Kloman collaborates with other executive leaders to refine service models and enhance the efficiency of advisor-facing programs. Through the management of core business functions, Kloman drives the firm's commitment to advisor success and operational excellence. The President & Chief Operating Officer monitors industry trends to proactively adjust operational strategies and maintain a competitive edge. By focusing on the intersection of technology and human expertise, Kloman ensures that the firm remains a leader in providing the tools and support necessary for advisor independence.

    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, directs the firm's regulatory compliance framework and risk management strategies. By overseeing the adherence to industry standards, Brillhart ensures that the firm and its independent advisors operate within a secure and ethical environment. This leadership role involves developing compliance policies that protect both the firm and its clients while facilitating advisor growth. Justin Brillhart collaborates with the executive team to integrate compliance solutions into the firm's broader business tools, making regulatory adherence a seamless part of practice management. Through the management of complex compliance requirements, Brillhart supports the firm's reputation for integrity and professional excellence. The Advisor, Chief Compliance Officer, Financial Advisor, Investment Advisor Representative, President monitors regulatory changes to proactively update internal protocols. By balancing risk mitigation with business enablement, Brillhart empowers advisors to pursue independence with confidence and security.

    Thava Kanaganathan - Chief Technology Officer

    Thava Kanaganathan, the Chief Technology Officer at Commonwealth, architects the digital infrastructure and software solutions that empower independent financial advisors. By directing the development of proprietary technology tools, Kanaganathan ensures that advisors possess the digital capabilities required for modern practice management and client engagement. This leadership role involves overseeing cybersecurity protocols, data integration, and the continuous evolution of the firm's technology stack. Thava Kanaganathan collaborates with the executive team to align technical innovation with the firm's broader business goals and advisor needs. Through the implementation of advanced software platforms, Kanaganathan drives operational efficiency and enhances the user experience for advisors across the country. The Chief Technology Officer manages the technical roadmap to ensure the firm remains at the forefront of financial technology. By prioritizing robust and intuitive digital solutions, Kanaganathan supports the firm's mission to provide advisors with the tools necessary for sustained independence and growth.

    Erin Rainwater - Vice President & Chief of Staff

    Erin Rainwater, the Vice President & Chief of Staff at Commonwealth, coordinates strategic initiatives and facilitates communication across the executive leadership team. By managing the flow of information and prioritizing key projects, Rainwater ensures that the firm's leadership remains aligned on critical business objectives. This role involves overseeing special projects that impact the firm's overall strategy and advisor support programs. Erin Rainwater acts as a central point of contact for complex organizational issues, driving consensus and ensuring the efficient execution of corporate goals. Through the management of executive workflows, Rainwater enhances the productivity of the leadership team and supports the firm's commitment to advisor-focused service. The Vice President & Chief of Staff monitors the progress of strategic initiatives to ensure timely delivery and high-quality outcomes. By fostering collaboration and operational clarity, Rainwater directly contributes to the firm's ability to provide consistent and effective support to independent financial advisors.

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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 Tina Reesman (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), Tina Reesman (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.