Dean Health Plan Executive and Leadership Team

May, 2026

Leadership Overview

Dean Health Plan has 4 executives leading key functions including strategy, finance, human resources, and operations.

Driven by a commitment to integrated healthcare, Dean Health Plan manages a school of medical professionals and a multi-specialty physicians group affiliated with St. Mary's Hospital, providing essential primary and specialty care services across Wisconsin.

Leadership Roles at Dean Health Plan

  • President & Chief Executive Officer - Stephen Olson
  • Senior Vice President & Chief Financial Officer - Steven Caldwell
  • President - Julie Perez
  • Senior Vice President Chief Human Resources Officer - John Haeberle
  • Stephen Olson - President & Chief Executive Officer

    Stephen Olson, the President & Chief Executive Officer at Dean Health Plan, directs the overarching strategy and operational execution for the organization. Olson guides the company's vision, ensuring alignment with its mission to manage a school of medical professionals and a multi-specialty physicians group. This leadership role involves setting strategic priorities, fostering innovation in healthcare delivery, and driving the organization's growth and market position. Olson oversees the integration of primary and specialty care services, ensuring high-quality patient outcomes and operational efficiency across all affiliated clinics and St. Mary's Hospital. The President & Chief Executive Officer's responsibilities extend to cultivating key relationships with healthcare partners and stakeholders, solidifying Dean Health Plan's presence in Madison, Wisconsin, and beyond. Stephen Olson's executive oversight ensures the continued development of medical professionals and the expansion of comprehensive healthcare solutions.

    Steven Caldwell - Senior Vice President & Chief Financial Officer

    Steven Caldwell, the Senior Vice President & Chief Financial Officer at Dean Health Plan, manages all financial operations and fiscal strategy. Caldwell oversees budgeting, financial planning, and investment strategies, ensuring the fiscal health and sustainability of the organization. This role is critical in managing the financial aspects of the multi-specialty physicians group and its affiliation with St. Mary's Hospital. Caldwell's responsibilities include optimizing financial performance, managing revenue cycles, and ensuring compliance with all financial regulations within the healthcare sector. The Senior Vice President & Chief Financial Officer also plays a key part in securing funding and managing capital expenditures to support the expansion of primary and specialty care services. By implementing robust financial controls and reporting mechanisms, Steven Caldwell drives financial accountability and supports strategic decision-making across Dean Health Plan's operations in Wisconsin.

    Julie Perez - President

    Julie Perez, the President at Dean Health Plan, directs specific operational divisions and strategic initiatives within the healthcare system. Perez focuses on enhancing the delivery of primary care services, such as family and internal medicine, across the network of clinics. This leadership role involves optimizing patient access, improving service quality, and ensuring seamless integration of care pathways. Perez collaborates closely with clinical leadership to advance specialty care offerings, including cardiology, mental health, and orthopedics, aligning these services with market demands and patient needs. The President's responsibilities extend to driving operational excellence and efficiency throughout the organization, supporting the broader goals of Dean Health Systems. By overseeing key functional areas, Julie Perez contributes significantly to the organization's mission of providing comprehensive and accessible healthcare solutions in Wisconsin.

    John Haeberle - Senior Vice President Chief Human Resources Officer

    John Haeberle, the Senior Vice President Chief Human Resources Officer at Dean Health Plan, leads all human capital management initiatives. Haeberle is responsible for developing and implementing strategies related to talent acquisition, employee relations, compensation, and benefits for the organization's medical professionals and staff. This leadership position is vital in supporting the operational needs of the multi-specialty physicians group and its affiliated hospital. Haeberle focuses on fostering a positive and productive work environment, ensuring that Dean Health Plan attracts and retains top talent in primary and specialty care fields. The Senior Vice President Chief Human Resources Officer also oversees organizational development and change management, crucial for adapting to the evolving healthcare landscape. By championing employee engagement and professional development, John Haeberle ensures the workforce is equipped to deliver exceptional patient care and advance the company's mission.

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    Frequently Asked Questions Regarding Dean Health Plan Top Executives and Leadership Team

    Who leads Dean Health Plan?
    Dean Health Plan is led by Stephen Olson (President & Chief Executive Officer), along with executives such as Steven Caldwell (Senior Vice President & Chief Financial Officer) and Julie Perez (President).
    Who is part of Dean Health Plan’s executive team?
    The executive team of Dean Health Plan includes leaders such as Stephen Olson (President & Chief Executive Officer), Steven Caldwell (Senior Vice President & Chief Financial Officer), Julie Perez (President) and other senior executives.
    How many executives does Dean Health Plan have?
    Dean Health Plan has 4 executives leading key business areas.
    What roles are included in Dean Health Plan’s leadership team?
    The leadership team of Dean Health Plan includes roles such as President & Chief Executive Officer, Senior Vice President & Chief Financial Officer, President, Senior Vice President Chief Human Resources Officer.